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Page 1

Shailendra Kumar’s Chemistry For IIT/AIEEE/AIPMT ORGANIC CHEMISTRY

SCIENCE TUTORIALS; Opp. Khuda Baksh Library, Ashok Rajpath, Patna - 4
PIN POINT STUDY CIRCLE; Opp. Mahual Kothi, Near International School, Alpana Market, Patna

1

A SHORT PROBLEM BOOK

IN

ORGANIC
CHEMISTRY

Shailendra Kumar
www.shailendrakrchemistry.wordpress.com

Page 2

Shailendra Kumar’s Chemistry For IIT/AIEEE/AIPMT ORGANIC CHEMISTRY

SCIENCE TUTORIALS; Opp. Khuda Baksh Library, Ashok Rajpath, Patna - 4
PIN POINT STUDY CIRCLE; Opp. Mahual Kothi, Near International School, Alpana Market, Patna

2

Unit - I, General Questions on Structure and Bonding

1. How many electrons occupy the bonding molecular orbitals of a CN triple bond?

(a) 2 (b) 4

(c) 6 (d) 8

2. Which of the following species is not amphoteric ?

(a) NH
3

(b) HF

(c) NH
4

(+) (d) HCO
3

(–)

3. What is the relationship of the two structures shown below?

(a) they are identical

(b) they are conformations of the same structure

(c) they are constitutional isomers

(d) they are different compounds with different compositions

4. Which of the following molecules will not have a dipole moment?

(a) CH
3
Cl (b) CH

3
OCH

3

(c) CH
2
Cl

2
(d) CCl

4

5. Which of the following molecules has a dipole moment?

(a) CBr
4

(b) CH
2
=CH

2

(c) BF
3

(d) SO
2

6. Which of the following molecules has a linear shape?

(a) NH
3

(b) H
2
S

(c) CO
2

(d) H
2
CO

7. Which of the following intermediates is pyramidal in shape?

(a) H
3
C(+) (b) H

2
C:

(c) H
3
C:(-) (d) HC=C:(-)

8. In which compound does carbon have the highest oxidation state?

(a) CH
4

(b) HCN

(c) H
2
CO (d) CH

2
Cl

2

9. Which of the following statements applies to a C
10

H
14

O
2
compound?

(a) it may have 2 double bonds and 2 rings (b) it may have 3 double bonds and 0 rings

(c) it may have 1 triple bond and 3 rings (d) it may have 0 double bonds and 3 rings

10. What functional group is present in the terpene camphor?

(a) hydroxy (b) carboxy

(c) carbonyl (d) oxy

Page 38

Shailendra Kumar’s Chemistry For IIT/AIEEE/AIPMT ORGANIC CHEMISTRY

SCIENCE TUTORIALS; Opp. Khuda Baksh Library, Ashok Rajpath, Patna - 4
PIN POINT STUDY CIRCLE; Opp. Mahual Kothi, Near International School, Alpana Market, Patna

3 8

Unit - VI, Amines and Related Nitrogen Compounds

1. Which of the following is a 3º-amine?

(a) 1-methylcyclohexylamine (b) triethylamine

(c) tert-butylamine (d) N-methylaniline

2. Which of the following compounds is cyclopentyldiethylamine?

3. Which of the following is a proper name for CH
2
=CHCH

2
NHCH

3
?

(a) allylmethylamine (b) 4-amino-1-pentene

(c) 2-amino-4-pentene (d) N-methyl-1-propenamine

4. Which of the following is tetrabutylammonium iodide?

(a) C
4
H

9
NH

3
+ I– (b) C

4
H

9
N(CH

3
)

3
+ I–

(c) (C
4
H

9
)

4
N+ I– (d) (CH

3
)

4
N+ I–

5. Which of the following is N,N-dimethylaniline?

6. Which of the following is a proper name for (CH
3
)

2
CHCH

2
NHCH

2
CH

2
CH(CH

3
)

2
?

(a) 2,7-dimethyl-4-azaoctane (b) butylpentylamine

(c) 2,7-dimethylpropylbutylamine (d) 3-amino-2,7-dimethyloctane

7. Ethylmethylamine cannot be resolved under normal conditions. Why?

(a) the favored configuration is not chiral.

(b) it isomerizes rapidly with the achiral isomer trimethylamine.

(c) the nitrogen atom rapidly inverts its configuration leading to a racemic mixture.

(d) the C–N bond is not stable under conditions used for resolution

8. Which of the following is pyridine?

9. Which of the following is the strongest base in aqueous solution?.

(a) (CH
3
)

3
N (b) (CH

3
)

2
NCH

2
CH

2
OH

(c) CH
3
CH

2
CH

2
NHOH (d) (CH

3
)

4
NOH

Page 39

Shailendra Kumar’s Chemistry For IIT/AIEEE/AIPMT ORGANIC CHEMISTRY

SCIENCE TUTORIALS; Opp. Khuda Baksh Library, Ashok Rajpath, Patna - 4
PIN POINT STUDY CIRCLE; Opp. Mahual Kothi, Near International School, Alpana Market, Patna

3 9

10. Which of the following is the strongest Brønsted base?

11. Dibutylamine, (C
4
H

9
)

2
NH, and anisole, C

6
H

5
OCH

3
, have similar boiling points, and are relatively insoluble

in water. How might a mixture of these compounds be separated into the pure components?

(a) i) dissolve mixture in ether; ii) extract the anisole into 10% aqueous NaOH

(b) i) dissolve mixture in ether; ii) extract the amine into 10% aqueous HCl

(c) i) dissolve mixture in ether; ii) extract the amine into 10% aqueous NaOH

(d) i) dissolve mixture in ether; ii) extract the anisole into 10% aqueous HCl

12. Which of the following is the strongest Brønsted acid?

13. Which of the following is the strongest Brønsted base?

14. Which of the following is the weakest Brønsted base?

15. Which of the following is the weakest Brønsted base?

16. Which of the following is the strongest Brønsted base?

Page 75

Shailendra Kumar’s Chemistry For IIT/AIEEE/AIPMT ORGANIC CHEMISTRY

SCIENCE TUTORIALS; Opp. Khuda Baksh Library, Ashok Rajpath, Patna - 4
PIN POINT STUDY CIRCLE; Opp. Mahual Kothi, Near International School, Alpana Market, Patna

7 5

66. Which of the following is not a common component of both DNA and RNA?

(a) ribose (b) phosphate

(c) cytosine (d) adenine

67. Which of the following is not a component of RNA?

(a) adenine (b) phosphate

(c) cytosine (d) thymine

68. Which of the following is purine base?

(a) guanine (b) indole

(c) cytosine (d) thymine

69. Which of the following is a pyrimidine base?

(a) imidazole (b) guanine

(c) cytosine (d) adenine

70. The H-bonded base pair shown on the right represents which of the following?

(a) adenine-thymine (b) guanine-cytosine

(c) adenine-cytosine (d) adenine-guanine

71. Which of the following is a nucleoside?

72. In DNA replication the complementary nucleotide sequence for 5'-ACGT-3' is which of the following?

(a) 3'-ACGT-5' (b) 3'-TGCA-5'

(c) 5'-AGCT-3' (d) 5'-TCGA-3'

73. What is the complementary RNA sequence for the DNA segment AATCAGTT?

(a) AAUCAGUU (b) CCAUCGAA

(c) AACUGAUU (d) UUAGUCAA

74. How many nucleotides are needed to code for a specific amino acid?

(a) one (b) two

(c) three (d) four

Page 76

Shailendra Kumar’s Chemistry For IIT/AIEEE/AIPMT ORGANIC CHEMISTRY

SCIENCE TUTORIALS; Opp. Khuda Baksh Library, Ashok Rajpath, Patna - 4
PIN POINT STUDY CIRCLE; Opp. Mahual Kothi, Near International School, Alpana Market, Patna

7 6

ANSWERS

1. B
2. A
3. B
4. C
5. A
6. D
7. D
8. B
9. A
10. B
11. D
12. C
13. D
14. B
15. D
16. B
17. C
18. B
19. A
20. A
21. D
22. C
23. D
24. B
25. C
26. B
27. A
28. D
29. C
30. C
31. A
32. C
33. D
34. B
35. A
36. D
37. C

38. D
39. B
40. C
41. D
42. A
43. B
44. C
45. A
46. D
47. C
48. A
49. B
50. C
51. B
52. A
53. B
54. A
55. D
56. A
57. A
58. B
59. D
60. C
61. C
62. A
63. D
64. B
65. A
66. A
67. D
68. A
69. C
70. B
71. C
72. B
73. D
74. C

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