Question

How many of the following amines will undergo diazotization ?
tert butyl amine, ethanamine, aniline, N-methyl-aniline, p-toluidine, m-chloro-anilines, 2-phenylethanamine, o-anisidine, 2, 4, 6-tribromo aniline.

Answer 1

Hint: Firstly, we have to understand the concept of diazotization. The diazotization reaction is the reaction in which an aromatic primary amine gets converted into its diazonium salt. Only primary aromatic amines can undergo diazotization.

Complete Step by Step Solution:
We have to check which of the given compounds are aromatic primary amines.
(1) Tert butyl amine – It is an aliphatic amine. Hence, it cannot undergo diazotization.
(2) Ethanamine – It is an aliphatic amine. Hence, it cannot undergo diazotization.
(3) Aniline – In this compound, the nitrogen of an amino group is attached to a phenyl group. It is a primary aromatic amine. Hence, it can undergo diazotization.
(4) N-methyl-aniline – The nitrogen of the amino group is attached to two carbons in this compound, making it a secondary amine. Hence, it cannot undergo diazotization.
(5) p-toluidine – In this compound, the methyl group is in para position to the amino group. It is a primary aromatic amine. Hence, it can undergo diazotization.
(6) m-chloro-anilines - The chloro group is in meta position to the amino group in this compound. It is a primary aromatic amine. Hence, it can undergo diazotization.
(7) 2-phenylethanamine It is an aliphatic amine. Hence, it cannot undergo diazotization.
(8) o-anisidine - In this compound, the methoxy group is in ortho position to the amino group. It is a primary aromatic amine. Hence, it can undergo diazotization.
(9) 2,4,6-tribromo aniline – In this compound, 3 bromo groups are present along with the amino group. It is a primary aromatic amine. Hence, it can undergo diazotization.
Hence, among the given amines, five amines will undergo diazotization.

Note: The structure of each of the compounds should be known to identify whether it is a primary aromatic amine or not.