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Reactions of Aryl Amines (Diazo Salts)

An aromatic p...

Question

An aromatic primary amine A with molecular formula $C_{6} H_{7} N$ undergoes diazotisation to give B. B when the aqueous solution of B is boiled it gives C. Identify A,B and C.

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Solution

Compound A with molecular formula $C_{6} H_{7} N$ is Aniline $(C_{6} H_{5} N H_{2})$
Compound B is Benzene diazonium chloride $(C_{6} H_{5} - N = N - C l)$
Compound C is phenol $(C_{6} H_{5} O H)$
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Q. Compound A of molecular formula

C_{3} H_{6} O

does not reduce not reduce Tollen's reagent nod Fehling's solution. Compound A undergoes Clemmensen reduction to give compound B of molecular formula

C_{3} H_{8}

. Compound A in the presence of Conc.

H_{2} S O_{4}

condenses is give air aromatic compound C of molecular formula

C_{9} H_{12}

.
Identify B and C. Explain the reactions.

Q. An excess of compound 'A' (molecular formula C₃H₈O) is treated with acidified potassium dichromate to form a product 'B' (molecular formula C₃H₆O). 'B' forms a shining silver mirror on warming with ammoniacal silver nitrate. 'B' when treated with an aqueous solution of H₂NCONHNH_2,HCl and sodium acetate, it gives a product 'C'. Identify the structure of 'C'

Q. From analysis and molecular weight determination, the molecular formula of (A) is

C_{3} H_{7} N O

. The compound gave following reactions.
(i) On hydrolysis it gives an amine (B) and a carboxylic acid (C)
(ii) Amine (B) reacts with benzene sulphonyl chloride and gives a product which is insoluble in aqueous sodium hydroxide solution.
(iii) Acid (C) on reaction with Tollen's reagent gives a silver mirror what are A, B and C.
Explain the reactions.

A

' (molecular formula

C_{3} H_{8} O

is treated with acidified potassium dichromate to form a product '

B

' (molecular formula

C_{3} H_{6} O

B

' forms a shining silver mirror on warming with ammoniacal silver nitrate. '

B

' when treated with an aqueous solution of

H_{2} N C O N H N H_{2}

and sodium acetate gives a product '

C

'. Identify the structure of '

C

^{'} A^{'}

(molecular formula

C_{3} H_{8} O

) is treated with acidified potassium dichromate to form a product

^{'} B^{'}

(molecular formula

C_{3} H_{6} O

^{'} B^{'}

forms a shining silver mirror on warming with ammoniacal silver nitrate.

^{'} B^{'}

when treated with an aqueous solution of

N H_{2} C O N H N H_{2}, H C l

and sodium acetate gives a product

^{'} C^{'}

. Identify the structure of

^{'} C^{'}

.

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Reactions of Aryl Amines (Diazo Salts)

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