1.

Explain Gabriel phthalimide synthesis for the

AMINES
preparation of methanamine. 3. Explain Carbylamine reaction with an example.
Ans: Phthalimide reacts with KOH to form potassium Ans: Ex 1: When methanamine is treated with chloroform and
phthalimide which is on treatment with methyl alcoholic solution of KOH, methyl isocyanide is obtained
chloride gives N-Methyl phthalimide which on CH3NH2 + CHCl3 + 3KOH (alc) ⎯⎯ → CH3NC + 3KCl + 3H2O
hydrolysis with sodium hydroxide gives methanamine.
O O O
Ex 2: When ethanamine is treated with chloroform and
KOH CH Cl alcoholic solution of KOH, ethyl isocyanide is obtained.
NH ⎯⎯⎯⎯
→
- +
3 →
N K ⎯⎯⎯⎯ N CH3
C2H5NH2 + CHCl3 + 3KOH (alc) ⎯⎯ → C2H5NC + 3KCl + 3H2O
O O O
O
4. Between CH3NH2 and C6H5NH2 which is more basic? Why?
ONa NaOH Ans: CH3NH2 is more basic due to +I effect of CH3 group.
+ H3C NH2
ONa
5. Arrange the following amines in the order of their increasing
O
2. Explain Hoffmann’s Bromamide reaction with an basic strength in aqueous solution. (CH3)3N, (CH3)2NH,
example. (CH3)NH2.
Ans: Ex 1: Acetamide on treatment with Br2 in the Ans: Increasing order is (CH3)3N < (CH3)NH2 < (CH3)2NH
presence of KOH or NaOH at about 343K gives
methanamine 6. Explain Tests to distinguish 1o, 2o and 3o amines by using
CH3CONH2 +Br2 + 4KOH ⎯⎯ → CH3NH2 + 2KBr + Hinsberg’s reagent.
K2CO3 + 2H2O Ans: Benzene sulphonyl chloride is known as Hinsberg’s
reagent
Ex 2: Propanamide on treatment with Br2 in the (a) Primary amines react with benzenelsulphonyl chloride to
presence of KOH or NaOH at about 343K gives form product which is soluble in alkali i.e NaOH or KOH
ethanamine (b) Secondary amines react with benzenesulphonyl chloride to
CH3 CH2CONH2 + Br2 + 4KOH ⎯⎯ → CH3CH2NH2 + 2KBr + form product which is insoluble in alkali.
K2CO3 + 2H2O (c) Tertiary amines do not react with benzenesulphonyl chloride
7. Explain Diazotisation reaction with an example. Or 10. How is aniline converted into phenyl isocyanide? Write
Name the product obtained and write the reaction the equation.
when nitrous acid treated with aniline at 273-278K Ans: Aniline reacts with chloroform and alcoholic solution of
Ans: Aniline react with Nitrous acid 273 K -278K or KOH, phenyl isocyanide is obtained
0o-5oC to form diazonium salt. This reaction is also called C6H5NH2 + CHCl3 + 3KOH (alc) ⎯⎯ → C6H5NC +3KCl + 3H2O
as diazotisation reaction.
NaNO2 + 2 HCl
C6H5NH2 ⎯⎯⎯⎯⎯
273− 278 K
→ C6 H 5 − N 2+Cl − + NaCl + 2H2O 11. Write the major product formed in the following
conversion:
i) When nitrous acid is treated with methylamine
8. Explain the reduction of nitrobenzene to aniline.
Ans: When nitrobenzene is reduced in presence of H2 in ii) Benzene diazonium chloride is treated with KI
Pd or Sn in HCl or Fe in HCl to form aniline. Ans: i) Methyl alcohol ii) Iodobenzene
NO 2 NH2
12. Give the IUPAC name of i) CH3-NH-CH2CH3
ii) (CH3)2-N-CH2-CH3 iii) CH3CH2NH2 (iv) (CH3)2-N-C6H5
⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯⎯
H 2 /Pd and ethanol or Sn + HCl or Fe + HCl
→ Ans: i) N-methylethanamine
ii) N,N-dimethylethanamine
9. What is the action of bromine water on iii) ethanamine
benzenamine (Aniline) at room temperature?
iv) N,N-dimethylbenzenamine
Ans: Aniline reacts with bromine water to form
2, 4, 6-tribromoaniline
NH2 NH2 13. Between ammonia and aniline, which is more basic?
Ans: Ammonia
Br Br
Br + Water
2
+ 3Br2 ⎯⎯⎯⎯⎯⎯→ 14. Why aromatic primary amines cannot be prepared by
Gabriel synthesis?
Ans: because aryl halides do not undergo nucleophilic
Br
substitution with the anion formed by phthalimide.