Organic Chemistry Some Basic Principles &

Techniques

Question1
In Carius method for estimation of halogens, 180 mg of an organic
compound produced 143.5 mg of AgCl . The percentage composition
of chlorine in the compound is _________ %. (Given : molar mass in
g mol of Ag : 108, Cl : 35.5 )
−1

JEE Main 2025 (Online) 22nd January Morning Shift

Answer: 20

Solution:
To find the percentage composition of chlorine in an organic compound using the Carius method, we follow
these steps:

Calculate Millimoles of AgCl:

Since 143.5 mg of AgCl is produced, and the molar mass of AgCl is 143.5 g/mol, the millimoles of AgCl is:
mg
Millimoles of AgCl = 143.5

143.5 mg/mmol
= 1 mmol

Determine Millimoles of Cl:

In AgCl, there is a 1:1 ratio of Ag to Cl, so the millimoles of Cl are equal to that of AgCl:

Millimoles of Cl = 1 mmol

Calculate Mass of Cl:

Using the molar mass of Cl (35.5 g/mol), the mass of Cl is:

Mass of Cl = 35.5 × 10 −3
g = 35.5 mg

Compute Percentage by Mass of Cl:

The total mass of the organic compound is 180 mg, so the percentage of chlorine is:
 mg
Cl by mass = (
35.5
% ) × 100 = 19.72%
180 mg

Round to the Nearest Integer:

Rounding 19.72% to the nearest integer gives 20%.

Thus, the percentage composition of chlorine in the compound is approximately 20%.

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Question2
The possible number of stereoisomers for 5-phenylpent-4-en-2-ol is
________.

JEE Main 2025 (Online) 24th January Evening Shift

Answer: 4

Solution:

n( stereogenic unit) = 2, 2 2
= 4 stereoisomers are possible.

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Question3
The hydrocarbon (X) with molar mass 80 g mol −1
and 90% carbon
has _______ degree of unsaturation.

JEE Main 2025 (Online) 24th January Evening Shift

Answer: 3

Solution:

Mass of carbon = 80×90

100
= 72gm

Number of C-atoms = 72

12
= 6

Mass of hydrogen = 80×10

800
= 8gm

Number of H -atoms = 8
1
= 8

So molecular formula C 6
H8

D.U. = 6 + 1 − 8/2 = 7 − 4 = 3

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Question4
The total number of structural isomers possible for the substituted
benzene derivatives with the molecular formula C H is________. 9 12

JEE Main 2025 (Online) 3rd April Evening Shift

Answer: 8

Solution:
MF = C 9 H 12
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Question5
The IUPAC name of the following compound is :

JEE Main 2025 (Online) 22nd January Morning Shift

Options:

A. 5-Methoxycarbonly-2-methylhexanoic acid

B. Methyl-5-carboxy-2-methylhexanoate.

C. 2-Carboxy-5-methoxycarbonylhexane.

D. Methyl-6-carboxy-2,5-dimethylhexanoate.

Answer: A

Solution:
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Question6
The incorrect statements regarding geometrical isomerism are :

(A) Propene shows geometrical isomerism.

(B) Trans isomer has identical atoms/groups on the opposite sides of

the double bond.

(C) Cis-but-2-ene has higher dipole moment than trans-but-2-ene.

(D) 2-methylbut-2-ene shows two geometrical isomers.

(E) Trans-isomer has lower melting point than cis isomer.

Choose the correct answer from the options given below :

JEE Main 2025 (Online) 22nd January Morning Shift

Options:

A. (A) and (E) Only

B. (A), (D) and (E) Only

C. (C), (D) and (E) Only

D. (B) and (C) Only

Answer: B

Solution:
(A) CH 3 − CH = CH 2 . GI is not possible

(B) Trans isomer has identical atoms/groups on the opposite side of double bond.

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Question7
How many different stereoisomers are possible for the given
molecule?

JEE Main 2025 (Online) 22nd January Morning Shift

Options:

A. 2

B. 1

C. 3

D. 4

Answer: D

Solution:

To determine the number of different stereoisomers for a molecule, use the formula:
Number of stereoisomers = 2
n

where n is the number of chiral centers in the molecule.

For the given molecule, there are 2 chiral centers, so:

n = 2

Therefore, the number of possible stereoisomers is:

2
2 = 4

This means there are 4 different stereoisomers possible for the molecule in question.

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Question8
The most stable carbocation from the following is :

JEE Main 2025 (Online) 22nd January Evening Shift

Options:

A.

B.
C.

D.

Answer: C

Solution:
Due to +M effect of -OMe at para position

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Question9
The correct stability order of the following species/molecules is :

JEE Main 2025 (Online) 23rd January Morning Shift

Options:

A. q > r > p

B. q > p > r

C. p > q > r

D. r > q > p

Answer: A

Solution:
q is aromatic r is nonaromatic p is antiaromatic

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Question10
Which one of the carbocations from the following is most stable?

JEE Main 2025 (Online) 24th January Morning Shift

Options:

A.

B.

C.

D.

Answer: C
Solution:
Carbocation intermediate is stabilised by +I, +M& hyperconjugation effect. Since in option 2 carbocation is
in conjugation with stronger +M group −OCH hence it will be most stable.
3

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Question11
Identify correct statement/s :

(A) −OCH and −NHCOCH are activating group.

3 3

(B) −CN and -OH are meta directing group.

(C) -CN and −SO 3H are meta directing group.

(D) Activating groups act as ortho - and para directing groups.

(E) Halides are activating groups.

Choose the correct answer from the options given below :

JEE Main 2025 (Online) 24th January Evening Shift

Options:

A. (A), (C) and (D) only

B. (A), (B) and (E) only

C. (A) and (C) only

D. (A) only

Answer: A

Solution:
(B) −CN is meta directing But -OH is ortho / pera directing.

(E) Halides are deactivating groups.

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Question12
In the given structure, number of sp and sp hybridized carbon 2

atoms present respectively are :

JEE Main 2025 (Online) 24th January Evening Shift

Options:

A. 3 and 5

B. 3 and 6

C. 4 and 5

D. 4 and 6

Answer: A

Solution:

Number of sp and sp hybridised carbon atom are 3 and 5.

2

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Question13
The correct order of stability of following carbocations is :

JEE Main 2025 (Online) 28th January Morning Shift

Options:

A. A > B > C > D

B. C > B > A > D

C. B > C > A > D

D. C > A > B > D

Answer: D

Solution:

Solution :-

C is aromatic due to ⊕ve charge hence it is most stable

A have more resonance structure

B have less resonance structure

D have only hyper conjugation

Consider First Aromaticity > Resonance > Hyper conjugation

Ans. D < B < A < C

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Question14
Given below are two statements:

Statement I: and are isomeric compounds.

Statement II: and are functional

group isomers.

In the light of the above statements, choose the correct answer from
the options given below:

JEE Main 2025 (Online) 28th January Evening Shift

Options:

A.
Statement I is false but Statement II is true

B.
Both Statement I and Statement II are true

C.
Statement I is true but Statement II is false

D.
Both Statement I and Statement II are false

Answer: B

Solution:
Statement - I → True

Statement - I → True

1o Amine and 2o Amine are different functional groups, hence both are functional group isomers.

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Question15
Total number of nucleophiles from the following is :

JEE Main 2025 (Online) 29th January Morning Shift

Options:

A.
4

B.
6

C.
5

D.
7

Answer: C
Solution:
Nucleophiles are electron rich species and can provide electrons for making new bonds.

Nucleophiles are nucleus loving species

* typically have a −ve (negative) charge or non-bonding electron pair available for making a new bond.

Nucleophiles are Lewis bases.

NH 3 - It is a nucleophile.

NH 3 has a lone pair of electrons on the nitrogen atom which allows it to be a nucleophile since it can provide
electrons to form a new bond.

PhSH - It is a nucleophile

Lone pair of electrons are present on the sulphone atom and hence it is a nucleophile. The lone pair of
electrons are readily donate to form new bonds. with electrophiles.

(CH 3 )
2
S - It is a nucleophile

The lone pair of electrons on the sulphur atom makes this molecule nucleophile.

H 2 C = CH 2 − It is a nuclophile

Alkenes are nulleophiles because they have a high electron' density in their conbon-conbon double bond. The
π bondin CH = CH is a region of high election density.
2 2

OH - It is a nucleophile

Hydroxide ion is a nucleophile, not an electrophile. It is negatively changed and election rich. The electrons
are easily donated.

H3 O
⊕
- It is not a nucleophile

Hychonium ion is an electrophile. It can gain a pair of electrons from a nucleophile. Also, it is positively
changed.

(CH 3 ) 2 CO - It is not a nucleophile.

Acetone

primarily acts as an electrophile in reactions. It can readily accepts electron pairs from other molecules due to
the partial positive charge on the carbonyl carbon atom.
- It is not a nucleophile.

It is an imine compound

and generally act as electrophile in reactions. The carbon in the C = N double bond is electrophile and
attacked by nucleophiles.

So, the nucleophiles are

−
NH 3 , PhSH, (CH 3 ) 2 S, CH 2 = CH 2 , OH

Total number of nucleophiles is 5

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Question16
Match List - I with List - II.

List - I (Structure) List - II (IUPAC Name)

(A)

(I) 4-Methylpent-1-ene

(B) (CH3)2C(C3H7)2 (II) 3-Ethyl-5-methylheptane

(C)

(III) 4,4-Dimethylheptane

(D) (IV) 2-Methyl-1,3-pentadiene

Choose the correct answer from the options given below :

JEE Main 2025 (Online) 29th January Morning Shift

Options:

A.
(A)-(II), (B)-(III), (C)-(IV), (D)-(I)

B.
(A)-(II), (B)-(III), (C)-(I), (D)-(IV)

C.
(A)-(III), (B)-(IV), (C)-(I), (D)-(II)

D.
(A)-(III), (B)-(II), (C)-(I), (D)-(IV)

Answer: A

Solution:
(A)
The substituents are written in the alphabetical order. So, ethyl is first and then methyl. Sok, lowest number is
given for ethyl. 3-ethyl. And methyl has position 5. 5-methyl.

The parent chain has seven carbon atoms. So, the base name heptane.

IUPAC name : 3-ethyl-5-methylheptane

(A) Match with (II) 3-ethyl-5-methylheptane

(B)

Substituents get the same position when numbering is done from both ends. So, the substituent name (prefix)
is 4,4-dimethyl. The parent chain has seven carbon atoms. So, the base name is heptane.

IUPAC name : 4,4-dimethylheptane

(B) Match with (III) 4,4-dimethylheptane.

(C)

Double bond has higher priority than the methyl group. So, the numbering is given as

Smallest possible position is 1 and 3 for the double bond present. So, 1, 3-diene is correct.

Methyl substituent is at position 2.

So, the prefix is 2-methyl-1,3

The parent chain has five carbon atoms and the base name is penta.

Include diene as suffix to penta- as pentadien.

So, IUPAC name is

2-methyl-1,3-pentadiene

(C) Match with (IV) 2-methyl-1,3-pentadiene.

(D)

Double bond has higher priority than methyl substituent. So, position 1 is for double bond and position 4 is
for −CH substituent. Prefix is 4-methyl.
3

Parent has five carbon atoms. So, the base name penta. The suffix used is ene for the double bond. So 'a'
eliminated and written as pentane.

IUPAC name : 4-methylpent-1-ene

(D) match with (I) 4-methylpent-1-ene

The matching is written as

(A) - (II)

(B) - (III)

(C) - (IV)

(D) - (I)

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Question17
Given below are two statements :

Statement (I): In partition chromatography, stationary phase is thin

film of liquid present in the inert support.

Statement (II): In paper chromatography, the material of paper acts

as a stationary phase.
In the light of the above statements, choose the correct answer from
the options given below :

JEE Main 2025 (Online) 29th January Evening Shift

Options:

A.
Statement I is true but Statement II is false

B.
Statement I is false but Statement II is true

C.
Both Statement I and Statement II are false

D.
Both Statement I and Statement II are true

Answer: A

Solution:
Statement I : Correct

Partition chromatography - The separation of components between two liquid phases. The stationary phase is
a thin film of liquid present on an inert support. The liquid film allows for the separation of substances based
on their solubilities between the stationary phase and mobile phase.

Statement II : False

In paper chromatography, the paper itself does not act as the stationary phase. The stationary phase is the
water trapped within the pores of the paper. The paper serves as a support for the water layer.

So, Statement I is correct and Statement II is incorrect.

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Question18
Given below are two statements :
Statement (I): On nitration of m-xylene with HNO , H SO followed 3 2 4

by oxidation, 4-nitrobenzene-1,3-dicarboxylic acid is obtained as the

major product.

Statement (II) : −CH group is o/p-directing while −NO group is

3 2

m-directing group.

In the light of the above statements, choose the correct answer from
the options given below :

JEE Main 2025 (Online) 29th January Evening Shift

Options:

A.
Statement I is true but Statement II is false

B.
Both Statement I and Statement II are true

C.
Both Statement I and Statement II are false

D.
Statement I is false but Statement II is true

Answer: B

Solution:

Statement I : Correct

Nitration of m-xylene follows electrophilic aromatic substitution mechanism. First step is the generation of
electrophile NO (nitronium ion) and then the electrophile attacks the benzene ring. Methyl groups are
+

2
ortho-para directing groups. The NO in ortho position is not possible in this case due to the two
+
2

neighbouring methyl groups. The nitro group is bonded to the para-position.

On oxidation, the methyl groups get converted to carboxylic acid groups. (−CH ) to −COOH conversion).
3

So, the statement is correct.

Statement II : Correct

− CH group (methyl group) is ortho-para directing and −NO group (nitro group) is meta directing.
3 2

− CH group ⟶ electron donating group

3

− NO group ⟶ electron withdrawing group.

2

Electron donating groups push electrons towards the ring and increase electron density. Electron donating
groups give ortho-para directing products. Electron withdrawing groups pull electrons away from the ring
and decrease electron density. Electron withdrawing groups give meta-directing products. So, the statement is
correct.

So, both statement I and statement II are true.

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Question19
Designate whether each of the following compounds is aromatic or
not aromatic.

JEE Main 2025 (Online) 2nd April Morning Shift

Options:

A. a, c, d, e, h aromatic and b, f , g not aromatic

B. b, e, f , g aromatic and a, c, d, h not aromatic

C. a, b, c, d aromatic and e, f , g, h not aromatic

D. e, g aromatic and a, b, c, d, f , h not aromatic

Answer: A

Solution:
Aromatic compounds

, are not aromatic, these compounds do not follow Huckel's rule

b, f , g

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Question20
Consider the following compound (X)

The most stable and least stable carbon radicals, respectively,

produced by homolytic cleavage of corresponding C − H bond are :

JEE Main 2025 (Online) 2nd April Morning Shift

Options:

A. III, II

B. II, IV

C. I, IV

D. II, I

Answer: D

Solution:

II most stable carbon radical due to resonance stablise

I least stable carbon radical due to no stabilising factor.

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Question21
In 3,3-dimethylhex-1-en-4-yne, there are _________sp ,_________ 3

sp and_________ sp hybridised carbon atoms respectively.

2

JEE Main 2025 (Online) 2nd April Evening Shift

Options:

A. 4, 2, 2

B. 2, 4, 2

C. 3, 3, 2

D. 2, 2, 4
Answer: A

Solution:

3 2
4 − sp , 2 − sp , 2 − sp

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Question22
The least acidic compound, among the following is:

JEE Main 2025 (Online) 3rd April Morning Shift

Options:

A. B

B. D

C. A

D. C

Answer: B
Solution:

C.B. of terminal alkyne will be sp hybridisation and loculised. In other C.B. will be resonance stablised.

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Question23
Identify the correct statements from the following.

Choose the correct answer from the options given below:

JEE Main 2025 (Online) 3rd April Morning Shift

Options:

A. B & C Only

B. C & D Only

C. A,B & C Only

D. A & B Only

Answer: D

Solution:
In option C are momologoes to each - other and option D are only organic molecule not isomers.

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Question24
Given below are two statements :

Statement I : Hyperconjugation is not a permanent effect.

Statement II : In general, greater the number of alkyl groups

attached to a positively charged Catom, greater is the
hyperconjugation interaction and stabilization of the cation.

In the light of the above statements, choose the correct answer from
the options given below

JEE Main 2025 (Online) 3rd April Evening Shift

Options:

A. Statement I is false but Statement II is true

B. Statement I is true but Statement II is false

C. Both Statement I and Statement II are false

D. Both Statement I and Statement II are true

Answer: A

Solution:
Hyperconjugation is considered a permanent effect because it does not rely on the presence of an external
reagent to occur. Therefore, Statement I is false. However, Statement II is true; the presence of more alkyl
groups results in more alpha hydrogen atoms (α − H), which enhances hyperconjugation. This increased
hyperconjugation leads to greater stabilization of the carbocation.

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Question25
What is the correct IUPAC name of

JEE Main 2025 (Online) 3rd April Evening Shift

Options:

A. 3-Bromo-2-hydroxy-5-nitrobenzoic acid

B. 2-Hydroxy-3-bromo-5-nitrobenzoic acid

C. 3-Bromo-4-hydroxy-1-nitrobenzoic acid

D. 5-Nitro-3-bromo-2-hydroxybenzoic acid

Answer: A

Solution:
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Question26
The correct order of basicity for the following molecules is :

JEE Main 2025 (Online) 4th April Evening Shift

Options:

A. R > P > Q

B. P > Q > R

C. R > Q > P

D. Q > P > R

Answer: C

Solution:
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Question27
In which pairs, the first ion is more stable than the second?

JEE Main 2025 (Online) 4th April Evening Shift

Options:

A. (A) & (B) only

B. (B) & (D) only

C. (A) & (C) only

D. (B) & (C) only

Answer: A

Solution:

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Question28
The IUPAC name of the following compound is:

JEE Main 2025 (Online) 4th April Evening Shift

Options:

A. 4-Hydroxyhept-6-en-1-yne

B. Hept-1-en-6-yn-4-ol

C. Hept-6-en-1-yn-4-ol

D. 4-Hydroxyhept-1-en-6-yne

Answer: B

Solution:

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Question29
Which of the following is the correct IUPAC name of given organic
compound (X)?
JEE Main 2025 (Online) 7th April Morning Shift
Options:

A. 4-Bromo-3-methylbut-2-ene

B. 1-Bromo-2-methylbut-2-ene

C. 3-Bromo-3-methylprop-2-ene

D. 2-Bromo-2-methylbut-2-ene

Answer: B

Solution:
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Question30
The number of optically active products obtained from the complete
ozonolysis of the given compound is :

JEE Main 2025 (Online) 7th April Evening Shift

Options:

A.
4

B.
0

C.
2

D.
1

Answer: B

Solution:
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Question31
The descending order of basicity of the following amines is :

(D) CH 3 NH 2
(E) (CH 3 ) 2 NH

Choose the correct answer from the options given below :

JEE Main 2025 (Online) 7th April Evening Shift

Options:

A.
E>A>D>C>B

B.
E>D>A>B>C

C.
E>D>B>A>C

D.
B>E>D>A>C

Answer: C

Solution:
E>D>B>A>C

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Question32
What is the correct IUPAC name of the compound?
JEE Main 2025 (Online) 8th April Evening Shift
Options:

A.
1-Ethylcyclopent-2-en-3-ol

B.
4-Ethylcyclopent-2-en-1-ol

C.
1-Ethyl-3-hydroxycyclopent-2-ene

D.
4-Ethyl-1-hydroxycyclopent-2-ene

Answer: B

Solution:
JEE Main 2025 (Online) 8th April Evening Shift Chemistry - Basics of Organic Chemistry Question 15
English Explanation

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Question33
Match the LIST-I with LIST-II
LIST-I LIST-II
A. Carbocation I. Species that can supply a pair of electrons.
B. C-Free radical II. Species that can receive a pair of electrons.
C. Nucleophile III. sp2 hybridized carbon with empty p-orbital.
 LIST-I LIST-II
D. Electrophile IV. sp2/sp3 hybridized carbon with one unpaired electron.

Choose the correct answer from the options given below:

JEE Main 2025 (Online) 8th April Evening Shift

Options:

A.
A-IV, B-II, C-III, D-I

B.
A-II, B-III, C-I, D-IV

C.
A-III, B-IV, C-I, D-II

D.
A-III, B-IV, C-II, D-I

Answer: C

Solution:

(A) Carbocation → sp hybridised carbon with empty P-orbital

2
(B) Carbon free radical → sp 2
/sp
3
hybridised carbon with one unpaired electron.

(C) Nuecleophile → species of that can supply a pair of electron.

(D) Electrophile → species that can receive a pair of electron.

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Question34
The set of meta directing functional groups from the following sets
is:

[1-Feb-2024 Shift 2]
Options:

A.
−CN, −NH2, −NHR, −OCH
3

B.
−NO2, −NH2, −COOH, −COOR

C.
−NO , −CHO, −SO H, −COR
2 3

D.
−CN, −CHO, −NHCOCH3, −COOR

Answer: C

Solution:

All are −M, Hence meta directing groups.

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Question35
Following Kjeldahl's method, 1g of organic compound released
ammonia, that neutralised 10 mL of 2MH2SO4. The percentage of
nitrogen in the compound is_______ %.

[1-Feb-2024 Shift 2]
Answer: 56

Solution:
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Question36
Increasing order of stability of the resonance structure is :
[24-Jan-2023 Shift 1]
Options:

A. C, D, B, A

B. C, D, A, B

C. D, C, A, B

D. D, C, B, A

Answer: B

Solution:
Solution:
No option is matching the correct answer.
Order should be : C < A < B < D

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Question37
Given below are two statements, one is labelled as Assertion A and
the other is labelled as Reason R. Assertion A : Benzene is more
stable than hypothetical cyclohexatriene.
Reason R : The delocalized π electron cloud is attracted more
strongly by nuclei of carbon atoms. In the light of the above
statements, choose the correct answer from the options given below:
[24-Jan-2023 Shift 2]
Options:

A. A is true but R is false.

B. A is false but R is true.

C. Both A and R are correct and R is the correct explanation of A.

D. Both A and R are correct but R is NOT the correct explanation of A.

Answer: C

Solution:
Solution:
Assertion - A : Benzene is more stable than cyclohexatriene (True)
Reason −R : Delocalised π − e cloud lies B.M.O so more attracted by nuclei of carbon atom.
(True & Correct Explanation)

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Question38
Which of the following conformations will be the most stable?
[25-Jan-2023 Shift 1]
Options:

A.

B.

C.
D.

E.

Answer: A

Solution:
Solution:
Conformation

has lowest vanderwaal and torsional strain. Hence it must be most stable.

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Question39
In sulphur estimation. 0.471g of an organic compound gave 1.4439g
of barium sulphate.
The percentage of sulphur in the compound is ________ (Nearest
Integer)
(Given: Atomic mass Ba: 137u : S : 32u, O : 16u )
[25-Jan-2023 Shift 1]

Answer: 42

Solution:

Solution:
32 weight of BaSO4 formed
\%sulphur = × × 100
233 weight of organic compound
= 32 × 1.4439 × 100
233 0.471
= 42.10
Nearest integer 42

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Question40
The isomeric deuterated bromide with molecular formula C4H8 DBr
having two chiral carbon atoms is
[25-Jan-2023 Shift 2]
Options:

A. 2-Bromo-1-deuterobutane

B. 2-Bromo-2-deuterobutane

C. 2-Bromo-3-deuterobutane

D. 2-Bromo-1-deutero-2-methylpropane

Answer: C

Solution:
Solution:

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Question41
Match List I with List II.

Choose the correct answer from the options given below :-

[25-Jan-2023 Shift 2]
Options:

A. A-III, B-IV, C-I, D-II

B. A-IV, B-III, C-I, D-II

C. A-II, B-III, C-I, D-IV

D. A-III, B-I, C-IV, D-II

Answer: D

Solution:
Solution:

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Question42
Identify the correct order for the given property for following
compounds
Choose the correct answer from the option given below :-
[29-Jan-2023 Shift 1]
Options:

A. (B), (C) and (D) only

B. (A), (C) and (E) only

C. (A), (C) and (D) only

D. (A), (B) and (E) only

Answer: B

Solution:

Solution:
Boiling point of alkyl halide increases with increase in size, mass of halogen atom and size of alkyl
group
Boiling point of isomeric alkyl halide decreases with increase in branching
Density increases with increase in atomic mass of halogen atom

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Question43
Compound that will give positive Lassaigne's test for both nitrogen
and halogen is
[29-Jan-2023 Shift 1]
Options:

A. N2H4 ⋅ HCl

B. CH3NH2 ⋅ HCl
C. NH4 Cl

D. NH2 OH . HCl

Answer: B

Solution:
Solution:
Na
CH3NH2 ⋅ HCl ──────▶ NaCN and NaCl
fusion
NaCN gives +ve test for nitrogen and
NaCl gives +ve test for halogen

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Question44
Following chromatogram was developed by adsorption of compound
' A ' on a 6 cm TLC glass plate. Retardation factor of the compound
' A ' is ×10−1.

[29-Jan-2023 Shift 1]

Answer: 6

Solution:
Solution:
Rf = Distance moved by the substance frombase line
Distance move dby the solvent frombase line
3.0 cm −1
= = 0.6 or 6 × 10
5.0 cm

-------------------------------------------------------------------------------------------------

Question45
The most stable carbocation for the following is:

[30-Jan-2023 Shift 2]
Options:

A. c

B. d

C. b

D. a

Answer: A

Solution:

Solution:

The +M effect of NH2 is stabilizing the carbocation.

-------------------------------------------------------------------------------------------------

Question46
Match items of column I and II

Correct match is:

[31-Jan-2023 Shift 1]
Options:

A. A-(iii), B-(iv), C-(ii), D-(i)

B. A-(i), B-(iii), C-(ii), D-(iv)

C. A-(ii), B-(iii), C-(iv), D-(i)

D. A-(ii), B-(iv), C-(i), D-(iii)

Answer: C

Solution:
Solution:
A. H2O ∕ CH2Cl2 → ii, CH2Cl2 > H2O (density) so they can be separated by differential solvent
extraction.
B.
iii. column chromatography Due to H-bonding in

it can be separated from

by column chromatography.
C. Kerosene / Naphthalene → iv. Fractional distillation.
Due to different B.P. of kerosene and Naphthalene it can be separated by fractional distillation.
D. C6H12O6 ∕ NaCl→ i. Crystallization.
NaCl (ionic compound) can be crystallized.

-------------------------------------------------------------------------------------------------

Question47
Consider the following reaction
Propanal + Methanal = ─────────▶
(i)dil. NaOH
Product B
(ii)∆ (C5H8O3)
(iii) NaCN
(iv)H3O+

The correct statement for product B is. It is

[31-Jan-2023 Shift 1]
Options:

A. optically active and adds one mole of bromine

B. racemic mixture and is neutral

C. racemic mixture and gives a gas with saturated NaHCO3 solution

D. optically active alcohol and is neutrall

Answer: C

Solution:

Solution:
OH−
CH3 − CH2 − CHO + HCHO →
Δ
Carboxylic acid will give CO2 gas, with NaHCO3 solution

-------------------------------------------------------------------------------------------------

Question48
An organic compound [A](C4H11N), shows optical activity and gives
N2 gas on treatment with HNO2. The compound [A] reacts with
PhSO2 Cl producing a compound which is soluble in KOH. The
structure of A is:
[31-Jan-2023 Shift 2]
Options:

A.

B.

C.
D.

Answer: D

Solution:

Solution:
C4H11N releases N2 with HNO2 i.e. it is primary amine.
After reacting with Hinsberg reagent it forms a compound which is soluble in KOH,
Hence, the amine is primary.

-------------------------------------------------------------------------------------------------

Question49
In Dumas method for the estimation of N2, the sample is heated with
copper oxide and the gas evolved is passed over:
[31-Jan-2023 Shift 2]
Options:

A. Ni

B. Copper gauze

C. Pd

D. Copper oxide

Answer: B

Solution:
Solution:
Duma's method.
The nitrogen containing organic compound, when heated with CuO in a atmosphere of CO2, yields
free N2 in addition to CO2 and H2O.

(
CxHyNz + 2x + y CuO→
2 )
2 2 2 (
xCO2 + y H2O + z N2 + 2x + y Cu )
Traces of nitrogen oxides formed, if any, are reduced to nitrogen by passing the gaseous mixture
over heated copper gauze.

-------------------------------------------------------------------------------------------------

Question50
In the following halogenated organic compounds the one with
maximum number of chlorine atoms in its structure is :
[31-Jan-2023 Shift 2]
Options:

A. Chloral

B. Gammaxene

C. Chloropicrin

D. Freon -12

Answer: B

Solution:
Solution:
-------------------------------------------------------------------------------------------------

Question51
Resonance in carbonate ion (CO32−) is

Which of the following is true?

[1-Feb-2023 Shift 1]
Options:

A. It is possible to identify each structure individually by some physical or chemical

method.

B. All these structures are in dynamic equilibrium with each other.

C. Each structure exists for equal amount of time.

D. CO32− has a single structure i.e., resonance hybrid of the above three structures.

Answer: D

Solution:
Solution:
Resonating structure are hypothetical and resonance hybrid is real structure which is weighted
average of all the resonating structures.

-------------------------------------------------------------------------------------------------

Question52
The total number of chiral compound/s from the following is
________.
[1-Feb-2023 Shift 1]

Answer: 2

Solution:

Solution:
-------------------------------------------------------------------------------------------------

Question53
All structures given below are of vitamin C. Most stable of them is :
[1-Feb-2023 Shift 2]
Options:

A.

B.

C.

D.
Answer: A

Solution:

Solution:
H-bonding stabilised vitamin C

-------------------------------------------------------------------------------------------------

Question54
Given below are two statements:
Statement I : Sulphanilic acid gives esterification test for carboxyl
group.
Statement II : Sulphanilic acid gives red colour in Lassigne's test for
extra element detection.
In the light of the above statements, choose the most appropriate
answer from the options given below :
[1-Feb-2023 Shift 2]
Options:

A. Statement I is correct but Statement II is incorrect.

B. Both Statement I and Statement II are incorrect.

C. Both Statement I and Statement II are correct.

D. Statement I is incorrect but Statement II is correct.

Answer: D

Solution:
Solution:

Does not show esterification test.

Presence of both sulphur and nitrogen give red colour in Lassigne's test.

-------------------------------------------------------------------------------------------------

Question55
Testosterone, which is a steroidal hormone, has the following
structure.

The total number of asymmetric carbon atom ∕ s in testosterone is

________.
[1-Feb-2023 Shift 2]

Answer: None

Solution:

Solution:
-------------------------------------------------------------------------------------------------

Question56
Match List I with List II

Choose the correct answer from the options given below:

[6-Apr-2023 shift 1]
Options:

A. A-II, B-IV, C-I, D-III

B. A-IV, B-II, C-I, D-III

C. A-II, B-I, C-IV, D-III

D. A-III, B-I, C-IV, D-II

Answer: D
Solution:
Solution:
Nitrogen detection by lassaigne's method
Na + C + N → NaCN
6 NaCN + FeSO4 → Na4[Fe(CN)6] + Na2SO4
Na4[Fe(CN)6] + Fe3+ → Fe4[Fe(CN)6]3
(Prussian blue)
Sulphur detection by Sodium nitroprusside
Na2[Fe(CN)5 NO] + Na2S → Na4[Fe(CN)5 NOS]
[Purple]
Phosphorus detection by ammonium molybdate
Na3PO4 + 3HNO3 → H3PO4 + 3NaNO3
H3PO4 + 12(NH4)2MoO4 + 21HNO3 →
(NH4)3PO4 ⋅ 12MoO3 + 21NH4NO3 + 12H2O
(canary yellow)
Halogen give specific coloured ppt with AgNO3(aq)
NaCl + AgNO3(aq) → AgCl + NaNO3
(White)
NaBr + AgNO3(aq) → AgBr + NaNO3
(Pale yellow )
NaI + AgNO3(aq) → AgI + NaNO3
( Yellow )

-------------------------------------------------------------------------------------------------

Question57
From the figure of column chromatography given below, identify
incorrect statements.
A. Compound 'c' is more polar than ' a ' and ' b '
B. Compound ' a ' is least polar
C. Compound ' b ' comes out of the column before 'c' and after ' a '
D. Compound ' a ' spends more time in the column Choose the
correct answer from the options given below :-
[6-Apr-2023 shift 2]
Options:

A. A, B and C only

B. B, C and D only

C. A, B and D only

D. B and D only

Answer: A

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question58
The strongest acid from the following is
[6-Apr-2023 shift 2]
Options:

A.
B.

C.

D.

Answer: A

Solution:
Solution:
Strongest acid from the following is
−NO2 group has more EWG nature so more acidic,

-------------------------------------------------------------------------------------------------

Question59
The descending order of acidity for the following carboxylic acid is -
A. CH3 COOH
B. F3C − COOH
C. ClCH2 − COOH
D. BrCH2 − COOH
Choose the correct answer from the options given below:
[8-Apr-2023 shift 2]
Options:

A. D > B > A > E > C

B. B > D > C > E > A

C. E > D > B > A > C

D. B > C > D < E > A

Answer: B

Solution:

Solution:
Acidity α stability of conjugate base
Stability order
F3C − COO− > F − CH2 − COO− > Cl − CH2 − COO− > Br − CH2 − COO− > CH3COO−

-------------------------------------------------------------------------------------------------

Question60
The correct IUPAC nomenclature for the following compound is :

[8-Apr-2023 shift 2]
Options:

A. 2-Methyl-5-oxohexanoic acid

B. 2-Formyl-5-methylhexan-6-oic acid

C. 5-Formyl-2-methylhexanoic acid

D. 5-Methyl-2-oxohexan-6-oic acid

Answer: A

Solution:

Solution:

-------------------------------------------------------------------------------------------------

Question61
Using column chromatography mixture of two compounds ' A ' and
' B ' was separated. 'A' eluted first, this indicates ' B ' has
[10-Apr-2023 shift 1]
Options:

A. high Rf , weaker adsorption

B. high Rf , stronger adsorption

C. low Rf , stronger adsorption

D. low Rf , weaker adsorption

Answer: C

Solution:

Solution:
More Polar the compound, the more it will adhere to the adsorbent and the smaller the distance it
will travel from baseline, and Lower its Rf value.
B has Low Rf value and strong Adsoption
Rf = distance covered by substance from base line
total distance covered by solvent form base line

-------------------------------------------------------------------------------------------------

Question62
The decreasing order of hydride affinity for following carbonations
is:

Choose the correct answer from the options given below:

[10-Apr-2023 shift 2]
Options:

A. C, A, D, B

B. A, C, B, D

C. A, C, D, B
D. C, A, B, D

Answer: D

Solution:

Solution:
1
Stability of carbocation ∝ Hydride affinity

-------------------------------------------------------------------------------------------------

Question63
The correct order for acidity of the following hydroxyl compound is
:

Choose the correct answer from the options given below:

[10-Apr-2023 shift 2]
Options:

A. E > C > D > A > B

B. D > E > C > A > B

C. E > D > C > B > A

D. C > E > D > B > A

Answer: A
Solution:
Solution:
Acidity ∝ stability of conjugate base
Stability order

Activity →E > C > D > A > B

-------------------------------------------------------------------------------------------------

Question64
In Carius tube, an organic compound ' X′ is treated with sodium
peroxide to form a mineral acid ' Y′.The solution of BaCl2 is added
to ' Y′ to form a precipitate ' Z′ '.' Z ' is used for the quantitative
estimation of an extra element. ' X ' could be
[10-Apr-2023 shift 2]
Options:

A. Chloroxylenol

B. Methionine

C. A nucleotide

D. Cytosine

Answer: B

Solution:

Solution:
Carious method is used for quantitative analysis of sulfur

So Methionine is correct answer

-------------------------------------------------------------------------------------------------

Question65

Where Nu = Nucleophile
Find out the correct statement from the options given below for the
above 2 reactions.
[11-Apr-2023 shift 1]
Options:

A. Reaction (I) is of 1 st order and reaction (II) is of 2 nd order

B. Reaction (I) and (II) both are 2 nd order

C. Reaction (I) and (II) both are 1 st order

D. Reaction (I) is of 2 nd order and reaction (II) is of 1 st order

Answer: A

Solution:

Solution:

-------------------------------------------------------------------------------------------------

Question66
Thin layer chromatography of a mixture shows the following
observation :
The correct order of elution in the silica gel column chromatography
is
[11-Apr-2023 shift 1]

Options:

A. B, A, C

B. C, A, B

C. A, C, B

D. B, C, A

Answer: C

Solution:
Solution:

According to the observation, A is more mobile and interacts with the mobile phase more than C,
and C is more drawn to the mobile phase than B.
Hence, the correct order of elution in the silica gel column chromatography is - B < C < A
-------------------------------------------------------------------------------------------------

Question67
Compound from the following that will not produce precipitate on
reaction with AgNO3 is :
[11-Apr-2023 shift 2]
Options:
A.

B.

C.

D.

Answer: B

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question68
The number of possible isomeric products formed when 3-chloro-1-
butene reacts with HCl through carbocation formation is _________
[11-Apr-2023 shift 2]

Answer: 4

Solution:
Solution:

Total Possible Isomeric product = 1 + 3 = 4

-------------------------------------------------------------------------------------------------

Question69
Correct statements for the given reaction are :

A. Compound ' B' is aromatic

B. The completion of above reaction is very slow
C. 'A' shows tautomerism
D. The bond lengths of C − C in compound B are found to be same
Choose the correct answer from the options given below:
[12-Apr-2023 shift 1]
Options:

A. A,B and C only

B. A, C and D only
C. B, C and D only

D. A, B and D only

Answer: B

Solution:

Solution:

(i) B is Aromatic
(ii) Completion of reaction is very fast due to formation of aromatic compound
(iii) A show keto-enol tautomerism
(iv) B is aromatic so C − C bond length are same.

-------------------------------------------------------------------------------------------------

Question70
Three organic compounds A, B and C were allowed to run in thin
layer chromatography using hexane and gave the following result
(see figure). The Rf value of the most polar compound is ______
×10−2.

[12-Apr-2023 shift 1]
Answer: 25

Solution:
Solution:
Most polar compound - C - because of lowest moulmerls in upper direction
Rf = Dis tan ce covered by compound = 2 = 0.25 = 25 × 10−2
Dis tance covered by solvent 8

-------------------------------------------------------------------------------------------------

Question71
The major product for the following reaction is :

[13-Apr-2023 shift 2]
Options:

A.

B.

C.

D.
Answer: B

Solution:

Solution:

-------------------------------------------------------------------------------------------------

Question72
Given below are two statements, one is labelled as Assertion A and
the other is labelled as Reason R. Assertion A : Order of acidic
nature of the following compounds is A >B > C.

Reason R : Fluoro is a stronger electron withdrawing group than

Chloro group.
In the light of the above statements, choose the correct answer from
the options given below :
[13-Apr-2023 shift 2]
Options:

A. Both A and R are correct and R is the correct explanation of A

B. A is false but R is true

C. Both A and R are correct but R is NOT the correct explanation of A

D. A is true but R is false

Answer: C

Solution:

Solution:
Acidic strength α − I effect
α I effect
+I
F, Cl exerts -1 effect, Methyl exerts +I effect, C is least acidic.
Among A and B; since inductive effect is distance dependent, Extent of −I effect is higher in A
followed by B even though F is stronger electron withdrawing group than Cl. Thus, A is more acidic
than B.

-------------------------------------------------------------------------------------------------

Question73
Given below are two statements :
Statement I : Tropolone is an aromatic compound and has 8π
electrons.
Statement II : π electrons of >C = O group in tropolone is involved
in aromaticity
In the light of the above statements, choose the correct answer from
the options given below :
[13-Apr-2023 shift 2]
Options:

A. Statement I is false but Statement II is true

B. Statement I is true but Statement II is false

C. Both Statement I and Statement II are true

D. Both Statement I and Statement II are false

Answer: B

Solution:
Solution:

Tropolone is an aromatic compound and has 8π electrons ( 6πe−are endocyclic and 2πe−are
exocyclic) and π electrons of C = O group in tropolone is not involved in aromaticity.

-------------------------------------------------------------------------------------------------

Question74
0.400g of an organic compound (X) gave 0.376g of AgBr in Carius
method for estimation of bromine. \% of bromine in the compound
(X) is ______ . (Given: Molar mass
AgBr = 188gmol−1, Br = 80gmol−1 )
[13-Apr-2023 shift 2]

Answer: 40

Solution:
Solution:
mole of AgBr = 0.376
188
mole of Br− = mole of AgBr = 0.376
188
 mass of Br− = 0.376 × 80
188
−
% of Br = 0.376 × 80 ×
100 = 40%
188 × 0.4

-------------------------------------------------------------------------------------------------

Question75
Which of the following statement is correct for paper
chromatography?
[15-Apr-2023 shift 1]
Options:

A. Water present in the pores of the paper forms the stationary phase.

B. Water present in the mobile phase gets absorbed by the paper which then forms the
stationary phase

C. Paper sheet forms the stationary phase.

D. Paper and water present in its pores together form the stationary phase.

Answer: A

Solution:

Solution:
Fact

-------------------------------------------------------------------------------------------------

Question76
Number of electrophilic centres in the given compound is

[24-Jun-2022-Shift-1]
Answer: 3

Solution:
Solution:
Given compounds :

Number of electrophilic centres = 3

-------------------------------------------------------------------------------------------------

Question77
Arrange the following carbocations in decreasing order of stability.
A

[24-Jun-2022-Shift-2]
Options:

A. A > C > B

B. A > B > C

C. C > B > A

D. C > A > B

Answer: A

Solution:
Solution:

Carbocation (A) is stabilised by hyperconjugation due to 4α hydrogen atoms. Carbocation (C) is

also stabilised by hyperconjugation due to 4 a hydrogen atoms but destabilised by −1 effect of O-
atom. Carbocation (B) is most stable as it is stabilised by resonance.
∴ Correct decreasing order of stability is B > A > C

-------------------------------------------------------------------------------------------------

Question78
0.2g of an organic compound was subjected to estimation of nitrogen
by Dumas method in which volume of N2 evolved (at STP) was
found to be 22.400 mL. The percentage of nitrogen in the compound
is ______[nearest integer]
−1
(Given : Molar mass of N2 is 28gmol . Molar volume of N2 at
STP : 22.4L )
[24-Jun-2022-Shift-2]

Answer: 14

Solution:

Solution:
Given volume of N2 = 22.400 mL
22.400 = 10−3
∴ Moles of N2 = mole
22400
∴ Moles of N atoms = 2 × 10−3 mole
∴ Weigh of N atoms = 14 × 2 × 10−3 mole
= 28 × 10− 3 mole
∴% of N atom in the compound
28 × 10−3
= × 100
0.2
= 14

-------------------------------------------------------------------------------------------------

Question79
Phenol on reaction with dilute nitric acid, gives two products. Which
method will be most efficient for large scale separation?
[25-Jun-2022-Shift-1]
Options:

A. Chromatographic separation

B. Fractional Crystallisation

C. Steam distillation

D. Sublimation

Answer: C

Solution:

Solution:

o-Nitrophenol and p-Nitrophenol can be easily separated by steam distillation.

-------------------------------------------------------------------------------------------------
Question80
In the following structures, which on is having staggered
conformation with maximum dihedral angle?
[25-Jun-2022-Shift-1]
Options:

A.

B.

C.

D.
Answer: C

Solution:

Solution:

It is the staggered conformation with maximum dihedral angle.

-------------------------------------------------------------------------------------------------

Question81
The IUPAC name of ethylidene chloride is :
[25-Jun-2022-Shift-1]
Options:

A. 1-Chloroethene

B. 1-Chloroethyne

C. 1,2-Dichloroethane

D. 1,1-Dichloroethane

Answer: D

Solution:
Solution:
Ethylidene chloride is CH3 − CHCl2, its IUPAC name is 1,1-Dichloromethane.

-------------------------------------------------------------------------------------------------

Question82
Given below are two statements : one is labelled as Assertion A and
the other is labelled as Reason R.
Assertion A : A mixture contains benzoic acid and napthalene. The
pure benzoic acid can be separated out by the use of benzene.
Reason R : Benzoic acid is soluble in hot water.
In the light of the above statements, choose the most appropriate
answer from the options given below.
[25-Jun-2022-Shift-2]
Options:

A. Both A and R are true and R is the correct explanation of A.

B. Both A and R are true but R is NOT the correct explanation of A.

C. A is true but R is false.

D. A is false but R is true.

Answer: D

Solution:

Solution:
Since, both benzoic acid and naphthalene will dissolve in benzene. Hence assertion is wrong.
Benzoic acid is almost insoluble in cold water but soluble in hot water. Hence Reason is true

-------------------------------------------------------------------------------------------------

Question83
Given below are two statements :
Statement I : In 'Lassaigne's Test', when both nitrogen and sulphur
are present in an organic compound, sodium thiocyanate is formed.
Statement II : If both nitrogen and sulphur are present in an organic
compound, then the excess of sodium used in sodium fusion will
decompose the sodium thiocyanate formed to give NaCN and Na2 S.
In the light of the above statements, choose the most appropriate
answer from the options given below :
[26-Jun-2022-Shift-1]
Options:

A. Both Statement I and Statement II are correct.

B. Both Statement I and Statement II are incorrect.

C. Statement I is correct but Statement II is incorrect.

D. Statement I is incorrect but Statement II is correct.

Answer: A

Solution:

Solution:
Both statement I \& statement II are correct
NaSCN + 2 Na → NaCN + Na2S

-------------------------------------------------------------------------------------------------

Question84
Compound 'P' on nitration with dil. HNO3 yields two isomers (A)
and (B). These isomers can be separated by steam distillation.
Isomers (A) and (B) show the intramolecular and intermolecular
hydrogen bonding respectively. Compound (P) on reaction with
conc. HNO3 yields a yellow compound ' C ', a strong acid. The
number of oxygen atoms is present in compound ' C '_____
[26-Jun-2022-Shift-1]

Answer: 7

Solution:

Solution:
-------------------------------------------------------------------------------------------------

Question85
The correct order of nucleophilicity is
[26-Jun-2022-Shift-2]
Options:

A. F− > OH−

B.

C.

D. NH2− > NH3

Answer: D

Solution:
Solution:

NH3 ⟶ NH2− + H+
Acid Conjugate base

Conjugate base of acid is always a stronger nucleophile.

-------------------------------------------------------------------------------------------------

Question86
Total number of possible stereoisomers of dimethyl cyclopentane
is____
[27-Jun-2022-Shift-1]

Answer: 6

Solution:
Solution:

Dimethyl cyclopentane

will show stereo isomerism, Its stereo isomers are

will show stereo isomerism, Its stereo isomers are

-------------------------------------------------------------------------------------------------

Question87
Which of the following is most stable?
[27-Jun-2022-Shift-2]
Options:

A.

B.

C.

D.

Answer: A

Solution:
Solution:

1,3-cyclohexadiene is most stable because it is a neutral molecule. All others are intermediates and
hence less stable.

-------------------------------------------------------------------------------------------------

Question88
0.25g of an organic compound containing chlorine gave 0.40g of
silver chloride in Carius estimation. The percentage of chlorine
present in the compound is_____ [in nearest integer]
(Given : Molar mass of Ag is 108gmol−1 and that of Cl is 35.5gmol−1
)
[27-Jun-2022-Shift-2]

Answer: 40

Solution:
Solution:
Given, weight of organic compound = 0.25g
0.4
Moles of AgCl =
M
Molecular mass of AgCl(M ) = 143.5 gm
∴ Moles of AgCl = 0.4
143.5
0.4
∴ Mass of Cl = × 35.5
143.5
Mass % of Cl in the organic compound
 35.5 × 0.4
143.5
= × 35.5
0.25
= 39.58
≃40

-------------------------------------------------------------------------------------------------

Question89
Which one of the following techniques is not used to spot
components of a mixture separated on thin layer chromatographic
plate?
[28-Jun-2022-Shift-1]

Options:

A. I2 (Solid)

B. U.V. Light

C. Visualisation agent as a component of mobile phase

D. Spraying of an appropriate reagent

Answer: C

Solution:
Solution:

TLC is a technique used to separate mixture of compounds based on differences in polarity. In TLC
a glass plate coated with a stationary phase is spotted with the mixture to be separated.

-------------------------------------------------------------------------------------------------

Question90
Which of the following structure are aromatic in nature?
[28-Jun-2022-Shift-1]
Options:

A. A, B, C, and D

B. Only A and B

C. Only A and C

D. Only B, C and D

Answer: B

Solution:
Solution:
A and B are aromatic as they are cyclic, planar and has 4n + 2πe−(n = 1)

-------------------------------------------------------------------------------------------------

Question91
The formula of the purple colour formed in Laissaigne's test for
sulphur using sodium nitroprusside is
[28-Jun-2022-Shift-1]
Options:

A. NaFe[Fe(CN)6]

B. Na[Cr(NH3)2(NCS)4]

C. Na2[Fe(CN)5(NO)]
D. Na4[Fe(CN)5(NOS)]

Answer: D

Solution:
Solution:
S2− + [Fe(CN)5 NO) ]2− → [Fe(CN)5(NOS)]4−

-------------------------------------------------------------------------------------------------

Question92
In the estimation of bromine, 0.5g of an organic compound gave
0.40g of silver bromide. The percentage of bromine in the given
compound is ____% (nearest integer)
(Relative atomic masses of Ag and Br are 108u and 80u,
respectively).
[28-Jun-2022-Shift-1]

Answer: 34

Solution:

Solution:
188g AgBr has 80g of Br
∴0.4 gAgBr = 80 × 0.4
188
% of Br in given organic compound
= 80 × 0.4 × 100
188 × 0.5
≈34%

-------------------------------------------------------------------------------------------------

Question93
The correct IUPAC name of the following compound is :
[28-Jun-2022-Shift-2]
Options:

A. 4-methyl-2-nitro-5-oxohept-3-enal

B. 4-methyl-5-oxo-2-nitrohept-3-enal

C. 4-methyl-6-nitro-3-oxohept-4-enal

D. 6-formyl-4-methyl-2-nitrohex-3-enal

Answer: C

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question94
Kjeldahl's method was used for the estimation of nitrogen in an
organic compound. The ammonia evolved from 0.55g of the
compound neutralised 12.5 mL of 1MH2SO4 solution. The
percentage of nitrogen in the compound is______ . (Nearest integer)
[29-Jun-2022-Shift-1]
Answer: 64

Solution:

Solution:
Meq of H2SO4 used by NH3 = 12.5 × 1 × 2 = 25
25 × 10−3 × 14 × 100
% of N in the compound = = 63.6
0.55
Meq. of H2SO4 = Meq. of NH3
12.5 × 1 × 2 = 25 meq. of NH3
= 25 millimoles of NH3
So Millimoles of ' N′ = 25
Moles of ' N′ = 25 × 10−3
wt. of N = 14 × 25 × 10−3
14 × 25 × 10−3
%N = × 100
0.55
= 63.66
≈64%

-------------------------------------------------------------------------------------------------

Question95
Observe structures of the following compounds

The total number of structures/compounds which possess

asymmetric carbon atoms is ______________.
[29-Jun-2022-Shift-1]

Answer: 3

Solution:
Solution:

Number of compounds containing asymmetric carbons are three.

-------------------------------------------------------------------------------------------------

Question96
Which of the following carbocations is most stable?
[29-Jun-2022-Shift-2]
Options:

A.

B.

C.

D.

Answer: D

Solution:
Solution:

Is most stable carbocation

-------------------------------------------------------------------------------------------------

Question97
The number of chiral alcohol(s) with molecular formula C4H10O
is_____
[29-Jun-2022-Shift-2]

Answer: 2

Solution:

Solution:

Out of which only two are chiral

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Question98
While estimating the nitrogen present in an organic compound by
Kjeldahl's method, the ammonia evolved from 0.25g of the
compound neutralized 2.5mL of 2M H 2SO4. The percentage of
nitrogen present in organic compound is
[25-Jul-2022-Shift-1]

Answer: 56

Solution:

Solution:
NH3 gas is neutralized by 2.5 mL of 2MH2SO4
∴ Moles of NH3 neutralized = 2.5 × 2 × 2 millimole = 10 × 10−3 moles
∴ Weight of N present in the compound will be
−3
= 10 × 10 × 14
= 0.14g
∴% of ' N′ in compound
= 0.14 × 100
0.25
= 56%

-------------------------------------------------------------------------------------------------

Question99
The number of sp3 hybridised carbons in an acyclic neutral
compound with molecular formula C4H 5N is
[25-Jul-2022-Shift-1]

Answer: 1

Solution:

Solution:
DU = 4 + 1 − ( 5 −2 1 ) = 3
H3 C − CH = CH − C ≡ N
↑
sp3
CH2 = C = CH = CH = NH
3
Zero sp carbon

-------------------------------------------------------------------------------------------------

Question100
Arrange the following in decreasing acidic strength:

[25-Jul-2022-Shift-2]
Options:

A. A > B > C > D

B. B > A > C > D

C. D > C > A > B

D. D > C > B > A

Answer: A

Solution:
Solution:
The correct order of acid strength is

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Question101
The separation of two coloured substances was done by paper
chromatography. The distances travelled by solvent front, substance
A and substance B from the base line are 3.25cm, 2.08cm and
1.05cm, respectively. The ratio of Rf values of A to B is_____
[25-Jul-2022-Shift-2]

Answer: 2

Solution:
Solution:
Distance travelled by the substance
Rf =
Distance travelled by the solvent front
2.08
(Rf )A =
3.25
1.05
(Rf )B =
3.25
(Rf )A
≃2
(Rf )B

-------------------------------------------------------------------------------------------------

Question102
The total number of monobromo derivatives formed by he alkanes
with molecular formula C5H 12 is (excluding stereo isomers)
[25-Jul-2022-Shift-2]
Answer: 8

Solution:

Solution:

It is sum of distance of z from (3√2 , 0) and (0, p√2 ) For minimising, z should lie on AB and AB = 5√2
(AB)2 = 18 + 2p2
p = ±4

-------------------------------------------------------------------------------------------------

Question103
∙
C + CH4 → A + B
A and B in the above atmospheric reaction step are :
[26-Jul-2022-Shift-1]
Options:

A. C2H6 and Cl2

∙
B. CHCl2 and H2

∙
C. CH3 and HCl

D. C2H6 and HCl

Answer: C

Solution:

Solution:
 ∙ ∙
Cl + CH4 ⟶ ˙CH 3 + HCl

-------------------------------------------------------------------------------------------------

Question104
Which technique among the following, is most appropriate in
separation of a mixture of 100 mg of p nitrophenol and picric acid?
[26-Jul-2022-Shift-1]
Options:

A. Steam distillation

B. 2 − 5 ft long column of silica gel

C. Sublimation

D. Preparative TLC (Thin Layer Chromatography)

Answer: D

Solution:

Solution:
Thin layer chromatography is a technique used to isolate non-volatile mixtures.
Hence, mixture of p-nitrophenol and Picric acid is separated by TLC.

-------------------------------------------------------------------------------------------------

Question105
Which of the following compounds is not aromatic?
[26-Jul-2022-Shift-1]
Options:

A.
B.

C.

D.

Answer: C

Solution:

Solution:
[10] Annulene, although follow (4n + 2)π electron rule, but it is non-aromatic due to its non planar
nature. It is nonplanar due to repulsion of C − H bonds present inside the ring.

-------------------------------------------------------------------------------------------------

Question106
The correct stability order of the following diazonium salt is

[26-Jul-2022-Shift-1]
Options:

A. (A) > (B) > (C) > (D)

B. (A) > (C) > (D) > (B)

C. (C) > (A) > (D) > (B)

D. (C) > (D) > (B) > (A)

Answer: B

Solution:

Solution:

Since diazonium ion is a cation hence it is stabilized by electron donating groups and destabilized
by electron withdrawing group.
Hence Stability order should be A > C > D > B.

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Question107
The correct decreasing order of priority of functional groups in
naming an organic Question: compound as per IUFAC system of
nomenclature is
[26-Jul-2022-Shift-2]
Options:

A. −COOH > −CONH2 > −COCl > −CHO

B. SO3H > −COCl > −CONH2 > −CN

C. −COOR > −COCl > −NH2 > C = 0

D. −COOH > −COOR > −CONH2 > −COCl

Answer: B

Solution:

Solution:
−SO3H > −COCl > −CONH2 > −CN

-------------------------------------------------------------------------------------------------

Question108
Given below are two statements: one is labelled as Assertion A and,
the other is labelled as Reason R.
Assertion A: [6] Annulene, [8] Annulene and cis-[10] Annulene, are
respectively aromatic, not-aromatic and aromatic.

Reason R: Planarity is one of the requirements of aromatic systems.

In the light of the above statements, choose the most appropriate
answer from the options given below.
[27-Jul-2022-Shift-1]
Options:

A. Both A and R are correct and R is the correct explanation of A.

B. Both A and R are correct but R is NOT the correct explanation of A.

C. A is correct but R is not correct.

D. A is not correct but R is correct.

Answer: A

Solution:
Solution:
[6] Annulene is aromatic because it is planar.
[8] Annulene and [10] Annulene are both not aromatic because they are not planar. So, Assertion
(A) is not correct.
Reason (R) is correct because planarity is one of the requirements of aromatic system.

-------------------------------------------------------------------------------------------------

Question109
In Carius method of estimation of halogen, 0.45g of an organic
compound gave 0.36g of AgBr. Find out the percentage of bromine
in the compound.
(Molar masses : AgBr = 188gmol−1; Br = 80gmol−1 )
[27-Jul-2022-Shift-1]
Options:

A. 34.04%

B. 40.04%

C. 36.03%

D. 38.04%

Answer: A

Solution:
Solution:
Mass of organic compound = 0.45 gm
Mass of AgBr obtained = 0.36 gm
0.36
∴ Moles of AgBr =
188
0.36 × = 0.1532 gm
∴ Mass of Bromine = 80
188
∴%Br in compound = 0.1532 × 100 = 34.04%
0.45

-------------------------------------------------------------------------------------------------

Question110
Optical activity of an enantiomeric mixture is +12.6∘ and the specific
rotation of (+) isomer is +30∘ The optical purity is ________ %
[27-Jul-2022-Shift-1]

Answer: 42

Solution:

Solution:
Total rotation × 12 ⋅ 6
Optical purity = 10 = × 100
Specific rotation 30
= 42%

-------------------------------------------------------------------------------------------------

Question111
Match List - I with List - II.

Choose the correct answer from the options given below :

[27-Jul-2022-Shift-2]
Options:

A. (A) - (IV), (B) - (III), (C) - (I), (D) - (II)

B. (A) - (III), (B) - (I), (C) - (IV), (D) - (II)

C. (A) - (III), (B) - (IV), (C) - (II), (D) - (I)

D. (A) - (III), (B) - (IV), (C) - (I), (D) - (II)

Answer: D

Solution:

Solution:
(A) Chloroform + Aniline → (III) Distillation
(B) Benzoic acid + Napthalene → (IV) Crystallisation
(C) Water + Aniline → (I) Steam distillation
(D) Napthalene + Sodium chloride → (II) Sublimation

-------------------------------------------------------------------------------------------------

Question112
Match List - I with List - II.

Choose the correct answer from the options given below:

[28-Jul-2022-Shift-1]
Options:
A. (A) - (II), (B) - (I), (C) - (IV), (D) - (III)

B. (A) - (IV), (B) - (III), (C) - (I), (D) - (II)

C. (A) - (III), (B) - (IV), (C) - (I), (D) - (II)

D. (A) - (IV), (B) - (III), (C) - (II), (D) - (I)

Answer: C

Solution:

Solution:

-------------------------------------------------------------------------------------------------

Question113
Among the following marked proton of which compound shows
lowest pKa value?
[28-Jul-2022-Shift-1]
Options:

A.

B.
C.

D.
Answer: C

Solution:
Solution:

The conjugate base of compound (C) is stabilized by extended conjugation. Hence the indicated
proton of compound C is most acidic i.e. will have lowest pKa.

-------------------------------------------------------------------------------------------------

Question114
Given below are two statements: One is labelled as Assertion A and
the other is labelled as Reason R
Assertion A : Thin layer chromatography is an adsorption
chromatography.
Reason R: A thin layer of silica gel is spread over a glass plate of
suitable size in thin layer chromatography which acts as an
adsorbent.
In the light of the above statements, choose the correct answer from
the options given below
[28-Jul-2022-Shift-2]
Options:

A. Both A and R are true and R is the correct explanation of A

B. Both A and R are true but R is NOT the correct explanation of A

C. A is true but R is false

D. A is false but R is true

Answer: A

Solution:
Solution:
Thin layer chromoatography (TLC) is another type of adsorption chromatography, which involve
sepration of substance of a mixture ovel a thin layer of an adsorbent coated on glass plate.
A thin layer (about 0.2 mm thick) of an adsorbent (silica gel) or (Alumina) in spread overa glass
plate of suitable size. Hence Assertion (A) is correct and Reason (R) is correct explanation of (A)

-------------------------------------------------------------------------------------------------

Question115
A sample of 0.125g of an organic compound when analyzed by
Duma's method yields 22.78 mL of nitrogen gas collected over KOH
solution at 280K and 759 mm Hg. The percentage of nitrogen in the
given organic compound is ____(Nearest integer)
Given :
(a) The vapour pressure of water of 280K is 14.2 mm Hg.
(b) R = 0.082L atm K−1mol−1
[28-Jul-2022-Shift-2]
Answer: 22

Solution:

Solution:
P actual = 759 − 14.2 = 744.8 mmHg

nN = 744.8 × 22.78
2 760 × 0.0821 × 280 × 1000
= 0.000971 mol
Mass of N2 = 0.02719 gm
Percentage of nitrogen
= 0.0271 × 100 = 21.75 ≃ 22
0.125

-------------------------------------------------------------------------------------------------

Question116
Correct structure of γ-methylcyclohexane carbaldehyde is
[29-Jul-2022-Shift-2]
Options:

A.

B.

C.
D.

Answer: A

Solution:

Solution:

γ-Methyl cyclohexane carbaldehyde

-------------------------------------------------------------------------------------------------

Question117
Given below are two statements.
Statement 1: The compound
is optically active.

Statement II :

is mirror image of above compound A.

In the light of the above statement, choose the most appropriate
answer from the options given below.
[29-Jul-2022-Shift-2]
Options:

A. Both Statement I and Statement II are correct.

B. Both Statement I and Statement II are incorrect.

C. Statement I is correct but Statement II is incorrect.

D. Statement I is incorrect but Statement II is correct.

Answer: C

Solution:
Solution:

Compound (A) in Statement-I and compound in Statement-II is not the mirror image of (I).

-------------------------------------------------------------------------------------------------

Question118
Given below are two statements:
Statement I A mixture of chloroform and aniline can be separated
by simple distillation.
Statement II When separating aniline from a mixture of aniline and
water by steam distillation aniline boils below its boiling point.
In the light of the above statements, choose the most appropriate
answer from the options given below.
[26 Feb 2021 Shift 1]
Options:

A. Statement I is false but statement II is true

B. Both statement I and statement II are false

C. Statement I is true but statement II is false

D. Both statement I and statement II are true

Answer: D

Solution:

Solution:
Statement I is true, i.e. a mixture of chloroform and aniline can be separated by simple distillation.
Boiling points of chloroform (334K ) and aniline (457 K) differ largely. So, on boiling the\/mixture,
vapours of CH Cl 3 are formed first which is then condensed to pure liquid CH Cl 3.
Whereas, the vapours of aniline will form later and liquid aniline can be collected separately.
Statement II is also true, i.e. aniline and water can be separated by steam distillation technique.
Aniline is steam volatile but immiscible with water. So, a mixture of aniline and water will boil close
to but below 373K . After distillation, the mixture of aniline (bottom layer) and water (top layer) can
be separated by separating funnel.
So, both statements I and II are true (option-d).

-------------------------------------------------------------------------------------------------

Question119
Reagent, 1-naphthylamine and sulphanilic acid in acetic acid is used
for the detection of
[18 Mar 2021 Shift 1]
Options:

A. N 2O

B. N O3−

C. N O

D. N O2−

Answer: D

Solution:

Solution:
When a solution is acidified with acetic acid, sulphanilic acid and then 1-naphthylamine is added,
the red coloured precipitate obtain indicates presence of N O2−anions. For detection of N O2−
following test is used.
-------------------------------------------------------------------------------------------------

Question120
Nitrogen can be estimated by Kjeldahl's method for which of the
following compound?
[17 Mar 2021 Shift 2]
Options:

A.

B.

C.

D.

Answer: B

Solution:

Solution:
Nitrogen can be estimated by Kjeldahl's method for the benzyl amine as in this compound nitrogen
is not the part of ring and is free to react.
Because this method can be readily applied to the compound in which nitrogen is free to react with
the reagent. The compounds which have nitrogen in the ring (like pyridine), an azo compound, or in
nitro compounds are not readily converted into the ammonium sulphate by the action of sulphuric
acid.
-------------------------------------------------------------------------------------------------

Question121
Given below are two statements.
Statement I Retardation factor (Rf ) can be measured in
metre\/centimetre.
Statement II Rf value of a compound remains constant in all
solvents.
Choose the most appropriate answer from the options given below
[17 Mar 2021 Shift 1]
Options:

A. Statement I is true but statement II is false.

B. Both statement I and statement II are true.

C. Both statement I and statement II are false.

D. Statement I is false but statement II is true.

Answer: C

Solution:
Solution:

Rf = Distance moved by the substance from base line (x)

Distance moved by the solvent from base line (y)
Rf (Retardation factor is dimensionless)
Different compounds are differently adsorbed in various.
So, Rf value of a compound varies with solvent and it is not constant. Both statements I and II are
false.

-------------------------------------------------------------------------------------------------
Question122
In chromatography technique, the purification of compound is
independent of
[16 Mar 2021 Shift 1]
Options:

A. mobility or flow of solvent system

B. solubility of the compound

C. length of the column or TLC plate

D. physical state of the pure compound

Answer: D

Solution:

Solution:
In chromatography technique, the purification of compound is independent of physical state of the
pure compound (stationary phase). Chromatography is based on the principle of adsorbtion.
Different substances are differently adsorbed.
The technique of chromatography uses the difference in the rates at which the components of a
mixture move through a porous medium (stationary phase) under the influence of some solvent or
gas (moving phase).

-------------------------------------------------------------------------------------------------

Question123

Consider the above reaction where 6.1g of benzoic acid is used to get
7.8g of m-bromo benzoic acid. The percentage yield of the product is
......... . (Round off to the nearest integer). [Given : Atomic masses :
C = 12.0u, H = 1.0u, O = 16.0u, Br = 80.0u ]
[18 Mar 2021 Shift 2]
Answer: 78

Solution:

Solution:
Moles of benzoic acid
= 6.1 (weight)
122 (molecular weight)
= moles of m-bromobenzoic acid
So, weight of m-bromobenzoic acid
= 6.1 × 201g
122
= 10.05g
Actual weight
% yield = × 100
Theoretical weight
7.8
= × 100
10.05
= 77.61% = 78%

-------------------------------------------------------------------------------------------------

Question124
________ grams of 3-hydroxy propanal (M W = 74) must be
dehydrated to produce 7.8g of acrolein (M W = 56)(C3H 4O), if the
percentage yield is 64 (Round off to the nearest integer). [Given:
Atomic masses : C = 12.0u, H = 1.0u, O = 16.0u ]
[18 Mar 2021 Shift 1]

Answer: 16

Solution:

Solution:
On reaction
Δ
H O − CH 2 − CH 2 − CH O ⟶C3H 4O + H 2O
3-hydroxy propanal 64 Acrolein
(mol . wt = 74) (mol . wt = 56)
Let's assume required man of 3-hydroxypropanal be x to produce 0.64g acrolein.
∴ Number of moles = x/74
 x
Now, 7.8g of acrolein gives, × 0.64 = 7.8/56
74
⇒x = 16.10
or x ≅ 16.00

-------------------------------------------------------------------------------------------------

Question125
A reaction of 0.1 mole of benzylamine with bromomethane gave 23g
of benzyl trimethyl ammonium bromide. The number of moles of
−1
bromomethane consumed in this reaction are n × 10 , when
n = ........ (Round off to the nearest integer).
(Given : Atomic masses: C = 12.0u, H = 1.0u, N = 14.0u, Br = 80.0u
]
[18 Mar 2021 Shift 1]

Answer: 3

Solution:

Solution:
Benzylamine reacts with bromoethane to produce benzyl trimethyl ammonium bromide.
The reaction is as follows :

+ −
Ph − CH 2N H 2 + 3CH 3Br ⟶ PhCH 2N µ 3Br
w = 23g = 0.1mol
m 230
⇒0.1 × 3 = 03
Total moles of CH 3Br = 03 = 3 × 10−1mol .
-------------------------------------------------------------------------------------------------

Question126
Which purification technique is used for high boiling organic liquid
compound (decomposes near its boiling point)?
[22 Jul 2021 Shift 2]
Options:

A. Simple distillation

B. Steam distillation

C. Fractional distillation

D. Reduced pressure distillation

Answer: D

Solution:

Solution:
Reduced pressure distillation or vacuum distillation is used for the purification of high boiling
organic liquids which decomposes at or below their boiling point.

-------------------------------------------------------------------------------------------------

Question127
The metal that can be purified economically by fractional
distillation method is:
[20 Jul 2021 Shift 1]
Options:

A. Fe

B. Zn

C. Cu

D. Ni

Answer: B
Solution:

Solution:
Zinc can be purified economically by fractional distillation.

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Question128
0.8 g of an organic compound was analysed by Kjeldahl's method
for the estimation of nitrogen. If the percentage of nitrogen in the
compound was found to be 42%, then __________ mL of 1 M
H 2SO4 would have been neutralized by the ammonia evolved during
the analysis.
[25 Jul 2021 Shift 2]

Answer: 12

Solution:

Solution:
Organic compound : 0.8gm

(
wt. of N = 42 × 0.8 gm
100 )
42 × 0.8 2.4
mole of N = = mol
100 × 14 100
2.4
moles of N H 3 =
100
2N H 3 + H 2SO4 → (N H 4)2SO4
2.4 mole 1.2 mole
100 100
1.2 = 1 × V (l )
100
1.2
⇒V H SO = l = 12ml
2 4 100

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Question129
For above chemical reactions, identify the correct statement from
the following:
[20 Jul 2021 Shift 1]
Options:

A. Both compound 'A' and compound 'B' are dicarboxylic acids

B. Both compound 'A' and compound 'B' are diols

C. Compound 'A' is diol and compound 'B' is dicarboxylic acid

D. Compound 'A' is dicarboxylic acid and compound 'B' is diol

Answer: D

Solution:
Solution:

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Question130
Methylation of 10 g of benzene gave 9.2 g of toluene. Calculate the
percentage yield of toluene ______. (Nearest integer)
[22 Jul 2021 Shift 2]

Answer: 78

Solution:

Solution:
C6H 6 + CH 3Cl → C6H 5CH 3 + H Cl
10
78 (
10 × 92 gm⇒
78 )
Ay
= % yield = 9.2 × 78 × 100 ⇒ 78%
Ty 920

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Question131
When 0.15g of an organic compound was analyzed using Carius
method for estimation of bromine, 0.2397g of AgBr was obtained.
The percentage of bromine in the organic compound is ________.
(Nearest integer)
[Atomic mass : Silver = 108, Bromine = 80 ]
[20 Jul 2021 Shift 2]

Answer: 68

Solution:

Solution:
Moles of Br = Moles of AgBr obtained
0.2397 × 80g
⇒ Mass of Br =
188
therefore % Br in the organic compound
W
= Br × 100
WT
0.2397 × 80
= × 100 = 0.85 × 80
188 × 0.15
= 68
⇒ Nearest integer is '68'

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Question132
In Carius method, halogen containing organic compound is heated
with fuming nitric acid in the presence of :
[20 Jul 2021 Shift 2]
Options:

A. H N O3

B. AgN O3

C. CuSO4

D. BaSO4

Answer: B

Solution:
Solution:
Organic compound is heated with fuming nitric acid in the presence of silver nitrate in carius
method.
Lunar caustic (AgN O3) is used as reagent hare to distinguish Cl −, Br and I −respectively as follows.
AgN O3
Cl −(aq) ─────▸AgCl ↓ppt white
AgN O3
Br−(aq) ─────▸AgBr ↓ ppt pale yellow
AgN O3
I −(aq) ─────▸AgI ↓ ppt Dark yellow

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Question133
In the sulphur estimation, 0.471g of an organic compound gave
1.44g of barium sulphate. The percentage of sulphur in the
compound is .........%.
(Nearest integer)
(Atomic mass of Ba = 137u )
[26 Aug 2021 Shift 2]

Answer: 42

Solution:

Solution:
Atomic mass of sulphur is 32 g.
Molecular weight of BaSO4 is 233g.
So, weight of sulphur in BaSO4
= Atomic mass of sulphur × Weight of BaSO4
Molecular weight of BaSO4
= 32 × 1.44
233
Weight of sulphur
Percentage of sulphur = × 100
Weight of organic compound
= 32 × 1.44 × 100 = 41.98 ≃ 42%
233 0.471

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Question134
The number of stereoisomers possible for 1, 2 - dimethyl
cyclopropane is
[26 Aug 2021 Shift 2]
Options:

A. one

B. four

C. two

D. three

Answer: D

Solution:

Solution:
1, 2-dimethylcyclopropane is

Hence, stereoisomers are as follows

meso form in optically inactive, whereas enantiomeric pairs are optically active. Therefore, total
number of stereo isomers are three (3).

-------------------------------------------------------------------------------------------------

Question135
Arrange the following conformational isomers of n -butane in order
of their increasing potential energy

[31 Aug 2021 Shift 2]

Options:

A. II < III
B. I < IV < III < II

C. II < IV < III < I

D. I < III < IV < II

Answer: D

Solution:
Solution:
The order of potential energy of above conformations is

The fully eclipsed form is least stable due to repulsion between bulky (−CH3) methyl group at front
and rear carbon atom.
∴ It has maximum potential energy.
While the repulsion in anti form is minimum.
∴ It has minimum potential energy.

-------------------------------------------------------------------------------------------------
Question136
Given below are two statements.
One is labelled as Assertion (A) and the other is labelled as Reason
(R).
Assertion (A) A simple distillation can be used to separate a mixture
of propanol and propanone.
Reason (R) Two liquids with a difference of more than 20°C in their
boiling points can be separated by simple distillations.
In the light of the above statements, choose the most appropriate
answer from the
options given below.
[31 Aug 2021 Shift 1]
Options:

A. (A) is false but (R) is true.

B. Both (A) and (R) are correct but (R) is not the correct explanation of (A).

C. (A) is true but (R) is false

D. Both (A) and (R) are correct and (R) is the correct explanation of (A).

Answer: D

Solution:

Solution:
Propanol and propanone can be separated by simple distillation technique as difference in boiling
point of propanol and propanone is more than 20°C.
Boiling point of propanol = 97°C.
Boiling point of propanone = 56°C
Difference in boiling points = 41° C > 20°C
Hence, option (d) is correct.

-------------------------------------------------------------------------------------------------

Question137
The transformation occurring in Duma's method is given below

( )
C2H7N + 2x + y2 CuO → xCO2 + y2 H2O + 2z N2 + 2x + y2 Cu ( )
The value of y is ........ . (Integer answer)
[31 Aug 2021 Shift 2]

Answer: 7

Solution:

Solution:
For the reaction

( )
C2H7N + 2x + y CuO → xCO2 + y H2O + z N2 + 2x + y Cu
2 2 2 2 ( )
On reactant side number of H-atom = 7
y
On product side number of H-atom = × 2
2
y
7= ×2
2
∴y=7

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Question138
The number of moles of CuO, that will be utilised in Dumas method
for estimation nitrogen in a sample of 57.5g ofN, N-
dimethylaminopentane is ............ × 10−2 .(Nearest integer)
[27 Aug 2021 Shift 1]

Answer: 1125

Solution:

Solution:
In Dumas method,

( )
CxHyNz + 2x + y CuO → x CO2 + y H2O + z + 2x + y Cu
2 2 2 2 ( )
N, N-dimethylaminopentane has formula C7H17N.
So, relating with CxHyNz
x=7
y = 17
z=1
Molar mass of C7H17N = 115g
= 22.5 moles of CuO

( )
57.5g i.e. 57.5 C7H17N will utilise
115
= 22.5 × 57.5 moles of CuO
115
= 11.25g mol ≈ 1125 × 10−2 mol

-------------------------------------------------------------------------------------------------

Question139
In carius method for estimation of halogens, 0.2g of an organic
compound gave 0.188g of AgBr. The percentage of bromine in the
compound is ......... (Nearest integer)
[Atomic mass; Ag = 108, Br = 80]
[27 Aug 2021 Shift 1]

Answer: 40

Solution:

Solution:
Mass of bromine = 80 u
Mass of silver = 108 u
Mass of AgBr = 108 + 80 = 188 u
Weight of organic compound = 0.2 g
% of Br = Molar mass of Br × Weight of AgBr × 100
Molar mass of AgBr Weight of organic compound
= 80 × 0.188 × 100 = 40%.
188 0.2

-------------------------------------------------------------------------------------------------

Question140
The increasing order of basicity for the following intermediates is
(from weak to strong)
CH3
|
Θ
(i) H 3C − C|
CH3
 Θ
(ii) H 3C = CH − CH 2
Θ
(iii) H C ≡ C
Θ
(iv) CH 3
⊖

(v) CN
[Jan. 09,2020 (I)]
Options:

A. (iii) <(i) < (ii) < (iv) < (v)

B. (v) < (i) < (iv) < (ii) < ( iii )

C. (v) < ( iii ) < ( ii ) < (iv) < (i)

D. (iii) <(iv) < (ii) < (i) < (v)

Answer: C

Solution:

Solution:
Basicity order can be determined by the cummulative effect of the factors on the electron density of
concerned atom.

-------------------------------------------------------------------------------------------------

Question141
A flask contains a mixture of is hexane and 3 methyl pentane. One of
the liquids boils at 63∘ C while the other boils at 60∘ C. What is the
best way to separate the two liquids and which one will be distilled
out first?
[Jan. 08,2020(I)]
Options:

A. fractional distillation, isohexane

B. simple distillation, 3 -methylpentane

C. simple distillation, isohexane

D. fractional distillation, 3 -methylpentane

Answer: A

Solution:

Solution:
Liquid having lower boiling point comes out first in fractional distillation. Simple distillation can't be
used as boiling point difference is very small.
3-Methylpantane will show greater boiling point (63∘C) comparative to isohexane due to
symmetrical structure. Therefore isohexane distilled out first.

-------------------------------------------------------------------------------------------------

Question142
The correct order of stability for the following alkoxides is:

[Jan. 07, 2020 (II)]

Options:

A. (B) > (A) > (C)

B. (C) > (B) > (A)

C. (C) > (A) > (B)

D. (B) > (C) > (A)

Answer: B

Solution:

Solution:
Electron withdrawing group like (N O2) increase stability of alkoxide ion by dispersal of negative
charge.
In (B) and (C) structures negative charge is in conjugation with double bond and also stabilised by
electron withdrawing effect of nitro group.

-------------------------------------------------------------------------------------------------
Question143
The IUPAC name of the following compound is:

[Sep. 06, 2020 (II)]

Options:

A. 2 -nitro-4-hydroxymethyl-5-amino benzaldehyde

B. 3-amino-4-hydroxymethyl-5-nitrobenzaldehyde

C. 5-amino-4-hydroxymethyl-2-nitrobenzaldehyde

D. 4 -amino-2-formyl- 5 -hydroxymethyl nitrobenzene

Answer: C

Solution:

Solution:

5-Amino- 4 -hydroxymethyl-2-nitrobenzaldehyde

-------------------------------------------------------------------------------------------------

Question144
The IUPAC name of the following compound is :

[Sep. 04,2020 (I)]

Options:

A. 5-Bromo-3-methylcyclopentanoic acid

B. 4 -Bromo-2-methylcyclopentane carboxylic acid

C. 3-Bromo-5-methylcyclopentanoic acid

D. 3-Bromo-5-methylcyclopentane carboxylic acid

Answer: B

Solution:

Solution:

4-Bromo-2-methylcyclopentane carboxylic acid

-------------------------------------------------------------------------------------------------

Question145
The IUPAC name for the following compound is :

[Sep. 02, 2020 (I)]

Options:
A. 2,5 -dimethyl-5-carboxy-hex-3-enal

B. 2,5 -dimethyl-6-carboxy-hex-3-enal

C. 2,5 -dimethyl-6-oxo-hex-3-enoic acid

D. 6-formyl-2-methyl-hex-3-enoic acid

Answer: C

Solution:

Solution:

(2, 5 -dimethyl 1 − 6 -oxo-hex-3-enoic acid)

-------------------------------------------------------------------------------------------------

Question146
In an estimation of bromine by Carius method, 1.6g of an organic
compound gave 1.88g of AgBr. The mass percentage of bromine in
the compound is
(Atomic mass, Ag = 108, Br = 80gmol − 1 )
[NV, Sep. 06, 2020 (I)]

Answer: 50

Solution:
Solution:
Mass of organic compound = 1.6g
Mass of AgBr = 1.88g
1.88
Moles of Br = Moles of AgBr = = 0.01
188
Mass of Br = 0.01 × 80 = 0.80g
0.80 × 100
% of Br = = 50%
1.60
 Wt. of AgBr × Molar mass of Br ×
Alternate Method: % of Br = 100
W t . of O . C. AgBr
= 1.88 × 80 × 100 = 50%
1.6 188

-------------------------------------------------------------------------------------------------

Question147
Which one of the following compounds possesses the most acidic
hydrogen?
[Sep. 03,2020(I)]
Options:

A.

B. H 3C − C ≡ C − H

C.

D.

Answer: D

Solution:

Solution:
Acidic strength ∝−I , −M effect. Due to strong −I , and −M effect of three −COOCH 3 groups, it has
most acidic Hydrogen.

-------------------------------------------------------------------------------------------------
Question148
Glycerol is separated in soap industries by:
[Sep. 03,2020(I)]
Options:

A. Fractional distillation

B. Differential extraction

C. Steam distillation

D. Distillation under reduced pressure

Answer: D

Solution:

Solution:
Glycerol can be separated from spent-lye in soap industry by using reduce pressure distillation
technique.

-------------------------------------------------------------------------------------------------

Question149
What is the IUPAC name of the following compound?

[Jan. 10, 2019 (II)]

Options:

A. 3-Bromo-1, 2-dimethylbut-1-ene

B. 3-Bromo-3-methyl-1,2-dimethylprop-1-ene

C. 2-Bromo-3-methylpent-3-ene

D. 4-Bromo-3-methylpent-2-ene
Answer: D

Solution:
Solution:
IUPAC name: 4 -Bromo-3-methylpent- 2 -ene

-------------------------------------------------------------------------------------------------

Question150
The IUPAC name for the following compound is:

[April 12, 2019 (II)]

Options:

A. 3 -methyl-4-(3-methylprop-l-enyl)-l-heptyne

B. 3,5-dimethyl-4-propylhept-6-en-l-yne

C. 3-methyl-4-(1-methylprop-2-ynyl)-l-heptene

D. 3,5-dimethyl-4-propylhept-l-en-6-yne

Answer: D

Solution:
Solution:

3, 5 -dimethyl-4-propylhept- 1 -en-6-yne

-------------------------------------------------------------------------------------------------

Question151
The correct IUPAC name of the following compound is:

[April 9, 2019(I)]
Options:

A. 5-chloro-4-methyl-1-nitrobenzene

B. 2 -chloro-1-methyl-4-nitrobenzene

C. 3-chloro-4-methyl-1-nitrobenzene

D. 2 -methyl-5-nitro-1-chlorobenzene

Answer: B

Solution:
Solution:

2-Chloro-1-methyl-4-nitrobenzene

-------------------------------------------------------------------------------------------------

Question152
The IUPAC name of the following compound is:
CH3 OH
| |
H 3C − C H − C H − CH 2 − COOH
[April 8, 2019 (I)]
Options:

A. 4, 4-Dimethyl-3-hydroxybutanoic acid

B. 2-Methyl-3-hydroxypentan-5-oic acid

C. 3-Hydroxy-4-methylpentanoic acid

D. 4-Methyl-3-hydroxypentanoic acid

Answer: C

Solution:

Solution:

3-Hydroxy-4-methyl pentanoic acid

-------------------------------------------------------------------------------------------------

Question153
Which of the following compounds will show the maximum 'enol'
content?
[April 8, 2019 (II)]
Options:

A. CH 3COCH 2COOC2H 5

B. CH 3COCH 2COCH 3

C. CH 3COCH 3

D. CH 3COCH 2CON H 2

Answer: B

Solution:

Solution:
Enolic form of acetylacetone (b) is quite stable due to H-bonding which leads to stable 6 -
membered ring.

-------------------------------------------------------------------------------------------------

Question154
The increasing order of nucleophilicity of the following nucleophiles
is:
⊖
(i) CH 3CO2
(ii) H 2O
⊖
(iii) CH 3SO3
⊖

(iv) OH
[April 10, 2019 (II)]
Options:

A. (i) <(iv) < (iii) < (ii)

B. (ii) <( iii ) < ( iv )< (i)

C. (iv) <(i) < (iii) < (ii)

D. (ii) <(iii) < (i) < (iv)

Answer: D

Solution:

Solution:
If the lone pair donating tendency on oxygen is reduced, nucleophilicity reduced. This is because
the electron density of larger atoms is more readily distorted since the electrons are further from
the nucleus.
H 2O = Neutral molecule
O
||
CH 3SO3 = CH 3S−O− = Charged ion
⊖

||
O
CH 3COO = CH 3 − C−O = Charged ion
⊖ −

||
O
⊖
OH = Charged ion
Thus, the increasing order of nucleophilicity is:
⊖ ⊖
H 2O < CH 3SO3 < CH 3COO < OH

-------------------------------------------------------------------------------------------------

Question155
The IUPAC name of the following compound is:

[Online April 15, 2018(I)]

Options:

A. 3 -cthyl-4-methylhex-4-ene

B. 4,4 -diethyl-3-methylbut-2-ene

C. 4 -methyl-3-ethylhex-4-ene

D. 4 -ethyl-3-methylhex-2-ene

Answer: D

Solution:
Solution:

4-Ethyl-3-methylhex-2-cne

-------------------------------------------------------------------------------------------------

Question156
The increasing order of basicity of the following compounds is

[2018]
Options:

A. (i) < (ii) < (iii) < (iv)

B. ( ii ) < ( i ) < ( iii ) < ( iv )

C. (ii) <(i) < (iv) < (iii)

D. (iv) < (ii) < (i) < (iii)

Answer: C

Solution:

Solution:
-------------------------------------------------------------------------------------------------

Question157
The most polar compound among the following is:
[Online April 16, 2018]
Options:

A.

B.
C.

D.

Answer: C

Solution:

Solution:
Among the substituents attached to the given compounds, fluorine has maximum electronegativity.
so it will push electron pair towards itself. In option (b), the two F groups are attached opposite to
each other, thus net dipole moment will cancel out and reduce its polarity. In option (d), the F
groups are attached in slightly opposite direction, thus this also decreases its polarity. But in option
(c), the compound has the two F groups along same direction, thus net dipole moment will increase
in this direction and therefore it will exhibit maximum polarity. Hence the compound in option (c)
has maximum polarity.

-------------------------------------------------------------------------------------------------

Question158
On the treatment of the following compound with a strong acid, the
most susceptible site for bond cleavage is:

[Online April 15, 2018(II)]

Options:

A. O2 − C3

B. O5 − C6

C. C4 − O5

D. C1 − O2

Answer: B

Solution:
Solution:
The lone pair of electrons on O2 is involved in resonance with C = C. Hence O2 will not be
protonated. The lone pair of electrons on O5 is not involved in resonance with C = C. Hence, O5 will
be protonated. Chloride ion will then attack least substituted C atom (C6)

-------------------------------------------------------------------------------------------------

Question159
Two compounds I and II are eluted by column
chromatography(adsorption of I > II). Which one of the following is
a correct statement?
[Online April 15, 2018 (II)]
Options:

A. II moves slower and has higher Rp value than I

B. II moves faster and has higher Rf value than I

C. I moves faster and has higher Rf value than II

D. I moves slower and has higher Rf value than II

Answer: B

Solution:
Solution:
Since, adsorption of I > II, I is firmly attached to column (stationary phase). Hence, it moves slowly
and will cover little distance, while II is loosely attached to column (stationary phase). Hence, it
moves faster and will cover large distance.

-------------------------------------------------------------------------------------------------

Question160
The IUPAC name of the following compound is:

[Online April 8, 2017]

Options:

A. 1, 1− dimethyl-2-ethylcyclohexane

B. 2 - ethyl −1, 1 -dimethylcyclohexane

C. I-cthyl-2,2-dimethylcyclohexane

D. 2, 2-dimethyl-1-ethylcyclohexane

Answer: B

Solution:

Solution:
2-Ethyl-1,1-dimethylcyclohexane

-------------------------------------------------------------------------------------------------

Question161
In the following structure, the double bonds are marked as I, II, III
and IV

Geometrical isomerism is not possible at site(s):

[Online April 9, 2017]
Options:

A. III

B. I

C. I and III

D. III and IV

Answer: B

Solution:

Solution:

-------------------------------------------------------------------------------------------------
Question162
Which of the following statements is not true about partition
chromatography?
[Online April 8, 2017]

Options:

A. Mobile phase can be a gas

B. Stationary phase is a finely divided solid adsorbent

C. Separation depends upon equilibration of solute between a mobile and a stationary

phase

D. Paper chromatography is an example of partition chromatography

Answer: B

Solution:
Solution:
Partition chromatography is the process of separation whereby the component of the mixture get
distributed into two phases that may be liquid-liquid, liquid gas but not to solid-gas. Thus, it is not
possible that the stationory phase is a finally devided solid adsorbent in partition chromatography.

-------------------------------------------------------------------------------------------------

Question163
The increasing order of the boiling points for the following
compounds is :
(I) C2H 5OH
(II) C2H 5Cl
(III) C2H 5CH 3
(IV) C2H 5OCH 3
[Online April 9, 2017]

Options:

A. (III) < (IV) < (II) < (I)

B. (I V ) < (I I I ) < (I ) < (I I )

C. (I I ) < (I I I ) < (I V ) < (I )

D. (I I I ) < (I I ) < (I ) < (I V )

Answer: A

Solution:
Solution:
(I) C2H 5OH Hydrogen bonding Hydrogen bonding > dipole-dipole
(II) C2H 5Cl Dipole-dipole C2H 5Cl is more polar than C2H 5OCH 3 so, dipole-dipole C2H 5Cl >
dipole-dipoleC2H 5OCH 3
(III) C2H 5CH 3 Weak vander Waals yarces
(IV) C2H 5OCH 3 Dipole-dipole
Thus, boiling points order is
(I I I ) < (I V ) < (I I ) < (I ).

-------------------------------------------------------------------------------------------------

Question164
A mixture containing the following four compounds is extracted
with 1M HCl. The compound that goes to aqueous layer is :

[Online April 8,2017]

Options:

A. (I)

B. (II)

C. (III)

D. (IV)

Answer: B
Solution:

Solution:
When the given mixture is shaken with 1M H Cl , amine get protonated and becomes cation

( R N H ) , which does not dissolve in organic solvent but usually dissolve in H O due to its
2
⊕
2 2
charge. So, shaking with aqueous H Cl willpull amines into the aqueous phase and leave all other
compounds in organic layer.

-------------------------------------------------------------------------------------------------

Question165
The increasing order of the reactivity of the following halides for the
SN 1 reaction is
CH 3CH CH 2CH 3CH 3CH 2CH 2Cl
|
Cl
(I)
(II)
p − H 3CO − C6H 4 − CH 2Cl
(III)

[2017]
Options:

A. (I I I ) < (I I ) < (I )

B. (I I ) < (I ) < (I I I )

C. (I ) < (I I I ) < (I I )

D. (I I ) < (I I I ) < (I )

Answer: B

Solution:
Solution:
Since SN 1 reactions involve the formation of carbocation as intermediate in the rate determining
step, more the stability of carbocation higher will be the reactivity of alkyl halides towards SN 1
route. Since stability of carbocationsfollows order.
CH 3 − CH 2 − CH 2 < CH 3 − CH − CH 2 − CH 3
1∘ carbocation 2∘ carbocation
<p − H 3CO − C6H 4 − CH 2
Max . stable due to + M effect of − OCH3 group.

-------------------------------------------------------------------------------------------------
Question166
Which of the following molecules is least resonance stabilized?
[2017]
Options:

A.

B.

C.

D.

Answer: D

Solution:

Solution:
is nonaromatic and hence least resonance stabilized, whereas other three are aromatic.

-------------------------------------------------------------------------------------------------

Question167
The hydrocarbon with seven carbon atoms containing a neopentyl
and a vinyl group is:
[Online April 9, 2016]
Options:

A. 2,2 - dimethyl −4 - pentene

B. 4,4 - dimethyl pentene

C. isopropyl-2-butene

D. 2, 2- -dimethyl-3-pentene

Answer: B

Solution:
Solution:

4, 4− Dimethyl pentene

-------------------------------------------------------------------------------------------------

Question168
The absolute configuration of is:

[2016]
Options:

A. (2S, 3S)

B. (2R, 3R)

C. (2R, 3S)

D. (2S, 3R)

Answer: D

Solution:
Solution:
-------------------------------------------------------------------------------------------------

Question169
The distillation technique most suited for separating glycerol from
pent-l-ye in the soap industry is:
[2016]
Options:

A. Steam distillation.
B. Distillation under reduced pressure.

C. Simple distillation

D. Fractional distillation

Answer: B

Solution:
Solution:
Pent-l-ye and glycerol are separated by distillation under reduced pressure. Under the reduced
pressure, the liquid boil at low temperature and the temperature of decomposition will not reach.
e.g. glycerol boils at 290∘C with decomposition but at reduced pressure it boils at 180∘C without
decomposition.

-------------------------------------------------------------------------------------------------

Question170
Which of the following compounds will exhibit geometrical
isomerism?
[2015]
Options:

A. 2 - Phenyl −1 - butene

B. 1, 1− Diphenyl −1 - propene

C. 1 - Phenyl −2 - butene

D. 3 - Phenyl - 1 - butene

Answer: C

Solution:
Solution:
H
|
H 3C − C = CH − CH 2Ph
In 1 -phenyl-2-butene, the two groups around the doubly bonded carbons are different. This
compound can show cis-and trans-isomerism.

-------------------------------------------------------------------------------------------------

Question171
The optically inactive compound from the following is:
[Online April 10, 2015]
Options:

A. 2 - chloropropanal

B. 2 - chlorobutane

C. 2 - chloropentane

D. 2 - chloro −2 - methylbutane

Answer: D

Solution:
Solution:
The optically inactive compound must contains achiral carbon atom(s). Option (d) contains achiral
carbon atom

-------------------------------------------------------------------------------------------------

Question172
The number of structural isomers for C6H 14 is :
[Online April 11,2015]
Options:

A. 4

B. 3
C. 6

D. 5

Answer: D

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question173
Which of the following pairs of compounds are positional isomers ?
[Online April 11,2015]
Options:

A. CH 3 − CH 2 − CH 2 − C − CH 3 and CH 3 − CH 2 − C − CH 2 − CH 3
|| ||
O O

O
||
B. CH 3 − CH 2 − CH 2 − CH 2 − CH O and CH 3 − CH 2 − CH 2 − C − CH 3

C. CH 3 − CH 2 − CH 2 − C − CH 3 and CH 3 − CH − CH 2 − CH O
|| |
O CH3

CH 3
D. CH 3 − CH 2 − C − CH 2 − CH 3and CH CH − CH 2 − CH O
|| 3
O

Answer: A

Solution:
Solution:
Pentan-2-one and pentan-3-one are position isomers. (b), (c), (d) contain different compounds
aldehyde and ketones. These exhibit functional group is omerism.

-------------------------------------------------------------------------------------------------

Question174
In allene (C3H 4), the type(s) of hybridization of the carbon atoms is
(are):
[Online April 11, 2014]
Options:

A. sp and sp3

B. sp2 and sp

C. only sp2

D. sp2 and sp3

Answer: B

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question175
The correct IUPAC name of the following compound is:

[Online April 19, 2014]

Options:
A. 4 - methyl −3 - ethylhexane

B. 3 - ethyl −4 - methylhexane

C. 3,4 -ethylmethylhexane

D. 4 - ethyl - 3 - methylhexane

Answer: B

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question176
Which one of the following acids does not exhibit optical isomerism?
[Online April 12, 2014]
Options:

A. Lactic acid

B. Tartaric acid

C. Maleic acid

D. alpha -amino acids

Answer: C

Solution:

Solution:
Optically active compounds contain an asymmetric (chiral) carbon atom (a carbon atom attached to
four different atoms or groups). Therefore, all acids except maleic acid exhibit optical isomerism.
-------------------------------------------------------------------------------------------------

Question177
For which of the following molecule significant µ ≠ 0?

[2014]
Options:

A. Only (i)

B. (i) and (ii)

C. Only(iii)

D. (iii) and (iv)

Answer: D

Solution:

Solution:

In both the molecules the bond moments are not cancelling with each other and hence the
molecules has a resultant dipole.

-------------------------------------------------------------------------------------------------

Question178
In which of the following pairs A is more stable than B ?
[Online April 9, 2014]
Options:
A.

B.

C.

D. Ph3C∙, (CH 3)3C∙

Answer: D

Solution:
Solution:
Ph3˙C is more stable than (CH 3)3˙C because resonance stabilisation effect in Ph3˙C is more
pronounced as compared to hyperconjugation stabilisation effect in (CH 3)3˙C, overall stability
orderamong free radical is:
Triphenylmethyl > benzyl > allyl > tertiary alkyl > secondary > primary > methyl > vinyl

-------------------------------------------------------------------------------------------------

Question179
Arrange in the correct order of stability (decreasing order) for the
following molecules:
[Online April 22, 2013]
Options:

A. (I ) > (I I ) > (I I I ) > (I V )

B. (I V ) > (I I I ) > (I I ) ≈ (I )
C. (I ) > (I I ) ≈ (I I I ) > (I V )

D. (I I I ) > (I ) ≈ (I I ) > (I V )

Answer: D

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question180
A solution of (−) − 1− chloro −1− phenylethane in toluene racemises
slowly in the presence of a small amount of SbCl 5, due to the
formation of:
[2013]
Options:

A. carbanion

B. carbene

C. carbocation

D. free radical

Answer: C

Solution:
Solution:
Carbocations are planar, hence can beattacked on either sideto form racemic mixture.
SbCl 5 ⊕
Cl − CH − CH 3───────▶Ph − CH − CH 3 + SbCl 6− ⟶Ph − CH − CH 3 + SbCl 5
| Toluene |
Carbocation
ph Cl
(−) (d + l ) mixture

-------------------------------------------------------------------------------------------------

Question181
The order of stability of the following carbocations is:

[2013]
Options:

A. I I > I I > I

B. I I > I I I > I

C. I > I I > I I I

D. I I I > I > I I

Answer: D

Solution:
Solution:
Higher stability of allyl and benzyl carbocations is due to dispersal of positive charge by resonance
whereas in alkyl carbocations dispersal of positive charge on different hydrogen atoms is due to
inductive effect. Hence the correct order of stability will be

-------------------------------------------------------------------------------------------------

Question182
Which one of the following is most stable?
[Online April 9, 2013]
Options:

A.

B.

C.

D.
Answer: A

Solution:
Solution:
3∘ carbocations are most stable.

-------------------------------------------------------------------------------------------------

Question183
Given

In the above compounds correct order of reactivity in electrophilic

substitution reactions will be:
[Online April 25,2013]
Options:

A. B > A > C > D

B. D > C > B > A

C. A > B > C > D

D. B > C > A > D

Answer: A

Solution:
Solution:
−Cl and −CH 3 groups are o and p directing. They are electron releasing due to +M and
hyperconjugation effects. Further since such groups increase electron density in the nucleus, they
facilitate further electrophilic substitution and hence known as activating group. The activating
effect of these groups is in order of −CH 3 > −X but chlorine exceptionally deactive the ring due to
strong − I effect. Hence, it is difficult to carry out substitution in chlorobenzene than in benzene.
Further −N O2 is a deactivating group, hence deactivates the benzene nucleus, i.e. hinder the
further substitution. Thus nitrobenzene undergo electrophilic substitution with a great difficulty,
hence the correct order will be

-------------------------------------------------------------------------------------------------

Question184
In nucleophilic substitution reaction, order of halogens as incoming
(attacking) nucleophile is:
I − > Br−>Cl −
The order of halogens as departing nucleophile should be:
[Online April 25, 2013]
Options:

A. Br− > I −>Cl −

B. I −>Br− > Cl −

C. Cl − > Br− > I −

D. Cl − > I − > Br−

Answer: B

Solution:

Solution:
Since the leaving group breaks away as a base, it is easier to displace weaker bases as compared
to stronger bases. Thus less basic the substituent, the more easily it is displaced.
Since the basic strength of the given groups is in order.
I − < Br− < Cl −
Thus the order of halogen leaving groups is
I − > Br− > Cl

-------------------------------------------------------------------------------------------------
Question185
Which of the following cannot be represented by resonance
structures?
[Online May 7, 2012]
Options:

A. Dimethyl ether

B. Nitrate anion

C. Carboxylate anion

D. Toluene

Answer: A

Solution:
Solution:
Ethers, due to absence of delocalized pair of electrons do not show resonance.

-------------------------------------------------------------------------------------------------

Question186
The IUPAC name of the compound is

[Online May 7, 2012]

Options:

A. 1,2 -propoxide

B. propylene oxide

C. 1, 2− oxo propane

D. 1,2 -cpoxy propane

Answer: D
Solution:

Solution:
1,2 -Epoxy propane is the correct IUPAC name of given compound.

-------------------------------------------------------------------------------------------------

Question187
The IUPAC name of the following compound is

[Online May 19,2012]

Options:

A. (E)-2-hepten-4-yne

B. (Z ) − 5 -hepten- 3 -yne

C. (E)-5-hepten-3-yne

D. (Z)-2-hepten-4-yne

Answer: A

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question188
Dipole moment is shown by
[Online May 26, 2012]
Options:

A. 1,2 -dichlorobenzene
B. trans-2, 3 -dichloro-2-butene

C. 1,4 -chlorobenzene

D. trans-1,2-dinitroethene

Answer: A

Solution:

Solution:
In 1,2 -dichlorobenzene the two dipoles are at 60∘ (i.e. unsymmetric). Thus possesses dipole
moment.

-------------------------------------------------------------------------------------------------

Question189
How many cyclic structures are possible for C4H 6 ?
[Online May 7, 2012]
Options:

A. 3

B. 5

C. 6

D. 4

Answer: B

Solution:

Solution:
Five cyclic structures are possible for C4H 6. These are as following:

-------------------------------------------------------------------------------------------------

Question190
Maleic acid and fumaric acids are
[Online May 26,2012]
Options:

A. chain isomers

B. functional isomers

C. tautomers

D. geometrical isomers

Answer: D

Solution:
Solution:
Maleic acid and fumaric acids are geometrical isomers.

-------------------------------------------------------------------------------------------------
Question191
In the below mentioned compounds the decreasing order of
reactivity towards electrophilic substitution is

[Online May 12, 2012]

Options:

A. (iv) > (i) > (ii) > (iii)

B. (ii) >(iii) > (i) > (iv)

C. (iii) >(i) > (iv)> (ii)

D. (i) > (ii) > (iii) > (iv)

Answer: D

Solution:
Solution:
−OCH 3 and −CH 3 groups are activating group while −CF 3 is a deactivating group. Thus order is

-------------------------------------------------------------------------------------------------

Question192
The change in the optical rotation of freshly prepared solution of
glucose is known as:
[2011RS]
Options:

A. racemisation

B. specific rotation

C. mutarotation

D. tautomerism

Answer: C

Solution:
Solution:
When either of the two forms of glucose is dissolved in water, there is change in rotation till the
equilibrium value of +52.5∘. This is known as mutarotation
α − D(+) Glucose ⇌ Equilibrium mixture ⇌β − D − (+) Glucose
+111.5° +52.5∘ +19.5°

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Question193
Out of the following, the alkene that exhibits optical isomerism is
[2010]
Options:

A. 3-methyl-2-pentene

B. 4 -methyl-1-pentene

C. 3-methyl-1-pentene

D. 2 -methyl-2-pentene

Answer: C

Solution:
Solution:
 H *
|
H 2C = H C − C − CH 2 − CH 3
|
CH3
3- Methyl-1-pentene

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Question194
The correct order of increasing basicity of the given conjugate bases
(R = CH 3) is
[2010]
Options:

A. RCOO < H C ≡ C < R < N H 2

B. R < H C ≡ C < RCOO < N H 2

C. RCOO < N H 2 < H C ≡ C < R

D. RCOO < H C ≡ C < N H 2 < R

Answer: D

Solution:
Solution:
The corresponding conjugate acid are CH 3 COOH > CH ≡ CH > N H 3 > RH
Most acidic Least acidic

∴ the correct order of basicity is RCOO− < CH ≡ C− < N H 2 − < R−

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Question195
The IUPAC name of neopentane is
[2009]
Options:

A. 2, 2-dimethylpropane

B. 2-methylpropane
C. 2,2 -dimethylbutane

D. 2- methylbutane

Answer: A

Solution:
Solution:

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Question196
The alkene that exhibits geometrical isomerism is:
[2009]
Options:

A. 2 - methyl propene

B. 2 -butene

C. 2 - methyl −2 - butene

D. propene

Answer: B

Solution:
Solution:

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Question197
The number of stereoisomers possible for a compound of the
molecular formula CH 3 − CH = CH − CH (OH ) − M e is:
[2009]
Options:

A. 2

B. 4

C. 6

D. 3

Answer: B

Solution:
Solution:
CH 3 − CH = CH − C H CH
|
OH 3
It exhibits both geometrical as well as optical isomerism.
cis −R cis −S
trans - R trans - S

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Question198
Arrange the carbanions,
(CH 3)3C, CCl 3, (CH 3)2CH , C6H 5CH 2
order of their decreasing stability is
[2009]
Options:

A. (CH 3)2CH > CCl 3 > C6H 5CH 2 > (CH 3)3C

B. CCl 3 > C6H 5CH 2 > (CH 3)2CH > (CH 3)3C

C. (CH 3)3C > (CH 3)2CH > C6H 5CH 2 > CCl 3
D. C6H 5CH 2 > CCl 3 > (CH 3)3C > (CH 3)2CH

Answer: B

Solution:
Solution:

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Question199
The correct decreasing order of priority for the functional groups of
organic compounds in the IUPAC system of nomenclature is
[2008]
Options:

A. −COOH , −SO3H , −CON H 2, −CH O

B. −SO3H , −COOH , −CON H 2, −CH O

C. −CH O, −COOH , −SO3H , −CON H 2

D. −CON H 2 − CH O, −SO3H , −COOH

Answer: A

Solution:

Solution:
The correct order of priority for the given functional group is

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Question200
The absolute configuration of

[2008]
Options:

A. S, S

B. R, R

C. R, S

D. S, R

Answer: B

Solution:

Solution:
The absolute configuration is (R, R)
(use priority rules to get the absolute configuration)

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Question201
⊕
The electrophile, E attacks the benzene ring to generate the
intermediate σ− complex. Of the following, which σ− complex is
lowest energy?
[2008]
Options:

A.
B.

C.

D.

Answer: B

Solution:

Solution:
In option (b) the complex formed is with benzene whereas in other cases it is formed with
nitrobenzene with −N O2 group in different positions (o−, m−, p−). The complex formed with
nitrobenzene in any position of −N O2 group is less stablethan the complex formed with benzene,
so the most stable complex has lowest energy.

-------------------------------------------------------------------------------------------------

Question202
The IUPAC name of is

[2007]
Options:

A. 3-ethyl-4,4-dimethylheptane

B. 1,1 -diethyl-2,2-dimethylpentane

C. 4,4 -dimethyl −5, 5 -diethylpentane

D. 5,5 -dicthyl −4, 4 -dimethylpentane.

Answer: A

Solution:
Solution:

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Question203
Which one of the following conformations of cyclohexane is chiral?
[2007]
Options:

A. Boat

B. Twist boat

C. Rigid

D. Chair
Answer: B

Solution:

Solution:
Chiral conformation will not have plane of symmetry. Since twist boat does not have plane of
symmetry, it is chiral.

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Question204
Which of the following molecules is expected to rotate the plane of
plane-polarised light?
[2007]
Options:

A.

B.

C.
D.

Answer: B

Solution:
Solution:
The organic compounds which have chiral carbon atom (a carbon atom attached to four different
groups or atoms) and do not have plane of symmetry rotate plane polarised light.
CHO *
|
HO− C − H (* is asymmetric carbon)
|
CH2 OH

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Question205
Presence of a nitro group in a benzene ring
[2007]
Options:

A. deactivates the ring towards electrophilic substitution

B. activates the ring towards electrophilic substitution

C. renders the ring basic

D. deactivates the ring towards nucleophilic substitution.

Answer: A

Solution:
Solution:
Nitro group is electron withdrawing group, so it deactivates the ring towards electrophilic
substitution.

-------------------------------------------------------------------------------------------------

Question206
The IUPAC name of the compound shown below is :

[2006]
Options:

A. 3 -bromo-1-chlorocyclohexene

B. 1 -bromo-3-chlorocyclohexene

C. 2 -bromo-6-chlorocyclohex-1-ene

D. 6-bromo-2-chlorocyclohexene

Answer: A

Solution:
Solution:

3-Bromo-1-chlorocyclohexene

-------------------------------------------------------------------------------------------------

Question207
Increasing order of stability among the three main conformations
(i.e. Eclipse, Anti, Gauche) of 2 -fluorocthanol is
[2006]
Options:

A. Eclipse, Anti, Gauche

B. Anti, Gauche, Eclipse

C. Eclipse, Gauche, Anti

D. Gauche, Eclipse, Anti

Answer: A

Solution:
Solution:

Due to hydrogen bonding between H &F gauche conformation is most stable, hence the correct
order is Eclipse, Anti, Gauche

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Question208
The increasing order of stability of the following free radicals is
[2006]
Options:

A. (C6H 5)2˙CH < (C6H 5)3˙C < (CH 3)3˙C < (CH 3)2˙CH

B. (CH 3)2˙CH < (CH 3)3˙C < (C6H 5)2˙CH < (C6H 5)3˙C

C. (CH 3)3˙C < (CH 3)2˙CH < (C6H 5)2˙CH < (C6H 5)3˙C

D. (C6H 5)3˙C < (C6H 5)2˙CH < (CH 3)3˙C < (CH 3)2˙CH

Answer: B

Solution:
Solution:
The order of stability of free radicals
(C6H 5)3˙C > (C6H 5)2˙CH > (CH 3)3˙C > (CH 3)2˙CH
The stabilisation of first two is due to resonance and last two is due to hyper conjugation.

-------------------------------------------------------------------------------------------------

Question209
CH 3Br + N u− ⟶ CH 3 − N u + Br− The decreasing order of the rate
of the above reaction with nucleophiles (Nu ) A to D is
[N u− = (A)PhO, (B)AcO, (C)H O, (D)CH 3O−]
[2006]
Options:

A. A > B > C > D

B. B > D > C > A

C. D > C > A > B

D. D > C > B > A

Answer: C

Solution:
Solution:
− −
CH 3COO− < C6H 5O < OH < OCH 3
− −
e s are delocalised Max . e density on O

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Question210

The alkene formed as a major product in the above elimination

reaction is
[2006]
Options:

A.
B.

C.

D. CH 2 = CH 2

Answer: D

Solution:
Solution:
Hofmann's rule : When theoretically more than one type of alkenes are possible in eliminations
reaction, the alkene containing least alkylated (least substituted) double bond is formed as major
product. Hence

Note: Therefore less sterically hundred β -hydrogen is removed.

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Question211
Which types of isomerism is shown by 2,3 -dichlorobutane?
[2005]
Options:

A. Structural
B. Geometric

C. Optical

D. Diastereo

Answer: C

Solution:
Solution:

CH 2 − CH 2, 2, 3 -Dichlorobutane exhibits optical isomerism due to the presence of two asymmetric

carbon atoms.

-------------------------------------------------------------------------------------------------

Question212
Due to the presence of an unpaired electron, free radicals are:
[2005]
Options:

A. cations

B. anions

C. chemically inactive

D. chemically reactive

Answer: D

Solution:

Solution:
Free radicals are electrically neutral, unstable and very reactive on account of the presence of odd
electrons.

-------------------------------------------------------------------------------------------------

Question213
The decreasing order of nucleophilicity among the nucleophiles is
(A) CH 2C − O−
||
O

(B) CH 3O−
(C) CN −

[2005]
Options:

A. (C) > (B) > (A) > (D)

B. (B) > (C) > (A) > (D)

C. (D) > (C) > (B) > (A)

D. (A) > (B) > (C) > (D)

Answer: A

Solution:
Solution:
In moving down a group, the basicity and nucleophilicity are inversely related, i.e. nucleophilicity
increases while basicity decreases. In going from left to right across a period, the basicity and
nucleophilicity are directly related. Both of the characteristics decrease as the electronegativity of
the atom bearing lone pair of electrons increases. If the nucleophilic centre of two or more species
is same, nucleophilicity parallels basicity, i.e. more basic the species, stronger is its nucleophilicity.
Hence based on the above facts, the correct order of nucleophilicity will be
− − −
CN − > CH 3O > CH 3COO > H 3CC6H 4SO3
(C) (B) (A) (D)

-------------------------------------------------------------------------------------------------

Question214
The IUPAC name of the compound is
[2004]
Options:

A. 3,3 -dimethyl −1 - cyclohexanol

B. 1, 1 -dimethyl-3-hydroxy cyclohexane

C. 3, 3-dimethyl-1-hydroxy cyclohexanc

D. 1, l-dimethyl-3-cyclohexanol

Answer: A

Solution:

Solution:

3 , 3-Dimethyl - 1 cyclohexanol

-------------------------------------------------------------------------------------------------

Question215
Which one of the following does not have sp2 hybridised carbon?
[2004]
Options:

A. Acetonitrile

B. Acetic acid

C. Acetone

D. Acetamide

Answer: A

Solution:
Solution:

-------------------------------------------------------------------------------------------------

Question216
Which of the following will have a mesoisomer also?
[2004]
Options:

A. 2,3 - Dichloropentane

B. 2,3 -Dichlorobutane

C. 2-Chlorobutane

D. 2-Hydroxypropanoic acid

Answer: B

Solution:
Solution:
Note: Compounds containing two similar chiral Catoms have plane of symmetry and can exist in
meso form too.

-------------------------------------------------------------------------------------------------

Question217
Amongst the following compounds, the optically active alkane
having lowest molecular mass is
[2004]
Options:
H
|
A. CH 3 − C −◁
|
C2H 5

CH3
|
B. CH 3 − CH 2 − C H − CH 3

C. CH 3 − CH 2 − CH 2 − CH 3

D. CH 3 − CH 2 − C ≡ CH

Answer: A

Solution:
Solution:
Only 2 -cylcopropylbutane has a chiral centre,
H
|
CH 3 − C −◁
|
C2H 5

-------------------------------------------------------------------------------------------------

Question218
Which of the following compounds is not chiral?
[2004]
Options:

A. 1 -chloro-2-methyl pentane

B. 2 -chloropentane

C. 1 -chloropentane

D. 3 -chloro-2-methyl pentane

Answer: C
Solution:
Solution:
1 -chloropentane is not chiral while others are chiral in nature
1 *2 3 4 5
(a) Cl CH 2 C H CH 2CH 2CH 3
1 *2 3 4 5
(b) H 3C C H CH 2CH 2CH 3
|
Cl
1 2 3 4 5
(c) Cl CH 2CH 2CH 2CH 2CH 3
1 2 *3 4 5
(d) CH 3CH C H CH 2CH 3

-------------------------------------------------------------------------------------------------

Question219
The reaction

is fastest when X is
[2005, 2004]
Options:

A. OCOR

B. OC2H 5

C. N H 2

D. Cl

Answer: D

Solution:
Solution:
−Cl is the best leaving group among the given options.

-------------------------------------------------------------------------------------------------

Question220
Consider the acidity of the carboxylic acids:
(1) PhCOOH
(2) o − N O2C6H 4COOH
(3) p - N O2C6H 4COOH
(4) m - N O2C6H 4COOH
Which of the following order is correct?
[2004]
Options:

A. 2 > 4 > 1 > 3

B. 2 > 4 > 3 > 1

C. 1 > 2 > 3 > 4

D. 2 > 3 > 4 > 1

Answer: D

Solution:
Solution:
In carboxylic acids, presence of electron withdrawing substituent e.g. −N O2 disperses the negative
charge of the anion and stabilises it and hence increases the acidity of the parent acid.
Further o -isomer will have higher acidity than corresponding m -and p -isomers due to ortho and
high inductive effect of −N O2 group. Since nitro group at p position has more pronounced electron
withdrawing than −N O2 group at m -position, hence the correct order is:

-------------------------------------------------------------------------------------------------

Question221
Which of the following is the strongest base?
[2004]
Options:

A.

B.

C.

D.

Answer: D

Solution:

Solution:
Lone pair of electrons present on the nitrogen of benzyl amine is not involved in resonance.

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Question222
The general formula CnH 2nO2 could be for open chain
[2003]
Options:

A. carboxylic acids
B. diols

C. dialdehydes

D. diketones

Answer: A

Solution:

Solution:
CnH 2nO2 is general formula for carboxylic acid

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Question223
The IUPAC name of CH 3COCH (CH 3)2 is
[2003]
Options:

A. 2 -methyl-3-butanone

B. 4 -methylisopropyl ketone

C. 3 -methyl-2-butanone

D. Isopropylmethyl ketone

Answer: C

Solution:

Solution:
-------------------------------------------------------------------------------------------------

Question224
Among the following four structures I to IV,

it is true that
[2003]
Options:

A. only I and II are chiral compounds

B. only III is a chiral compound

C. only II and IV are chiral compounds

D. all four are chiral compounds

Answer: A

Solution:
Solution:
-------------------------------------------------------------------------------------------------

Question225
In the anion H COO− the two carbon-oxygen bonds are found to be
of equal length. What is the reason for it?
[2003]
Options:

A. The C = O bond is weaker than the C − O bond

B. The anion H COO− has two resonating structures

C. The anion is obtained by removal of a proton from the acid molecule

D. Electronic orbitals of carbon atom are hybridised

Answer: B

Solution:
Solution:
H COO− exists in following resonating structures
⊖
O O
|| |
H − C − O− ⟷ H − C = O
Hence in it both the carbon oxygen bonds are found equal.

-------------------------------------------------------------------------------------------------

Question226
Which of the following compounds has wrong IUPAC name?
[2002]
Options:

A.
CH 3 − CH 2 − CH 2 − COO − CH 2CH 3 → ethyl butanoate

B.

CH 3 − CH − CH 2 − CH O → 3 -methyl-butanol
|
CH3

C.
CH 3 − CH − CH − CH 3 → 2-methyl-3-butanol
| |
OH CH3

D.
O
||
CH 3 − C H − C − CH 2 − CH 3 → 2 -methyl-3-pentanone
|
CH3

Answer: C

Solution:
Solution:
According to IUPAC convention alcohols are having more priority than saturated [Link] the
IUPAC name of compound shown above is:
3 - methyl butan -2- ol

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Question227
In which of the following species is the underlined carbon having sp3
hybridisation?
[2002]
Options:

A. CH 3COOH

B. CH 3xCH 2OH

C. CH 3xCOCH 3

D. CH 2 = xCH − CH 3

Answer: B

Solution:
Solution:
In molecules (a), (c) and (d), the carbon atom has a multiple bond, only (b) has sp3 hybridisation.

-------------------------------------------------------------------------------------------------

Question228
A similarity between optical and geometrical isomerism is that
[2002]
Options:

A. each forms equal number of isomers for a given compound

B. if in a compound one is present then so is the other

C. both are included in stereoisomerism

D. they have no similarity

Answer: C

Solution:

Solution:
Both differ in the arrangement of group in space, therefore grouped under sterio-isomerism.
-------------------------------------------------------------------------------------------------

Question229
Which of the following does not show geometrical isomerism?
[2002]
Options:

A. 1,2 - dichloro-1-pentene

B. 1,3 -dichloro- 2 -pentene

C. 1,1 -dichloro-1-pentene

D. 1,4 -dichloro- 2 -pentene

Answer: C

Solution:
Solution:
1 2 3 4 5
(a) Cl CH = CCH 2CH 2CH 3
|
Cl
Cl
1 2 3 | 4 5
(b) Cl CH 2CH = C − CH 2CH 3
1 2 3 4 5
(c) Cl 2C = CH CH 2CH 2CH 3
1 2 3 4 5
(d)Cl CH 2CH = CH CH CH 3
|
Cl

-------------------------------------------------------------------------------------------------

Question230
Racemic mixture is formed by mixing two
[2002]
Options:

A. isomeric compounds

B. chiral compounds

C. meso compounds
D. enantiomers with chiral carbon

Answer: D

Solution:
Solution:
A mixture of equal amount of two enantiomers is called a racemic mixture.

-------------------------------------------------------------------------------------------------

Question231
Following types of compounds (as I, II)

CH 3CH = CH CH 3 CH 3 C HOH
(I) |
CH2CH3
(II)

are studied in terms of isomerism in:

[2002]
Options:

A. chain isomerism

B. position isomerism

C. conformers

D. stereoisomerism

Answer: D

Solution:
Solution:
Stereoisomerism, isomers differ in the arrangement of groups in space. The two structures show
stereoisomerism. Structure I shows geometrical isomerism as it contains two different atoms or
groups H and CH 3 attached to each carbon containing double bond.

cis-butene trans-butene Structure II shows optical isomerism as it contains a chiral carbon

(attached to four different groups) atom.
-------------------------------------------------------------------------------------------------

Question232
Arrangement of (CH 3)3C−, (CH 3)2CH − CH 3 − CH 2 − when
attached to benzyl or an unsaturated group in increasing order of
inductive effect is
[2002]
Options:

A. (CH 3)3C− < (CH 3)2CH − < CH 3 − CH 2 −

B. CH 3 − CH 2 − < (CH 3)2CH − < (CH 3)3C−

C. (CH 3)2CH − 4(CH 3)3C− < CH 3 − CH 2 −

D. (CH 3)3C− < CH 3CH 2 − < (CH 3)2CH −

Answer: B

Solution:
Solution:
−CH 3 group has +I effect, as number of −CH 3 group increases, the inductive effect increases.
Therefore the correct order is
CH 3 − CH 2 − < (CH 3)2CH − < (CH 3)3C−

-------------------------------------------------------------------------------------------------

Question233
The functional group, which is found in amino acid is
[2002]
Options:
A. - COOH group

B. N H 2 group

C. −CH 3 group

D. both (a) and (b).

Answer: D

Solution:
Solution:
Amino acids contain −N H 2 and −COOH groups, e.g glycine H 2N CH 2COOH .

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