A) alcohols
B) amines
C) alkylhalides
D) hydrogens in hydrocarbons
Correct Answer: B
Solution :
Diethyl oxalate is used for distinguishing primary, secondary and tertiary amines (Hermanns method) (i) The primary \[(1{}^\circ )\] amine forms the corresponding substituted oxamide which is usually a crystalline solid. \[\underset{COO{{C}_{2}}{{H}_{5}}}{\overset{COO{{C}_{2}}{{H}_{5}}}{\mathop{|}}}\,+\begin{matrix} H-NHR \\ H-NHR \\ \end{matrix}\xrightarrow[{}]{{}}\underset{CONHR}{\overset{CONHR}{\mathop{|}}}\,+2{{C}_{2}}{{H}_{5}}O\] (ii) The secondary amine forms a diethyl oxamic ester which is generally a liquid. \[\underset{COO{{C}_{2}}{{H}_{5}}}{\overset{COO{{C}_{2}}{{H}_{5}}}{\mathop{|}}}\,+HN{{R}_{2}}\xrightarrow[{}]{{}}\underset{COO{{C}_{2}}{{H}_{5}}}{\overset{CON{{R}_{2}}}{\mathop{|}}}\,+{{C}_{2}}{{H}_{5}}OH\] (iii)The tertiary amine under these conditions does not react at all since it does not contain a replaceable hydrogen atom.
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