Single Choice Correct:

Q.1 Identify the species not capable of acting as an electrophile.

(A) BCl3 (B) AlCl3 (C) NH 4 (D) H+

Q.2 Identify the strongest nucleophile amongst the following in aqueous medium.
(A) HS (B) OH (C) F (D) NH 2

Q.3 Which free radical is the most stable one?

  

(A) CH2 (B) CH2 (C) (CH3)3C (D) (CH3)2CH

NO2

Q.4 Which is the most stable singlet carbene among the following?
.. .. .. ..
(A) CF2 (B) CCl2 (C) CBr2 (D) CI2

Q.5 Which of the following species cannot function as an electrophile?

..
(A) HCl (B) CCl2 (C) SiF4 (D) CH2=CH2

Q.6 Which of these species are electrophiles:

(A) CO2 (B) CCl4 (C) AlCl3 (D) All of these

Q.7 In which of the following molecules all the effects namely inductive, mesomeric and
hyperconjugation operate:
(A) Cl (B) COCH3 (C) CH3 (D)

CH3 CH3
Q.8 For the following reactions:
(I)  (II) 
Cl + Cl, H1° Cl + Cl, H2°


(III) (IV) 
CH2Cl CH2 + Cl, H3° Cl + Cl, H4°

The correct decreasing order of enthalpies of formation of carbocation is

(A) H1o > H o2 > H o3 > H o4 (B) H o4 > H1o > H o2 > H o3
(C) H o3 > H o2 > H1o > H o4 (D) H o2 > H1o > H o4 > H o3

Q.9 Which of the following reaction intermediates are electrophilic in character?

(1) Carbocation (2) Carbanion (3) Free radicals (4) Singlet carbenes
(A) Only (1) (B) (1) and (3) (C) (1) and (4) (D) (1), (2), (3) and (4)

Q.10 Consider the following three halides

(A) CH3CH2Cl (B) CH2=CHCl (C) HCCCl

Arrange these three compounds in decreasing order of CCl bond length.

(A) (A) > (B) > (C) (B) (C) > (B) > (A) (C) (B) > (C) > (A) (D) (A) > (C) > (B)
Q.11 The most stable free radical is
Me

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

Q.12 Which of the following compounds give white precipitate with AgNO3?
Cl Cl CH2Cl

(I) (II) (III)

(A) (I) and (II) (B) (II) and (III) (C) (I) and (III) (D) none of these

Q.13 Which one of the compounds behaves as an electrophile as well as nucleophile?

(A) Acetone (B) Cyanide ion (C) Nitrite ion (D) Sulphite ion

Q.14 Which one of the following has the highest nucleophilicity?

(A) F (B) OH (C) CH3 (D) NH 2

Q.15 Melting point of which compound is maximum?

(A) Chlorobenzene (B) odichlorobenzene
(C) mdichlorobenzene (D) pdichlorobenzene

Q.16 Which one of the following compound is least soluble in water?

(A) Phenol (B) onitrophenol (C) mnitrophenol (D) pnitrophenol

Q.17 Which compound will have lowest boiling point?

O O O O O O
N N N O O
OH N
(a) (b) (c) (d) HO OH
OH
HO OH
OH OH OH
Q.18 Which of the following is protic solvent?
O
(A) HCOOH (B) CH3CN (C) C2H5OC2H5 (D)

Q.19 Arrange the following compounds in the decreasing order of hetrolytic bond dissociation energy of
CCl bond.

CH2Cl CH2Cl CH2Cl CH2Cl

OCH3

OCH3
OCH3
(I) (II) (III) (IV)
(A) (II) > (III) > (IV) > (I) (B) (III) > (I) > (II) > (IV)
(C) (I) > (II) > (III) > (IV) (D) (IV) > (III) > (II) > (I)
 I
O2 N 3 2 NO 2
1
Q.20 4 6 Which of the following statements is true about this molecule:
5
NO 2
(A) C5  N bond is longer than C1  N and C3  N bonds.
(B) C5N bond is shorter than C1  N bond and latter is shorter than C3N bond.
(C) All three C  N bonds are of same length
(D) Cl  N and C3  N bonds are of same length but they are longer than C5  N bond.

2
3
1
Q.21 Which of the following statements is true about this molecule.
4

(A) Cl  C2 and C3  C4 bonds are of same length

(B) Cl  Cl2 bond is shorter than C3  C4 bond
(C) Cl  C2 bond is longer than C3  C4 bond
(D) Cl  C2 and C2  C3 bonds are of same length

NH2 NH2 NH2

Q.22 I. II. III.

CHO
The order of the C  N bond lengths among these compounds is :
(A) III > I > II (B) II > I > III (C) III > II > I (D) I > II > III
Q.23 The order of the C  O bond lengths among these compounds is :
OH OH OH

I. II. III.
NO 2
NO 2

(A) I > II > III (B) III > II > I (C) II > I > III (D) III > I > II

Q.24 Which of the following compounds do not have all C  O bonds of same length :

(A) CO2 (B) HCOOH (C) CO 32  (D) HCO O

Q.25 Which Among of the following compounds do not have all C  C bonds of same length :

(A) (B) (C)  (D) O

Q.26 Among the following compounds which has longest C  O bond :

O O O O
(A) C (B) C (C) C (D) C
H H H F H NH 2 H OH
Q.27 HOC  N HN  C  O
( Cyanic acid ) ( Isocyanic acid )
Loss of proton from these two acids produces :
(A) same anion (B) different anions (C) same cation (D) different cations

Q.28 I. CH2  CH  CH  CH3 II. CH2  CH  CH  CH3

Br Br

Ionization of these compounds produces :Br and
(A) same cation (B) different cations (C) same anion (D) different anions

Q.29 The order of H  N  H bond angle is :

I. NH2 II. NH3 III. CH3  NH2 IV . CH3  C  NH2

O
(A) IV > I > II > III (B) I > IV > II > III (C) I > IV > III > II (D) II < III < I < IV
O
Q.30 The correct order of  C  bond length is :
O
I. CH3  C  Cl II. CH3  C  OH III.CH3  C  O  C  CH3 IV. CH3  C  NH2
O O O O
 
V. CH3  C  O Na
O

(A) IV > V > II > III > I (B) I < II < III < IV < V
(C) IV > II > V > III > I (D) V > IV > II > III > I

Q.31 I II. III. IV .

 

 
Resonance energies of these cations are in the order :
(A) I > II > IV > III (B) IV > III > I > II (C) IV > III > II > I (D) II > I > III > IV

  
Q.32 I. II. III.
O N
H order :
Resonance energies of these cations are in the
(A) II > I > III (B) I > II > III (C) III > II > I (D) III > I > II

Q.33 I. II. III.

Which of the following choice is the correct order of resonance energy of these molecules :
(A) I > II > III (B) III > II > I (C) II > I > III (D) III > I > II
Q.34 I. CH2 = CH  F II. CH2 = CH  OH III. CH2 = CH  NH2
Which of the following choice is the correct order of resonance energy of these molecules:
(A) I > II > III (B) III > II > I (C) II > I > III (D) II > III > I

O O
Q.35 I. CHO II.  C  OCH3 III.  C  NH2

Arrange these groups in decreasing order of their electron  withdrawing power in resonance:
(A) I > II > III (B) I > III > II (C) III > II > I (D) II > III > I

Q.36 I.  CH = CH2 II. CH=CHOCH3 III. CH=CHNO2

Arrange these groups in decreasing order of their electron  donation power in resonance:
(A) II > III > I (B) III > II > I (C) II > I > III (D) III > I > II

Q.37 In which of the following molecules   electron  density in ring is maximum :


NO2 O NH 2 OCH3
(A) (B) (C) (D)

Q.38 The   electron density in ring is maximum in :

CH 3 CH 2  CH 3 H 3 C  CH  CH3 CH3
C  CH3
(A) (B) (C) (D)
CH3


OH HO HO
Q.39 I. CH3 II. CH3 III. 
CH3
CH3  C  N CH 3  C N CH3 CH3  C  N
 CH3
CH3
The stability order of these canonical structure is :
(A) I > II > III (B) II > III > I (C) I > III > II (D) III > I > II
CH2  CH  OCH3  
Q.40 C H 2  CH  O CH3
I. II.

 
CH2  CH  NHCH3 C H 2  CH  NH CH 3
I. II.
Which of the following statements is true about the contribution of I and II in respective resonance
hybrids:
(A) Both I and II have same contributions
(B) I contributes more than II
(C) I contributes less than II
(D) It is not possible to judge their relative contributions
O O O O
Q.41 (I) H  C  OH (II) H  C  O  H (III) H  C

 OH (IV) H  C

OH


Which of the following order is correct for stability of the four contributing structures?
(A) I > II > III > IV (B) I > II > IV > III (C) I > III > II > IV (D) I > IV > III > II
 O
Q.42 I. O Br II. Br III. N Br
CH 3

Br
The ease of ionisation of these compounds to produce is in the order as:
(A) I > II > III (B) III > I > II (C) II > III > I (D) III > II > I

CH3
Q.43 CH3O  CH  CH  CH2  Cl CH3O  CH2  CH2  Cl N  CH  CH  CH2  Cl
CH3
I. II. III.

The order of the ease of ionisation of these compounds to produce carbocations and Cl is :
(A) I > III > II (B) III > I > II (C) II > III > I (D) II > I > III

Q.44 Which of the following C  H bond is weakest for homolytic fission ?

H CH 2H

(A) (B) (C) CH3-H (D) H

Q.45 The correct order of CH1 , CH2 , CH3 bond energies is :

CH3
H3  CH  CH  C  CH2
(A) C  H3 > C  H1 > C  H2 (B) C  H3 > C  H2 > H
C2HH11
(C) C  H2 > C  H1 > C  H3 (D) C  H1 > C  H3 > C  H2

CH  CH  CH2
Q.46 The order of ease of removal of hydrogen
H2 H3 H4
H1

(A) H1 > H4 > H3 > H2 (B) H2 > H3 > H4 > H1

(C) H3 > H2 > H4 > H1 (D) H4 > H3 > H2 > H1

Q.47 H Arrange the B.E. of (CH) bonds indicated by , , 

H 3C
H
H
H
(A) C  H   C  H   C  H   C  H  (B) C  H   C  H   C  H   C  H
(C) C  H   C  H   C  H   C  H  (D) C  H   C  H   C  H   C  H 
Q.48 The correct order of stability of following redicals is :
 


 
I II III IV V

(A) I > II > V > III >IV (B) IV > II > I > V > III
(C) IV > II > I > III > V (D) II > IV > I > V > III

Q.49 Hetrolytic cleavage is easiest in :

CH3
I. CH3  Cl II. CH3  CH 2  Cl III.CH 3  C| H  Cl IV. CH3  C  Cl
CH3 CH3
(A) I (B) II (C) III (D) IV

Q.50 Stability of alkyl carbocations can be explained by

(A) inductive effect (B) hyper conjugation
(C) resonance (D) electromeric effect

Q.51 Which of the following will form precipitates with aq. AgNO3?

(A) —Br (B) —Br (C) —Br (D) Br

ASSERTI ON & REASONI NG TYPE

Read the following question and choose the correct answer:

(A) If both Assertion and Reason are true and the Reason is correct explanation of the Assertion.
(B) If both Assertion and Reason are true, but Reason is not correct explanation of the Assertion.
(C) If Assertion is true, but Reason is false.
(D) If Assertion is false, but the Reason is true.

Q.1 Assertion : o – Hydroxyacetophenone is less acidic than its meta isomer.

Reason : The conjugate base of o–hydroxyacetophenone is more stable than that of meta
isomer.

Q2. Assertion : CHF3 is less acidic than CHCl3.

Reason : Electron withdrawing groups increase the acidic nature.
(A) A (B) B (C) C (D) D

Q3. Assertion : 7–Bromo–1,3,5–cycloheptatriene exists as ionic compound.

Reason : Tropylium ion is aromatic and is stable.
(A) A (B) B (C) C (D) D
Q4. Assertion : Water is a good solvent for ionic compounds but poor one for covalent compounds.
Reason : Hydration energy of ions releases sufficient energy to overcome lattice energy and
break hydrogen bonds in water while covalent bonded compounds interact so weakly
that even van der Waals' forces between molecules of covalent compounds cannot
be broken.
(A) A (B) B (C) C (D) D
Q5. Assertion : In benzyne, two out of six carbon atoms are sp-hybridized.
Reason : It contains a carbon–carbon triple bond containing a –bond formed by lateral
overlap of sp2 hybridised orbitals.
(A) A (B) B (C) C (D) D

Q6. Assertion : Singlet carbene has a linear structure.

Reason : The carbon atom in singlet carbene is sp2–hybridized.
(A) A (B) B (C) C (D) D

Q7. Assertion : Heterolytic fission involves the breaking of a covalent bond in such a way that both
the electrons of the shared pair are carried away by one of the atoms.
Reason : Heterolytic fission occurs readily in polar covalent bonds.
(A) A (B) B (C) C (D) D

Q8. Assertion : HC  C is more stable than H2C = C.

Reason : HC  C has more scharacter than H2C = C.
(A) A (B) B (C) C (D) D

Q9. Assertion : o-hydroxy benzoic acid is much more acidic than benzoic acid.
Reason : Anion formed from o-hydroxy benzoic acid is stabilized by intramolecular hydrogen
bond.
(A) A (B) B (C) C (D) D

COMPREHENSI ON TYPE

Comprehension # 1

Hydrogen of carbon is acidic in nature when functional group is strong electron withdrawing
group such as NO2, COOR, CN etc. If carbon is present between two electron withdrawing
groups, the acidity of an hydrogen is even greater. Aldehydes and ketones having hydrogen
exist in solution as an equilibrium mixture of two isomeric forms, the keto form and the enol form.
The anions formed by deprotonation of hydrogen bear most of the negative charge on oxygen and
are referred to as enolate ions.

Q1. Which one of the following compound has maximum pKa value?
O
(A) CH3CHO (B) CH3NO2 (C) CH3CCH3 (D) CH3COOC2H5
Q2. Which of these compounds contains active methylene group?
O COOC2H5 CN
(A) CH3CCH2COOC2H5 (B) CH2 (C) CH2 (D) all of these
COOC2H5 NO2

O
NH2–/
Q3. (A). The Compound (A) should be
O
O O O
.. ..
..
(A) O (B) O (C) O (D) none of these

Comprehension # 2

Hyperconjugation involves the conjugation between –electrons of a single carbon hydrogen bond
and the –electron of the adjacent multiple bond. It is also called no bond resonance because in the
different canonical forms, no bond is shown between carbon and hydrogen atom of the alkyl group.
The necessary and sufficient conditions for Hyperconjugation are:
(i) Compound should have at least one sp2 hybrid carbon of either alkene, carbocation or alkyl
free radical.
(ii) –carbon with respect to sp2 hybrid carbon should have at least one hydrogen.

Q.4 Which of the following carbonium ions will show highest number of hyperconjugative forms?
CH3 CH3
  

(A) CH3CH2 (B) CH3CH (C) CH3C (D) CH3CH2–C
CH3 CH3 CH3

Q5. In which of the following species hyperconjugation is possible?

CH3

(A) CH3CH2 (B) C6H5–CH3 (C) CH2=CH2 (D) CH3C–HC=CH2
CH3

Q6. Which of the following free radicals will not show the phenomena of Hyperconjugation?
.
CH CH3
. 2 .
(A) CH3 (B) (C) CH3CH2 (D) CH3CH.

Comprehension # 3

Electron releasing groups decrease the strength of any acid and increase the strength of any base.
Strength of any acid is also influenced because of H-Bonding. Resonance influences electron density
to a large extent than any other effect and hence it influences strength of acid or base of very large
extent.
 H COOH H COOH
C C
Maleic acid Fumaric acid
C C
H COOH HOOC H

Q7. Compare the values of second dissociation constant (K a 2 ) of maleic acid and that of fumaric acid.
(A) They are equal.
(B) Maleic acid has higher K a 2 than Fumaric acid.
(C) Fumaric acid has higher K a 2 than maleic acid.
(D) none of these.

Q8. Most basic nitrogen atom in following molecule is

II NH CH3
2
IV
CH3—N==C—CH—N—CH3
I
III NH
CH3
(A) I (B) II (C) III (D) IV

Q9. Weakest acid among the following is

OH OH OH OH

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

NO2 CH3 OCH3 Cl

Q10. Which one of the following compounds is most acidic?
OH
OH OH
(A) (B) Cl—CH2—CH2—OH (C) (D)
CH3 NO2

Q11. C6H5—C—C6H5 ; C6H5—CH2 ; H2C = CH—CH2 ;

C6H5
I II III IV
Correct order of stability of above carbocations is

(A) I > IV > II > III (B) IV > I > II > III (C) I > II > IV > III (D) III > II > IV > I
Q12. Consider the following carbanions

CH3O CH2 ; O2N CH2 ; CH2

(I) (II) (III)

Correct order of their stability is

(A) II > III > I (B) I > II > III (C) III > II > I (D) I > III > II
Comprehension # 4

In general, electron withdrawing effect increases acidity, whereas electron releasing effect increases
basicity. But irrespective of the nature of the effect of substituent, ortho substituted benzoic acids are
stronger acid than benzoic acid. However, an ortho substituent aniline is always weaker base than
aniline. The net result of Ieffect and Reffect will decide the acid or base strength. The Ieffect acts
from all positions, but the Reffect is produced only if the substituent is either at ortho or para
positions.
Q13. The decreasing order of acid strength of the following compounds is
COOH COOH COOH COOH COOH COOH

NO2 CH3 Cl NH2 OH

(I) (II) (III) (IV) (V) (VI)
(A) (II) > (IV) > (I) > (III) > (VI) > (V) (B) (II) > (I) > (IV) > (V) > (III) > (VI)
(C) (II) > (IV) > (I) > (V) > (III) > (VI) (D) (II) > (I) > (IV) > (III) > (VI) > (V)

Q14. The compound with minimum pKb or maximum pKa value of its conjugate acid is
NH2
NH2 NH2 NH2
OMe

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

Q15. Arrange the following compounds in the decreasing order of basic strength
(I) Aniline (II) omethylaniline (III) mmethylaniline (IV) pmethyl aniline
(A) (I) > (II) > (III) > (IV) (B) (IV) > (III) > (II) > (I)
(C) (IV) > (III) > (I) > (II) (D) (II) > (I) > (III) > (IV)

Q16. The correct order of acid strength is

(A) mcresol > phenol > ocresol > pcresol (B) phenol > mcresol > pcresol > ocresol
(C) ocresol > mcresol > pcresol > phenol (D) pcresol > mcresol > ocresol > phenol

Q17. Arrange the following compounds in the decreasing order of their acidic strength.
COOH COOH COOH
CH3 CMe3 H3C CH3

(I) (II) (III)

(A) (I) > (II) > (III) (B) (II) > (I) > (III) (C) (III) > (II) > (I) (D) (II) > (III) > (I)

Q18. Which is the correct increasing order of basic strength of the following compounds?
NH2 NH2 NH2 NH2
Cl CH3 NO2

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

 (A) (I) < (II) < (III) < (IV) (B) (III) < (I) < (IV) < (II)
(C) (III) < (I) < (II) < (IV) (D) (IV) < (III) < (II) < (I)

Q19. Arrange the following compounds in decreasing order of their acidic strength.
COOH COOH COOH COOH
NO2 OCH3 OH

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

(A) (I) > (II) > (III) > (IV) (B) (II) > (III) > (I) > (IV)
(C) (III) > (II) > (I) > (IV) (D) (I) > (III) > (II) > (IV)

Q20. Which one of the following is most acidic in character?

(A) (B) (C) (D) CH2=CH–CH3

Q21. Which one of the following phenols will have the lowest pKa value?
CH3 CH3
OH H3C OH H3C OH OH
(A) (B) (C) (D)
CH3 O2N H3C NO2 H3 C
NO2 CH3 NO2

Q22. Which one of the following compounds is the strongest acid?

(A) CH2=CH–COOH (B) CHC–COOH (C) CH3–CH2–COOH (D) CH3–COOH

Q23. Arrange the following compounds in the decreasing order of their acidic strength.
COOH
(I) CH3COOH (II) COOH–COOH (III) CH2 (IV) HOOC–(CH2)2–COOH
COOH
(A) (II) > (IV) > (III) > (I) (B) (I) > (II) > (III) > (IV)
(C) (II) > (III) > (IV) > (I) (D) (II) > (I) > (IV) > (III)

MATCH THE COLUMN TYPE

Q.1 Column I Column II

(A) Hydrogen bonding 1. CH3NH2

(B) Aromatic 2. Benzyne

(C) Electrophile 3. SO3

(D) Nucleophile 4. Tropolyium cation

Q.2 Column I Column II
(A) Group donates electrons inductively but does not donate or
1. – OCH3
withdraw electron by resonance.
(B) Group withdraws electrons inductively and withdraws
2. – Cl
electrons by resonance.

(C) Group deactivates the benzene ring and directs ortho/para. 3.  NH 3
(D) Group withdraws electron inductively, donates electrons by 4. – CH3
resonance, and activates the ring. 5. – NO2

Q.3 Column I Column II

(A) NO2 1. – M effect

O
(B) NH–C–CH3 2. +I effect

(C) Cl 3. –I effect

(D) N=O 4. + M effect

Q.4 Column I Column II

1. aromatic
(A)

2. nonaromatic
(B)


3. antiaromatic
(C)
N
..
4. paramagnetic
CH2
(D)

Q.5 Column I Column II

(A) Trichloroacetic acid is more acidic than acetic 1. Hyperconjugation
acid.
 2. I effect
(B) Allyl carbocation (CH 2 CH C H 2 ) is more
stable than npropyl carbocation.
(C) Propene is more stable than ethene. 3. Resonance
 4. Octet rule
(D) RCO+ is more stable than R C  O
Q.6 Column I Column II
(A) (CH3)4N+ 1. Not an electrophile.
(B) [(CH3)3C]3C+ 2. Not a nucleophile.
(C) C6 H11 NH3 3. No resonance stabilisation.
4. No hyperconjugation stabilisation.

ANASWER KEY
SINGLE CHOICE CORRECT

1. C 2. A 3. A 4. A 5. D 6. D 7. B

8. B 9. C 10. A 11. D 12. C 13. A 14. C

15. D 16. D 17. D 18. A 19. B 20. D 21. B

22. A 23. B 24. B 25. B 26. C 27. A 28. A

29. A 30. D 31. C 32. A 33. A 34. B 35. A

36. C 37. B 38. A 39. D 40. B 41. A 42. B

43. B 44. D 45. A 46. B 47. A 48. C 49. D

50. AB 51. BD
ASSERTION AND REASONING
1. D 2. B 3. A 4. A 5. D 6. D 7. B
8. A 9. A
COMPREHENSION TYPE
1. D 2. D 3. A 4. C 5. AB 6. AB 7. C
8. A 9. C 10. D 11. B 12. A 13. A 14. D
15. C 16. B 17. C 18. C 19. C 20. B 21. C
22. B 23. C
MATCH THE COLUMNS
1. (A  1) (B  2, 4) (C  2, 3, 4) (D  1, 3)
2. (A  4) (B  2, 5) (C  2) (D  1)
3. (A  1, 3) (B  3, 4) (C  1, 3, 4) (D  1, 3, 4)
4. (A  2) (B  3, 4) (C  1) (D  1, 4)
5. (A  2) (B  3) (C  1) (D  4)
6. (A  1, 2, 3, 4) (B  2, 3, 4) (C  1, 2, 3, 4)