Solution

Class 12 - Chemistry

Amines
Section A

(c) NH2 > OH- > NH3 > H2O

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1.
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Explanation: NH2  > OH > NH3 > H2O. Due to higher electronegativity of O than N atom, the O-H bond is
more polar than the N-H bond. Hence, O-H is more acidic in nature than the N-H bond. Now, NH2 and OH
have a negative charge due to which they are more basic than NH3 and H2O.

2. (d) Aromatic primary amines

Explanation: In Gabriel's phthalimide reaction, the potassium salt of phthalimide is formed. It reacts
readily with the primary alkyl halide to form the corresponding alkyl derivative. But aryl halide
(C6H5X) does not react with potassium salt of phthalimide. Because C-X bond in haloarene (alkyl halide) is
difficult to be cleaved due to a partial double-bond character. Hence, do not undergo SN2 reaction
with potassium salt of phthalimide. So, aromatic primary amines cannot be prepared by Gabriel
phthalimide synthesis.
3. (a) Sandmeyer reaction ; Gattermann reaction
Explanation: The Cl-, Br-, and CN- nucleophiles can easily be introduced in the benzene ring of benzene
diazonium salt in the presence of Cu(I) ion. This reaction is called the Sandmeyer reaction.
Chlorine or bromine can be introduced in the benzene ring by treating the benzene diazonium salt solution
with corresponding halogen acid in the presence of copper powder. This is referred to as the Gattermann
reaction.
4. (d) CH3OH
∘ ∘
0 −5 C

Explanation: CH3NH2 + HNO3 −−−−→  CH3OH + N2 + H2O

5. (c) Gabriel phthalimide synthesis

Explanation:
Gabriel phthalimide synthesis is used to get primary amine is prepared from alkyl halide without any
change in the number of carbon atoms.

6. (b) 2 – butanamine
Explanation: Sec – Butylamine is the common name of 2-butanamine (CH3CH2CHNH2CH3).

7. (c) Butanamine
Explanation: In Hoffmann bromamide reaction, the amine formed has one carbon less than the amide.
RCONH2 + Br2 + 4NaOH  →  RNH2 + Na2CO3 + 2NaBr + 2H2O

8. (a) IV
Explanation: Hydrocarbon are more volatile than the amine.
Section B

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 9. a. Alkylamines are stronger bases because alkyl groups are electron releasing (+I effect) leading to high
electron density on the nitrogen atom. In arylamines, aryl group is electron withdrawing (- Effect). The
lone pair of electrons on nitrogen are delocalized due to resonance with the benzene ring.
b. CH3 NH2 + HNO2 → CH3 OH
M ethyla min e M ethanol

PCl K CN

−−→ C H3 C l −−−→
Chloromethane
Na/ C2 H5 OH

C H3 C ≡ N −−−−−−−→ C H3 C H2 N H2
Ethane nitrile 4(H) Ethyla min e

10. Carbylamine reaction: When primary amine reacts with and C HC l3 KOH, offensive smelling isocyanide is
formed.
C2 H5 NH2 + CHC l3 + 3KOH → C2 H5 N ≡ C + 3KCl + 3H2 O
Ethanamine Ethyl insocyanide

H2 /Pd

11. R − NH2 + CHC l3 + 3KOH → R − NC −−−−−−−→ R − NH − C H3

o o
1 A min e Alkyl isocyanide 1 A min e
(Re duction)

Carbylamine reaction is shown by 1o amine only which results in the replacement of two hydrogen atoms
attached to N atom of -NH2 group by one carbon atom in heating with choloform to form isocyanide or
carbylamine. On catalytic reduction, the isocyanide will give a secondary amine with one methyl group.
12. i. Conversion of CH3–CH2–Cl into CH3–CH2–CH2–NH2 involve the following steps:

ii. Conversion of C6H5–CH2–Cl into C6H5–CH2–CH2–NH2 involve the following steps:

13. i. Sandmeyer reaction:

ii. Coupling reaction:

14. i. C2 H5 C l + K C N → C2 H5 = C ≡ N + K C l

C2 H5 C l + AgC N → C2 H5 − N = C + AgC l

These reactions show CN- as an ambident nucleophile which possesses two nucleophilic centres.
ii. Hinsberg test:
The reaction of benzenesulphonyl chloride (Hinsberg reagent, C6H5SO2Cl) with primary amine yields N-
ethyl benzene sulphonyl amide which is soluble in alkali.
In the reaction with secondary amine N, N-diethyl benzene sulphonamide is formed which is insoluble in
alkali. Tertiary amine does not react with benzene sulphonyl chloride.

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