2.

Amines

1. How are amines classified? Give their general formulae.

Amines are classified into three types. That is primary, secondary and
tertiary depending on whether one, two (or) three hydrogen atoms of
ammonia have been replaced by alkyl group.
R R
NH3 R NH2 NH R N
R R
Ammonia Primary secondary Tertiary
amine amine amine
2. How benzene diazonium chloride is converted to Chloro benzene?

Benzene diazonium chloride is treated with cuprous chloride (CuCl) to form

Chlorobenzene. The reaction is known as Sandmeyer reaction.
+ -
N2Cl + CuCl Cl
Benzene
Chloro benzene
diazonium chloride

3. How would obtain ethylamine from acetaldehyde?

When acetaldehyde is treated with ammonia in the presence of nickel

reduction takes place to form ethyl amine.

Ni
H3C CHO + NH3
+ H2 H3C CH2 NH2

4. Explain coupling reaction with example?

The diazonium ions are joined (or) coupled to the ring of phenol (or)
aromatic amines are called Diazo- coupling reaction.

+ - OH-
N2Cl + OH N N OH
Benzene
diazonium chloride phenol p-Hydroxy azobenzene

5. What happens when aniline is warmed with acetyl chloride?

Aniline is treated with acetyl chloride to form acetanilide.
NH2 HN CO CH3

+ H3C CO Cl

Aniline Actanilide

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6. Explain Gabriel phthalimide reaction with an example.

CO CO
KOH
NH CH3CH2Br
NK
- H2O - KBr
CO CO
Phthalimide
CO
COOH
OH- /H2O
NCH2CH3 + H3C CH2 NH2

CO Ethyl amine
COOH

7. How do you convert methyl nitrile into ethylamine?

Methyl nitrile is treated with Lithium aluminum hydride to form ethyl

amine.
LiAlH4
H3C CN + 2 H2 H3C CH2 NH2
Methyl nitrile Ethyl amine

8. Write a note on Hofmann’s degradation reaction.

Converting an amide to an amine having one carbon atom less than the
starting amide is called Hofmann’s degradation (or) rearrangement. It is
carried out in presence Br2 and NaOH.
H3C CO NH2 + Br2 + 3 NaOH H3C NH2 + 2 NaBr + NaHCO3 + H2O
Acetamide Methyl amine

9. How is benzene diazonium chloride converted to p-Hydroxy azobenzene?

Benzene diazonium chloride reacts with phenol to form p-Hydroxy

azobenzene. It is an example for coupling reaction.

OH-
N 2Cl
+ OH NH NH OH

Benzenediazonium Phenol p-Hyydroxyazobenzene

chlorede

10. Write the structure and IUPAC name of tri methyl amine.

H3C N CH3
N,N-Dimethyl methanamine
CH3

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 11. Arrange the following compounds in the order of increasing basic
strength and give reasons. Ammonia, methyl amine and dimethyl amine.

H3C
NH > H3C NH2 > NH3
H3C
Di methyl amine Methyl amine Ammonia
This is because the alkyl groups are electron releasing. They increase the
electron density around the nitrogen, thereby increasing the availability
of the lone pair of electrons. The greater the number of electron releasing
alkyl groups, the greater the availability of nitrogen’s lone pair and
stronger the base.

12. How does benzene diazonium chloride react with β-Napthol in NaOH?
Give chemical equation. What is the name of this equation?

β-Napthol (2-naphthol.) reacts with benzene diazonium chloride in

alkaline solution at 0-5 o C to form 1-phynylazo 2- Napthol.It is a
coupling reaction.

N N
OH
OH
OH-
N 2Cl
+
Benzenediazonium 2-Naphthol 1-Phenylazo-2-naphthol
chlorede

13. How primary, secondary and tertiary aliphatic amines do reacts with
nitrous acid?

1. Primary amines react with nitrous acid to form alcohol and nitrogen
gas.
H3 C NH2 + HONO H3 C OH + N2 + H2 O
Methanamine Methanol

2. Secondary amines react with nitrous acid to form N-nitrosoamines

which are water insoluble yellow oils. The process which involves
replacement of hydrogen on nitrogen by nitro group called nitrosation.
R R
R N H + HONO - H2O
R N N O + H2O
secondary Nitrosoamine
amine (yellow oil)
3. Tertiary amines (R3N) having no available hydrogen on nitrogen. so
simply form soluble tri alkyl ammonium salts of nitrous acid, which is
soluble in water.

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14. Describe Hinsberg test to distinguish primary, secondary and tertiary
amines.

This involves the treatment with benzene sulphonyl chloride (Hinsberg

reagent), then made alkaline with aqueous with NaOH.
1. The primary amines give N-alklylbenzene sulphonamide. This forms
salt with NaOH, which is soluble in water.

H H +
NaOH Na
-
SO 2Cl +H N R
- HCl
SO 2 N R SO 2 N R

N-alkylbenzene soluble
Primary amine salt
sulphonamide (insoluble)

2. The secondary amines gives N,N- dialklylbenzene sulphonamide. This

do not form salt with NaOH (no acidic hydrogen) and insoluble in alkali
solution.
R R
NaOH
SO 2Cl + H N R
- HCl
SO 2 N R No reaction

secondary N,N-dialkylbenzene
amine sulphonamide (insoluble)

3. The tertiary amines do not react with reagent because no acidic

hydrogen is available.

*******

45. How is acetone converted into isopropyl amine?

When acetone is treated with ammonia in the presence of nickel reduction

takes place to form ethyl amine.
O NH2
Ni
H3C C CH3 + NH3 + H2
150 oC
H3C CH CH3
Acetone
Isopropyl amine

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