Haloalkanes and Haloarenes

Question1
Consider the following sequence of reactions:

11.25 mg of chlorobenzene will produce ___________×10 −1

mg of product B.

(Consider the reactions result in complete conversion.)

[Given molar mass of C, H, O, N and Cl as 12, 1, 16, 14 and 35.5 g mol −1

respectively]

JEE Main 2025 (Online) 28th January Morning Shift

Answer: 93

Solution:
 −3 −1 −3
11.25 × 10 x × 10 × 10
=
112.5 93
−1
x × 10 = 93 × 0.1

x = 93mg

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Question2

Consider the above sequence of reactions. 151 g of 2-bromopentane is made to react. Yield of major
product P is 80% whereas Q is 100%.

Mass of product Q obtained is________ g.

(Given molar mass in gmol −1

H : 1, C : 12, O : 16, Br : 80 )

JEE Main 2025 (Online) 2nd April Evening Shift

Answer: 184

Solution:
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Question3
Given below are two statements :

Statement I : CH 3 − O − CH 2 − Cl will undergo S N1 reaction though it is a primary halide.

Statement II :

will not undergo S N2 reaction very easily though it is a primary halide.

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

JEE Main 2025 (Online) 22nd January Morning Shift

Options:

A. Both Statement I and Statement II are incorrect

B. Both Statement I and Statement II are correct

C. Statement I is correct but Statement II is incorrect

D. Statement I is incorrect but Statement II is correct

Answer: B

Solution:
+

CH 3 − O − CH 2 − Cl will undergo S N1 mechanism because CH 3 − O− C H 2 is highly stable.

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

Question4

The maximum number of RBr producing 2-methylbutane by above sequence of reactions

is__________ . (Consider the structural isomers only)

JEE Main 2025 (Online) 22nd January Evening Shift

Options:

A. 5

B. 3

C. 4

D. 1

Answer: C

Solution:
Mg H2 O

−
−
RBr → RMgBr → R − H
dry Ether

Hence, RBr Can be

Total 4 Structural isomers.

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Question5
Propane molecule on chlorination under photochemical condition gives two di-chloro products, " x "
and " y ". Amongst " x " and " y ", " x " is an optically active molecule. How many tri-chloro
products (consider only structural isomers) will be obtained from " x " when it is further treated with
chlorine under the photochemical condition?

JEE Main 2025 (Online) 23rd January Morning Shift

Options:
A. 4

B. 2

C. 3

D. 5

Answer: C

Solution:

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Question6
The ascending order of relative rate of solvolysis of following compounds is :

JEE Main 2025 (Online) 23rd January Evening Shift

Options:

A. (C) < (D) < (B) < (A)

B. (D) < (A) < (B) < (C)

C. (D) < (B) < (A) < (C)

D. (C) < (B) < (A) < (D)

Answer: B

Solution:
Solvolysis or S N
1 ∝ stability of carboccation Stability order

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Question7
Identify the products [A] and [B], respectively in the following reaction:
JEE Main 2025 (Online) 23rd January Evening Shift
Options:

A.

B.

C.

D.

Answer: B

Solution:
A is phenol and B is para benzoquinone.

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Question8
Following are the four molecules "P", "Q", "R" and "S".
 Which one among the four molecules will react with H − Br (aq) at the fastest rate?

JEE Main 2025 (Online) 24th January Morning Shift

Options:

A. Q

B. S

C. P

D. R

Answer: A

Solution:

Addition of H − Br to alkene follows electrophilic addition mechanism. In the rate determining step a carbocation intermediate is formed. Among P, Q, R & S
(aq)

compound Q will form most stable carbocation intermediate since it is resonance stabilized.

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Question9
Given below are two statements:

Statement I: The conversion proceeds well in the less polar medium.

−
HO
(−)
CH 3 − CH 2 − CH 2 − CH 2 − Cl
− → CH 3 − CH 2 − CH 2 − CH 2 − OH + Cl

Statement II: The conversion proceeds well in the more polar medium.

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

JEE Main 2025 (Online) 24th January Morning 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: D

Solution:

Transition state (less charge density)

⇒ This reaction will proceed faster in less polar medium which will not increase the activation energy value.

Transition state (Higher charge density)

⇒ This reaction will proceed faster in more polar medium which will decrease the activation energy value.

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Question10
The structure of the major product formed in the following reaction is :

JEE Main 2025 (Online) 24th January Evening Shift

Options:

A.
B.

C.

D.

Answer: B
 Solution:

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Question11
The products A and B in the following reactions, respectively are
Ag−NO 2 AgCN

−
A ⟷ CH 3 − CH 2 − CH 2 − Br → B

JEE Main 2025 (Online) 28th January Morning Shift

Options:

A. CH 3 − CH 2 − CH 2 − ONO, CH 3 − CH 2 − CH 2 − CN

B. CH 3 − CH 2 − CH 2 − NO 2 , CH 3 − CH 2 − CH 2 − CN

C. CH 3 − CH 2 − CH 2 − ONO, CH 3 − CH 2 − CH 2 − NC

D. CH 3 − CH 2 − CH 2 − NO 2 , CH 3 − CH 2 − CH 2 − NC

Answer: D

Solution:
Ag−NO 2 AgCN

CH 3 − CH 2 − CH 2 − NO 2 ⟶ CH 3 − CH 2 − CH 2 − Br ⟶ CH 3 − CH 2 − CH 2 − NC
(A) (B)

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Question12
The major product of the following reaction is:

JEE Main 2025 (Online) 28th January Evening Shift

Options:

A.
6-Phenylhepta-3,5-diene

B.
6-Phenylhepta-2,4-diene

C.
2-Phenylhepta-2,4-diene

D.
2-Phenylhepta-2,5-diene

Answer: C

Solution:

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Question13
Which among the following halides will generate the most stable carbocation in the nucleophilic
substitution reaction?

JEE Main 2025 (Online) 29th January Evening Shift

Options:

A.

B.

C.
D.

Answer: B

Solution:

A nucleophilic substitution reaction is a chemical reaction in which an electron rich molecule (nucleophile) replaces a functional group in an electron deficient
molecule (electrophile). Carbocation formation occurs in SN mechanism (unimolecular nucleophilic substitution).
1

Carbocation is formed in the first step when the bond between carbon and the leaving group breaks. The nucleophile attack on the carbocation occurs in the second
step.

The general stability order of carbocation is

Tertiory > Secondary > Primary

The stability order including allyl carbocation, benzyl carbocation, phenyl carbocation and triphenyl methyl ((P h) 3
C
+
) carbocation is

Phenyl < Allyl < Benzyl < Triphenyl methyl

(1)

Carbocation formed from this halide is

Allylic carbocation stability is due to the resonance delocalization of the positive change across the adjacent double bond.

(2)

Stable due to the delocalization of positive change across all three phenyl rings.

(3)

Benzyl carbocation stability is because of the positive charge delocalization across the aromatic ring. So, it is mole stable than allylic carbocation but less stable
than Ph C+ carbocation.
3

(4)

Delocalization is possible for the adjacent double bond. So, most stable carbocation is
The answer is option (2)

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Question14
In the following series of reactions identify the major products A&B respectively

JEE Main 2025 (Online) 3rd April Evening Shift

Options:

A.
B.

C.

D.

Answer: B

Solution:

Both reactions are electrophilic substitution reaction, I st is sulphonation and II nd is halogenation :

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Question15
Given below are two statements :

Statement (I) : Alcohols are formed when alkyl chlorides are treated with aqueous potassium
hydroxide by elimination reaction.

Statement (II) : In alcoholic potassium hydroxide, alkyl chlorides form alkenes by abstracting the
hydrogen from the β-carbon.
In the light of the above statements, choose the most appropriate answer from the options given below
:

JEE Main 2025 (Online) 4th April Evening Shift

Options:

A. Both Statement I and Statement II are incorrect

B. Both Statement I and Statement II are correct

C. Statement I is incorrect but Statement II is correct

D. Statement I is correct but Statement II is incorrect

Answer: C

Solution:

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Question16
Consider the following molecule(X).

The major product formed when the given molecule (X) is treated with HBr(1eq) is :

JEE Main 2025 (Online) 4th April Evening Shift

Options:

A.
B.

C.

D.
 Answer: A

Solution:

Among the given options, the major product decided by stability of carbocation formed in
intermediate.

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Question17
Which one of the following reactions will not lead to the desired ether formation in major proportion?

JEE Main 2025 (Online) 8th April Evening Shift

Options:

A.

+
–
B. iso-
BuO Na +sec − BuBr ⟶ Bu − O− sec- iso -Bu

C.
 +
–
t
D. t
BuO Na +EtBr ⟶ Bu − O − Et

Answer: B

Solution:

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Question18
Choose the correct set of reagents for the following conversion.

JEE Main 2025 (Online) 8th April Evening Shift

Options:

A. Cl 2/ anhy ⋅AlCl 3; Br 2 /Fe; alc. KOH

B. Cl 2 /Fe; Br 2 / anhy. AlCl ; aq. KOH

3

C. Br 2 /Fe; Cl 2 , Δ ; alc. KOH

D. Br 2/ anhy. AlCl 3; Cl 2 , Δ; aq. KOH

Answer: C

Solution:
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Question19

'P' is

JEE Main 2025 (Online) 8th April Evening Shift

Options:

A.

B.

C.
D.

Answer: C

Solution:
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Question20
The correct statement regarding nucleophilic substitution reaction in a chiral alkyl halide is ;
[27-Jan-2024 Shift 1]
Options:

A. Retention occurs in SN1 reaction and inversion occurs in SN2 reaction.

B. Racemisation occurs in SN1 reaction and retention occurs in SN2 reaction.

C. Racemisation occurs in both SN1 and SN2 reactions.

D. Racemisation occurs in SN 1 reaction and inversion occurs in SN2 reaction.

Answer: D

Solution:

Solution:

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Question21
Identify B formed in the reaction.
excess NH3 NaOH
Cl − (CH2)4 − Cl ────────▶ A ────────▶ B + H2O + NaCl
[27-Jan-2024 Shift 2]
Options:

A.

B. H2N − (CH2)4 − NH2

+ +
C. ClNH3 − (CH2)4 − NH3Cl−

D.
Answer: B

Solution:

Solution:

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Question22
Which among the following halide/s will not show SN1 reaction:
(A) H2C = CH − CH2 Cl
(B) CH3 − CH = CH − Cl

Choose the most appropriate answer from the options given below:
[27-Jan-2024 Shift 2]

Options:

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

B. (A) and (B) only

C. (B) and (C) only

D. (B) only

Answer: D

Solution:

Solution:

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Question23

Given below are two statements : one is labelled as Assertion A and the other is labelled as Reason R :
Assertion A : Aryl halides cannot be prepared by replacement of hydroxyl group of phenol by halogen
atom.
Reason R : Phenols react with halogen acids violently. In the light of the above statements, choose the
most appropriate from the options given below:
[29-Jan-2024 Shift 1]
Options:

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

B. A is false but R is true

C. A is true but R is false

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

Answer: C

Solution:

Solution:

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Question24
Alkyl halide is converted into alkyl isocyanide by reaction with
[29-Jan-2024 Shift 2]
Options:

A. NaCN

B. NH4 CN

C. KCN

D. AgCN

Answer: D

Solution:

Solution:

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Question25

The final product A, formed in the following multistep reaction sequence is:

[30-Jan-2024 Shift 1]
Options:

A.

B.

C.

D.

Answer: B

Solution:

Solution:

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Question26
Given below are two statements:
Statement - I: High concentration of strong nucleophilic reagent with secondary alkyl halides which
do not have bulky substituents will follow SN2 mechanism.
Statement - II: A secondary alkyl halide when treated with a large excess of ethanol follows SN1
mechanism.
In the the light of the above statements, choose the most appropriate from the questions given below:
[30-Jan-2024 Shift 2]
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: D

Solution:

Solution:

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Question27
2-chlorobutane +Cl2 → C4H8Cl2 (isomers)
Total number of optically active isomers shown by C4H8Cl2, obtained in the above reaction is____
[30-Jan-2024 Shift 2]

Answer: 6

Solution:

Solution:

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Question28

The total number of hydrogen atoms in product A and product B is_____

[31-Jan-2024 Shift 1]

Answer: 10

Solution:

Solution:

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Question29
The correct order of reactivity in electrophilic substitution reaction of the following compounds is :

[31-Jan-2024 Shift 2]
Options:

A. B > C > A > D

B. D > C > B > A

C. A > B > C > D

D. B > A > C > D

Answer: D

Solution:

Solution:

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Question30
Given below are two statements : one is labelled as Assertion (A) and the other is labelled as Reason
(R).
Assertion (A) : Haloalkanes react with KCN to form alkyl cyanides as a main product while with
AgCN form isocyanide as the main product.
Reason (R) : KCN and AgCN both are highly ionic compounds.
In the light of the above statement, choose the most appropriate answer from the options given below:
[1-Feb-2024 Shift 1]
Options:

A. (A) is correct but (R) is not correct

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

C. (A) is not correct but (R) is correct

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

Answer: A

Solution:

Solution:

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Question31
Identify A and B in the following sequence of reaction

[1-Feb-2024 Shift 1]
Options:

A.

B.
C.

D.

Answer: B

Solution:
Solution:

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Question32
Acid D formed in above reaction is :

[1-Feb-2024 Shift 2]
Options:

A. Gluconic acid

B. Succinic acid

C. Oxalic acid

D. Malonic acid

Answer: B

Solution:

Solution:

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Question33
Assertion A : Hydrolysis of an alkyl chloride is a slow reaction but in the presence of NaI, the rate of
the hydrolysis increases.
Reason R: I−is a good nucleophile as well as a good leaving group.
In the light of the above statements, choose the correct answer from the options given below.
[24-Jan-2023 Shift 1]
Options:

A. A is false but R is true

B. A is true but R is false

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

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

Answer: C

Solution:

Solution:
The rate of hydrolysis of alkyl chloride improves because of better Nucleophilicity of I−.

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Question34
Number of moles of AgCl formed in the following reaction is

[24-Jan-2023 Shift 1]

Answer: 2

Solution:
Solution:
Benzylic and tertiary carbocations are stable.

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Question35
Maximum number of isomeric monochloro derivatives which can be obtained from
2,2,5,5tetramethylhexane by chlorination is
[24-Jan-2023 Shift 2]

Answer: 3

Solution:
Solution:
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Question36
Decreasing order towards SN 1 reaction for the following compounds is:

[30-Jan-2023 Shift 2]
Options:

A. a > c > d > b

B. a > b > c > d

C. b > d > c > a

D. d > b > c > a

Answer: C

Solution:

Solution:
The rate of SN 1 reaction depends upon stability of carbocation which follows the order

(b) > (d) > (c) > (a)

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Question37
The correct order of melting point of dichlorobenzenes is
[31-Jan-2023 Shift 1]
Options:

A.
B.

C.

D.

Answer: D

Solution:
Solution:

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Question38
Identify the incorrect option from the following:
[1-Feb-2023 Shift 1]
Options:
A.

B.

C.

D.

Answer: B

Solution:

Solution:
In alcoholic KOH, elimination reaction takes place.

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Question39
For the reaction:
Acetone
RCH2 Br + I−──────▶ RCH2I + Br−
major

The correct statement is :

[6-Apr-2023 shift 1]
Options:

A. The transition state formed in the above reaction is less polar than the localised anion.

B. The reaction can occur in acetic acid also.

C. The solvent used in the reaction solvates the ions formed in rate determining step.

D. Br−can act as competing nucleophile.

Answer: A

Solution:
Solution:
This is finkelstein reaction

Clearly, the transition state is less polar than free anions. Br−and I−
Acetic acid is protic which does not support SN2 Acetone does not solvate anion Br−gets precipitated and hence can not compete with I−
So only (1)is correct

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Question40
Choose the halogen which is most reactive towards SN1 reaction in the given compounds (A, B, C, &
D)

[8-Apr-2023 shift 1]
Options:

A. A − Br(a); B − I(a); C − Br(b); D − Br(a)

B. A − Br(b); B − I(a); C − Br(a); D − Br(a)

C. A − Br(b); B − I(b); C − Br(b); D − Br(b)

D. A − Br(a); B − I(a); C − Br(a); D − Br(a)

Answer: A

Solution:

Solution:
(A)

→ Because formed intermediate carbocation formed by Br(a) get stabilised by conjugation with phenyl
(B)
→ Because the intermediate carbocation formed by I(a) become more stable by conjugation
(C)

→ Because, we con't remove Br(a) from bridge head carbon (Bredt's rule)
(D)

→ Because, formed intermediate by Br(a), 3∘ carbocation is more stable (stability of carbocation 3∘ > 2∘ > 1∘ )

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Question41
The correct order of reactivity of following haloarenes towards nucleophilic substitution with aqueous
NaOH is

Choose the correct answer from the options given below:

[8-Apr-2023 shift 2]
Options:

A. D > B > A > C

B. A > B > D > C

C. C > A > D > B

D. D > C > B > A

Answer: A

Solution:
Solution:
1
Rate α EWG α
EDG
NO2 → − Meffect
OMe → +M effect

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Question42
Choose the correct answer from the options given below:
[10-Apr-2023 shift 1]
Options:

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

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

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

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

Answer: D

Solution:

Solution:

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Question43
The major product ' P ' formed in the given reaction is:

[10-Apr-2023 shift 2]

Options:

A.

B.

C.

D.

Answer: A

Solution:

Solution:
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Question44
2-Methyl propyl bromide reacts with C2H5O−and gives ' A ' whereas on reaction with C2H5 OH it
gives ' B '. The mechanism followed in these reactions and the products ' A ' and ' B ' respectively are
:
[13-Apr-2023 shift 1]
Options:

A. SN1, A = tert-butyl ethyl ether; SN1, B = 2-butyl ethyl ether

B. SN2, A = 2-butyl ethyl ether; SN2, B = iso-butyl ethyl ether

C. SN, A = iso-butyl ethyl ether; SN1, B = tert-butyl ethyl ether

D. SN1, A = tert-butyl ethyl ether; SN2, B = iso-butyl ethyl ether

Answer: C

Solution:
Solution:

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Question45
Match List I with List II
I - Bromopropane is reacted with reagents in List I to give product in List II
Choose the correct answer from the options given below :
[13-Apr-2023 shift 2]
Options:

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

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

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

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

Answer: D

Solution:

Solution:
CH3 − CH2 − CH2 − Br + KOH(Alc) → CH3 − CH = CH2
(Allene)
CH3 − CH2 − CH2 − Br + KCN(Alc) → CH3 − CH2 − CH2 − CN
(Nitrle)
CH3 − CH2 − CH2 − Br + AgNO + CH3 − CH2 − CH2 − NO2 + AgBr↓
(Niroallkane)
CH3 − CH2 − CH2 − Br + CH3 − COOAg → CH3 − COO − CH2 − CH2 − CH3 + AgBr↓
(Ester)

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Question46
The major product in the Friedel-Craft acylation of chlorobenzene is :
[15-Apr-2023 shift 1]
Options:

A.

B.

C.
D.

Answer: D

Solution:
Solution:

Chlorine is ortho/para directing, para is major.

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Question47

[24-Jun-2022-Shift-1]
Options:

A.

B.
C.

D.

Answer: D

Solution:
Solution:

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Question48

Consider the above reaction. The number of pi electrons present in the product ' P ' is_____
[24-Jun-2022-Shift-2]
Answer: 2

Solution:

Solution:

The given reaction undergoes nucleophilic substitution by SN2 mechanism at room temperature
∴ No. of π electrons present in P = 2

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Question49
The major product in the reaction

[25-Jun-2022-Shift-1]
Options:

A. t-Butyl ethyl ether

B. 2,2-Dimethyl butane

C. 2-Methyl pent-1-ene

D. 2-Methyl prop-1-ene

Answer: D

Solution:
Solution:
We have been given a bulky base, hence elimination will take place & not substitution.

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Question50
In the given reaction 'A' can be

[25-Jun-2022-Shift-2]
Options:
A. benzyl bromide

B. bromobenzene

C. cyclohexyl bromide

D. methyl bromide

Answer: B

Solution:

Solution:

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Question51
The major product of the following reaction is :

[27-Jun-2022-Shift-1]
Options:

A.

B.
C.

D.

Answer: A

Solution:

Solution:

It is bimolecular nucleophilic substitution (SN2) which occur at benzylic carbon by inversion in configuration. This reaction cannot undergo
substitution at benzene ring.

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Question52
The major product (P) in the reaction

[28-Jun-2022-Shift-1]
Options:

A.

B.

C.

D.

Answer: C

Solution:

Solution:

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Question53
The correct structure of product 'A' formed in the following reaction.
O
||
NaOD −(Ph is − C6H5)
PhCHO + PH . CHO ───────▶ A + Ph − C − O
in D2O

is
[28-Jun-2022-Shift-1]
Options:

A.

B.

C.

D.

Answer: A

Solution:

Solution:

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Question54
In the above reaction 'A' is
[28-Jun-2022-Shift-2]
Options:

A.

B.

C.

D.

Answer: C

Solution:

Solution:

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Question55
The stable carbocation formed in the above reaction is

[29-Jun-2022-Shift-2]
Options:
⊕
A. CH3CH2CH2

⊕
B. CH3CH2

⊕
C. CH3 − CH − CH3

D.

Answer: C

Solution:

Solution:
+
Initially CH3 − CH2 − CH2 is formed. On rearrangement CH3 − CH − CH3 stable carbocation is formed.

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Question56
Two isomers (A) and (B) with Molar mass 184g ∕ mol and elemental composition C, 52.2%; H, 4.9%
and Br 42.9% gave benzoic acid and p-bromobenzoic acid, respectively on oxidation with KMnO4.
Isomer 'A' is optically active and gives a pale yellow precipitate when warmed with alcoholic AgNO3.
Isomer ' A ' and ' B ' are, respectively
[29-Jun-2022-Shift-2]
Options:

A.

B.

C.
D.

Answer: C

Solution:

Solution:

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Question57

Considering the above reactions, the compound ' A′ and compound ' B ' respectively are :
[29-Jul-2022-Shift-1]
Options:

A.

B.

C.
D.

Answer: C

Solution:

Solution:

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Question58
Compound 'A' undergoes following sequence of reactions to give compound ' B '.
The correct structure and chirality of compound ' B ' is
[where Et is −C2H5 ]

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

A.

B.

C.

D.
Answer: C

Solution:

Solution:

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Question59
The product formed in the first step of the reaction of

with excess M g ∕ E t2O (E t = C2H 5) text

[24 Feb 2021 Shift 1]
Options:

A.

B.

C.

D.

Answer: D

Solution:

Solution:
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Question60
The major product of the following reaction is

[31 Aug 2021 Shift 2]

Options:

A.

B.

C.

D.

Answer: D

Solution:

Solution:
In the given reaction E2 elimination reaction takes place in which two substituents are removed from a molecule to form double bond (alkene).

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Question61
The correct order of reactivity of the given chlorides with acetate in acetic acid is
[31 Aug 2021 Shift 1]
Options:

A.
B.

C.

D.

Answer: A

Solution:

Solution:

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Question62
The major product (A) formed in the reaction given below is

[27 Aug 2021 Shift 2]

Options:

A.

B.

C.

D.

Answer: B

Solution:

Solution:
On reaction of haloalkane with methoxide ion, alkene is formed.

⊖
● OCH3 will act as a base due to its small size and high electron density and therefore, abstracts proton to form double bond which is in conjugation
with aromatic ring.
⊖
⊖
● The OCH3 when acts as nucleophile undergoes nucleophilic substitution and replaces Br to form ether, which is a minor product.
So, option (b) is correct.

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Question63
In the following sequence of reactions the P is

[27 Aug 2021 Shift 1]

Options:

A.

B.

C.

D.

Answer: A

Solution:

Solution:
In the first step, Grignard reagent is obtained. In the second step, acid-base reaction occurs. Due to presence of an acidic hydrogen in alcohol,
neutralisation reaction takes place that produces alkane and water.
The reaction is

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

Question64
The major product formed in the following reaction is

[26 Aug 2021 Shift 1]

Options:
A.

B.

C.

D.

Answer: A

Solution:

Solution:

2 - methylbut - 1, 3 - diene 1 - bromo 3 - methylbut - 2 - ene

This addition is known as 1, 4 - addition.
Mechanism This reaction can undergoes two pathways Path A

Out of the two intermediates formed in two paths, the path B intermediate is more stable as it has more stable carbocation. So, major product will
be formed because of path B.

1, 2 -addition product is formed at low temperature and will be less stable as double bond is less substituted. 1, 4 - addition is thermodynamically
stable product as double bond is more substituted. As diene is in excess and HBr is limited in reaction, so diene cannot be formed.
So option (b) is incorrect.

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

Question65
Excess of isobutane on reaction with Br2 in presence of light at 125°C gives which one of the following,
as the major product?
[26 Aug 2021 Shift 1]
Options:
A.

B.

C.

D.

Answer: D

Solution:

Solution:
Excess of isobutane reacts with Br2 in presence of light at 125°C gives 1 - bromo - 2 - methyl propane as major product.

Mechanism The above reaction is halogenation of alkane via free radical substitution reaction.
Initiation step
hv
Br2→Br● + Br●
Propagation step

Reactivity order of abstraction of H towards bromination of alkane as more stable alkyl free radical is formed as follows
3°H > 2°H > 1°H
Since, isobutane is in excess, so dibromination of single isobutane is not favourable reaction. This make (a) and (b) incorrect options.

-------------------------------------------------------------------------------------------------
Question66

Consider the given reaction, the product A is

[26 Aug 2021 Shift 2]
Options:

A.

B.

C.

D.

Answer: C

Solution:

Solution:

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

Question67
Among the following compounds I - IV, which one forms a yellow precipitate on reacting sequentially
with
(i) NaOH
(ii) dil. HNO3
(iii) AgNO3 ?

[26 Aug 2021 Shift 1]

Options:

A. II

B. IV

C. I

D. III

Answer: B

Solution:
Solution:

This compound halide will only give yellow ppt. as benzyl carbocation formed shown below is highly stable by conjugation.

Other compounds halide cannot be removed because their corresponding carbocation is highly unstable.

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

Question68
In the following sequence of reactions,
H + ∕ H 2O
KIO
C 3 H6 ─────▶A────▶B +C
dil. KOH

The compounds B and C respectively are

[1 Sep 2021 Shift 2]
Options:

A. Cl3 COOK, HCOOH

B. Cl3 COOK, CH3I

C. CH3, HCOOK

D. CHI3, CH3 COOK

Answer: D
Solution:

Solution:
Propene (C3H6) undergoes acidic hydrolysis to give A which is 2° alcohol. This alcohol undergoes iodoform reaction in presence of KIO and dil.
KOH to give iodoform along with potassium salt of carboxylic acid.
This reaction is known as iodoform test.

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

Question69
The decreasing order of reactivity towards dehydrohalogenation (E 1) reaction of the following
compounds is:

[Jan. 08,2020 (I)]

Options:

A. D > B > C > A

B. B > D > A > C

C. B > D > C > A

D. B > A > D > C

Answer: A

Solution:

Solution:
E 1 reaction proceeds via carbocation formation, therefore greater the stability of carbocation, faster will be the E 1 reaction. Thus correct decreasing
order of the given halides towards dehydrohalogenation by E 1 is
D>B>C>A

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

Question70
Consider the following reactions:
conc. H 2SO4

(1) (CH 3)3CCH (OH )CH 3───────▶

alc KOH
(2) (CH 3)2CH CH (Br)CH 3───────▶
(CH 3)3O−K
⊕

(3) (CH3)2CH CH (Br)CH 3 ───────▶

∆
(4) −CH 2 − CH O─────▶
Which of these reaction(s) will not produce Saytzeff product?
[Jan. 07,2020 (I)]
Options:
A. (1), (3) and (4)

B. (4) only

C. (3) only

D. (2) and (4)

Answer: C

Solution:

Solution:
CH3
conc. H2SO4 |
(A) (CH3)3 CCH(OH) CH3 ───────▶ CH3 − C = C − CH3
|
CH3
CH3
alc . KOH |
(B) (CH3)2 CHCH(Br) CH3 ──────▶ CH3 − C = CH − CH3
CH3
1 − BuO−K+ |
(C) (CH3)2 CHCH(Br) CH3 ───────▶ CH3 − CH − CH = CH2
Due to bulky nature of tertiary butoxide, the least hindered hydrogen is eliminated. Therefore, Hoffiman product is formed.
CH3
∆ |
(D) (CH3)2 C − CH2 − CHO ────▶ CH3 − C = CH − CHO
|
OH

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Question71
In the following reaction sequence, structures of A and B, respectively will be:

[Jan. 07, 2020 (II)]

Options:

A.

B.

C.

D.
Answer: C

Solution:

Solution:

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

Question72
The decreasing order of reactivity of the following organic molecules towards AgNO3 , solution is:

(C) CH3CHCH3
|
CI

(D)CH3CHCH2NO2
|
CI
[Sep. 04,2020 (I)]

Options:

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

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

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

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

Answer: D

Solution:

Solution:
Given reaction is SN 1 reaction. In SN 1 reaction Rate of reaction ∝ Stability of C+

−CI ⊕
(C) CH3 − CH − CH3─────▶CH3 − CH − CH3
| (2°)
CI (iii)
−CI ⊕
(D) CH3 − CH − CH2 − NO2─────▶CH3 − CH − CH2 − NO2
| (iv)
(−1)
CI
+
Stability of C : ii > i > iii > iv
Reactivity order :B > A > C > D

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

Question73
Which of the following compounds will form the precipitate with aq. AgN O3 solution most readily?
[Sep. 04,2020 (II)]
Options:

A.

B.

C.

D.

Answer: D

Solution:
Solution:
Ease of precipitation of AgBr depends upon the rate of formation of carbocation.

Most stable carbocation due to +R effect of N .

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

Question74
Among the following compounds, which one has the shortest C - Cl bond?
[Sep. 04,2020 (II)]
Options:

A.

B.

C. H3C − CI

D.

Answer: D

Solution:

Solution:
Due to conjugation of lonepair of Cl with π bond, partial double bond character decreases bond length that's why compound (d) has shortest C − Cl
bond length.

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

Question75
The mechanism of SN1 reaction is given as:

A student writes general characteristics based on the given mechanism as:

(1) The reaction is favoured by weak nucleophiles.
⊕
(2) R would be easily formed if the substituents are bulky.
(3) The reaction is accompanied byracemization.
(4) The reaction is favoured by non-polar solvents. Which observations are correct?
[Sep. 03,2020 (I)]
Options:

A. (1) and (2)

B. (1) and (3)

C. (1), (2) and (3)

D. (2) and (4)

Answer: C

Solution:

Solution:
Above reaction is SN 1 reaction as it proceeds via formation of carbocation. Polar protic solvent is more suitable for SN 1 and so racemisation takes
place.

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

Question76
The total number of monohalogenated organic products in the following (including stereoisomers)
(i)H ∕ Ni∕∆ 2
reaction is _________. A ────────▶
(Simplest optically active alkene) (ii)X2 ∕∆

[NV, Sep. 03,2020 (I)]

Answer: 8

Solution:

Solution:

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

Question77
The major product in the following reaction is:

[Sep. 03,2020 (II)]

Options:

A.

B.

C.

D.

Answer: C

Solution:

Solution:

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

Question78
Which of the following compounds will show retention in configuration on nucleophic substitution by
OH− ion?
[Sep. 02,2020 (I)]
Options:
Br
|
A. CH3 − C − H
|
C6H13

B. CH3 − CH − Br
|
C6H 5

C. CH3 − CH − Br
|
CH3
D. CH3 − CH − CH2 Br
|
C2H 5

Answer: D

Solution:

Solution:
OH
S NI + 1.2H− shift + |
CH3 − CH − CH2 Br ─────▶ CH3 − CH − CH2─────▶CH3 − C − CH3─────▶CH3 − C − CH3
| | | |
C2H 5 C2H 5 C2H 5 C2H 5

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

Question79
The major product obtained from E 2 -elimination of 3-bromo-2-fluoropentane is:
[Sep. 02,2020 (II)]
Options:
Br
|
A. CH3CH2 − CH − CH = CH2

B. CH3CH2 CH = C − F
|
CH3

F
|
C. CH3 − CH = CH − CH − CH 3

Br
|
D. CH3 − CH2 − C − CH = CH3

Answer: B

Solution:

Solution:

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

Question80
Consider the reaction sequence given below:

Which of the following statements is true?

[Sep. 02,2020 (II)]
Options:

⊖ ⊖
A. Changing the base from OH to OR will have no effect on reaction (2).
B. Changing the concentration of base will have no effect on reaction (1).

C. Doubling the concentration of base will double the rate of both the reactions.

D. Changing the concentration of base will have no effect on reaction (2).

Answer: B

Solution:

Solution:
First reaction is SN 1 in which rate does not depend on conc. of nucleophile but depends on reactant conc. Second reaction is E 2 reaction in which
rate depends on conc. of base as well as reactant conc. Therefore, changing in the concentration of base will have no effect on rate of reaction ( 1
).

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

Question81
The decreasing order of reactivity of the following compounds towards nucleophilic substitution (SN 2)
is :

[Sep. 03,2020 (II)]

Options:

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

B. (I I ) > (I I I ) > (I V ) > (T )

C. (I I I ) > (I I ) > (I V ) > (I )

D. (I V ) > (I I ) > (I I I ) > (I )

Answer: B

Solution:

Solution:
SN 2 reactions depend upon −I and −M effect on substrate. On increasing −I and −M effect, rate of SN 2 reaction will increase.

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

Question82
(i) KOH atc
The major product of the following reaction is: CH3CH2CH − CH2 ───────▶
(ii) Na NH2 in liq . NH2
| |
Br Br

[Jan. 12,2019(II)]
Options:

A. CH3 CH = C = CH2
B. CH3CH2CH − CH2
| |
NH2 NH2

C. CH3 CH = CHCH2NH2

D. CH3CH2C ≡ CH

Answer: D

Solution:

Solution:

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

Question83
The major product of the following reaction is:

[Jan. 10,2019(I)]
Options:

A.

B.

C.

D.

Answer: A

Solution:

Solution:
Dehydrohalogenation ( β -elimination) occurs as:

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

Question84
Which hydrogen in compound (E) is easily replaceable during bromination reaction in presence of
light?
CH3 − CH2 − CH = CH2
δ γ β α

[Jan. 10,2019(I)]
Options:

A. α - hydrogen

B. γ - hydrogen

C. δ - hydrogen

D. β - hydrogen

Answer: B

Solution:

Solution:
Allylic H is easily replaced due to the greater stability of allylic free radical.
hv
CH3 − CH2 − CH = CH2 + Br2────▶CH3 − CH − CH = CH2
|
Br

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

Question85
The major product of the following reaction is:

[Jan. 9, 2019(I)]
Options:

A.

B.

C.
D.

Answer: A

Solution:

Solution:

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

Question86
The major product of the following reaction is:

[Jan. 10,2019(II)]
Options:

A.

B.

C.

D.

Answer: D
Solution:

Solution:
Sodium borohydride is a selective reducing agent. It reduces carbonyl group to alcoholic group, N methylimino group (M eN = CH −) to 2∘ amines,
but does not reduce an isolated carbon-carbon double bond. Reaction involved:

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

Question87
An 'Assertion' and a 'Reason' are given below. Choose the correct answer from the following options:
Assertion (A): Vinyl halides do not undergo nucleophilic substitution easily. Reason (R): Even though
the intermediate carbocation is stabilized by loosely held π -clectrons, the cleavage is difficult because
of strong bonding.
[April 12, 2019 (II)]
Options:

A. Both (A) and (R) are wrong statements.

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

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

D. (A) is a correct statement but (R) is a wrong statement.

Answer: D

Solution:

Solution:

Due to partial double bond character of C -halogen bond, halogen leaves with great difficulty, if at all it does. Hence, vinyl halides do not undergo
nucleophilic substitution easily. So, assertion is correct.

Intermediate carbocation is not stabilised by loosely heldπ electrons because empty orbital, being at 90∘ , cannot overlap with p -orbitals of π bond.
So, reason is wrong.

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

Question88
Increasing rate of SN 1 reaction in the following compounds is :

[April 10, 2019 (I)]

Options:

A. (A) < (B) < (C) < (D)

B. (B) < (A) < (C) < (D)

C. (B) < (A) < (D) < (B)

D. (A) < (B) < (D) < (C)

Answer: B

Solution:

Solution:
The rate of SN 1 is decided by the stability of carbocation formed in the rate determining step.

Carbocation(D) is most stable due to +R effect of −OCH 3 group; (C) is stabilised by +I and +H effects of the CH 3 group; (B) is least stable due to −
I effect of MeO group and (A) is stabilised by −CH 3 as well as phenyl group. So increasing order of rate of SN 1 is
(B) < (A) < (C) < (D)

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

Question89
CH3 CH3 OH
|
The major product of the following reaction is CH3 − C = CHCH3─────▶
|
H |
Br

[April 10, 2019 (I)]

Options:
CH3
|
A. CH3 − C = CH = CH2
|
H

CH3
|
B. CH3 − C = CHCH3

CH3
|
C. CH3 − C = CH2 CH3
|
OCH3

CH3
|
D. CH3 − C = CHCH3
| |
H OCH3
Answer: C

Solution:

Solution:

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

Question90
The major product ' Y ' in the following reaction is:

[April 10, 2019 (II)]

Options:

A.

B.

C.

D.

Answer: C

Solution:

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

Question91
Increasing order of reactivity of the following compounds for SN 1 substitution is:

[April 9, 2019 (II)]

Options:

A. (B) < (C) < (D) < (A)

B. (B) < (C) < (A) < (D)

C. (B) < (A) < (D) < (C)

D. (A) < (B) < (D) < (C)

Answer: C

Solution:

Solution:
In SN 1 reaction carbocation acts as an intermediate.

Carbocation produced by (C) is more stable than carbocation produced by (D) due to +I effect of −OCH 3 group.
Further in (A) there is formation of tertiary carbocation after rearrangement while (B) is primary carbocation.

So, the correct order is (C) > (D) > (A) > (B)

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

Question92
Which of the following potential energy (PE) diagrams represents the SN I reaction?
[April 9, 2019 (II)]
Options:
A.

B.

C.

D.

Answer: A

Solution:

Solution:
The SN 1 reaction energy diagram illustrates the dominant part of the substrate with respect to the reaction rate. The rate determining step is the
formation of the intermediate carbocation.

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

Question93
The major product of the following reaction is:

[April 8,2019 (1)]

Options:

A.
B.

C.

D.

Answer: D

Solution:

Solution:

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

Question94
The major product of the following reaction is:

[2018]
Options:

A.
B.

C.

D.

Answer: B

Solution:

Solution:
CH 3O− is a strong base and strong nucleophile, so favourable condition is SN 2 ∕ E 2.
The given alkyl halide is 2∘ and β carbons are 4∘ and 2∘, so sufficiently hindered, thus E 2 dominates over SN 2

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

Question95
The major product of the following reaction is:

[Online April 16,2018]

Options:

A.

B.
C.

D.

Answer: C

Solution:

Solution:

Inversion takes place at the carbon containing bromine atom.

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

Question96
Which of the following will most readily give the dehydrohalogenation product?
[Online April 15,2018(I)]
Options:

A.

B.

C.

D.
Answer: A

Solution:

Solution:
Here dehydrohalogenation goes by E 1cB and most stable carbanion formation is favoured in (a).

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

Question97
The major product of the following reaction is:
KOH, CH OH 3
CH3CHCH2CHCH2CH3 Br ───────▶
heat
| |
Br Br

[Online April 8,2017]

Options:

A. CH2 = CHCH2 CH = CHCH3

B. CH2 = CHCH = CHCH2CH3

C. CH3 CH = C = CHCH2CH3

D. CH3 CH = CH − CH = CHCH3

Answer: D

Solution:

Solution:
KOH . CH3 OH∕∆
CH3 − CH − CH2 − CH − CH2 − CH3───────────▶CH3 − CH = CH − CH = CH2 − CH3
| | E2 (Saytzeff product)
Br Br

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

Question98
CH3
| C2H5 ONa
The major product of the following reaction is C6H5CH2 − C
|
− CH2 − CH3───────▶
C2H5 OH
Br

[Online April 8,2017]

Options:
CH3
|
A. C6H5CH2 − C − CH2 − CH3
|
OC2H5

CH3
|
B. C6H5 CH − C − CH2 − CH3
|
CH3

C. C6H5 CH = C − CH2 − CH3

|
CH3

D. C6H5CH2 − C = CH2
|
CH2CH3

Answer: C

Solution:

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

Question99
In the following reaction sequence:
KOH(aq) (i)CH3 Mg Br Anhy . ZnCI2 + Conc . HCL
────────▶ II ────────▶ III ──────────────▶ given turbidity immediately
I
(C3H6CI2) (ii)H2O ∕ H+

The compound I is :
[Online April 9,2017]
Options:

A. CH2 − CH − CH3
| |
CI CI

B. CH2 − CH2 − CH3

| |
CI CI

C. CH − CH − CH2 − CH3
|
CI

CI
|
D. CH3 − C − CH3
|
CI

Answer: D

Solution:

Solution:

CI OH OH
| O
KOH | −H2O || (I)CH3 MgBr | Anhy . ZnCl3 + HCl
H3C − C − CH3────────▶CH3 − C − CH3────────▶CH3 − C − CH3────────▶CH3 − C − CH3─────────▶ (CH3)3 CI
| | |
CI (aq.) (II) (II)H2O ∕ H
⊕ Lucas Test Given turbidity immediately
OH CH3
(C3H6CI2) Unstable 3° alcohal
(I)
-------------------------------------------------------------------------------------------------

Question100
The major product obtained in the following reaction is:

[2017]
Options:

A. (±)C6H 5CH (OtBu)CH 2C6H 5

B. C6H 5CH = CH C6H 5

C. (+)C6H 5CH (OtBu)CH 2C6H 5

D. (−)C6H 5CH (OtBu)CH 2C6H 5

Answer: B

Solution:
Solution:

Elimination reaction is highly favoured if (a) Bulkier base is used (b) Higher temperature is used Hence in given reaction biomolecular elimination
reaction provides major product.

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

Question101
Which one of the following reagents is not suitable for the elimination reaction?

[Online April 10,2016]

Options:

A. NaI

B. NaOEt ∕ EtOH

C. NaOH ∕ H2O

D. NaOH ∕ H2O − EtOH

Answer: A

Solution:

Solution:
Alkyl chloride or bromide undergo substitution and get converted to an alkyl iodide on treatment with a solution of sodium iodide in acetone. e.g.
acetone
CH 3CH 2CH 2Br + N aI ───────▶CH 3CH 2CH 2I + N aBr
This reaction is also known as Finkelstein Reaction.

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

Question102
The synthesis of alkyl fluorides is best accomplished by:
[2015]
Options:

A. Finkelstein reaction

B. Swarts reaction

C. Free radical fluorination

D. Sandmeyer's reaction

Answer: B

Solution:

Solution:
Alkyl fluorides are more conveniently prepared by heating suitable chloro − or bromo-alkanes with organic fluorides such as
AsF 3, SbF 3, CoF 2, AgF , H g2F 2 etc. This reaction is called Swarts reaction.
CH 3Br + AgF ⟶ CH 3F + AgBr
2CH 3CH 2Cl + H g2F 2 ⟶ 2CH 3CH 2F + H g2Cl 2

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

Question103
A compound A with molecular formula C10H 13Cl gives a white precipitate on adding silver nitrate
solution. A on reacting with alcoholic KOH gives compound B as the main product. B on ozonolysis
gives C and D. C gives Cannizaro reaction but not aldol condensation. D gives aldol condensation but
not Cannizaro reaction. A is:
[Online April 10,2015]
Options:

A. C6H5 − CH2 − CH2 − CH2 − CH2 − Cl

B. C6H5 − CH2 − CH2 − CH − CH3
|
CI

C.

D.

Answer: C

Solution:

Solution:
Compound A reacts with [Link] to give compound B which on further ozonolysis gives C (does not contains α − H atom ) and D (contains α − H
atom ). This reaction sequence can be achieved by compounds in option (a) and (c). Since compound A gives white ppt. with AgN O3 preferable
option will be (c) as tert alkyl reacts with AgN O3 more quickly.

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

Question104
In SN 2 reactions, the correct order of reactivity for the following compounds:
CH3 Cl, CH3CH2 Cl, (CH3)2 CHCl and (CH3)3 CCl is:
[2014]
Options:

A. CH3 Cl > (CH3)2 CHCl > CH3CH2 Cl > (CH3)3 CCl

B. CH3 Cl > CH3CH2 Cl > (CH3)2 CHCl > (CH3)3 CCl

C. CH3CH2 Cl > CH3 Cl > (CH3)2 CHCl > (CH3)3 CCl

D. (CH3)2 CHCl > CH3CH2 Cl > CH3 Cl > (CH3)3 CCl

Answer: B

Solution:

Solution:
Steric hindrance around the carbon atom having Cl will slow down the SN 2 reaction, hence lesser the hindrance, faster will be the reaction. So, the
order of reactivity is CH 3Cl > (CH 3)CH 2 − Cl > (CH 3)2CH − Cl > (CH 3)3CCl

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

Question105
For the compounds CH 3Cl , CH 3Br, CH 3I and CH 3F , the correct order of increasing C-halogen
bond length is:
[Online April 9,2014]
Options:

A. CH 3F < CH 3Cl < CH 3Br < CH 3I

B. CH 3F < CH 3Br < CH 3Cl < CH 3I

C. CH 3F < CH 3I < CH 3Br < CH 3Cl

D. CH 3Cl < CH 3Br < CH 3F < CH 3I

Answer: A

Solution:

Solution:
The correct order of increasing bond length is
CH 3F < CH 3Cl < CH 3Br < CH 3I

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

Question106
In a nucleophilic substitution reaction:
DM F
R − Br + Cl −─────▶R − Cl + Br−
which one of the following undergoes complete inversion of configuration?
[Online April 9. 2014]
Options:

A. C6H 5CH C6H 5Br

B. C6H 5CH 2Br

C. C6H 5CH CH 3Br

D. C6H 5CCH 3C6H 5Br

Answer: C

Solution:

Solution:
C6H 5CH CH 3Br being an optically active secondary alkyl bromide undergoes SN 2 nucleophilic substitution reaction. Hence it undergoes complete
inversion of configuration.

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

Question107
The major organic compound formed by the reaction of 1, 1, 1 -trichloroethane with silver powder is:
[2014]
Options:

A. Acetylene

B. Ethene

C. 2 - Butyne

D. 2 - Butene

Answer: C
Solution:

Solution:
CI
|
2 CI − C − CH3 + 6 Ag─────▶ CH3C = CCH3 + 6 AgCI
| 2 − butyne
CI
1, 1, 1 − trichloroethane

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

Question108
Chlorobenzne reacts with trichloro acetaldehyde in the presence of H 2SO4

The major product formed is:

[Online April 11, 2014]
Options:

A.

B.

C.

D.

Answer: C

Solution:
Solution:
Chloral on reaction with chlorobenzene in the presence of a catalytic amount of sulphuric acid forms DDT (dichloro diphenyl trichloro ethane).

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

Question109
The major product formed when 1,1,1 -trichloro propane is treated with aqueous potassium
hydroxide, is:
[Online April 19, 2014]
Options:

A. propyne

B. 1 -propanol

C. 2 -propanol

D. propionic acid

Answer: D

Solution:
Solution:
O
heat ||
CI3C − CH2CH3 + KOH─────▶(OH)3C − CH2CH3 + 3 KCI ─────▶ CH3CH2C OH
1, 1, 1 − trichloro − propane propionic acid

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

Question110
The order of reactivity of the given haloalkanes towards nucleophile is :
[Online April 23,2013]
Options:

A. RI > RBr > K Cl

B. RCl > RBr > RI

C. RBr > RCl > RI

D. RBr > RI > RCl

Answer: A

Solution:
Solution:
For a given alkyl group, the order of reactivity is
R − I > R − Br > R − Cl > R − F
, decreasing halogen reactivity.
increasing bond energy
This order depends on the carbon-halogen bond energy; the carbon-fluorine bond energy is maximum and thus fluorides are least reactive while
carbon iodine bond energy is minimum hence iodides are most reactive.
-------------------------------------------------------------------------------------------------

Question111
Compound (A), C8H 9Br, gives a yellow precipitate when warmed with alcoholic AgN O3. Oxidation of
(A) gives an acid (B), C8H 6O−. (B) easily forms anhydride on heating. Identify the compound (A).
[2013]
Options:

A.

B.

C.

D.

Answer: D

Solution:
Solution:

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Question112
The Wurtz-Fittig reaction involves condensation of :
[Online April 22. 2013]
Options:
A. two molecules of aryl halides

B. one molecule of each of aryl-halide and alkyl-halide.

C. one molecule of each of aryl-halide and phenol.

D. two molecules of aralkyl-halides.

Answer: B

Solution:

Solution:
Reaction between alkyl halides, aryl halides and sodium in presence of dry ether to give substituted aromatic compounds is known as Wurtz fitting
reaction C6H 5Cl + 2N a + Cl CH 3 ⟶ C6 H 5 CH 3 + 2N aCl
T ol uene

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Question113
Alkyl halides react with dialkyl copper reagents to give
[2005]
Options:

A. alkenyl halides

B. alkanes

C. alkyl copper halides

D. alkenes

Answer: A

Solution:
Solution:
In Corey House synthesis of alkanes alkyl halides react with lithium dialkyl cuprate
R′X + LiR2Cu ⟶ R′ − R + RCu + LiX

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Question114
Aryl fluoride may be prepared from arene diazonium chloride using:
[Online April 9. 2013]
Options:

A. H BF 4 ∕∆

B. H BF 4 ∕ N aN O2Cu, ∆

C. CuF ∕ H F

D. Cu ∕ H F

Answer: A

Solution:

Solution:
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Question115
Elimination of bromine from 2 -bromobutane results in the formation of -
[2005]
Options:

A. Predominantly 2 -butyne

B. Predominantly 1-butene

C. Predominantly 2 -butene

D. Equimolar mixture of 1 and 2 -butene

Answer: C

Solution:

Solution:
Br
| Alc . KOH
-+9 CH3 − CH − CH2 − CH3───────▶CH3 − CH = CH − CH3 + HBr
The formation of 2 -butene is in accordance to Saytzeff's rule (more substituted alkene is formed).

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Question116
A major component of Borsch reagent is obtained by reacting hydrazine hydrate with which of the
following?
[Online April 22. 2013]
Options:

A.

B.

C.

D.
Answer: C

Solution:
Solution:
The major component of Borsch reagent is 2,4 dinitrophenyl hydrazine which can be obtained by reaction of 2,4 -dinitrochloro benzene and
hydrazine

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Question117
How many chiral compounds are possible on monochlorination of 2 - methyl butane?
[2012]
Options:

A. 8

B. 2

C. 4

D. 6

Answer: D

Solution:

Solution:
CI
| ⋆
CH2 − CH − CH2 − CH3
|
CH3
(R + S)
CI
|
CH3 − CH − CH − CH3
| ⋆
CH3
(R + S)
Four monochloro derivatives are chiral.

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Question118
Phenyl magnesium bromide reacts with methanol to give
[2005]
Options:

A. a mixture of toluene and M g(OH )Br

B. a mixture of phenol and M g(M e)Br

C. a mixture of anisole and M g(OH )Br

D. a mixture of benzene and M g(OM e)Br

Answer: D

Solution:
Solution:
CH 3OH + C6H 5M gBr ⟶ CH 3OM gBr + C6H 6

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Question119
AgCN Reduction
C2H 5Br───────▶X ───────▶Y, Here Y is
Zn − Hg ∕ HCl

[Online May 7, 2012]

Options:

A. Ethyl methyl amine

B. n -propylamine

C. Isopropylamine

D. Ethylamine

Answer: B

Solution:

Solution:

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Question120
The compound formed on heating chlorobenzene with chloral in the presence of concentrated
sulphuric acid, is
[2004]
Options:

A. freon

B. DDT

C. gammexene

D. hexachlorocthane

Answer: B

Solution:

Solution:
DDT is prepared by heating chlorbenzene and chloral with concentrated sulphuric acid

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Question121
Which of the following statements is wrong?
[Online May 12, 2012]
Options:

A. Ethyl chloride on reduction with Z n -Cu couple and alcohol gives ethane.

B. The reaction of methyl magnesium bromide with acetone gives butanol- 2 .

C. Alkyl halides follow the following reactivity sequence on reaction with alkenes. R − I > R − Br > R − Cl > R − I

D. C2H 4Cl 2 may exist in two isomeric forms

Answer: D

Solution:
Solution:

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Question122
Bottles containing C6H 5I and C6H 5CH 2I lost their original labels. Theywere labelled A and B for
testing. A and B were separately taken in test tubes and boiled with N aOH solution. The end solution
in each tube was made acidic with dilute H N O3 and then some AgN O3 solution was added.
Substance B gave a yellow precipitate. Which one of the following statements is true for this
experiment?
[2003]
Options:

A. A is C6H 5CH 2I
B. B is C6H 5I

C. Addition of H N O3 was unnecessary

D. A is C6H 5I

Answer: D

Solution:
Solution:
NaOH HNO3 ∕ H+
C6H5I─────▶C6H6 ONa ─────▶
(A)
AgNO3
C6H5 OH ─────▶ No yellow ppt.
NaOH HNO3 ∕ H+ AgNO3
C6H5CH2I─────▶C6H5CH2 ONa ─────▶ C6 H5 CH2 OH ─────▶ yellow ppt.
(B)
Since benzyl iodide gives yellow ppt. hence this is compound B and A is phenyl iodide (C6H5I).

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Question123
The reaction:
H 2O

(CH 3)3C − Br───────▶(CH 3)3 − C − OH

[2002]
Options:

A. elimination reaction

B. substitution reaction

C. free radical reaction

D. displacement reaction.

Answer: D

Solution:
Solution:
The hydrolysis of t -butyl bromide is an example of SN 1 reaction.

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Question124
Among the following, the molecule with the lowest dipole moment is
[Online May 19,2012]
Options:

A. CH Cl 3

B. CH 3Cl

C. CH 2Cl 2

D. CCl 4

Answer: D

Solution:
Solution:
CCl 4 is a nonpolar moleculas and it has symmetrical tetrahedral structure. Although each of the c -cl bond is polar but the resultant of all there
dipole moments is zero.

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Question125
Consider the following bromides :

The correct order of SN I reactivity is

[2010]
Options:

A. B > C > A

B. B > A > C

C. C > B > A

D. A > B > C

Answer: A

Solution:

Solution:

Since SN 1 reactions involve the formation of carbocation as intermediate in the rate determining step, more is the stability of carbocation higher will
be reactivity of alkyl halides towards SN 1 route. Now we know that stability of carbocations follows the order : 3∘ > 2∘ > 1∘ , soSN 1 reactivity should
also follow the same order.
3∘ > 2∘ > 1∘ > Methyl ( SN 1 reactivity)

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Question126
The organic chloro compound, which shows complete sterochemical inversion during a SN 2 reaction,
is
[2008]
Options:

A. (C2H 5)2CH Cl

B. (CH 3)3CCl
C. (CH 3)2CH Cl

D. CH 3Cl

Answer: D

Solution:

Solution:
SN 2 reaction is favoured by small groups on the carbon atom attached to halogen. So, the order of reactivity is
CH 3Cl > (CH 3)2CH Cl > (CH 3)3CCl > (C2H 5)2CH Cl

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Question127
Which of the following is the correct order of decreasing SN 2 reactivity?
[2007]
Options:

A. R2CH X > R3CX > RCH 2X

B. RCH 2X > R3CX > R2CH X

C. RCH 2X > R2CH X > R3CX

D. R3CX > R2CH X > RCH 2X ( X is a halogen )

Answer: C

Solution:

Solution:
In SN 2 mechanism transition state is pentavelent. For bulky alkyl group it will havesterical hinderance and smaller alkyl group will favour the SN 2
mechanism. So the decreasing order of reactivity of alkyl halide towards SN 2 mechanism is
RCH 2X > R2CH X > R3CX

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Question128
Reaction of trans 2 -phenyl-1-bromocyclopentane on reaction with alcoholic KOH produces
[2006]
Options:

A. 1-phenylcyclopentene

B. 3-phenylcyclopentene

C. 2 -phenyleyclopentene

D. 4 -phenylcyclopentene

Answer: A

Solution:

Solution:
The reaction is dehydrohalogenation

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Question129
Fluorobenzene (C6H 5F ) can be synthesized in the laboratory
[2006]
Options:

A. by direct fluorination of benzene with F2 gas

B. by reacting bromobenzene with NaF solution

C. by heating phenol with HF and KF

D. from aniline by diazotisation followed by heating the diazonium salt with HBF4

Answer: D

Solution:
Solution:

Conversion of (I) to (II) is known as Balz-schilmann reaction.

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Question130
The structure of the major product formed in the following reaction is

[2006]
Options:

A.

B.
C.

D.

Answer: B

Solution:

Solution:

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Question131
Tertiary alkyl halides are practically inert to substitution by SN 2 mechanism because of
[2005]
Options:

A. steric hindrance

B. inductive effect

C. instability

D. insolubility

Answer: A

Solution:

Solution:
Due to steric hindrance tertiary alkyl halides do not react by SN 2 mechanism, they react by SN 1 mechanism. SN 2 mechanism is followed in case of
primary and secondary alkyl halides.

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