OUR OWN HIGH SCHOOL, DUBAI

SUBJECT: CHEMISTRY
QUESTION BANK
CHAPTER-13-AMINES

SECTION – A
The following questions are multiple-choice questions with one correct answer.
Each question carries 1 mark.

1 An optically active amine (C5H13N) on treatment with aq. NaNO2/HCl forms an optically inactive [1]
alcohol (C5H12O) with evolution of N2 gas. The amine is

(a) 1-pentanamine
(b) 2-pentanamine
(c) 3-pentanamine
(d) 2-methylbutanamine

2 The most reactive amine towards dilute hydrochloric acid is ___________. [1]

3 Amides can be converted into amines by the reaction named [1]

(a) Hoffmann degradation

(b) Ammonolysis
(c) Carbylamine
(d) Diazotization

4 Which of the following would not be a good choice for reducing nitrobenzene to aniline? [1]

(a) LiAlH4
(b) H2/Ni
(c) Fe and HCl
(d) Sn and HCl

5 Which of the following is the strongest base? [1]

6 The name of the compound ‘B’ in the following series of reactions, is [1]

(a) propan-1-amine
(b) propan-2-amine
(c) butan-1-ol
(d) butan-2-ol

7 Aniline when acetylated, the product on nitration followed by alkaline hydrolysis gives [1]

(a) acetanilide
(b) o-nitro acetanilide
(c) p-nitroaniline
(d) m-nitroaniline

8 The compound, which does not react with CH3COCl is [1]

(a) RNH2
(b) R2NH
(c) R3N
(d) all of these

9 [1]
An organic compound A on reduction gives compound B, which on reaction with trichloro methane and
caustic potash forms C. The compound 'C' on catalytic reduction gives N-methyl benzenamine, the
compound 'A' is:

(a) Nitrobenzene
(b) Nitromethane
(c) Methanamine
(d) Benzamine

10 [1]
The end product in the following sequence is

(a) CH3NH2
(b) C2H5NH2
(c) CH3CN
(d) CH3COONH4
11 The least basic among the following is: [1]
(a) (CH3)2NH
(b) CH3NH2
(c) (CH3)3N
(d) C6H5NH2

12 The compound obtained by heating a mixture of a primary amine and chloroform with ethanolic [1]
potassium hydroxide (KOH) is

(a) an alkyl cyanide

(b) a nitro compound
(c) an alkyl isocyanide
(d) an amide

13 Which of the following is formed when an alkyl primary amine reacts with nitrous acid? [1]

(a) Alkyl nitrite

(b) Secondary amine
(c) Nitroalkane
(d) Alcohol

14 The conversion of benzene diazonium chloride to bromobenzene can be accomplished by [1]

(a) Reimer-Tiemann reaction

(b) Friedel-Crafts reaction
(c) Gattermann reaction
(d) Azo-Coupling reaction

15 Which of the following amines are insoluble in water? [1]

(a) Methanamine
(b) Ethanamine
(c) Propanamine
(d) Benzenamine

16 The best reagent for converting 2-phenylpropanamide into 2-phenylpropanamine is: [1]

(a) excess H2
(b) Br2 in aqueous NaOH
(c) iodine in the presence of red phosphorus
(d) LiAlH4 in ether

17 Reduction of CH3CH2NC with hydrogen in presence of Ni or Pt as catalyst gives [1]

 (a) CH3CH2NH2
(b) CH3CH2NHCH3
(c) CH3CH2NHCH2CH3
(d) (CH3)3N

18 The correct IUPAC name for CH2=CHCH2NHCH3 is [1]

(a) Allyl methylamine

(b) 2-amino-4-pentene
(c) 4-aminopent-1-ene
(d) N-methylprop-2-en-1-amine

19 The best reagent for converting, 2-phenylpropanamide into 1-phenylethanamine is: [1]

(a) excess H2/Pt

(b) NaOH/Br2
(c) NaBH4/methanol
(d) LiAlH4/ether

20 Amongst the following, the strongest base in aqueous medium is: [1]

(a) CH3NH2
(b) NCCH2NH2
(c) (CH3)2NH
(d) C6H5NHCH3

SECTION – B
The questions in this section are Assertion – Reason type of questionsChoose the correct answer
out of the following choices.
(i) Both assertion and reason are true, and reason is the correct explanation of the
assertion.
(ii) Both assertion and reason are true but reason is not the correct explanation of
assertion.
(iii) Assertion is not true but reason is true.
(iv) Both assertion and reason are false.

21 Assertion: Aromatic 1°amines can be prepared by Gabriel phthalimide synthesis. [1]

Reason: Aryl halides undergo nucleophilic substitution with anion formed by phthalimide.

22 Assertion: Only a small amount of HCl is required in the reduction of nitro compounds with iron [1]
scrap and HCl in the presence of steam.
Reason: FeCl2 formed gets hydrolyzed to release HCl during the reaction.

23 Assertion: Amines are basic in nature. [1]

Reason: Amines have lone pair of electrons on nitrogen atom.
24 Assertion: Acetanilide is less basic than aniline. [1]
Reason: Acetylation of aniline results in decrease of electron density on nitrogen.

25 Assertion: Nitration of aniline can be conveniently done by protecting the amino group by [1]
acetylation.
Reason: Acetylation increases the electron-density in the benzene ring.

26 Assertion: Aniline does not undergo Friedel-Crafts reaction. [1]

Reason: –NH2 group of aniline reacts with AlCl3 (Lewis acid) to give acid-base reaction.

27 Assertion: Acylation of amines gives a monosubstituted product whereas alkylation of amines [1]
gives
poly-substituted product.
Reason: Acyl group sterically hinders the approach of further acyl groups

28 Assertion: Nitrating mixture used for carrying out nitration of benzene consists of conc. [1]
HNO3+ conc. H2SO4
Reason: In presence of H2SO4, HNO3 acts as a base and produces NO2+ ions.

29 1. Assertion: Only a small amount of HCl is required in the reduction of nitro compounds with iron [1]
scrap and HCl in the presence of steam.
Reason: FeCl2 formed gets hydrolyzed to release HCl during the reaction.

30 1. Assertion: N-Ethylbenzene sulphonamide is soluble in alkali. [1]

Reason: Hydrogen attached to nitrogen in sulphonamide is strongly acidic.

SECTION - C
The following questions are very short answer type and you may answer them
in minimum twosentences.

31 Give the structures of A and B in the following sequence of reactions: [2]

32 How will you distinguish between the following pairs of compounds? [2]
(i) Aniline and Ethanamine
(ii) Aniline and N-methylaniline

33 Account for the following, supporting your answer with diagrams or equations [2]
wherever possible:
(a) Diazonium salts of aromatic amines are more stable than those of aliphatic amines.
(b) Methylamine in water reacts with ferric chloride to precipitate hydrated ferric
oxide.
34 Arrange the following in decreasing order of pkb giving reason: [2]
(a) Aniline, p-nitroaniline and p-toluidine
(b) C2H5NH2, (C2H5)2NH, (C2H5)3N in gaseous state

[2]
35 Write the structures of A, B and C in the following:

36 Write the structures of main products when benzene diazonium chloride reacts with the [2]
following reagents:
(i)CuCN/KCN
(ii) H𝟐O

37 Arrange the following compounds in increasing order of solubility in water: [2]

𝑪𝟔𝑯𝟓𝑵𝑯𝟐, (𝑪𝟐𝑯𝟓)𝟐𝑵𝑯, 𝑪𝟐𝑯𝟓𝑵𝑯2

38 (a) Illustrate Sandmeyer’s reaction with an equation. [2]

(b) Explain, why (CH3)2NH is more basic than (CH3)3N in aqueous solution.

39 (i) Complete the reaction with the main product formed: [2]

(ii) Convert Bromoethane to Propanamine.

40 (i) Draw the zwitter ion structure for sulphanilic acid. [2]
(ii) How can the activating effect of –NH2 group in aniline be controlled?

SECTION – D
The following questions are long answer type and you may answer them in
minimum three sentences with relevant equations / diagrams

41 Give reasons: [3]

(i) Aniline does not undergo Friedel-Crafts reaction.
(ii) Aromatic primary amines cannot be prepared by Gabriel’s phthalimide synthesis.
(iii) Aliphatic amines are stronger bases than ammonia.

42 Write equations involved in the following reactions: [3]

(i) Ethanamine reacts with acetyl chloride.
(ii) Aniline reacts with bromine water at room temperature.
(iii) Aniline reacts with chloroform and ethanolic potassium hydroxide.
43 (a) Write the IUPAC name for the following organic compound: [3]
(CH3CH2)2NCH3
(b) Write the equations for the following:
(i) Gabriel phthalimide synthesis
(ii) Hoffmann bromamide degradation

44 Write reasons for the following: [3]

(i) Ethylamine is soluble in water whereas aniline is insoluble.
(ii) Amino group is o- and p-directing in aromatic electrophilic substitution reactions, but
aniline on nitration gives a substantial amount of m-nitroaniline.
(iii) Amines behave as nucleophiles.

45 [3]
How will you carry out the following conversions?
(i) Nitrobenzene to Aniline
(ii) Ethanamide to Methanamine
(iii) Ethanenitrile to Ethanamine

SECTION – E
The following are long answer type questions

46 1. A colorless substance ‘A’ (C6H7N) is sparingly soluble in water and gives a water-soluble [5]
compound ‘B’ on treating with mineral acid. On reacting with CHCl3 and alcoholic potash ‘A’
produces an obnoxious smell due to the formation of compound ‘C’. Reaction of ‘A’ with
benzene sulphonyl chloride gives compound ‘D’ which is soluble in alkali. With NaNO 2 and HCl,
‘A’ forms compound ‘E’ which reacts with phenol in alkaline medium to give an orange dye ‘F’.
Identify compounds ‘A’ to ‘F’.
1.

47 Predict the reagent or the product in the following reaction sequence. [5]
48 (a)How will you convert the following: [5]
(i) Phenol to N-phenylethanamide.
(ii) Chloroethane to methanamine.
(iii) Propanenitrile to ethanol.

(b) Account for the following:

(i) Tertiary amines do not undergo acylation reaction.
(ii) Amines are more basic than comparable alcohols.

49 Passage:
Amines constitute an important class of organic compounds derived by replacing one or more
hydrogen atoms of ammonia molecule by alkyl/aryl groups. Amines are usually formed from
nitro compounds, halides, amides, etc. They exhibit hydrogen bonding which influences their
physical properties. Alkyl amines are found to be stronger bases than ammonia. In aromatic
amines, electron releasing and withdrawing groups, respectively increase and decrease their
basic character. Reactions of amines are governed by availability of the unshared pair of
electrons on nitrogen. Influence of the number of hydrogen atoms at nitrogen atom on the type
of reactions and nature of products is responsible for identification and distinction between
primary, secondary and tertiary amines. Reactivity of aromatic amines can be controlled by
acylation process.

(a) Why does aniline not give Friedel-Crafts reaction? [1]

(b) How can you distinguish between CH3CH2NH2 and (CH3CH2)2NH by Hinsberg test? [1]
(c) (a) Write the structures of A and B in the following reactions: [2]
 OR

How will you convert the following: (a) Benzoic acid to aniline (b) Aniline to p-
bromoaniline
50 Amines are alkyl or aryl derivatives of ammonia formed by replacement of one or more
hydrogen atoms. Alkyl derivatives are called aliphatic amines and aryl derivatives are known as
aromatic amines. The presence of aromatic amines can be identified by performing dye test.
Aniline is the simplest example of aromatic amine. It undergoes electrophilic substitution
reactions in which - NH2 group strongly activates the aromatic ring through delocalization of lone
pair of electrons of N-atom. Aniline undergoes electrophilic substitution reactions. Ortho and
para positions to the -NH2 group become centers of high electrons density. Thus, -NH2 group is
ortho and para-directing and powerful activating group.
Answer the following questions:
(a) Give one chemical test to distinguish between Cyclohexylamine and aniline [1]
(b) Predict the product and write equation when Oxidation of aniline with manganese [1]
dioxide and sulphuric acid
(c) What happens when [2]
(i) Aniline reacts with nitrating mixture
(ii) Aniline on bromination
OR
Give reason:
Acetylation of aniline reduces its activation effect.

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