Q. Diethyl oxalate is used for distinguishing primary, secondary and tertiary

A) Alcohols
B) Amines
C) Alkyl halides
D) Hydrogens in hydrocarbons
Explanation

(b)
Dimethyl oxalate is used for distinguishing primary, secondary and tertiary amines (Hofmann’s method).
The primary ($1{^\circ}$) amine forms the corresponding substituted oxamide which is usually a crystalline solid.
$COOC_{2}H_{5}\ \ \ \ \ H - NHR$ $CONHR$
$|$ $+$ $\rightarrow$ $|$ $+ 2C_{2}H_{5}OH$
$COOC_{2}H_{5}\ \ \ H - NHR$ $CONHR$
The secondary amine forms a diethyl oxamic ester which is generally a liquid.
$\ \ \ COOC_{2}H_{5}\ \ \ \ \$ $CONR_{2}$
$|$ $+ NHR_{2}$ $\rightarrow$ $|$ $+ C_{2}H_{5}OH$
$COOC_{2}H_{5}$ ${COOC}_{2}H_{5}$
The tertiary amine under these conditions does not react at all since it does not contain a replaceable hydrogen atom.

Dr. Abubacker
Reviewed by Dr. Abubacker

Physics Educator & NEET/JEE Specialist

Ph.D. in Physics with 19+ years of teaching experience.

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