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General Organic Chemistry

(GOC)

By ACiD Sir

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Practice Sheet – 1 TOPIC : GOC BY ACiD SIR

1. Which of the following compound is electrophile

(1) SO3 (2) Na+ (3) FΘ (4) NH3

2. Which of the following compound is nucleophile

•
(1) H2O (2) :CCl2 (3) CH3 (4) None of these

3. Which is most acidic compound:

(1) C2H5COOH (2) CH3CH2CH2COOH (3) CH3COOH (4) HCOOH

4. Maximum –I effect is exerted by the group

(1) –C6H5 (2) –OCH3 (3) –Cl (4) –NO2

5. Which of the following is most stable:

(1) CH3 (2) CH2= CH (3) CH≡ C (4) CH3–C≡ C

6. What is the decreasing order of strength of the bases,

OH , NH2 , , CH3–CH2

(I) (II) (III) (IV)

(1) IV > II > III > I (2) III > IV > II > I (3) I > II > III > IV (4) II > III > I > IV

7. The stability of given free radicals in decreasing order is:

•
(a) CH3 − CH2
•
(b) CH3 − C H2 − CH3 (c) H3C–C–CH3
. •
(d) CH3
CH3

(1) c > d > a > b (2) a > b > c > d (3) c > b > d > a (4) c > b > a > d

8. Which of the following substituted carboxylic acids has the highest Ka value:

(1) CH3–CH2–CH–COOH (2) CH3–CH–CH2–COOH

Cl Cl

(3) CH 2–CH 2–CH 2–COOH (4) CH3–CH–CH2–COOH

Cl Br

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9. Examine the following two structures for the anilinium ion and choose the correct statement from

the ones given below.

I II

(1) II is not an acceptable canonical structure because carbonium ions are less stable than

ammonium ion.

(2) II is not an acceptable canonical structure because it is non-aromatic.

(3) II is not an acceptable canonical structure because the nitrogen has 10 valence electrons.

(4) II is an acceptable canonical structure.

10. Find the stability order of given resonating structures:

(I) (II)

O
⊕
(III) ⊕ N (IV)
O

(1) I > II > III > IV (2) I > III > II > IV (3) I > III > IV > II (4) IV > I > III > II

11. Classify the following compounds in aromatic, non aromatic and antiaromatic.

H
B 
(1) (2) (3) (4)

12. Most stable carbocation is:

⊕ ⊕
(1) CH2=CH (2) CH 2=CH–CH 2 (3) (4)

13. Least stable carbonium ion in the following will be:

(1) (2) ⊕ (3) (4) ⊕

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14. Arrange stability of the given carbocations in decreasing order:
⊕ ⊕ ⊕ ⊕
CH2 CH2 CH2 CH2

OCH3 OH NH2 Cl

I II III IV

(1) I > II > III > IV (2) III > II > I > IV

(3) IV > I > II > III (4) III > I > II > IV

15. Arrange the carbanions, in order of their decreasing stability:

(1) (2)

(3) (4)

16. Acidic strength order is:-

(1) (2) (3) (4)

(1) 4 > 1 > 2 > 3 (2) 3 > 1 > 2 > 4 (3) 4 > 3 > 1 > 2 (4) 3 > 4 > 2 > 1

17. Which of the following is most stable carbocation?

(1) (2) (3) (4)

ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17
Ans. 1 1 4 4 3 1 4 1 3 3 1, 2, 3, 4 4 4 2 2 4 1

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Practice Sheet–2

Inductive Effect

1. The inductive effect:

(1) Implies the atom’s ability to cause bond polarization

(2) Increases with increase of distance

(3) Implies the transfer of lone pair of electrons from more electronegative atom to the lesser

electronegative atom in a molecule

(4) Implies the transfer of lone pair of electrons from lesser electronegative atom to the more

electronegative atom in a molecule

2. The correct order of increasing acid strength of the compounds:

(a) CH3CO2H (b) MeOCH2CO2H (c) CF3CO2H (d)

(1) d < a < c < b (2) d < a < b < c (3) a < d < c < b (4) b < d < a < c

3. Which of the following groups has the highest +I effect:

(1) CH3— (2) CH3CH2— (3) (CH3)2 CH— (4) (CH3)3 C—

4. Pair of groups exerting (–I) effect is:

(1) –NO2 and –CH3 (2) –NO2 and –Cl (3) –Cl and –CH3 (4) –CH3 and –C2H5

5. The correct order of increasing basic strength of the bases NH3, CH3NH2 and (CH3)2NH is:

(1) NH3 < CH3NH2 < (CH3)2NH (2) CH3NH2 < (CH3)2NH < NH3

(3) CH3NH2 < NH3 < (CH3)2NH (4) (CH3)2NH < NH3 < CH3NH2

6. Correct order of acidic strength is:

(1) HCOOH > CH3COOH > C2H5COOH (2) C2H5COOH > CH3COOH > HCOOH

(3) HCOOH > C2H5COOH > CH3COOH (4) CH3COOH > HCOOH > C2H5COOH

7. Considering the basic strength of amines in aqueous solution, which one has the smallest pKb

value ?

(1) (CH3)3N (2) C6H5NH2 (3) (CH3)2NH (4) CH3NH2

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⊕
8. The number of electrons present in the valence shell of carbon of CH3 CH2 ion bearing +ve charge:

(1) 8 (2) 7 (3) 6 (4) 4

9. The hybridisation of C of methylcarbanion is:

(1) sp3 (2) sp2 (3) sp (4) All of these

10. Carbanion of CH3CHΘ2 has geometry:

(1) Planar (2) Pyramidal

(3) Squar bipyramidal (4) All of the above

11. Hybridisation of CH3 is:

(1) sp3 (2) sp2 (3) sp (4) Not certain

12. Which of the following presents the correct order of the acidic strength in the given compounds:

(1) FCH2COOH > CH3COOH > BrCH2COOH > ClCH2COOH

(2) BrCH2COOH> ClCH2COOH > FCH2COOH > CH3COOH

(3) FCH2COOH >ClCH2COOH > BrCH2COOH > CH3COOH

(4) CH3COOH > BrCH2COOH > ClCH2COOH > FCH2COOH

13. The correct order of decreasing acid strength of trichloroacetic acid (A), trifluoroacetic acid (B),

acetic acid (C) and formic acid (D) is:

(1) B > A > D > C (2) B > D > C > A (3) A > B > C > D (4) A > C > B > D

14 The decreasing order of –I effect of the orbitals is:

I. sp II. sp2 III. sp3

(1) I > II > III (2) III > II > I (3) I > III > II (4) II > III > I

Resonance Effect

15. Ortho-nitrophenol is less soluble in water than p- and m-nitrophenols because:

(1) o-nitrophenol is more volatile in steam than those of m- and p-isomers.

(2) o-nitrophenol shows intramolecular H-bonding

(3) o-nitrophenol shows intermolecular H-bonding

(4) Melting point of o-nitrophenol is lower than those of m- and p-isomers

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16. The correct order of acid strength of the following compounds is:

A. Phenol B. p-Cresol C. m-Nitrophenol D. p-Nitrophenol

(1) D > C > A >B (2) B > D > A >C (3) A > B > D >C (4) C > B > A >D

17. Among the following compounds, the most acidic is:

(1) p-nitrophenol (2) p-hydroxybenzoic acid

(3) o-hydroxybenzoic acid (4) p-toluic acid

18. An aromatic molecule will not:

(1) have 4n π electrons (2) have (4n + 2) π electrons

(3) be planar (4) be cyclic

19. Amongst the following, the most basic compound is:

(1) C6H5NH2 (2) p-NO2 – C6H4NH2

(3) m-NO2 – C6H4NH2 (4) C6H5CH2NH2

20. Amongst the following the most basic compound is:

(1) aniline (2) benzylamine (3) p–nitroaniline (4) acetanilide

21. The increasing order of stability of the following free radicals is:

• • • • • • • •
(1) (C6H5)3 C <(C6H5)2 CH <(CH3)3 C <(CH3)2 CH (2) (C6H5)2 CH <(C6H5)3 C <(CH3)3 C <(CH3)2 CH

• • • • • • • •
(3) (CH3)2 CH <(CH3)3 C <(C6H5)3 C <(C6H5)2 CH (4) (CH3)2 CH <(CH3)3 C <(C6H5)2 CH <(C6H5)3 C

22. Arrange basic strength of the given compounds in decreasing order:

(a) CH3–CH2–NH2 (b) CH2=CH–NH2 (c) C6H5–NH2

(1) a > b > c (2) a > c > b (3) c > b > a (4) b > c > a

23. Which of the following is the strongest base:

(1) (2) (3) (4)

24. Which of the following has maximum pKa:

(1) CH2FCOOH (2) CH2ClCOOH (3) CH3COOH (4) HCOOH

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25. The number of π electrons in benzene are:

(1) 8πe– (2) 3πe– (3) 6πe– (4) 2πe–

26. In benzene C–C bond length between all carbons are equal because of:

(1) Tautomerism (2) sp2 hybridization (3) Isomerism (4) Resonance

27. The order of stability of the following resonating structures is:

(1) II > I > III (2) I > III > II (3) I > II > III (4) III > II > I

28. Which of the following is most stable:

⊕ ⊕ ⊕ ⊕
(1) CH3 (2) CH3– CH 2 (3) CH3– CH –CH3 (4) CH2=CH– CH 2

29. Which of the following is least stable carbocations:

⊕ ⊕ ⊕ ⊕
(1) CH2= CH (2) CH3– CH 2 (3) (Ph)2 C H (4) Ph CH 2

30. Which one of the carbanions is most stable:

(1) (2) (3) (4)

31. Which of the following substituents will decrease the acidity of phenol:

(1) –NO2 (2) –CN (3) –CH3 (4) –CHO

32. Choose the most stable Carbocation:

⊕ ⊕
(1) CH3–CH=CH– CH2 (2) CH2=CH–CH –CH3
⊕ ⊕
(3) CH2=C –CH2–CH3 (4) CH2=CH–CH2 – CH2

33. Most stable carbonium ion in the following will be:

⊕
(1) ⊕ (2) ⊕ (3) CH2 (4) ⊕

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34. Consider the following compounds:

Arrange these compounds in decreasing order of their basicity:

(1) a > b > c > d (2) b > c > a > d (3) d > a > c > b (4) d > a > b > c

35. Which free radical is the most stable:

(1) (2) (3) (4)

36. Which of the following is heterocyclic aromatic species ?

(1) (2) (3) (4)

37. Which nitrogen is protonated readily in the guanidine?

(1) 1 (2) 2 (3) 3 (4) All with equal rate

38. Which of the following shows the correct order of decreasing acidity:

(1) PhCO2H > PhSO3H > PhCH2OH > PhOH

(2) PhSO3H > PhOH > PhCO2H > PhCH2OH

(3) PhCO2H >PhOH > PhCH2OH > PhSO3H

(4) PhSO3H > PhCO2H > PhOH > PhCH2OH

39. Which nitrogen in LSD (Lysergic acid and diethylamide) is most basic:

(1) I (2) II (3) III (4) All are equally basic

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40. (A) (B) (C)

Choose the incorrect statement:

(1) A is more basic than C (2) B is more basic than A
(3) B is more basic than C (4) All are aromatic bases

41. (I) (II)

(IV)
(III)

The correct order of decreasing basicity of the above compound is:

(1) I > II > III > IV (2) II > I > IV > III (3) III > IV > II > I (4) II > I > III > IV

42. The order of acidic strength of the hydrogen atoms (Hα, Hβ, Hγ) in the given molecule is:

(1) Hγ > Hα > Hβ (2) Hγ > Hβ > Hα (3) Hβ > Hγ > Hα (4) Hβ > Hα > Hγ

43. Which one of the following is least basic in character ?

(3) (4)
(1) (2)

44. Among the following the compound having the most acidic alpha-hydrogen is:
(1) CH3CHO (2) CH3COCH3

(3) (4) CH3–CO–CH2–CO2CH3

45. Which of the following resonance structures contributes is the most stable ?

(1) (2) (3) (4)

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46. Which of the following group has (+M) effect ?

(1) (2) (3) (4)

47. Which of the following molecules, in pure form, is unstable at room temperature ?

(1) (2) (3) (4)

48. and are:

(1) Resonating structures (2) Tautomers

(3) Geometrical isomers (4) Optical isomers

49. Which one of the following compounds is most acidic:

(1) (2) (3) (4) ClCH2CH2OH

50. Which one of the following compounds has the most acidic nature

(1) (2) (3) (4)

51. Mesomeric effect is the resonance of:

(1) π- electrons and lone pair

(2) σ- electrons only

(3) π and σ-electrons both

(4) π- electrons only

52. Which of the following is wrong about resonance:

(1) Resonating structures having same energy have same contribution

(2) All resonating structures have same number of unpaired electron.

(3) All resonating structures have same number of bond pair electrons.

(4) All resonating structures have same amount of net charge.

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Hyperconjugation Effect

53. Select the most stable carbocation among the following:

(1) (2)

(3) (4)

54. Among the following alkenes

(I) 1-butene (II) trans-2-butene

(III) cis-2-butene (IV) Isobutylene

the order of decreasing stability is:

(1) II > I > III > IV (2) III > IV > I > II (3) IV > I > II > III (4) IV > II > III > I

55. Correct order of stability is:

(1) CH2=CH2 > CH3–CH=CH2 > (CH3)2C=CH2 (2) CH2=CH2 < CH3–CH=CH2 < (CH3)2C=CH2

(3) CH2=CH2 < (CH3)2C=CH2 < CH3–CH=CH2 (4) CH3–CH=CH2 < CH2=CH2 < (CH3)2C=CH2

56. Arrange the Stability of following:

I II III

(1) I < II < III (2) II < I < III (3) I < III < II (4) II < III < I

57. Which of the following alkene is most stable:

(1) (2) (3) (4)

58. Compare heat of hydrogenation of the following:

(i) (ii) (iii)

(1) i > ii > iii (2) iii > ii > i

(3) ii > iii > i (4) ii > ii > iii

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59. Give the decreasing order of hyperconjugative effect of R in R–CH = CH2, where R is:

I. Me – II. Et–
III. Me2CH– IV. Me3C–

(1) I > II > III > IV (2) IV > III > II > I (3) II > I > III > IV (4) IV > III > I > II

60. Correct order of stability is:

(1) 1-butene > trans-2-butene > cis-2-butene
(2) trans-2-butene > 1-butene > cis-2-butene
(3) trans-2-butene > cis-2-butene > 1-butene
(4) cis-2-butene > trans-2-butene > 1-butene

61. Which amongst the following is the most stable carbocation:

(1) (2) (3) (4)

Electromeric Effect

62. Electromeric effect:

(1) Comes into play at the demand of attacking reagent.
(2) Involves displacement of electrons in a sigma bond.
(3) Comes into play in the molecule when at least one atom has unshared pair of electrons.
(4) Is permanent effect.

63. Which statement is correct for electromeric effect:

(1) It is a temporary effect
(2) It is the property of π bond
(3) It takes place in presence of reagent, i.e., electrophile or nucleophile
(4) All are correct

ANSWER KEY
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25
Ans. 1 2 4 2 1 1 3 3 1 2 2 3 1 1 2 1 3 1 4 2 4 1 4 3 3
Que. 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50
Ans. 4 3 4 1 1 3 2 3 3 2 3 1 4 2 1 2 4 1 3 4 3 2 1 1 2
Que. 51 52 53 54 55 56 57 58 59 60 61 62 63
Ans. 1 3 3 4 2 3 3 2 1 3 3 1 4

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Practice Sheet–3

1. Which of the following is most stable:

(1) (2) (3) F– (4) Cl–

2. In the anion HCOO–, the two carbon-oxygen bonds are found to be equal length. What is the reason
for it:
(1) the C=O bond is weaker than the C–O bond
(2) the anion HCOO– has two equivalent resonating structures
(3) the electronic orbitals of carbon atom are hybridized
(4) the anion is obtained by removal of proton from the acid molecule

3. Rank the following radicals in order of

Decreasing stability:

I II

III IV
(1) III > II > I > IV (2) III > II < I < IV (3) II > III > II > IV (4) III < II < I < IV

4. Which is the decreasing order of acidity in,

(I) HCOOH (II) CH3COOH (III) CH3CH2COOH (IV) C6H5COOH
(1) I > II > III > IV (2) IV > III > II > I (3) IV > I > II > III (4) I > IV > II > III

5. Which is maximum acidic compound:

COOH

(3) (4)
(1) (2)
OCH3

6. Which is most stable carbanion:

(1) (2) (3)

(4) CH2=CH– CH –CH=CH2

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7. Arrange (all dibasic acid) in increasing order of their Ka value:

oxalic acid, succinic acid,

I II

malonic acid, adipic acid

III IV

(1) III < II < I < IV (2) II < III < I < IV (3) IV < II < III < I (4) II < I < III < IV

8. Consider the following compounds

CH3–CH2–NH2 CH3– –NH2

I II III

Correct order of their basic strength is:

(1) I < II < III (2) II > I > III (3) III > II < I (4) II < III < I

9. Arrange the following in decreasing of their basic nature:

H
I II III

(1) I > II > III (2) I > III > II (3) III < II > I (4) II > I > III

10. Give the correct order of increasing acidity of the following compounds:

(I) (II) (III) (IV)

(1) II < I < IV < III (2) IV < II < I < III (3) I < II < IV < III (4) IV < I < II < III

11. Which of the following pairs does not represent canonical structures ?

(1) and

(2) and

(3) and

(4) and

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12. Which is aromatic species:

(1) –2 (2) (3) (4) All the above

13. The hybridization states of the nitrogen atoms in pyridine, piperidine and pyrrole are respectively:

are respectively:

(1) sp2, sp3 and sp2 (2) sp2, sp3 and sp3

(3) sp3, sp3 and sp3 (4) sp2, sp2 and sp2

14. Select an acid from each pair having stronger conjugate base:

(A) H2O H2 S
(I) (II)

(B) CH 3 – C ≡ CH CH 3 – CH = CH 2
(I) (II)

(C)

(1) I, I, II (2) II, I, I (3) I, II, I (4) I, II, II

15. Match the column-I and column-II and select the answer:

Column-I Column-II
O
(a) C–OH + NaHCO3 (p) NH3
14

14
(b) (q) C O 2

(c) (r) CO2

(d) (s) H2

(1) (a-r), (b-q), (c-s), (d-p) (2) (a-q), (b-r), (c-s), (d-p)

(3) (a-s), (b-q), (c-r), (d-p) (4) (a-p), (b-s), (c-q), (d-r)

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16. What is the order of acidic strength of the labelled H atoms:

(1) Ha > Hc > Hb (2) Hb > Hc > Ha (3) Hc > Ha > Hb (4) Ha > Hb > Hc

17. Consider the following bases:

(I) o-nitroaniline
(II) m-nitroaniline

(III) p-nitroaniline

Order of the base strength is:

(1) II > III > I (2) II > I > III (3) I > II > III (4) I > III > II

18. Increasing order of base strength of the following is:

I. CH3NH2 II. (CH3)2NH III. (CH3)3N IV. C6H5NH2

V. C6H5CH2NH2

(1) IV < V < I < II < III (2) IV < V < III < I < II

(3) IV < III < V < I < II (4) IV < V < I < III < II

19. Which of the following compound is not resonance stabilized ?

(1) (2) (3) (4)

20. Which of the following ketonic compound is the least stable ?

(3) (4)
(1) (2)

21. The correct order of stability for the following species is:

⊕ ⊕
O
(I) (II)
⊕
O ⊕
(III) (IV)

(1) II > IV > I > III (2) I > II > III > IV (3) II > I > IV > III (4) I > III > II > IV

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22. Which of the following represent the decreasing order of Ka values ?

(1) (ii) > (i) > (iii) > (iv) (2) (ii) > (iii) > (i) > (iv)

(3) (i) > (ii) > (iii) > (iv) (4) (ii) > (iv) > (i) > (iii)

23. Which of the following compounds will not give effervescence with sodium bicarbonate ?

(1) C6H5CO2H (2)

(3) C6H5OH (4)

24. The compound that does not liberate CO2, on treatment with aqueous sodium bicarbonate solution,

is:

(1) Benzoic acid (2) Benenesulphonic acid

(3) Salicylic acid (4) Carbolic acid

25. Among the following strongest acid is:

(1) CH3COOH (2) C6H5COOH

(3) m-CH3OC6H4COOH (4) p-CH3OC6H4COOH

26. The strongest base among the following is:

(3) (4)
(1) (2)

27. Among the following the dissociation constant (Ka) is highest for:

(1) C6H5OH (2) C6H5CH2OH (3) CH3C≡CH (4) CH3NH3+Cl–

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28. Among the following the aromatic molecule is:

(1) (2)
(3) (4)

29. Pyridine is less basic than triethylamine because:

(1) Pyridine has aromatic character
(2) Nitrogen in pyridine is sp2 hybridized
(3) Pyridine is a cyclic system
(4) In pyridine, lone pair of nitrogen is delocalized

30. Among the following the weakest base is:

(1) C6H5CH2NH2 (2) C6H5CH2NHCH3 (3) O2NCH2NH2 (4) CH3NHCHO

31. Which of the following orders is correct for the energy required for homolytic cleavage of indicated
C–H bonds?
H3

H2
H1

(1) H1 > H2 > H3 (2) H3 > H1 > H2 (3) H2 > H1 > H3 (4) H3 > H2 > H1

32. The decreasing order of stability of following cations is

⊕ ⊕ ⊕ ⊕
CH2 CH2 CH2 CH2

OH NH2 CH3 Cl
(P) (Q) (R) (S)

(1) P > Q > R > S (2) Q > S > R > P (3) Q > P > S > R (4) Q > P > R > S

33. The decreasing order of stability of following anions is

Θ Θ Θ Θ
CH2 CH2 CH2 CH2

NO2 CN CH3
(P) (Q) (R) (S)

(1) P > Q > R > S (2) S > R > Q > P (3) Q > P > R > S (4) P > Q > S > R

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34. Polarization in acrolein as:

(1) = –CHO (2) = –CHO

(3) =CH– (4) =CH–

35. Which of the following order of acidic strength is correct:

(1) RCOOH > ROH > HOH > HC≡CH (2) RCOOH > HOH > ROH > HC≡CH

(3) RCOOH > HOH > HC≡CH > ROH (4) RCOOH > HC≡CH > HOH > ROH

36. Which of the following is more basic than aniline:

(1) Diphenyl amine (2) Triphenyl amine

(3) p-nitro aniline (4) Benzyl amine

37. The stability of carbanions in the following:

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

is in the order of:

(1) (d)>(b)>(c)>(a) (2) (a)>(c)>(b)>(d) (3) (a)>(b)>(c)>(d) (4) (b)>(c)>(d)>(a)

38. Given are cyclohexanol (I), acetic acid (II) 2,4,6-trinitrophenol (III) and phenol (IV). In these the order

of decreasing acidic character will be:

(1) III > II > IV > I (2) II > III > I > IV (3) II > III > IV > I (4) III > IV > II > I

39. Which of the following will not be soluble in sodium hydrogen carbonate?

(1) 2,4,6-trinitrophenol (2) Benzoic acid

(3) o-nitrophenol (4) Benzenesulphonic acid

40.

Which statement is incorrect in respect of the above reaction ?

(1) Product is aromatic

(2) Product has high dipole moment

(3) Product has less resonance energy

(4) Product is soluble in polar solvent

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+ + • •
41. Hybridisaiton of carbon in CH3 , CF3 , CH3 , CF3 is respectively

(1) sp2, sp2, sp2, sp3

(2) sp2, sp2, sp3, sp2

(3) sp2, sp3, sp2, sp2

(4) sp3, sp2, sp2, sp2

42. The correct decreasing order of stability of I, II and III carbocaitons is :

+
(I) CH3 − CH − CH3

+
(II) CH3 − CH − COCH3

+
(III) CH3 − CH − OCH3

(1) I > II > III (2) II > III > I (3) III > I > II (4) II > I > III

ANSWER KEY
Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25
Ans. 4 2 1 4 2 1 3 4 2 2 4 1 1 4 1 3 1 2 3 1 4 1 3 4 3
Que. 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42
Ans. 3 4 1 2 4 3 4 4 4 2 4 3 1 3 3 1 3

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Practice Sheet–4

1. Statement I: Tropylium cation is aromatic in nature

Statement II: The only property that determines its aromatic behaviour is its planar structure.

(1) Both Statement I and Statement II are correct.

(2) Both Statement I and Statement II are incorrect.

(3) Statement I is correct but Statement II is incorrect.

(4) Statement I is incorrect but Statement II is correct.

⊕ ⊕ ⊕ ⊕
2. Statement I: Me3 C is more stable than Me2 CH and Me2 CH is more stable than the Me CH2 .

Statement II: Greater the number of hyperconjugative structures, more is the stability of

carbocation.

(1) Both Statement I and Statement II are correct.

(2) Both Statement I and Statement II are incorrect.

(3) Statement I is correct but Statement II is incorrect.

(4) Statement I is incorrect but Statement II is correct.

3. Statement I: Cyclopentadienyl anion is much more stable than allyl anion.

Statement II: Cyclopentadienyl anion is aromatic in nature.

(1) Both Statement I and Statement II are correct.

(2) Both Statement I and Statement II are incorrect.

(3) Statement I is correct but Statement II is incorrect.

(4) Statement I is incorrect but Statement II is correct.

4. Statement I: The pKa value of acetic acid is lower than that of phenol.

Statement II: Phenoxide ion is more resonance stabilized than acetate ion.

(1) Both Statement I and Statement II are correct.

(2) Both Statement I and Statement II are incorrect.

(3) Statement I is correct but Statement II is incorrect.

(4) Statement I is incorrect but Statement II is correct.

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⊕ ⊕
5. Statement I: CH 3 – C H2 is more stable than C H3 due to hyperconjugation.
⊕
Statement II : Hyperconjugation in CH 3 – C H2 involves following overlapping:

(1) Both Statement I and Statement II are correct.

(2) Both Statement I and Statement II are incorrect.
(3) Statement I is correct but Statement II is incorrect.
(4) Statement I is incorrect but Statement II is correct.

6. Match the terms mentioned in Column I with the terms in Column II

Column I Column II
(i) Carbocation (a) cyclohexane and 1- hexene
(ii) Nucleophile (b) Conjugation of electrons of
C–H σ bond with empty p-
orbital present at adjacent
positively charged carbon.
(iii) Hyperconjugation (c) sp2 hybridised carbon with
empty p-orbital
(iv) Isomers (d) Ethyne
(v) sp hybridization (e) Species that can receive a
pair of electrons

(vi) Electrophile (f) Species that can supply a

pair of electrons

(1) (i) → (c), (ii) → (f ), (iii) → (b), (iv) → (a), (v) → (d), (vi) → (e)
(2) (i) → (f), (ii) → (c ), (iii) → (b), (iv) → (a), (v) → (d), (vi) → (e)
(3) (i) → (c), (ii) → (f ), (iii) → (a), (iv) → (b), (v) → (d), (vi) → (e)
(4) (i) → (c)), (ii) → (f), (iii) → (b), (iv) → (d), (v) → (a), (vi) → (e)

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7. Match the intermediates given in Column I with their probable structure in Column II.

Column I Column II

(i) Free radical (a) Trigonal planar

(ii) Carbocation (b) Pyramidal

(iii) Carbanion (c) Linear

(1) (i) → (a), (ii) → (a), (iii) → (b) (2) (i) → (b), (ii) → (c), (iii) → (a)

(3) (i) → (a), (ii) → (b), (iii) → (c) (4) (i) → (a), (ii) → (b), (iii) → (b)

8. Match the ions given in Column I with their nature given in Column II.

Column I Column II
..
i CH3 − O
⊕
(a) Stable due to
..− CH2
resonance

ii F3C – C
⊕
(b) Destabilised

due to inductive

effect

iii (c) Stabilised by

hyperconjugation

iv ⊕
CH3 − CH − CH3 (d) A secondary

carbocation

(1) (i) → (a), (b), (ii) → (b), (iii) → (b), (iv) → (c), (d)

(2) (i) → (a), (b), (d), (ii) → (a), (iii) → (b), (iv) → (c), (d)

(3) (i) → (a), (b), (d), (ii) → (b), (iii) → (b), (iv) → (b), (d)

(4) (i) → (a), (c), (d), (ii) → (b), (iii) → (b), (iv) → (c), (d)

ANSWER KEY

Que. 1 2 3 4 5 6 7 8
Ans. 3 1 1 3 3 1 1 1

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Practice Sheet–5 (Previous Year Questions)

1. In which of the following compounds, the C – Cl bond ionisation shall give most stable carbonium

ion? [AIPMT – 2015]

(1) (2)
(3) (4)

2. Consider the following compounds

.
CH3 Ph
.
CH3–C–CH .
Ph–C–Ph
CH3
CH3
I II III

Hyperconjugation occurs in: [AIPMT – 2015]

(1) II only (2) III only (3) I and III (4) I only

3. The correct statement regarding the basicity of arylamines is: [NEET-I – 2016]

(1) Arylamines are generally less basic than alkylamines because the nitrogen lone-pair electrons

are delocalized by interaction with the aromatic ring π electron system

(2) Arylamines are generally more basic than alkylamines because the nitrogen lone-pair electrons

are not delocalized by interaction with the aromatic ring π electron system.

(3) Arylamines are generally more basic than alkylamines because of aryl group.

(4) Arylamines are generally more basic than alkylamines, because the nitrogen atom in arylamines

is sp-hybridized.

4. The pair of electron in the given carbanion, , is present in which of the following orbitals?

[NEET-I – 2016]

(1) 2p (2) sp3 (3) sp2 (4) sp

5. Which among the given molecules can exhibit tautomerism? [NEET-II - 2016]

(1) Both I an II (2) Both II and III (3) III only (4) Both I and III

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6. The correct order of strengths of the carboxylic acid: [NEET-II - 2016]

is:
(1) III > II > I (2) II > I > III (3) I > II > III (4) II > III > I

7. The correct increasing order of basic strength for the following compounds is: [NEET – 2017]

(1) II < III < I (2) III < I < II (3) III < II < I (4) II < I < III

8. Which of the following is correct with respect to -I effect of the substituents ? (R = alkyl)
[NEET(UG) 2018]
(1) –NH2 < –OR < –F (2) –NR2 < –F < –OR
(3) –NR2 > –OR > –F (4) –NR2 < –OR > –F

9. The correct order of the basic strength of methyl substituted amines in aqueous solution is
[NEET(UG) 2019]
(1) (CH3)2NH > CH3NH2 > (CH3)3N (2) (CH3)3N > CH3NH2 > (CH3)2NH
(3) (CH3)3N > (CH3)2NH > CH3NH2 (4) CH3NH2 > (CH3)2NH > (CH3)3N

10. The compound that is most difficult to protonate is [NEET(UG) 2019]

O O O
(1) H H (2) H C H (3) H C CH3 (4) Ph O H
3 3

11. The most stable crbocation among the following is [NEET(UG) 2019(ODISHA)]
⊕ ⊕
(1) (CH3)3CH– CH –CH3 (2) CH3–CH2– CH –CH2–CH3
⊕ ⊕
(3) CH3– CH –CH2–CH2–CH3 (4) CH3–CH2– CH2

12. A tertiary butyl carbocation is more stable than a secondary butyl carbocation because of which of
the following ? [NEET(UG) 2020]
(1) Hyperconjugation
(2) –I effect of –CH3 groups
(3) +R effect of –CH3 groups
(4) –R effect of –CH3 groups

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13. Which of the following substituted phenols is the strongest acid?
[NEET(UG) 2020(COVID-19)]
OH OH OH OH

(1) (2) (3) (4)

NO2 OCH3 C2H5 CH3

14. Which compound amongst the following is not an aromatic compound? [NEET - 2022]

(1) (2) (3) (4)

Θ ⊕ ⊕

15. Given below are two statements: [NEET(UG) 2022]

Statement I : The acidic strength of monosubstituted nitrophenol is higher than phenol because of
electron withdrawing nitro group.
Statement II : o-nitrophenol, m-nitrophenol and p-nitrophenol will have same acidic strength as
they have one nitro group attached to the phenolic ring.
In the light of the above statements, choose the most appropriate answer from the options given
below:
(1) Both Statement I and Statement II are correct.
(2) Both Statement I and Statement II are incorrect.
(3) Statement I is correct but Statement II is incorrect.
(4) Statement I is incorrect but Statement II is correct.

16. Consider the following compounds/species: [NEET(UG) 2023]


(i) (ii) (iii) (iv)

⊕
(v) (vi) (vii)

The number of compounds/species which obey Huckel’s rule is ______.

(1) 4 (2) 6 (3) 2 (4) 5

17. Which amongst the following Compounds /species is least basic ? [NEET(UG) 2023]

(1) (2) (3) (4)

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18. The most stable carbocation among the following is: [NEET(UG) 2024]
CH3

⊕ ⊕
(1) CH2 (2)

CH3 CH3
⊕
CH CH
(3) H3C CH CH3 (4) CH3 CH2
⊕ CH3

19. The correct order of decreasing acidity of the following aliphatic acids is : [NEET(UG) 2025]
(1) HCOOH > CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH
(2) HCOOH > (CH3)3CCOOH > (CH3)2CHCOOH > CH3COOH
(3) (CH3)3CCOOH > (CH3)2CHCOOH > CH3COOH > HCOOH
(4) CH3COOH > (CH3)2CHCOOH > (CH3)3CCOOH > HCOOH

20. Among the given compounds I-III, the correct order of bond dissociation energy of C − H bond
marked with * is : [NEET(UG) 2025]

(1) III > II > I (2) II > III > I (3) II > I > III (4) I > II > III

21. The correct order of decreasing basic strength of the given amines is: [NEET(UG) 2025]
(1) N-ethylethanamine > ethanamine > N-methylaniline > benzenamine
(2) benzenamine > ethanamine > N-methylaniline > N-ethylethanamine
(3) N-methylaniline > benzenamine > ethanamine > N-ethylethanamine
(4) N-ethylethanamine > ethanamine > benzenamine > N-methylaniline

ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21
Ans. 2 2 1 4 3 4 4 1 1 4 3 1 1 4 3 1 2 2 1 3 1

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Practice Sheet–6 (JEE Mains & JEE Advanced NEET Oriented Questions)

1. The increasing order of pKb for the following compounds will be : [JEE(Main)-2020]
N

N NH ,
NH2—CH=NH , CH3NHCH3
(A) (C)
(B)
(1) (A) < (B) < (C) (2) (C) < (A) < (B) (3) (B) < (A) < (C) (4) (B) < (C) < (A)

2. The correct order of stability for the following alkoxides is: [JEE(Main)-2020]
O– O– O–
O2N
NO2 NO2
(A) (B) (C)
(1) (C) > (B) > (A) (2) (C) > (A) > (B) (3) (B) > (C) > (A) (4) (B) > (A) > (C)

3. Arrange the following compounds in increasing order of C—OH bond length: methanol, phenol,
p–ethoxyphenol [JEE(Main)-2020]
(1) phenol < methanol < p-ethoxyphenol (2) phenol < p-ethoxyphenol < methanol
(3) methanol < p-ethoxyphenol < phenol (4) methanol < phenol < p-ethoxyphenol

4. The correct order of heat of combustion for following alkadienes is: [JEE(Main)-2020]

(a) (b) (c)

(1) (a) < (b) < (c) (2) (b) < (c) < (a) (3) (c) < (b) < (a) (4) (a) < (c) < (b)

5. Which of the following has the shortest C—Cl bond? [JEE(Main)-2020]

(1) Cl–CH=CH–OCH3 (2) Cl–CH=CH–CH3
(3) Cl–CH=CH2 (4) Cl–CH=CH–NO2

6. The decreasing order of basicity of the following amines is: [JEE(Main)-2020]

NH2
N NH2

H
(I) (II) (III) (IV)
(1) (I) > (III) > (IV) > (II) (2) (III) > (I) > (II) > (IV)
(3) (III) > (II) > (I) > (IV) (4) (II) > (III) > (IV) > (I)

7. Among the following compounds, which one has the shortest C—Cl bond? [JEE(Main)-2020]

H3C
H3C Cl
(1) H3C—Cl (2) H C (3) (4)
3

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8. Which one of the following compounds is non-aromatic ? [JEE(Main)-2021]
⊕

(1) (2) (3) (4)

⊕
O

9. The correct order of acid character of the following compounds is : [JEE(Main)-2021]

OH COOH COOH COOH

NO2 CH3
(I) (II) (III) (IV)
(1) II>III>IV>I (2) III>II>I>IV (3) IV>III>II>I (4) I>II>III>IV

10. A. Phenyl methanamine B. N,N-Dimethylaniline [JEE(Main)-2021]

C. N-Methyl aniline D. Benzenamine
Choose the correct order of basic nature of the above amines.
(1) D > C > B > A (2) D > B > C > A
(3) A > C > B > D (4) A > B > C > D

11. In the following molecule, [JEE(Main)-2021]

a
H3C
b c
C C—O
H H
Hybridisation of Carbon a, b and c respectively are :
(1) sp3, sp2, sp2 (2) sp3, sp2, sp (3) sp3, sp, sp (4) sp3, sp, sp2

12. Among the following, the aromatic compounds are: [JEE(Main)-2021]

(A) O (B) (C) (D)

Θ ⊕

Choose the correct answer from the following options:

(1) (A) and (B) only (2) (A), (B) and (C) only
(3) (B), (C) and (D) only (4) (B) and (C) only

13. Which of the following is least basic? [JEE(Main)-2021]

•• •• ••
(
(1) CH3CO NH ) 2
( ) ••
(2) CH3CO NH C2H5 (
(3) CH3H5 2 N ) (4) (CH H )
3 5 2
NH

14. Which of the following is an aromatic compound ? [JEE(Main)-2021]

⊕
Θ
(1) Θ (2) (3) (4)
Θ

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⊕ ⊕
⊕ ⊕
15. [JEE(Main)-2021]

Among the given species the Resonance stabilised carbocations are:

(1) (C) and (D) only (2) (A), (B) and (C) only
(3) (A), (B) and (D) only (4) (A) and (B) only

16. Which one of the following compounds does not exhibit resonance ? [JEE(Main)-2021]
CH2OH
(1) CH3CH2CH2CONH2 (2)

(3) CH3CH2OCH = CH2 (4) CH3CH2CH = CHCH2NH2

17. Which one of the following compounds will liberate CO2, when treated with NaHCO3?
[JEE(Main)-2021]
⊕Θ ⊕ Θ
(1) (CH3 )4 NOH (2) (CH3 )3 NHCl

(3) CH3NH2 (4)

18. Which one among the following resonating structures is not correct? [JEE(Main)-2021]
⊕ ⊕ ⊕ ⊕ ⊕
(1) ⊕ (2) (3) ⊕ (4)

19. Which among the following is the strongest acid ? [JEE(Main)-2021]

(1) (2) (3) (4)CH3CH2CH2CH3

20. Given below are two statements: [JEE(Main)-2021]

Statement I : Aniline is less basic than acetamide.
Statement II : In aniline, the lone pair of electrons on nitrogen atom is delocalised over benzene
ring due to resonance and hence less available to a proton.
Choose the most appropriate option;
(1) Both statement I and statement II are true.
(2) Both statement I and statement II are false.
(3) Statement I is true but statement II is false.
(4) Statement I is false but statement II is true.

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21. Given below are two statements: [JEE(Main)-2021]
Statement I: Hyperconjugation is a permanent effect.
 +

Statement II: Hyper conjugation in ethyl cation  CH3 − CH2  involves the over lapping of Csp2 − H1s
 
bond with empty 2p orbital of other carbon.
Choose the correct option:
(1) Both statement I and statement II are true
(2) Statement I is incorrect but statement II is true
(3) Statement I is correct but statement II is false
(4) Both Statement I and statement II are false.

22. Which one of the following compounds is not aromatic? [JEE(Main)-2021]

(1) (2) (3) (4)

⊕
CH2

⊕ ⊕ ⊕
23. CH2 = CH CH3 — CH2 HC ≡ C
A B C D

The correct order of stability of given carbocation is : [JEE(Main)-2021]

(1) C > A > D > B (2) D > B > C > A (3) A > C > B > D (4) D > B > A > C

24. Which of the following is an example of conjugated diketone? [JEE(Main)-2022]

O
(1) (2) CH3 —C—CH2 O

(3) (4)

25. Which of the following structures are aromatic in nature ? [JEE(Main)-2022]

(1) A, B, C and D (2) Only A and B (3) Only A and C (4) Only B, C and D

26. Which of the following carbocations is most stable? [JEE(Main)-2022]

⊕
(1) (2) (3) ⊕ (4)
⊕

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27. Arrange the following in decreasing acidic strength. [JEE(Main)-2022]

(1) A > B > C > D (2) B > A > C > D (3) D > C > A > B (4) D > C > B > A

28. Which of the following compounds is not aromatic ? [JEE(Main)-2022]

(1) (2) (3) (4)

29. Which of the following is not an example of benzenoid compound ? [JEE(Main)-2022]

(1) (2) (3) (4)

30. 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. [JEE(Main)-2022]

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.
(1) Both A and R are correct and R is the correct explanation of A.
(2) Both A and R are correct but R is NOT the correct explanation of A
(3) A is correct but R is not correct
(4) A is not correct but R is correct

31. Among the following marked proton of which compound shows lowest pKa value ?
[JEE(Main)-2022]

(1) (2)

(3) (4)

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32. Which among the following is the strongest Bronsted base? [JEE(Main)-2022]

(1) (2) (3) (4)

33. Increasing order of stability of the resonance structure is : [JEE(Main)-2023]

Θ ⊕
OHC OHC
NH2 NH2
A. ⊕ B. Θ
⊕
Θ +
Θ NH2
H OCH
C. NH2 D.

(1) C < D < B < A (2) C < A < B < D (3) D < C < A < B (4) D < C < B < A

34. Given below are two statements, one is labelled as Assertion A and the other is labelled as Reason R.

[JEE(Main)-2023]

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:

(1) A is true but R is false.

(2) A is false but R is true.

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

(4) Both A and R are correct but R is NOT the correct explanation of A.

35. The correct order in aqueous medium of basic strength in case of methyl substituted amines

is : [JEE(Main)-2023]

(1) Me2NH > MeNH2 > Me3N > NH3

(2) Me2NH > Me3N > MeNH2 > NH3

(3) NH3 > Me3N > MeNH2 > Me2NH

(4) Me3N > Me2NH > MeNH2 > NH3

36. The increasing order of pKa for the following phenols is [JEE(Main)-2023]
(1) 2,4-Dinitrophenol (2) 4-Nitrophenol

(3) 2,4,5-Trimethylphenol (4) Phenol

(5) 3-Chlorophenol

(1) 1 < 2 < 5 < 4 < 3 (2) 3 < 4 < 5 < 2 < 1

(3) 4 < 2 < 5 < 3 < 1 (4) 5 < 3 < 4 < 2 < 1

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37. The most stable carbocation for the following is: [JEE(Main)-2023]
NH2 NH2 NH2 NH2

⊕ ⊕
⊕
(a) ⊕
(b) (c) (d)
(1) c (2) d (3) b (4) a

38. The correct order of pKa values for the following compounds is: [JEE(Main)-2023]
OH OH OH OH

N NO2
(a) (b) (c) (d)
(1) c > a > d > b (2) b > d > a > c (3) b > a > d > c (4) a > b > c > d

39. Resonance in carbonate ion (CO23− ) is [JEE(Main)-2023]

O O– O–
C C C
–
O O– –
O O O O–
Which of the following is true?
(1) It is possible to identify each structure individually by some physical or chemical method.
(2) All these structures are in dynamic equilibrium with each other.
(3) Each structure exists for equal amount of time.
2−
(4) (CO3 ) has a single structure i.e., resonance hybrid of the above three structures

40. Given below are two statements: [JEE(Main)-2023]

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:
(1) Both Statement I and Statement II are true
(2) Statement I is true but Statement II is false
(3) Statement I is false but Statement II is true
(4) Both Statement I and Statement II are false

41. Given below are two statements, one is labelled as Assertion A and the other is labelled as Reason
R. [JEE(Main)-2023]
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:
(1) A is false but R is true
(2) Both A and R are correct and R is the correct explanation of A
(3) Both A and R are correct but R is NOT the correct explanation of A
(4) A is true but R is false

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42. Compound from the following that will not produce precipitate on reaction with AgNO3 is :
[JEE(Main)-2023]
Br
(1) (2) Br

(3) Br (4) CH=CH–CH2–Br

43. Among the following compounds, the one which shows highest dipole moment is [JEE(Main)-2023]
O

(1) (2)

(3) (4)

44. Which of the following has highly acidic hydrogen ? [JEE(Main)-2024]

CH3
H3 C CH2 CH2 H3 C
(1) C C CH3 (2)
O O O
O
H3 C CH2 C O
C CH2 CH3 C CH3
O H3 C C
(3) (4)
O

45. Which of the following is strongest Bronsted base [JEE(Main)-2024]

H
N
(1) (2) NH

NH2 H
N
..
(3) (4)

46. The set of meta directing functional groups from the following sets is : [JEE(Main)-2024]

(1) −CN, −NH2 , −NHR, −OCH3 (2) −CN, −CHO, −NHCOCH3 , −COOR

(3) −NO2 , −NH2 , −COOH, −COOR (4) −NO2 , −CHO, −SO3H, −COR

47. The functional group that shows negative resonance effect is : [JEE(Main)-2024]

(1) −OH (2) −OR (3) −COOH (4) −NH2

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48. Ionic reactions with organic compounds proceed through : [JEE(Main)-2024]

(A) homolytic bond cleavage

(B) heterolytic bond cleavage

(C) free radical formation

(D) primary free radical

(E) secondary free radical

Choose the correct answer from the options given below :

(1) (A) only (2) (C) only (3) (B) only (4) (D) and (E) only

49. The difference in energy between the actual structure and the lowest energy resonance structure

for the given compound is [JEE(Main)-2024]

(1) electromeric energy (2) ionization energy

(3) hyperconjugation energy (4) resonance energy

50. The interaction between π bond and lone pair of electrons present on an adjacent atom is

responsible for [JEE(Main)-2024]

(1) Resonance effect (2) Electromeric effect

(3) Inductive effect (4) Hyperconjugation

51. Which of the following molecule/species is most stable? [JEE(Main)-2024]

⊕ ⊕ ..
(1) (2) (3) (4)

52. A species having carbon with sextet of electrons and can act as electrophile is called

[JEE(Main)-2024]

(1) pentavalent carbon (2) carbon free radical

(3) carbocation (4) carbanion

53. Among the given organic compounds, the total number of aromatic compounds is______.

[JEE(Main)-2024]
..

(A) (B) (C) (D)

Θ
(1) 1 (2) 2 (3) 3 (4) 4

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54. Among the following, total number of meta directing functional groups is (Integer based)

–OCH3, –NO2, –CN, –CH3, –NHCOCH3, –COR, –OH, –COOH, –Cl. [JEE(Main)-2024]

55. Which one the following compounds will readily react with dilute NaOH ? [JEE(Main)-2024]

(1) C6H5CH2OH (2) C2H5OH (3) CH3( )3 COH (4) C6H5OH

56. The shape of carbocation is : [JEE(Main)-2024]

(1) trigonal planar (2) diagonal pyramidal

(3) tetrahedral (4) diagonal

57. Which of the following are aromatic? [JEE(Main)-2024]

(A) (B) (C) (D)

(1) B and D only (2) A and C only (3) A and B only (4) C and D only

58. Correct order of basic strength of Pyrrole , Pyridine and Piperidine is:

[JEE(Main)-2024]

(1) Piperidine > Pyridine > Pyrrole

(2) Pyrrole > Pyridine > Piperidine

(3) Pyridine > Piperidine > Pyrrole

(4) Pyrrole > Piperidine > Pyridine

59. Relative stability of the contributing structures is: [JEE(Main)-2024]

O O– O+
..
..

.. .. .. .. ..
II + I – I
CH2=CH–C–H CH2–CH=C–H ..
CH2–CH=C-H
(I) (II) (III)

(1) (I) > (III) > (II) (2) (I) > (II) > (III)

(3) (II) > (I) > (III) (4) (III) > (II) > (I)

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60. For the given compounds, the correct order of increasing pKa value : [JEE(Main)-2024]

(A) OH (B) O2N OH

OCH3
NO2
(C) HO (D)
OH
(E) OH OCH3

(1) (E) < (D) < (C) < (B) < (A)
(2) (D) < (E) < (C) < (B) < (A)
(3) (E) < (D) < (B) < (A) < (C)
(4) (B) < (D) < (C) < (A) < (E)

61. The correct stability order of the following resonance structures of CH3 − CH = CH − CHO is
[JEE(Main)-2024]

(1)II > III > I (2)III > II > I (3)I > II > III (4)II > I > III

62. Match List -I with List II: [JEE(Main)-2024]

List-I Mechanism steps List–II Effect

(A) (I) –E effect

(B) (II) –R effect

(C) (III) +E effect

(D) (IV) +R effect

Choose the correct answer from the options given below :

(1) (A) - (IV), (B) - (III), (C) - (I), (D) - (II)
(2) (A) - (III), (B) - (I), (C) - (II), (D) - (IV)
(3) (A) - (II), (B) - (IV), (C) - (III), (D) - (I)
(4) (A) - (I), (B) - (II), (C) - (IV), (D) - (III)

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63. What will be the decreasing order of basic strength of the following conjugate bases?

−
OH,RO,CH3COO,CI [JEE(Main)-2024]

(1) CI > OH > RO > CH3COO

(2) RO > OH > CH3COO > CI

(3) OH > RO > CH3COO > CI

(4) Cl > RO > OH > CH3COO

64. Which among the following is incorrect statement? [JEE(Main)-2024]

(1) Electromeric effect dominates over inductive effect

(2) The electromeric effect is, temporary effect

(3) The organic compound shows electromeric effect in the presence of the reagent only

( )
(4) Hydrogen ion H+ shows negative electromeric effect

65. Number of molecules from the following which can exhibit hydrogen bonding is____(nearest integer)
NO2
CH3OH,H2O, C2H6,C6H6, HF,NH3 [JEE(Main)-2024]
OH

66. Number of carbocation from the following that are not stabilized by hyperconjugation is………...

[JEE(Main)-2024]

67. Total number of aromatic compounds among the following compounds is _______.

[JEE(Main)-2024]

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68. How many compounds among the following compounds show inductive, mesomeric as well as

hyperconjugation effects? [JEE(Main)-2024]

69. The most stable carbocation from the following is : [JEE(Main)-2025]

(1) (2)

(3) (4)

70. The correct stability order of the following species/molecules is : [JEE(Main)-2025]

(1) q > r > p (2) r > q > p (3) q > p > r (4) p > q > r

71. Which one of the carbocations from the following is most stable ? [JEE(Main)-2025]

(1)

(2)

(3)

(4)

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72. Identify correct statement/s : [JEE(Main)-2025]

(A) −OCH3 and −NHCOCH3 are activating group

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

(C) -CN and −SO3H 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 :

(1) (A), (C) and (D) only (2) (A), (B) and (E) only

(3) (A) only (4) (A) and (C) only

73. The correct order of stability of following carbocations is : [JEE(Main)-2025]

(1) A > B > C > D (2) B > C > A > D (3) C > B > A > D (4) C > A > B > D

74. Which among the following halides will generate the most stable carbocation in Nucleophillic

substitution reaction? [JEE(Main)-2025]

(1) (2)

(3) (4)

75. Consider the following compound (X) [JEE(Main)-2025]

The most stable and least stable carbon radicals, respectively, produced by homolytic cleavage of

corresponding C − H bond are :

(1) I, IV (2) III, II (3) II, I (4) II, IV

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76. The correct order of basic nature in aqueous solution for the bases [JEE(Main)-2025]

NH3 ,H2 N − NH2 ,CH3CH2NH2 , (CH3CH2 ) NH and (CH3CH2 ) N is :

2 3

(1)
(
NH3 < H2 N − NH2 < CH3CH2 N ) 3
(2)
(
H2 N − NH2 < NH3 < CH3CH2 N ) 3

(
< CH3CH2NH2 < CH3CH2 NH )
2
(
< CH3CH2NH2 < CH3CH2 NH ) 2

NH2 − NH2 < NH3 < CH3CH2NH2 NH3 < H2 N − NH2 < CH3CH2NH2
(3) (4)
( ) (
< CH3CH2 N < CH3CH2 NH
3
)
2
( ) (
< CH3CH2 NH < CH3CH2 N
2
) 3

77. Designate whether each of the following compounds is aromatic or not aromatic. [JEE(Main)-2025]

(1) a, c, d, e, h aromatic and b, f, g not aromatic.

(2) e, g aromatic and a, b, c, d, f, h not aromatic.

(3) b, e, f, g aromatic and a, c, d, h not aromatic.

(4) a, b, c, d aromatic and e, f, g, h not aromatic.

78. The least acidic compound, among the following is: [JEE(Main)-2025]

(1) B (2) C (3) D (4) A

79. Given below are two statements : [JEE(Main)-2025]

Statement I : Hyperconjugation is not a permanent effect.

Statement II : In general, greater the number of alkyl groups attached to a positively charged C-

atom, 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

(1) Statement I is true but statement II is false

(2) Botn statement I and statement II are false

(3) Statement I is false but statement II is true

(4) Bot statement I and statement II are true

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80. Given below are two statements. [JEE(Main)-2025]
4 3 2 1 4 3 2 1
Statement I: The dipole moment of CH3 − CH = CH− CH = 0 is greater than CH3 − CH2 − CH2 − CH =
0

Statement II: C1–C2 bond length of CH3 − CH = CH − CH = O is greater than C1–C2 bond length of
4 3 2 1
CH3 − CH2 – CH2 − CH =
O
4 3 2 1
In the light of the above statements, choose the correct answer from the options given below:
(1) Statement I is false but Statement II is true
(2) Both Statement I and Statement II are false
(3) Statement I is true but Statement II is false
(4) Both Statement I and Statement II are true

81. The correct order of basicity for the following molecules is : [JEE(Main)-2025]

(1) P > Q > R (2) R > P > Q (3) Q > P > R (4) R > Q > P

82. In which pairs, the first ion is more stable than the second? [JEE(Main)-2025]

(A) (B)

(C) (D)

(1) (B) & (D) only (2) (A) & (B) only (3) (B) & (C) only (4) (A) & (C) only

83. Which of the following compounds is least likely to give effervescence of CO2 in presence of aq.

NaHCO3? [JEE(Main)-2025]

(1) (2)

(+) (−)
(3) Ph − NH3 Cl (4)

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84. Match the LIST-I with LIST-II [JEE(Main)-2025]

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.

D. Electrophile IV. sp2/sp3 Hybridized carbon with one unpaired electron.

Choose the correct answer from the options given below :

(1) A-IV, B-II, C-III, D-I (2) A-II, B-III, C-I, D-IV

(3) A-III, B-IV, C-II, D-I (4) A-III, B-IV, C-I, D-II

2Moles NaNH
2 → A. The product (A) will be:
85.  [JEE(Advanced)-2007]

(1) (2)

(3) (4)

86. The correct acidity order of the following is: [JEE(Advanced)-2007]

(1) (III) > (IV) > (II) > (I)

(2) (IV) > (III) > (I) > (II)

(3) (III) > (II) > (I) > (IV)

(4) (II) > (III) > (IV) > (I)

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87. Amongst the following, the number of compounds soluble in aqueous NaOH is:

[JEE(Advanced)-2010]

88. The total number of contributing structures showing hyperconjugation (involving C–H bonds) for
the following carbocation is. [JEE(Advanced)-2011]

89. Among the following compounds, the most acidic is: [JEE(Advanced)-2011]
(1) p-Nitrophenol (2) p-Hydroxybenzoic acid
(3) o-Hydroxybenzoic acid (4) p–Toluic acid

90. Which of the following molecules, in pure from, is (are) unstable at room temperature?
[JEE(Advanced)-2012]

(1) (2) (3) (4)

91. The hyper conjugative stabilities of tert-butyl cation and 2-butene, respectively, are due to
(1) σ→π (empty) and σ→π∗ electron delocalizations [JEE(Advanced)-2013]
(2) σ→σ∗ and σ→π electron delocalizations
(3) σ→π (filled) and σ→π electron delocalizations
(4) p (filled)→σ∗ and σ→π∗ electron delocalizations

92. The compound that does NOT liberate CO2, on treatment with aqueous sodium bicarbonate solution,
is– [JEE(Advanced)-2013]
(1) Benzoic acid (2) Benzene sulphonic acid
(3) Salicylic acid (4) Carbolic acid (phenol)

93. The correct order of acidity for the following compounds is: [JEE(Advanced)-2016]

(1) I > II > III > IV (2) III > I > II > IV
(3) III > IV > II > I (4) I > III > IV > II

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94. Among the following, the number of aromatic compound (s) is– [JEE(Advanced)-2017]

95. The order of basicity among the following compounds is [JEE(Advanced)-2017]

(1) II > I > IV > III (2) IV > I > II > III (3) I > IV > III > II (4) IV > II > III > I

96. The correct order of acid strength of the following carboxylic acids is: [JEE(Advanced)-2019]

(1) I > II > III > IV (2) I > III > II > IV (3) II > I > IV > III (4) III > II > I > IV

97. Consider the depicted hydrogen (H) in the hydrocarbons given below. The most acidic hydrogen (H)
is

(1) (2) (3) (4)

[JEE(Advanced)-2025]

ANSWER KEY

Que. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20
Ans. 3 1 2 1 4 3 3 2 1 4 1 4 1 1 4 4 2 4 1 4
Que. 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40
Ans. 3 1 3 3 2 4 1 3 1,2 4 3 4 2 3 1 1 1 2 4 2
Que. 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60
Ans. 3 1 1 1 1 4 3 3 4 1 1 3 3 4 4 1 1 1 2 4
Que. 61 62 63 64 65 66 67 68 69 70 71 72 73 74 75 76 77 78 79 80
Ans. 2 1 2 4 5 5 1 4 1 1 2 1 4 4 3 3 1 3 3 3
Que. 81 82 83 84 85 86 87 88 89 90 91 92 93 94 95 96 97
Ans. 4 2 4 4 3 1 4 6 3 2,3 1 4 1 5 2 1 2

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