Prayas JEE (2025)

MANTHAN

Chemistry General Organic Chemistry

Exercise-1 7. The order of decreasing stability of the carbanions is


(I) (CH3 )3 C 
(II) (CH3 ) 2 CH
INTRODUCTION, INDUCTIVE EFFECT

(III) CH3CH 
(IV) C6 H5 CH
1. The compound in which carbon uses only its sp3 hybrid 2 2

orbitals for bond formation is (a) I > II > III > IV (b) IV > III > II > I
(a) HCOOH (b) (NH2)2CO (c) IV > I > II > III (d) I > II > IV > III
(c) (CH3)3COH (d) (CH3)3C–CHO 8. Decreasing order of –I effect of the triad
2. A straight chain hydrocarbon has the molecular formula ⊕

C8H10. The hybridisation for the carbon atoms from one end [–NO2, – NH3 , –CN] is:
of the chain to the other are respectively sp3, sp2, sp2, sp3, ⊕ ⊕
(a) – NH3 > –NO2 > –CN (b) – NH3 > –CN > NO2
sp2, sp2, sp and sp. The structural formula of the hydrocarbon
⊕ ⊕
would be (c) –CN > –NO2 > – NH3 (d) –NO2 > –CN > – NH3
(a) CH3—C ≡ C—CH2—CH = CH—CH = CH2
9. Which of the following carbocation is least stable?
(b) CH3—CH2—CH = CH—CH2—C ≡ C—CH = CH2 ⊕
(c) CH3—CH = CH—CH2—C ≡ C—CH = CH2 (a) CH3 — C H — CH3
(d) CH3—CH = CH—CH2—CH = CH—C ≡ CH ⊕
(b) CH3 — CH 2 — C H 2
3. In the reaction,
⊕
Br— Br H2 (c) CH3—C—CH3
— C=C — BrCH2CH2Br
—

— Catalyst
1 2 H
H 3 4
CH3
The hybridisation states of carbon atoms 1, 2, 3 and 4 are
(a) 1 and 2: sp2; 3 and 4: sp3 CH3
—

⊕
(b) 1 and 2: sp2; 3 and 4: sp (d) CH3—C—CH—C6H5
(c) 1, 2, 3 and 4: sp
—

(d) 1 and 2: sp3; 3 and 4: sp2 CH3

4. Carbon atoms in the compound, (CN)4C2 are 10. Which of the following group/atom shows + I-effect?
(a) sp hybridized (b) sp2 hybridized (a) – OH (b) – OCH3 (c) – CH3 (d) – Cl
(c) sp and sp2 hybridized (d) sp, sp2 and sp3 hybridized 11. Which of the following can act as an electrophile?
5. Toluene has (a) H2O (b) SO3 (c) NH3 (d) ROR
(a) 6σ and 3π-bond
12. Which of the following can act as an electrophile?
(b) 9σ and 3π-bond
(a) AlCl3 (b) CN– (c) NH3 (d) CH3OH
(c) 9σ and 6π-bond
(d) 15σ and 3π-bond 13. Strongest nucleophile among the following is
6. Which one of the following order is correct regarding the (a) RNH2 (b) ROH
negative inductive effect of the substituents? (c) C6H5O – (d) CH3O–
(a) − NR 2 < −OR > −F 14. Inductive effect involves:
(a) Delocalisation of σ - electrons
(b) − NR 2 > −OR > −F
(b) Partial displacement of σ - electrons
(c) − NR 2 < −OR < −F (c) Delocalisation of π - electron
(d) − NR 2 > −OR < −F (d) Displacement of lone pair electrons

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RESONANCE, HYPERCONJUGATION, 22. The most stable carbanion among the following is
,
AROMATICITY CH2
15. Resonance structure of molecule does not have (a) (b)
(a) Identical arrangement of atoms.
, ,
(b) Nearly the same energy content. CH2 CH2
(c) The same number of paired electrons.
(d) Identical bonding (c) (d)
16. Which of the following will show aromatic behaviour?
OCH3 NO2
(a) (b)
23. Among the following, the aromatic compound/species is

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

17. Which of the following is the most stable cation?

+ + (c) (d)
(a) Ph 3C (b) Ph 2 CH
+ +
(c) Ph 3C CH 2 (d) PhCH 2 24. Which of the following is not an aromatic compound?
O
18. Which of the following resonating structures of 1‑methoxy-1,
3-butadiene is least stable? (a) (b)
⊕
(a) CH2–CH=CH–CH=O–CH3 +
⊕
(b) CH2=CH–CH–CH=O–CH3
⊕
(c) CH2–CH–CH=CH–O–CH3 (c) (d)
⊕
(d) CH2=CH–CH–CH–O–CH3
19. Which of the following is the decreasing order of stability?
⊕
(i) CH3–CH–CH3 25. The correct order of stability of following carbon free
⊕ radicals is:
(ii) CH3–CH–O–CH3 .
⊕ (CH3)3C
(iii) CH3–CH–CO–CH3
(I)
(a) (ii) > (i) > (iii) (b) (i) > (ii) > (iii)
(c) (iii) > (ii) > (i) (d) (ii) > (iii) > (i) • •
CH 3CH 2 CH 2 CH 3
20. Most stable carbocation amongst the following is:
(III) (IV)
+ + + +
CH 2 CH 2 CH 2 CH 2
(a) I > II > III > IV (b) IV > III > II > I
(c) II > III > I > IV (d) II > I > III > IV
(a) (b) (c) (d)
26. Which of the following is not a pair of resonating structures?

Cl NO 2 OCH3 (a) O and O

21. Which one is the most stable free radical?
CH 2
(b)

(a) (b) ,O
O
— —
—
(c) CH3—C — and CH3—C —+
• OH OH
(c) CH2 = CH—CH2 (d) CH3—C—CH3
—

CH3 (d) and

2
 27. Orbital interaction between the sigma bonds of a substitutent 34. Which of the following compound is least basic?
group and a neighbouring p-orbital is known as NH2 NH2 NH2 NH2
(a) Hyperconjugation (b) Inductive effect
(c) Steric effect (d) Dipole-dipole interactions
28. Which amongst the following is the most stable carbocation? (a) (b) (c) (d)
CH3
+ |
(a) CH3 − CH (b) CH3 − C+ NO2 OCH3 Cl CH3
| |
CH3 CH3 35. Which of the following orders of acidic strength is correct?
+ + (a) RCOOH > ROH > HOH > HC ≡ CH
(c) CH3 (d) CH3 CH 2
(b) RCOOH > HOH > ROH > HC ≡ CH
29. Which of the following is most stable alkene? (c) RCOOH > HOH > HC ≡ CH > ROH
H— H CH3— H
(a) — C=C — — (b) — C=C — — (d) RCOOH > HC ≡ CH > HOH > ROH
H H H H
CH3CH2 CH3— 36. Among the following compounds, the strongest acid
(c) (d) — CH— H
CH3 — C=C — — is:
H H
(a) HC ≡ CH (b) C6H6
ACIDIC STRENGTH AND BASIC STRENGTH (c) C2H6 (d) CH3OH
30. In the compound given below
37. Find the strongest acid among the following compounds:
(a) CH3CHCOOH (b)

—

NO2
(c) CH3CH2COOH (d) CH3CHCOOH

—
The correct order of the acidity of the positions (X), (Y) and CN
(Z) is 38. Find the correct order of Ka among the following compounds
(a) (Z) > (X) > (Y) (b) (X) > (Y) > (Z) HC ≡ C—CH2—COOH CH2 = CHCH2COOH
(c) (X) > (Z) > (Y) (d) (Y) > (X) > (Z)
(I) (II)
31. Most acidic compound among the following is:
CH3CH2CH2COOH
(a) OH
(III)
(a) I > II > III (b) II > I > III
(b) CO2H (c) III > II > I (d) I > III > II

(c) H3C CO2H INTRODUCTION TO REACTION MECHANISM

39. The presence of Chlorine atom on benzene ring makes the
(d) O2N CO2H second substituent enter at ______ position.
(a) Ortho (b) meta
32. Which of the following is the strongest base? (c) Para (d) Ortho & para

NH—CH3 40. Conversion of alkane into alkyl halide is an example of

(a) NH2 (b)
which of the following reaction?
(a) Electrophilic substitution
NH2
(c) (d) CH2—NH2 (b) Free radical addition
CH3 (c) Nucleophilic substitution
33. Which of the following is an aromatic compound? (d) Free radical substitution
41. Which of the following is most reactive towards E.S.R.?

(a) (b)
(a) (b)
N
(c) (d) Both (b) and (c) (c) (d)
N
3
 O 47. In amines, hybridisation state of N is:
+

—
—
O—C— NO2 (a) sp (b) sp2 (c) sp3 (d) sp3d
42. [P]
48. Which of the following is most basic?
The product [P] is: (a) Aniline (b) o–Nitroaniline
O NO2 (c) m–Nitroaniline (d) p–Nitroaniline

—
49. The most stable resonating structure of aniline is
(a) O—C
NH2
O
—
(b) O—C NO2 (a) (b)
O
—

(c) O2N O—C

NO2 (c) (d) All are equally stable

O
—

(d) O—C
50. Which of the following is most basic?
43. Nitration of benzene is
(a) Nucleophilic substitution (a) (b)
(b) Nucleophilic addition NH N
(c) Electrophilic substitution (c) RCN (d) C6H5NH2
(d) Electrophillic addition 51. The correct order of basic strength of substituted aniline is:
44. Consider the following compounds: (a) p–methylaniline > p–chloroaniline > p–aminoaceto
CH3 OH NO2 phenone
(b) p–methylaniline > p–aminoacetophenone > o–chloro
(I) (II) (III) (IV) aniline
(c) p–aminoacetophenone > p–methylaniline > p–
Correct order of their reactivity in electrophilic substitution chloroaniline
reaction would be: (d) p–aminoacetophenone > p–chloroaniline > p–
(a) I > II > III > IV (b) IV > III > II > I methylaniline
(c) III > II > I > IV (d) III > IV > I > II 52. Which of the nitrogen is protonated most readily in
guanidine?
MISCELLANEOUS
45. How many π-electrons are there in the following species?
,

(a) 1 (b) 2
(c) 3 (d) All are equally protonated
(a) 2 (b) 4 (c) 6 (d) 8
46. The number of benzylic hydrogen atoms in ethylbenzene 53. Which of the following compound is most acidic?
are: (a) Picric acid (b) p-nitrophenol
(a) 3 (b) 5 (c) 2 (d) 7 (c) m-nitrophenol (d) o,p-dinitrophenol

4
 Exercise-2 Codes :
SINGLE CORRECT TYPE QUESTIONS (a) A - Q ; B - R ; C - S ; D - P
1. Correct arrangement of the following acids in correct (b) A - R ; B - P ; C - S ; D -Q
Ka order is :- (c) A - S ; B - R ; C - P ; D - Q
(I) H3N–CH2–COOH (d) A - R ; B - S ; C - Q ; D – P
(II) NC–CH2–COOH
(III) H3C–CH2–COOH
–
(IV) OOC –CH2–COOH
(a) I > II > III > IV (b) II > I > III > IV 6. , pKa value of the compound decreases if X
(c) I > III > II > IV (d) IV > III > II > I

2. Which of them is false for order of – I effect is:-

(a) –F > –Cl > –Br > I (a) –NO2 (b) –NH2
 
(b) – NR 3  NH3  –NO2 (c) –OH (d) –OCH3
(c) –OCH3 > –OH > –NH2
7. Stability of:
(d)
(I) CH3–CH=CH–CH3

3. The order of basicity of halides is: CH3

|
(a) Cl– < Br– < I– < F– (II) CH3 – C = C – CH 3
(b) F– < I– < Br– < Cl– |
(c) I– < Br– < Cl– < F– CH3
(d) Cl– < F– < I– < Br–
(III) CH 3 – C = CH 2
4. Formic acid is considered as a hybrid of the four |
structures CH 3

(IV) CH3 – C = CH – CH 3
|
CH3
Which of the following order is correct for the stability in the increasing order is:
of the four contributing structures. (a) I < III < IV < II (b) I < II < III < IV
(a) I > II > III > IV (b) I > II > IV > III (c) I < IV < III < II (d) II < III < IV < I
(c) I > III > II > IV (d) I > IV > III > II
8. Spin multiplicity of Triplet nitrene is :
5. Match List- I with List- II and select the correct answer
using the codes given below – (a) 1 (b) 2
(c) 3 (d) 4
List-I (Stability) List -II (Reason)
(A) (P) Inductive effect 9. The correct order of increasing dissociation constant of
the following compound is :-

(B) (Q) Resonance

(C) (R) Hyperconjugation (a) II < IV < I < III

and resonance
(b) IV < III < I < II
(D) (S) Hyperconjugation (c) IV < II < I < III
and inductive (d) IV < I < II < III
effect

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10. In the following arrange the H (numbered) for their ease (b) [Link] > HOCH2. COOH>
of displacement during acid base reaction : [Link]
(c) [Link] > [Link] > [Link]
(d) CH3. COOH > [Link] >
(CH3)[Link]

(a) 1>2>3 (b) 3>2>1

(c) 3>1>2 (d) 2>3>1 15. Which of the following reacts with AgNO3 to give ppt.:

(a)

(b)

11.
(c)

Compare carbon-carbon bond rotation across I, II, III.

(a) I > II > III (b) I > III > II (d)
(c) II > I > III (d) II > III > I

12.

16. (A); Here (A) is :

The correct order of decreasing basic strengths of x, y
and z is :
(a) x > y > z (b) x > z > y
(c) y > x > z (d) y > z > x (a) (b)

13. Which nitorgen in LSD (Lysergic acid diethylamide) is

more basic : (c) (d)

17. Which of the following can give benzyne :

(a) I
(b) II (a)
(c) III
(d) All are equally basic
(b)
14. The acid strength of substituted carboxylic acids is
known to be dependent on the nature and position of
the substituent. In the following examples, an attempt (c)
has been made to arrange the acids in order of acid (d) All
strength, the strongest first. One of the series is 18. Hybridisation of arrow headed 'C' is
incorrect-which one :
(a) CH3.CH2CH(Cl).COOH > CH3 . (a) sp2 sp3 (b) sp3 sp3
CH(Cl).CH2COOH > [Link] (c) sp2 sp2 (d) sp3 sp3d
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19. Which of the following will not give 1, 2, shift : 21. Which of the following compounds are antiaromatic:-

(a) (I) (II)

(b) (III) (IV)

(c) (V) (VI)

(d) All (a) (III) and (VI) (b) (II) and (V)
(c) (I) and (V) (d) (V) and (VI)
20. The increasing order of stability of the following free
radicals is 22. Among the following, the least stable resonance
• • structure is -
(a) ( C6 H5 )3 C  ( C6 H5 )2 CH  ( CH3 )3
• •
C  ( CH3 )2 C H (a)

• •
(b) ( C6 H5 )2 CH  ( C6 H5 )3 C  ( CH3 )3
• •
C  ( CH3 )2 C H (b)

• •
(c) ( CH3 )2 CH  ( CH3 )3 C  ( C6 H5 )3
• •
C  ( C6 H 5 ) 2 C H (c)

• •
(d) ( CH3 )2 CH  ( CH3 )3 C  ( C6 H5 )2
• •
CH  ( C6 H5 )3 C (d)

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 Answer Key (Manthan)
Exercise-1
1. (c) 2. (d) 3. (a) 4. (c) 5. (d) 6. (c) 7. (b) 8. (a) 9. (b) 10. (c)
11. (b) 12. (a) 13. (d) 14. (b) 15. (d) 16. (d) 17. (a) 18. (c) 19. (a) 20. (c)
21. (a) 22. (d) 23. (c) 24. (b) 25. (d) 26. (d) 27. (a) 28. (b) 29. (b) 30. (b)
31. (d) 32. (d) 33. (d) 34. (a) 35. (b) 36. (d) 37. (a) 38. (a) 39. (d) 40. (d)
41. (b) 42. (c) 43. (c) 44. (c) 45. (c) 46. (c) 47. (c) 48. (a) 49. (a) 50. (a)
51. (a) 52. (a) 53. (a)

Exercise-2
1. (a) 2. (d) 3. (c) 4. (a) 5. (b) 6. (a) 7. (a) 8. (c) 9. (c) 10. (b)
11. (c) 12. (b) 13. (b) 14. (c) 15. (b, d) 16. (c) 17. (d) 18. (c) 19. (b) 20. (d)
21. (d) 22. (a)

Exercise-3 (PYQ’s)
1. (d) 2. [22] 3. (a, b) 4. (d) 5. [4] 6. (a) 7. (d) 8. (a) 9. (c) 10. (c)
11. (d) 12. (d) 13. (c) 14. [2] 15. (c) 16. (c) 17. (a) 18. (b) 19. (d) 20. [5]
21. (a) 22. (a) 23. (b) 24. [4] 25. (b) 26. (b) 27. (a) 28. (b) 29. (*) 30. (c)
31. (a) 32. (b) 33. (d) 34. (b) 35. (a)] 36. (d) 37. (a) 38. (b) 39. (*) 40. (d)
41. (d) 42. (b) 43. (b) 44. (b) 45. (a) 46. (a) 47. (c) 48. (b) 49. (a)

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