1

Nitrogen containing

organic compounds

2

1) The number of functional isomers

possible with C3H9N is _____

a) 2 b) 4 c)3 d)5

3

CH3CH2CH2NH2 or (CH3)2CHNH2

CH3CH2NHCH3,(CH3)3N

Hence the answer is (c) 3

4

2) An organic compound (x) containing

nitrogen on reduction with Fe / HCl

forms an amine which reacts with

NaNO2/H+ at 0°C to liberate nitrogen gas.

The compound (x) is _____

5

N2 liberation is possible when 1°amine is

not aryl (eg.: aniline). So the compound

(x) on reduction that gives a 1° amine that

is not aryl is (b)

Ans: (b)

6

3)

a) Amide and 1°amine

b)1°amine and nitrile

c) Amide and isonitrile

d) nitrite and isonitrile

4

32

2

1.Li AlHCHCl +AlcKOHBr /NaOH o

2.H OP Q R 2 amine

Pand R are:

7

If P is an amide we have

Hence P is an amide and R is isonitrile

Ans: (C) Amide and isonitrile

32 CHClBr /NaOH Re duction

(P) (Q) AlcKOHamide 1 a min e isonitrile 2 a min e

8

4) The variation in base strength of 1°, 2°,

3° methylamines in aqueous medium is

not due to ______

a) inductive effect

b) solvation effect

c) steric hindrance

d) resonance effect

9

In methylamines there is no resonance

effect to influence the base strength

Ans: (d) Resonance effect

10

5) Conjugate acid of

NH2 – CH2 - CH2 - COOH is ______

a) NH2 - CH2 - CH2 - COO-

b) +NH3- CH2 – CH2 - COOH

c) –NH - CH2 - CH2 - COOH

d) +NH3 - CH2 - CH2 - COO-

11

Conjugate acid can be obtained when a

basic group accepts H+.

In H2N-CH2-CH2-COOH , H2N accepts

H+ to form its conjugate acid

Ans: b)

12

6) Increase in base strength of

i) benzylamine ii) cyclohexylamine

iii) o-methoxyaniline is_______

a) iii < i < ii b) iii > ii > i

c) i > ii > iii d) ii < iii > i

13

Hence iii) is the weakest base and

ii) is the strongest

Ans: (a) iii < i < ii

14

7) Schotten Baumann reaction helps to

convert

a) 1° amine to 2°amine

b) 1°amine into N-substituted amide

c) amide into 1°amine

d) 1° amine into a quaternary salt

15

Benzoylation in presence of alkali is

Schotten Baumann reaction 1°amine react

to form N-substituted amide

Eg: C6H5COCl + C6H5NH2

C6H5CONHC6H5

Ans: b) 1° amine into N-substituted amide

16

8) CH3NH2 does not react with

a) NaOH

b) HCl

c) CH3COCl

d) C6H5SO2Cl

17

CH3NH2 is a base, does not react with

NaOH

Ans: (a) NaOH

18

9) Ethanamine and benzenamine can be

best distinguished using______

a) CHCl3 + Alc. KOH

b) CH3I

c) dil. HCl

d) Bromine water

19

C2H5NH2 and

both react with the reagents in a, b & c

but only benzenamine readily

decolourises orange colour of bromine

water.

Ans: d) Bromine water

20

10) Gabriel phthalimide synthesis is

used to prepare

a) amide

b) 1° aliphatic amine

c) amine

d) 1° aromatic amine

21

Take care to mark the correct answer.

Ans: (b) 1° aliphatic amine

22

11) Reagent that need not be used to

convert benzene into is____

a) KI b) HNO3

c) I2 d) HNO2

23

Ans: (C) I2

24

12)Alkyl halide

A and B are:

a) position isomers

b) functional isomers

c) metamers

d) chain isomers

25

X is R-CN R-CH2NH2 (A)

Y is R-NC R-NH-CH3 (B)

A and B are functional isomers

Ans: (b) functional isomers

26

13) N-methylbenzenamine reacts with

ethyliodide to form a salt that______

a) is achiral

b) is chiral

c) exhibits metamerism

d) exhibits geometric isomerism

27

N attached to four different groups is

chiral. Therefore the salt is chiral

Ans: (b) is chiral

28

14) p-nitroaniline

gives

a) p-diiodobenzene

b) p-iodobenzenamine

c) 2, 4-dinitrobenzene

d) p-iodonitrobenzene

21.NaNO /HCl 0 C

2.KI

29

NH2 +N2Cl- I I

NO2 NO2 NO2

Ans: (d) p-iodonitrobenzene

HClNaNO /2 KI

30

15) 0.3g of organic compound containing

C,O,H,N, ammonia

absorbed in 100ml of 0.1 M H2SO4.

Unreacted acid reacted with 20ml of

0.5 M NaOH. The percentage of nitrogen

in the compound could be____

a) 46 b) 56

c) 36 d) 66

kjeldhal 's

method

31

H2SO4 +2NaOHNa2SO4+ 2H2O

2NH3 + H2SO4 (NH4)2SO4

Initial amount of H2SO4 is 10 millimole

NH3 consumes 5millimole H2SO4

Amount NH3 =10millimole

% N =

Ans: a) 46

310 10 14 10046.6%

0.3

-

32

16) Coupling reaction between

benzene diazoniumchloride and phenol

involves the electrophile_________

6 5 6 5 2

6 5 2

a)C H b)C H N

c)C H O d) N

-

33

In , the electrophile is

Ans: (b) 6 5 2C H N

34

17) Zwitter ion is not formed by

R

a) H2N-CH-COOH

b) HOOC NH2

c) H2N SO3H

d) H2N-CH2-CH2-COOH

35

Zwitter ion is formed when there is transfer of H+ from acidic to basic group within a molecule. For this acidic or basic groups must be fairly strong. Options a, c, d, have either a strong acidic or strong basic group In option (b) NH2 is very weak, so also is COOH.

Ans: (b) HOOC NH2

36

18) CCl2 is an electrophile for_______

a) Hoffmann’s bromamide reaction

b) Carbylamine reaction

c) Sandmeyer’s reaction

d) Hinsberg test

37

In carbylamine reaction CHCl3 reacts

with alc. KOH to form CCl2 a neutral

electrophile

CHCl3 CCl2(dichlorocarbene)

Ans: (a) Carbylamine reaction

38

19)

is nitrated. The nitro group goes to

position________

a) c b) a

c) x d) y

39

In the molecule NH group is e-

releasing, ring activating, o,p directing,

but CO group is e- withdrawing, ring

deactivating, m – directing. Nitration

happens faster for the ring attached to

NH group. The NO2 group mainly goes

to para position (c).

Ans: (a) c

40

20)

X & Y have functional groups as

a) amine and phenol

b) amide and phenol

c) diazonium and phenol

d) nitrile and phenol

3n FeClin water warmX Y violet colour-

41

Y must be phenol to give violet colour

with n-FeCl3. Phenol is obtained from X

by hydrolysis. X must be a benzene

diazonium salt.

Ans: (c) X - diazonium group

Y - phenol

42

21) Amines are not

a) Lewis bases

b) Bronsted bases

c) nucleophiles

d) Arrhenius bases

43

All types of amines (1°, 2°, 3°) have a

lone pair of electrons on nitrogen.

Hence by definition they fit into a, b, c

but not d.

Ans: (d) Arrhenius base.

44

22) Ethanamine is not obtained by the

reduction of

a) methylcyanide

b) nitroethane

c) acetamide

d) ethylcyanide

45

223

Re NHCHCHduction

223

Re NHCHCHduction

223

Re NHCHCHduction

2223

Re NHCHCHCHduction

a) Methylcyanide – CH3CN

b) Nitroethane- C2H5NO2

c) Acetamide – CH3CONH2

d) Ethylcyanide–C2H5CN

Ans: (d) ethylcyanide

46

23) Which one of the following is most

reactive towards electrophilic

substitution reaction?

a) aniline

b) Acetanilide

c) benzamide

d) nitrobenzene

47

b, c, d have electron withdrawing groups,

which is ring deactivating. (a) has

electron releasing, ring activating group

Ans: (a) aniline

48

24) A tribromo derivative is obtained

when X is treated with bromine water. X

could be_______

a) acetophenone

b) acetanilide

c) o-cresol

d) m-toluidine

49

To get a tribromo derivative, the functional group must be strongly electron releasing group.(c) and (d) has it. But in (c) ortho position is blocked by CH3 group but not in (d). All o & p positions are free, hence m-toluidine on bromination forms tribromo derivative.

Ans: (d) m-toluidine

50

25)

C is ---------

a) C6H5COONH4 b) C6H5CH2NH2

c) C6H5NHCH3 d) C6H5COOH

2

4

2

HNO 0 C CuCN

6 5 2HCN

1.Li AlH

2.H O

C H NH A B

C

51

Ans: b) C6H5CH2NH2

52

26. In aniline, the polar effects due to NH2

group are

a) -I, - R

b) +I, +R

c) -I, +R

d) +I, -R

53

NH2 is electron releasing due to

resonance (+R) and electron

withdrawing due to high

electronegativity of N (-I).

Ans: c) –I, +R

54

27. In detection of nitrogen in an

organic compound via sodium fusion

extract, nitrogen is converted into

a) NH3

b) NaCN

c) NaNO3

d) N2

55

When nitrogen containing organic

compound is fused with sodium, the

compound formed is NaCN.

Ans: b) NaCN

56

28. Which of the following statements

is correct?

a) Amides are more basic than aliphatic amines

b) Electron withdrawing group increases the base strength of aniline

c) Diphenyl amine is less basic than aniline

d) Amines are stronger bases than ammonia

57

Ans:

c) Diphenyl amine

is less basic than aniline

58

29. The name of

a) ethylmethyl propylamine

b) sec-butyl methylamine

c) ethylmethyl isopropylamine

d) ethyl propylamine

59

It is a tertiary amine with alkyl groups

methyl, ethyl and isopropyl.

Ans: c) ethylmethyl isopropylamine

60

30. Benzene is converted into

The best sequence of reactions to do

this is

a) Methylation, nitration, reduction

b) Nitration, reduction, methylation

c) Methylation, reduction, nitration

d) Reduction, nitration, methylation

61

Ans: a) Methylation, nitration, reduction

62

31. Which one of these is neither a test

nor a method to prepare amines?

a) Hoffmann reaction

b) Carbylamine

c) Methylation

d) Sulphonation

63

Ans:

d) Sulphonation

64

32. X with NaOBr forms a 1° amine. X

could be

a) CH3CONHCH3

b) CH3COONH4

c) CH3CONH2

d) CH3NC

65

NaOBr is obtained from Br2/NaOH

X must be an amide (unsubstituted

RCONH2)

Ans: c) CH3CONH2

66

33. ethanenitrile on reduction forms

a) ethanamine

b) ethanamide

c) propanamine

d) propanamide

67

a) CH3CN CH3CH2NH2

ethanenitrile ethanamine

Ans: a) ethanamine

reduction

68

34. For maximum activity of sulpha

drugs, the minimum standard feature of

the drug should be

a)

b)

c)

d)

69

Ans:

c)

70

35. An aromatic compound with the

formula C7H9N cannot be

a) 1° amine

b) 2° amine

c) toluidine

d) 3° amine

71

3° amine is not possible.

Ans: d) tertiary amine

72

36. Aniline can be obtained by the

reduction of _____

a) benzonitrile b) benzamide

c) anilide d) nitrobenzene

73

C6H5CN C6H5CH2NH2

(benzonitrile)

C6H5CONH2 C6H5CH2NH2

(benzamide)

R-CONH-Ar RCH2NHAr

(anilide)

C6H5NO2 C6H5NH2

(nitrobenzene)

Ans: d) Nitrobenzene

reduction

reduction

reduction

reduction

74

37. p-hydroxy azobenzene is obtained

when

a) Phenol is coupled with azobenzene

b)p-hydroxyaniline is coupled with benzene

c)Phenol is coupled with bezenediazonium ion

d) Aniline is coupled with phenol

75

is obtained when phenol couples with

a benzene diazonium salt or ion

Ans: c) Phenol is coupled with

bezenediazonium ion

76

38. 1,3,5-tribromobenzene can be

obtained from aniline by a series of

reactions in the order

a) bromination, reduction, diazotisation b) bromination, diazotisation, boil with

ethanol c) carbylamine reaction, diazotisation,

boil with Br2 water d) bromination, heat with Zn dust, boil

with ethanol

77

Ans: b) bromination, diazotisation, boil in

C2H5OH

78

39. Enantiomers are possible for

a) ethylmethyamine

b) secondary butylamine

c) N, N-dimethyl aniline

d) trimethylammonium ion

79

Enantiomers are possible if the given

compound is chiral or has a chiral

carbon.

has a chiral carbon and hence is chiral.

Ans: b) sec-butylamine

80

40. Acetylation of aniline, makes it a) less reactive towards ESR & more

reactive towards oxidation

b) more reactive towards both ESR and oxidation

c) less reactive towards both ESR and oxidation

d) more reactive towards ESR but less reaction towards oxidation

81

Acetylation of aniline gives

which has electron withdrawing

group in the side chain

Ans:

c) less reactive towards both ESR and oxidation

82

41. Among i) aniline ii) benzaldehyde

iii) acetanilide iv) toluene,

the least and the most reactive towards

Friedel Craft’s alkylation is

a) i and iv b) iv and ii

c) iii and ii d) ii and i

83

Ans:

a) i and iv

84

42. Which one of the following gives a

product with Hinsberg reagent which is

insoluble in an alkali?

a) (CH3)3N

b) CH3CH2NH2

c) C6H5NHCH3

d) (CH3)2NC6H5

85

2° amine with Hinsberg reagent gives a

product insoluble in an alkali.

Ans: c) C6H5NHCH3

86

43. 2° amine reacts with NaNO2 and HCl

at 0° C to

a) form a 2° alcohol

b) liberate nitrogen gas

c) form a diazonium salt

d) form N-nitrosoamine

87

2° amine reacts with HNO2 liberated to

form N-nitrosoamine

Ans: d) form N-nitrosoamine

88

44. Aniline reacts with concentrated

H2SO4 at 450 K to give

a) phenol

b) sulphanilic acid

c) aniline hydrogensulphate

d) benzene sulphonic acid

89

Ans:

b) sulphanilic acid

90

45. The base strengths of the following

compounds decreases as

a) o-toluidine > aniline > o-nitroaniline

b) o-toluidine > o-nitroaniline > aniline

c) Aniline > o-nitroaniline > o-toluidine

d) o-nitroaniline<aniline<o-toluidine

91

Ans:

a) o-toluidine > aniline > o-nitroaniline

92

46. In the gaseous state the base strengths

of the following amine increases as:

a) CH3NH2<(CH3)2NH<(CH3)3N

b) (CH3)3N<CH3NH2<(CH3)2NH

c) (CH3)3N<(CH3)2NH<CH3NH2

d) CH3NH2<(CH3)3N<(CH3)2NH

93

In gaseous state only +I effect decides base

strength of amines.

Ans:

a) CH3NH2<(CH3)2NH<(CH3)3N

94

47. Gabriel phthalimide synthesis does not

involve

a) Neutralisation

b) Nucleophilic substitution

c) Hydrolysis

d) Hydration

95

Ans:

d) Hydration

96

48. A positive result for carbylamine test

will be obtained when the amine is

a) Aliphatic 1° amine only

b) Aromatic 1° amine only

c) 1° amine

d) 2° aliphatic amine

97

Ans:

c) 1° amine

98

49. Aniline and benzylamine can be best

distinguished using

a) NaNO2/ HCl at 0°C + b-naphthol in

NaOH

b) Hinsberg reagent

c) CHCl3 + alc.KOH

d) CH3COCl

99

Both are 1° amines, but aniline is an aryl

amine

Ans:

a) NaNO2/ HCl at 0°C + b-naphthol in

NaOH

100

50. Amide can be converted into 1° amine

by _____ reaction

a) Sandmeyer

b) Carbylamine

c) Hoffman’s bromamide

d) Rosenmund’s

101

Ans:

c) Hoffman’s bromamide

102

51. Which of the following statements is

correct?

i) Nitration of aniline gives meta isomer.

ii)Acetylation of aniline decreases the tendency of aniline to get oxidized.

iii) anilinium ion is a strong conjugate base.

iv) Aniline is an antioxidant.

a) i, ii, iv b) ii, iii c) ii, iii, iv d) iii, iv

103

Ans:

a) i, ii, iv

104

52. Number of resonance structures

possible for is

a) 2

b) 3

c) 4

d) 5

105

are the only two possible resonance

structures

Ans: a) 2

106

53. is done using the

reagent

a) H4P2O7

b) H3PO2

c) H3PO3

d) H3PO4

107

Ans:

b) H3PO2

108

54. Compounds P and Q that yield an

isocyanide when treated with alc. AgCN

and CHCl3/ alkali respectively are:

a) chlorobenzene and acetone

b) ethyl bromide and acetamide

c) methyl iodide and ethyl amine

d) ethyl alcohol and ethyl bromide

109

Ans:

c) methyl iodide and ethyl amine

110

55. An optically active compound A

(C8H11N) dissolves in HCl and answers

carbylamine test. The compound could

be

a) C6H5CH2CH2NH2

b) CH3NHCH2CH2C6H5

c) C6H5CH(NH2)CH3

d) C6H4(NH2) (C2H5)

111

Ans:

c) C6H5CH(NH2)CH3

112

56.

X is

a) KOH

b) NaNO3/ HCl

c) C2H5OH

d) NaNO2/ HCl

113

Ans:

d) NaNO2/ HCl

114

57. The pKb value is lowest for

a) C6H5NH2

b) C6H5(NH)CH3

c) (CH3)2NH

d) C6H5NHC6H5

115

Lower the pKb value, stronger is the base.

Among the options dimethyl amine in (c)

is the strongest base.

Ans: c) (CH3)2NH

116

58.

Z is

a) m-chlorophenol

b) resorcinol

c) catechol

d) m-nitroaniline

117

Ans: b) resorcinol

118

59.

X, Y, Z are

a) CH3OH, CH3NH2, CH3OH

b) CH3Cl, CH3NH2, CH3NO2

c) Cl-CH2-COOH, NH2-CH2-COOH,

HO-CH2-COOH

d) CH3COCl, CH3CONH2, CH3OH

119

Ans:

c) Cl-CH2-COOH, NH2-CH2-COOH,

HO-CH2-COOH

120

60. A mixture of aniline and nitrobenzene

can be separated using

a) NaOH solution

b) HCl acid

c) alcohol

d) ether

121

Aniline is basic hence dissolves in HCl

acid. Nitrobenzene remains undissolved

forms a separate layer, hence can be

separated.

Ans: b) HCl acid

122

61.

X should be

a) o-nitrobenzenamine

b) o-nitrobenzoic acid

c) m-nitrobenzoic acid

d) p-nitrobenzoic acid

123

Terphthalic acid is

Ans: d) p-nitrobenzoic acid

124

62. The reagent that will not help to

distinguish benzylamine from N-

methylbenzenamine is

a) CHCl3/ alc.KOH

b) C6H5SO2Cl

c) HNO2

d) HCl acid

125

Both of these react differently with

reagents in a, b and c but both dissolve in

HCl acid to form aqueous solution.

Ans: d) HCl acid

126

63. 1.78 g of an amine reacts with nitrous

acid at 0°C to liberate 4.48 dm3 of N2 at

STP. The molar mass of the amine is

_____ g mol-1.

a) 78

b) 89

c) 68

d) 48

127

= 0.02 mol nitrogen at STP 4.22

48.4

Mass of 0.02 mole of amine = 1.78g

Molar mass of the amine =

= 89 gmol-1

Ans: b) 89

1.78

0.02

128

64. Aniline can be purified by steam

distillation. Efficiency of steam

distillation can be increased by the

addition of

a) alcohol

b) HNO3

c) NaCl

d) benzene

129

When NaCl is dissolved, vapour pressure

of salt solution (water + salt) is lowered,

boiling point of water increases. Aniline

does not dissolve NaCl and hence gets

distilled more efficiently.

Ans: c) NaCl

130

65.

Y is

a) 2° amine

b) 3° amine

c) 1° amine

d) amide

131

Ans:

a) 2° amine