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ORGANIC CHEMISTRY
CHAPTER 4 AMINES
QUESTIONS FOR DISCUSSION
1. (CH3)3NH2 is a
1) primary amine 2) secondary amine
3) tertiary amine 4) quaternary amine
2. A secondary amine is
1) a compound with two NH2 groups
2) a compound with 2 carbon atoms and an – NH2 group
3) a compound with a – NH2 group on the carbon atom in number 2 position
4) a compound in which 2 of the hydrogens of NH3 have been replaced by organic groups
3. The reduction of nitrobenzene with tin and conc. HCl gives
1) methylamine
2) aniline
3) phenol
4) benzene
4. When benzamide is warmed with bromine in the presence of an alkali we get
1) aniline
2) m-bromobenzamide 3) bromobenzene
4) 2, 4, 6 – tribromobenzamide
5. In Hoffmann’s bromamide reaction carbon from – CONH2 group is lost as
2
1) CO
2) CO2
3) CO3
4) HCO3
6. Conversion of amide into an amine using bromine and potassium hydroxide is known as
1) Gabriel’s phthalimide synthesis
2) Etard’s reaction
3) Hoffmann’s synthesis
4) Reimer – Tiemann reaction
7. Identify the wrong statement
1) Carbyl amine is a cyanide 2) Due to its characteristic smell, methyl isocyanide is readily identified.
3) Production of carbyl amine can be used as a test for all the three types of amines
4) After carbyl amine test, contents of test tube is acidified to stop production of more carbyl amine.
8. Which one of the following statement is true?
1) Aniline cannot be directly nitrated
2) Aniline cannot be directly brominated
3) From aniline azo dyes can't be prepared 4) Aniline gives meta substitution product
9. Which of the following amines cannot be diazotized?
1) Aniline
2) α-naphthylamine
3) p-toluidine
4) benzylmine
NaOBr
10. In the reaction CH3CONH2  X, X is
1) CH3Br
2) CH4
3) CH3COBr
4) CH3NH2
11. Aniline on treatment with acetic anhydride gives
1) phenyl acetate
2) benzanilide
3) acetanilide
4) acetamide
CH2COCl
nitration
hydrolysis
12. C6H5NH2  A 
 B  C. Compound C is
1) acetanilide
2) o and p-nitro acetanilide
3) o and p-nitro aniline 4) m-nitro aniline
13. Which of the following will have highest pKb value?
1) NH3
2) CH3NH2
3) (CH3)2NH
4) (CH3)3N
14. Carbylamine test is used in the detection of
1) aliphatic secondary amine
2) aliphatic primary amine
3) aromatic primary amine
4) both aliphatic and aromatic primary amines
15. Which of the following is a quaternary ammonium salt?
1) CH3NH2
2) (CH3)2NH
3) (CH3)3N
4) [(CH3)4N]+I –
16. A gaseous carbon compound which answers the carbylamine test is soluble in HCl & solution
on treating with NaNO2 gives off N2 gas leaving behind a solution of wood spirit smell. It is
1) carbon monoxide
2) formaldehyde
3) methylamine
4) ethylamine
17. The formula C3H9N can represent
1) only a primary amine
2) a secondary amine 3) a tertiary amine
4) all the above
18. Which of the following amine will not react with nitrous acid to give nitrogen?
1) CH3NH2
2) CH3 – CH2 – NH2
3) (CH3)2 CH – NH2 4) (CH3)3N
19. C3H9N cannot represent
a) 10 amine
b) 20 amine
c) 30 amine
d) quarternary salt
20. Reaction of Aniline with Benzaldehyde is
1) condensation
2) polymerization
3) substitution 4) addition
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21. Hoffmann bromamide reaction is a convenient method for the preparation of
1) amines
2) acid amides
3) alcohols
4) amino acids
22. Which of the following would undergo Hoffmann reaction to give a primary amine?
1) RCONHCH3
2) R – CO – Cl
3) RCOOR
4) RCONH2
23. Methyl amine reacts with nitrous acid to give
1) nitromethane
2) methyl nitrate
3) methyl alcohol
4) hydrogen
24. Carbylamine test is answered by
1) methylamine
2) dimethylamine
3) trimethylamine
4) methylaniline
25. Which one of the following is the strongest base?
1) Ammonia
2) Methyl amine
3) Dimethyl amine
4) Aniline
26. Among the following compounds nitrobenzene, benzene, aniline and phenol, the strongest basic
behaviour in acid medium is exhibited by
1) phenol
2) aniline
3) nitrobenzene
4) benzene
27. When aniline is heated with chloroform & alcoholic KOH, the foul smelling product is
1) Phenyl isocyanide
2) phenol
3) benzonitrite
4) phenyl isocyanate
28. Which one of the following is the weakest base?
1) Dimethyl amine
2) Ammonia
3) Aniline
4) Methyl amine
29. Among the following , the least basic compound is
1) NH3
2) CH3NH2
3) C2H5NH2
4) C6H5NH2
30. A compound X is dissolved in dil. HCl. The solution is called in ice. To the ice cold solution
sodium nitrite is added. A colourless gas is liberated & ethyl alcohol is formed. Compound X is
1) ethyl amine
2) formaldehyde
3) aniline
4) acetaldehyde
31. Maximum number of molecules of CH3-I that can react with a molecule of methyl amine are
1) 1
2) 3
3) 2
4) 4
32. Reaction of primary amines with aldehyde yields
1) amide
2) Schiff’s bases
3) nitrite
4) nitro compound
33. Which one of the following is not an amine?
1) CH3NH2
2) C6H5 (CH3)2N
3) CH3CONH2
4) C6H5NH2
34. Acetamide is treated separately with following reagents. Which one would give methyl amine?
1) PCl5
2) NaOH + Br2
3) Sodalime
4) Conc. H2SO4
35. The starting compound in the manufacture of sulpha drugs is
1) benzaldehyde
2) aniline
3) methyl amine
4) salicylic acid
36. Para nitroaniline is prepared from aniline by
1) nitration followed by reduction
2) acetylation followed by nitration and then hydrolysis
3) oxidation followed by nitration
4) nitration
37. Among the following, the strongest base is
[IIT 2000]
a) C6H5NH2 b) p-NO2C6H4NH2 c) m-NO2 – C6H4NH2 (d) C6H5CH2NH2
38. The compound that will react most readily with NaOH to form methanol is
[IIT 2001]
(a) (CH3)4N+Ib) CH3OCH3
c) (CH3)4S+ I- d) (CH3)3 CCl
39. Which one of the following forms an alcohol with nitrous acid?
1) Methyl ethyl amine
2) Dimethyl aniline 3) Aniline
4) Ethyl amine
40. The correct order of basicities of the following compound is
1) CH3 – C(=NH) – NH2 2) CH3CH2NH2
3) (CH3)2NH 4) CH3 – CO – NH2
a) 2 > 1 > 3 > 4
(b) 1 > 3 > 2 > 4
c) 3 > 1 > 2 > 4
d) 1 > 2 > 3 > 4
41. Which of the following does not produce an amine?
a) Gabriel’s synthesis
b) Hoffmann reaction c) carbylamine reaction d) Mendius reaction.
42. Ethanamine is treated with nitrous acid at ordinary temperature, the products will be
a) ethanol only
b) ethanol, acetic acid, N2 and H2O
c) acetic acid, ethane and H2O
d) ethanol, ethane, N2 and ethyl chloride
43. What is the end product in the following sequence of reaction?
P2O5
H
Acetamide 
B
 A 

Zn / HCl
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44.
45.
46.
47.
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a) methanamine
b) Ethanamine c) Methyl isocyanide d) Methyl cyanide
Which of the following aniline is the weakest base?
a) NH3
b) C6H5CH2NH2
c) C6H5NH2
d) CH3NH2
Nitration of aniline is carried out after acylation because
a) Acylation activates the – NH2 group.
b) Oxidation can be prevented
b) otherwise meta product is formed
d) NH2 group undergoes reduction.
Among the compounds, Aniline (I), o-nitroaniline (II), p-nitroaniline (III) and m-nitroaniline
(IV), the order of increasing base strength is
a) II < III < I < IV
b) II < III < IV < I
c) I < II < III < IV
d) II < I < III < IV
The end product of the reaction
[C.P.M.T. 88]
5  B 
3  C is
C2 H5 NH2 2  
a) Ethyl cyanide
b) Ethylamine
c) Methylamine
d) Acetamide
48. Primary and secondary amines can be distinguished by
[AMU 88]
a) Br2 / KOH
b) HClO
c) HNO2
d) NH3
49. Which of the following amines will not respond to carbylamine reaction?
a) Ethylamine
b) (CH3)2 NH c) CH3 NH2
d) C6H5NH2
[CEET 91]
50. Aniline reacts with conc. HNO3 to give
[C.E.E.T.96]
NH2
NH2
a)
b)
HNO
H2N
PCl
NH
NO2
NO2
and
c)
d)
NO2
O
O
NO2
51. Which of the following is least alkaline?
a)
b)
O 2N
c)
NH2
[CPMT 97]
CH3O
NH2
NH2 d) All are equally basic
C6H5
52. Which of the following reactions does not yield an amine?
Na
a) RX + NH3 →
b) R – CH = N – OH + [H] 
C2H5OH
H
53.
54.
55.
56.
57.
58.
59.
60.
c) RCN + H2O 
d) R – CONH2 + 4 [H] 4 
Aniline is soluble in
a) H2O
b) NaOH
c) NaHCO3
d) HCl
The catalyst used to get aniline from chlorobenzene is
a) Platinum
b) Nickel
c) Cuprous oxide
d) Anhydrous ZnCl2
Aniline is dissolved in HCl. NaNO2 is added to it at 00C. The product is then treated with an
alkaline solution of β-napthol. This produces
a) A violet colour
b) Red dye
c) Green colour
d) Blue colour
Acetanilide finds applications in medicine as
a) A hypnotic
b) An antiseptic
c) An antipyretic
d) An analgesic
When aniline reacts with CH3I, the compound formed will be
a) C6H5NHCH3
b) C6H5N (CH3)2
c) C6H5N+ (CH3)3 I–
d) A mixture of (a), (b) and (c)
When aminomethane reacts with nitrous acid
a) Methanal and nitrogen are formed
b) Methanol and nitrogen are formed
c) Methyl diazonium salt is formed
d) Methyl nitrite is formed
A diazonium salt is obtained when nitrous acid reacts with
a) (CH3)2NH
b) C2H5 – NH – C2H5
c) C2H5 – NH2
d) C6H5NH2
NaNO2
H 2O
Identify ‘Y’ in the reaction, C6H5 – NH2  X 
 Y
LiAlH
HCl
3
300K
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a) C6H5 – Cl
b) C6H5 – OH
c) C6H5N2Cl
d) C6H5NHOH
61. Out of the following compounds which is most basic?
a) CH3 – NH2
b) (CH3)2NH
c) (CH3)3N
d) C6H5NH2
62. Aniline is purified by
a) Simple distillation b) Steam distillation c) Vacuum distillation d) Solvent extraction
63. Which compound when heated with methylamine and alcoholic KOH gives methyl isocyanide?
a) Dichloro methane
b) Methyl chloride
c) Trichloromethane
d) Carbon tetrachloride
64. Which of the following reactions are given by primary amines only?
a) Reaction with nitrous acid
b) Reaction with acetyl chloride
c) Reaction with benzoyl chloride
d) Reaction with chloroform and alcoholic KOH
65. When aniline is heated with glacial acetic acid in presence of anhy. ZnCl2, the product is
a) Acetamide
b) Acetanilide c) Phenyl acetamide
d) Phenyl acetanilide
66. Amongst the following the most basic compound is
a) Benzyl amine
b) Aniline
c) Acetanilide d) p-Bromoaniline
67. Which of the following statements is not correct regarding aniline?
a) It is less basic than ethylamine
b) it can be steam distilled
c) It reacts with sodium to give hydrogen
d) It is soluble in water
68. Aniline reacts with benzoyl chloride in the presence of NaOH to yield N-phenyl benzamide
(C6H5NHCOC6H5). The reaction is known as
a) Diazotisation
b) Cannizzaro reaction c) Schotten – Baumann reaction d) Coupling
69. The basic character of amines is due to
a) Presence of nitrogen atom
b) Tetrahedral structure
c) Lone pair of electrons on nitrogen atom d) High electronegativity of nitrogen
70. A diazonium salt reacts with phenol to give an azo dye. The reaction is called
a) Coupling
b) Diazotisation
c) Condensation
d) Sandmeyer reaction
71. Bromine water reacts with aniline to give
a) Tribromoaniline
b) o-Bromoaniline
c) p-Bromoaniline
d) m-Bromoaniline
72. When a primary amine is heated with CS2 in the presence of excess of mercuric chloride, it
gives isothiocyanates. This reaction is called
a) Hoffmann bromamide reaction
(b) Hoffmann mustard oil reaction
c) Perkins condensation
d) Hoffmann elimination reaction
73. Ethyl isocyanide on hydrolysis in acidic medium generates
[AIEEE 2002]
(a) Ethylamine salt and methanoic acid
b) Propanoic acid ammonium salt
c) ethanoic acid and ammonium salt
d) Methyl amine and salt ethanoic acid
74. Which of the following is the strongest base?
[AIEEE 2004]
a)
b)
c)
(d)
NH2
NHCH3
NH2
CH2NH2
CH3
75. Amongst the following the most basic compound is
[AIEEE 2005]
(a) Benzylamine
b) Aniline
c) Acetamide
d) p-nitroaniline
76. Which method is neither meant for synthesis nor for separation of amines? [AIEEE 2005]
a) Hinesberg method
b) Hoffmann method (c) Wurtz method
d) Curtius reaction
77. The most basic compound amongst the following is
[IIT 1990]
(a) Benzylamine
b) Aniline
c) p-Nitroaniline
d) Ethanamide
78. Reaction of cyclohexanone with dimethyl amine in the presence of catalytic amount of an acid
forms a compound if water during the reaction is continuously removed. The compound formed is
a) Schiff’s base
(b) An enamine
c) An imine
d) An amine [AIEEE 2005]
79. The IUPAC name for the amine CH3 – N(CH3) – C(C2H5) – CH2 – CH3 [IIT 1991]
(a) 3 – (N, N) 3 – Trimethyl pentanamine b) 3 (N, N – Trimethyl) – 3- amino pentane
c) 3 – N, N – Trimethyl pentanamine
d) 3 – (N, N – Dimethylamino) – 3- methyl pentane
80. Benzene diazonium chloride on reaction with phenol in weakly basic medium gives [IIT 1988]
a) Diphenyl ether (b) p-Hydroxyazobenzene c) Chlorobenzene d) Benzene
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QUESTIONS FOR PRACTICE
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