9.

AMINES
Class 12 - Chemistry
Time Allowed: 3 hours Maximum Marks: 70

General Instructions:

Read the following instructions carefully.

(a) There are 33 questions in this question paper with internal choice.

(b) SECTION A consists of 16 multiple -choice questions carrying 1 mark each.

(c) SECTION B consists of 5 short answer questions carrying 2 marks each.

(d) SECTION C consists of 7 short answer questions carrying 3 marks each.

(e) SECTION D consists of 2 case - based questions carrying 4 marks each.

(f) SECTION E consists of 3 long answer questions carrying 5 marks each.

(g) All questions are compulsory.

​(h) Use of log tables and calculators is not allowed.

Section A
1. The major product of the reaction between m-dinitro benzene with NH4HS is ______.

a) m-nitroaniline b) p-Dinitro benzene

c) m-Diamino benzene d) p-Diamino benzene

2. The Gabriel synthesis of amine undergoes which kind of reaction?

a) Nucleophilic substitution reaction (SN2) b) Elimination reaction

c) Electrophilic substitution reaction d) SN1

3. Amongst the given set of reactants, the most appropriate for preparing 2o amine is ________.

a) 1o R-NH2 + RCHO followed by H2 /Pt b) 1o R-Br (2 mol) + potassium phthalimide

followed by H3O+/heat

c) 2o R-Br + NaCN followed by H2 /Pt d) 2o R-Br + NH3

4. Which of the following is a 3o amine?

a) N-methylaniline b) Tert-butylamine

c) 1-methylcyclohexylamine d) Triethylamine
5. Propanamide on reaction with bromine in aqueous NaOH gives:

a) Ethanamine b) N-Methyl ethanamine

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 c) Propanamine d) Propanenitrile
6. Aniline does not undergo Friedel – Crafts reaction because:

a) Anilium ion deactivates any further reaction b) Aluminium chloride reacts with Aniline

c) All of these d) AlCl3 act as a catalyst

7. The correct increasing order of basic strength for the following compounds is ________.

I.

II.

III.

a) III < I < II b) III < II < I

c) II < III < I d) II < I < III

8. Sec – Butylamine is the common name of which compound?

a) N – ethylethanamine b) 2 – butanamine

c) N – methyl – 1 – propanamine d) 1 – butanamine

9. The gas evolved when methylamine reacts with nitrous acid is ________.

a) H2 b) N2

c) C2H6 d) NH3

10. Arrange the following in order of increasing basicity: aniline, p – nitroaniline, p – toluidine, and p – methoxyaniline.

a) p – nitroaniline < aniline< p – b) p – methoxyaniline p – nitroaniline <

methoxyaniline < p – toluidine aniline < p – toluidine

c) p – nitroaniline < aniline < p – toluidine < p d) aniline < p – methoxyaniline p –

– methoxyaniline nitroaniline < p – toluidine
11. Aniline reacts with NaNO2 and HCl at low temperature to give:

a) chloroaniline b) diazonium chloride

c) phenol d) nitroaniline
12. The nitrogen's lone pair in pyrrolidine is best described as occupying what type of orbital?

a) s b) sp2

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 c) sp3 d) sp

13. Assertion (A): Nitrobenzene does not undergo Friedel Craft alkylation.
Reason (R): Nitrobenzene is used as solvent in laboratory and industry.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

14. Assertion (A): Acylation of amines gives a monosubstituted product whereas alkylation of amines gives the
polysubstituted product.
Reason (R): Acyl group sterically hinders the approach of further acyl groups.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

15. Assertion (A): Nitrobenzene undergoes electrophilic substitution at m-position while nucleophilic substitution occurs at
o- and p- positions.
Reason (R): Nitro group in benzene ring significantly lowers the electron density at o- and p positions while at m-
position, the electron density is only originally lowered.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

16. Assertion (A): Acetamide reacts with Br2 in presence of methanolic CH3ONa to form methy! N-methylcarbamate.
Reason (R): Methyl isocyanate is formed as an intermediate which reacts with methanol to form methyl N-
methylcarbamate.

a) Both A and R are true and R is the correct b) Both A and R are true but R is not the
explanation of A. correct explanation of A.

c) A is true but R is false. d) A is false but R is true.

Section B
17. Write IUPAC name of the following:
1 2 3

C H3 − N H − C H2 − C H − C H
| 3

NO
2

18. Complete the following:

KCN LiAlH4

CH3 Br −−−→ A −−−−→ B

19. Give an example of diazotization.

20. Accomplish the following conversion: Nitrobenzene to benzoic acid.
21. Which amine in the following pair is a stronger base? Give reasons.
C H3 − C H − C H3 and C H3 − C H − C OOC H3
| |
NH NH
2 2

OR
An organic compound A, having the molecular formula C3H8O on treatment with Cu at 573 K, gives B. B does not

reduce Fehling's solution but gives a yellow precipitate of the compound C with I2/NaOH. Deduce the structures of

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 A, B and C.
Section C
22. Complete the following reactions:

a.

b.

c.

23. How will you carry out the following conversions?

i.

ii.

24. Give the structures of A and B in the following sequence of reactions:

NH3 NaOBr

i. C H 3 C OOH −
− −
→ A −−−−→ B
Δ
F e/H C l NaN O2 +H C l

ii. C 6 H5 N O2 −−−−→ A −−−−−−−−→ B

o o
0 −5 C
+
C uC N H2 O/H

iii. C 6 H5 N
2
+ −
Cl −−−−→ A −−−−−→ B
Δ

25. Give reasons:

i. Ammonolysis of alkyl halides is not a good method to prepare pure primary amines.
ii. Aniline does not give Friedel-Crafts reaction.
iii. Although -NH2 group is o/p directing in electrophilic substitution reactions, yet aniline on nitration gives good yield

of m-nitroaniline.
26. Write an equation of the reaction of aniline with benzoyl chloride and write the name of the product obtained.

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27. Identify the compounds A, B and C in the following equation:
aq. Br2 NaN O2 /H C l H3 P O2

−−−−→ (A) −−−−−−−→ (B) −−−−→ (C )

H NO2 Δ

28. An aromatic compound A (C7H6O2) on reaction with aqueous ammonia and heating forms compound B. B on

heating with Br2 and alcoholic potash forms a compound C of molecular formula C6H7N. Write the reactions

involved and identify A, B, C.

OR
Give one chemical test to distinguish between primary, secondary and tertiary amines.
Section D
29. Read the text carefully and answer the questions:
RCONH2 is converted into RNH2 by means of Hoffmann bromamide degradation. During the reaction amide is

treated with Br2 and alkali to get amine. This reaction is used to descend the series in which carbon atom is removed

as carbonate ion (CO 2−

3
) . Hoffmann bromide degradation reaction can be written as:

(a) Hoffmann bromamide degradation is used for the preparation of which amine?
(b) Which is the rate determining step in Hoffmann bromamide degradation which is shown above paragraph?
(c) Identify B in the following reaction.

(d) What are the constituent amines formed when the mixture of (i) and (ii) undergoes Hoffmann bromamide
degradation?

OR
Give IUPAC name of amine formed by Hoffman's degradation of Benzamide.
30. Read the text carefully and answer the questions:
Amines have a lone pair of electrons on nitrogen atom due to which they behave as Lewis base. Larger the value of
Kb or smaller the value of pKb stronger is the base. Amines are more basic than alcohols, ethers, esters, etc. The
basic character of aliphatic amines should increase with the increase of alkyl substitution. But it does not occur in a
regular manner as a secondary aliphatic amine is unexpectedly more basic than a tertiary amine in solutions.
Aromatic amines are weaker bases than ammonia and aliphatic amines. Electron-donating groups such as -CH3, -

OCH3, -NH2, etc., increase the basicity while electron-withdrawing substituents such as -NO2, -CN, halogens. etc.
decrease the basicity of amines. The effect of these substituents is more at p- than at m-positions.
(a) Arrange the following in increasing order of their basic strength:
C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2, (C2H5)2NH

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 (b) Arrange the following compounds in increasing order of their acidic strength:
Methylamine, dimethylamine, aniline, N-methylaniline
(c) Rearrange the following in increasing order of their basic strength:
p-toluidine, N, N-dimethyl-p-toluidine, p-nitroaniline, aniline
OR
Which is more acidic, RNH2 or ROH? Explain

(d) Which is more acidic, aniline or ammonia?

Section E
31. Identify A and B in the following reactions:

i.

NaGN LiAJ Hi

ii. C H 3 C H2 C H2 Br −−−−→ A −−−−→ B

iii.

OR
i. Tert-Butylamine cannot be prepared by the action of NH3 on tert-butyl bromic. Explain why?

ii. Suggest a convenient method for the preparation of tert-butylamine.

32. Account for the following:
i. Diazonium salts of aromatic amines are more stable than those of aliphatic amines.
ii. Amines are more basic than alcohols of comparable molecular masses.
OR
i. Write the structures of A and B in the following reactions:
+
C uC N H2 O/H

a. C6
H5 N
2
+ −
Cl −−−−→ A −−−−−→ B

NH3 NaOBr

b. C H 3 C OOH −
− −
→ A −−−−→ B
Δ

ii. Write the chemical reaction of methyl amine with benzoyl chloride and write the IUPAC name of the product
obtained.
iii. Arrange the following in the increasing order of their pKb values: C6H5NH2, NH3, C2H5NH2, (C2H5)2 NH

33. a. Write the reactions involved in the following:

i. Hoffmann bromamide degradation reaction
ii. Diazotisation
iii. Gabriel phthalimide synthesis
b. Give reasons:
i. (CH3)2NH is more basic than (CH3)3N in an aqueous solution.
ii. Aromatic diazonium salts are more stable than aliphatic diazonium salt.
OR
How will you convert
i. Ethanoic acid into methanamine

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ii. Hexanenitrile into 1-aminopentane
iii. Ethanamine into methanamine
iv. Nitromethane into dimethylamine
v. Propanoic acid into ethanoic acid

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