SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

1. The correct order of decreasing basic strength is :

NH2

N N N
H H
I II III IV
(A) I > II > III > IV (B) II > III > I > IV (C) II > IV > I > III (D) II > III > IV > I
2. The correct order of increasing dissociation constant of the following compound is :-

OH OH OH OH
NO2 NO2 NO2

NO2
NO2
NO2 NO2

I II III IV
(A) II < IV < I < III (B) IV < III < I < II (C) IV < II < I < III (D) IV < I < II < III
3. In the following arrange the H (numbered) for their ease of displacement during acid base reaction :
(2)
(3) OH
HO
H NaNH2(liquid NH3)
(1) 2 equivalent

(A) 1 > 2 > 3 (B) 3 > 2 > 1 (C) 3 > 1 > 2 (D) 2 > 3 > 1
4. Which one of the following is the strongest base in aqueous medium :-
(A) (C 2 H 5 ) 3 N (B) C 2 H 5 NH 2 (C) NH 3 (D) (C 2 H 5 ) 2 NH
5. The correct order of acid strength of the following compound is -

(I) CH3–C–CH3 (II) CH3–C–C–CH3 (III) CH3–C–CH2–C–CH3

O OO O O
(A) III > II > I (B) III > I > II (C) II > I > III (D) I > II > III
6. Which of the following shows the correct order of decreasing basicity in aqueous medium -
(A) (CH 3 ) 3 N > (CH 3 ) 2 NH > CH 3 NH 2 > NH 3 (B) (CH 3 ) 2 NH > (CH 3 ) 3 N > CH 3 NH 2 > NH 3
(C) (CH 3 ) 2 NH > CH 3 NH 2 > (CH 3 ) 3 N > NH 3 (D) (CH 3 ) 2 NH > CH 3 NH 2 > NH 3 > (CH 3 ) 3 N
7. For the compounds

N N N

H H
I II III
the order of basicity is -
(A) III > II > I (B) II > III > I (C) I > II > III (D) II > I > III
8. Which of the following shows the correct order of decreasing acidity-
(A) PhCO 2 H > PhSO 3 H > PhCH 2 OH > PhOH
(B) PhSO 3 H > PhOH > PhCO 2 H > PhCH 2 OH
(C) PhCO 2 H > PhOH > PhCH 2 OH > PhSO 3 H
(D) PhSO 3 H > PhCO 2 H > PhOH > PhCH 2 OH
7 9. Give the correct order of increasing acidity of the following compounds-

OH OH COOH CCH

I II III IV
(A) II < I < III < IV (B) IV < II < I < III (C) I < II < IV < III (D) IV < I < II < III
10. Which of the following is the most acidic
(A) CH 2 = CH 2 (B) HC  CH

(C) CH 2 =CHCH 2 CH=CH 2 (D)

11. Which of the following substituents will increase the acidity of phenol -
(A) –NO 2 (B) –CN (C) –CHO (D) – CH 3

12. (I) (II) (III)

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

(A) I > II > III (B) I > III > II (C) II > I > III (D) II > III > I
13. Which of the following s-bonds participate in hyperconjugation :

I V
H
H CH3
II
H IV
III
(A) I and II (B) I and V (C) I and V (D) III and IV

14. NH, N–H, N

O
(x) (y) (z)

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
15. Set the following in increasing order of their p K a values:

O O

(x) CH3—S—O—H (y) CH3—C—O—H (z) CH3—OH

O
(A) y > x > z (B) x < y < z (C) y > z > x (D) x < z < y
16. Rank the following alkenes in order of decreasing heats of hydrogenation (largest first):

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

(A) II > III > IV > I (B) II > IV > III > I (C) I > III > IV > II (D) I > IV > III > II
17. Which of the following molecules has all the effects : inductive, mesomeric and Baker Nathan effect ?
(A) C 2 H 5 Cl (B) CH 3 –CH=CH 2

(C) CH 2 =CH–CH=CH 2 (D) CH 3 –CH=CH –C–CH 3

O

18. Which nitorgen in LSD (Lysergic acid diethylamide) is more basic :

O
I III
H–N –C–N(C2H5)2
II
N
CH3
(A) I (B) II (C) III (D) all are equally basic
19. Which of the following substituted carboxylic acids has the highest K a value :

(A) CH 3 —CH 2 —CH— COOH (B) CH 3 —CH— CH 2 —COOH

Cl Cl
(C) CH2— CH 2 —CH 2 —COOH (D) CH 3 —CH— CH 2 —COOH
Cl Br
SELECT THE CORRECT ALTERNATIVES (ONE OR MORE THEN ONE CORRECT ANSWERS)

20. Which of the following compounds yield most stable carbanion after rupture of (C 1 –C 2 ) bond :

O O
(A) CH3—C—CCl3 (B) CH3—C—CBr3
1 2 1 2

O
(C) CH3—CH2—C—CI3 (D) None of these
1 2
 N N
21.
H NH2
pyrrole (I) pyridine (II) aniline (III)

Which is/are correct statements ?

(A) I is more basic than II (B) II is more basic than I and III
(C) III is more basic than II (D) all are aromatic bases
22. Following is true for stability between the two structures :


O O
(A) CH3–CH–CH=CH2 > CH3–C=CH–CH3

CH2
•
(B) CH 2=CH–CH=CH–CH 2• > CH2–C–CH–CH3

CH3
 
(C) CH2=C–CH2 > CH 3 –CH=CH– CH 2

O
(D) —O < CH3–C–O

23. Which have acidic hydrogen :

O
(A) CH 3 COOH (B) —OH (C) CH3—C—CH2—CN (D) NaNH2

24. C—C and C=C bond lengths are unequal in :

(A) Benzene (B) 1,3 buta-di-ene
(C) 1, 3 cyclohexa-di-ene (D) None
25. 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 has been made to arrange the acids in order of acid
strength, the strongest first. One of the series is incorrect-which one :
(A) CH 3 .CH 2 CH(Cl).COOH > CH 3 .CH(Cl).CH 2 COOH > CH 3 .CH 2 .CH 2 .COOH
(B) NO 2 .CH 2 .COOH > HOCH 2 . COOH > CH 3 .COOH
(C) Cl 3 C.COOH > BrCH 2 .COOH > FCH 2 .COOH
(D) CH 3 . COOH > CH 3 .CH 2 .COOH > (CH 3 ) 3 C.COOH
26. Which species is not aromatic :

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

N N
:
27. Select the correct option :
(A) carbonic acid is weaker acid than acetic acid
(B) the boiling points of acids are higher than corresponding alcohols
(C) chloroacetic acid is stronger acid than acetic acid
(D) phenol is more acidic than ethanol
28. Which reacts with AgNO 3 to give ppt. :

—Br
(A) —Br (B) –CH=CH–CH2Br (C) (D) —Br

29. Which statement is ture :

– –
(A) NH2
is stronger base than OH

(B) NH 2–OH is less basic than NH 3

(C) CH 3 –NH 2 is weaker base than N(CH 3 ) 3 in (aq) medium

NH2 CH2–NH2

(D) is weaker base than

30. Which is less acidic than phenol :

OH OH

—CH3 —NH2
(A) (B) CH 3 –OH (C) (D) H 2 O

31. The precursor carbocation to the product in the following reaction is :

H

C6H5 H C6H5
OH H


(A) C6H5 (B) C6H5  (C) either of the two (D) none of the two

32. Which of the following ion is formed in the following reaction :

H
OH O



(A) 
(B)
OH OH


CH2
(C) (D) All of three
OH
 OD
D NaOH
33. [Intermediate] P. Product is :
CO2 D

OD OD
HOOC D DOOC D
(A) (B)

OH
DOOC D
(C) (D) Reaction not possible

34. Predict the nature of A in the following reaction :

O
+ ClCH2COOC2H5 Base
(A)

Cl
O
CCOOC2H5
(A) (B)
CH2COOC2H5

O O
(C) CHCOOC2H5 (D) CHCOOC2H5

35. Which of the following intermediate is most likely to be formed during addition of HBr on crotonic acid :

CH 3 CH = CHCOOH + HBr(g)  CH 3 CH–CH 2 COOH :

Br
 
(A) CH 3 CH 2 – C HCOOH (B) CH 3 CH – CH 2COOH
OH
(C) CH3CH=CH–C–OH (D) none of these


36. Which will give most stable cation upon strong heating :

CH2–Cl Cl
CH2
(A) (B) (Ph) 3C–Cl (C) (D) CH
CH2–Cl

Cl
37. (A); Here (A) is :
—Cl
H


(A) (B) (C) 

(D)


 F

–F
38. Cl – C – C – F [X] ; Here [X] is :
Cl F

F F F F
(A) Cl – C = C – F (B) Cl – C = C – Cl (C) Cl – C = C – F (D) C l – C = C – F
Cl F Cl F

H3C CH3
H3C CH3 CHCl3
C C KOH
39. H H the reaction proceeds via :
H H

(A) carbene (B) Carbon free radical (C) Carbocation (D) Carbanion

Cl
:C Cl
40. (A) ; Here A is :
••
N
H
Cl
Cl
(A) (B) Cl
 (C) (D)
N N N
N
H
41. Which of the following can give benzyne :

Cl Cl
(A) NaNH2 (B)  (C) NaNH2 (D) All
H N2 Br

42. Dehydration of the following in increasing order is :

(I) –OH (II) –OH (III) –OH (IV) –OH

(A) I < II < III < IV (B) II < III < IV < I (C) I < III < IV < II (D) I < IV < II < III
43. Increasing tendency for SN1 and SN2 reaction is :

CH3
(I) CH 3 CH 2 CH 2 CH 2 Cl (II) CH3CH2CH – CH3 (III) CH3CHCH2 – Cl (IV) CH3–C – Cl
Cl CH3 CH3

(A) SN1 ; I < III < II < I V (B) SN2 ; IV < II < III < I
(C) (A) and (B) both are correct (D) Both incorrect
44. Cyclopentyl ethyl ether can be obtained by :

(A) –ONa+CH3CH2Br (B) –Br+CHCH

3 2ONa

(C) –OH+CH3CH2Cl (D) none is correct

45. Major product in the following reaction is :

–Br + KOCH2CH3 Product

(A) –OCH2CH3 (B) (C) —Br (D)

OCH2CH3

46. Mechanism of insertion reaction is of :

(A) One step for triplet carbene (B) Two step for singlet carbene
(C) One step for singlet carbene (D) Two step for both
H3C
1 
6 2 NH2
47. (P) . The most probable structure of intermediate P is :
5 –Cl
3
4

OCH3 OCH3 OCH3 OCH3

1 1 1 1
6 2 6 2 6 2 6 2
(A) (B) (C) (D)
5 3 5 3 5 3 5 3
4 4 4 4

CH3
1 
6 2 NH2
48. (A). The most probable structure of intermediate A is :
5 –Cl
3
4

CH3 CH3 CH3 CH3

1 1 1 1
6 2 6 2 6 2 6 2
(A) (B) (C) (D)
5 3 5 3 5 3 5 3
4 4 4 4

49. Hybridisation of arrow headed 'C' is

(A) sp 2 sp 3 (B) sp 3 sp 3 (C) sp 2 sp 2 (D) sp 3 sp 3 d

50. Which of the following is most strongest electrophile :

•• ••
(A) singlet H – N
•
• (B) triplet H – N
•
• (C) singlet –C (D) triplet –C–

51. In benzyne two external unshared electronic orbital :

(A) do not overlap to form a  bond (B) can overlap to form a complete  bond
(C) poorly overlap to form a ver y weak bond (D) contribute in benzene ring
52. Which of the following is aromatic intermediate :

•
•
(A) carbene (B) (C) Benzyne (D)
•
53. In which of the following case 'H' shift is more preferable than 'CH 3 ' shift :

CH3 CH3 H
 
(A) CH3–C–CH2 (B) CH3–C– CH–C–H
H CH3 H

CH3

(C) CH3–C–CH–CH3 (D) all
Ph

54. Which of the following will not give 1, 2, shift :

2
Hg

OH
(A) (CH 3 )3 C — C H 2 (B) (CH3)3C CH—CH2 (C) 
(D) all

55. Which of the following reactions is wrong :

 
(A) CH3CH2CHO OH
CH3 – CH – CHO

•
CH2CH3 CHCH3 + HCl
(B) Cl•

O O O O
(C) HO–C–H+ H– C–H  HO– C–H + H–C–H
H H

CH3
(D) CH3 –C 
Hydride
shifting
CH3 –CH–CH2
CH3 CH3

56. Methyl benzylic carbonium ion is the most stable one, hence it will react fastest consider the following
reaction :
Br CH3 SN2
+ OH (P) ; product (P) will be :
H H

H CH3 HO CH3
(A) (B)
HO H H H

OH
H CH3 CH3
H
(C) (D)
H H H H
OH
57. Consider the following reaction -
R – CH = CH2+ IN3  A , A is :

(A) R – CH – CH2N3 (B) R – CH – CH2I

I N3

(C) R – CH – CH2 (D) R – CH– CH

N N
I

58. + CHBr3 1 BuOK product ; product will be :

Br Br Br
(A) Br (B) Br
Br

Br
(C) (D)
Br

CH2

59. HBr major product will be :

Me CH2Br CH2Br CH3

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

CH3
O OH
60.  Product ; major product of the reaction can be :
O
CH3

O O O O

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

( i ) Zn
61. CH3COCH3 + BrCH2COOEt 
( ii ) H 2 O / H 
 (A) ; the product (A) is :

OCH3 OH
CH3
(A) C (B) CH3–C–CH2COOEt
CH3 Br
CH3

CH3 OH CH3 OCH2COOEt

(C) C (D) C
CH3 COOEt CH3 Br
 OH

62. Which carbocation is more likely to be formed in the dehydration of H :


 
(A) (B) (C) (D)


63. The most probable structure for (P) in the following reaction is :

conc H2SO4
2 (P)

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

64. Which of the following alcohols is dehydrated most readily with conc. H2SO4 ?

CHOHCH3 CHOHCH3 CHOHCH3 CHOHCH3

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

OCH3 NO2 Cl

65. Dehydration of alcohols by conc. H2SO4 takes palce according to following steps :

CH3 CH3 CH3

•• H  –H2O 
CH3–C–CHOH
2 •• step -I CH3–C–CHOH
2 2 step -II CH3–C–CH2
H H H


CH3 CH3
1,2–H shift –H
step -III CH3–C–CH3 step -IV CH2=C–CH3


the slowest and fastest steps in the above reaction are :

(A) step I is slowest, while III is fastest
(B) step II is slowest, while III is fastest
(C) step II is slowest, while IV is fastest
(D) all step proceed at equal rate