Step 1: Recall the carbylamine reaction.
The carbylamine reaction is a test for primary amines (aliphatic or aromatic). In this reaction, a primary amine reacts with chloroform (CHCl$_3$) and alcoholic KOH to form isocyanides (carbylamines), which have a very unpleasant odor.
General reaction:
\[
R–NH_2 + CHCl_3 + 3KOH \;\; \xrightarrow{\Delta} \;\; R–NC + 3KCl + 3H_2O
\]
Step 2: Check each option.
- (A) CH$_3$–CH$_2$–NH$_2$: This is a primary aliphatic amine. It gives the carbylamine test.
- (B) CH$_3$–NH$_2$: This is also a primary aliphatic amine, so it gives the carbylamine test.
- (C) CH$_3$–NH–CH$_3$: This is a secondary amine. Secondary (and tertiary) amines do not give the carbylamine reaction.
- (D) C$_6$H$_5$–NH$_2$: Aniline is a primary aromatic amine. It also gives the carbylamine test.
Step 3: Final Answer.
Thus, the amine which does not give the carbylamine reaction is the secondary amine, CH$_3$–NH–CH$_3$.
\[
\boxed{CH_3–NH–CH_3 \; \text{(secondary amine)}}
\]
Amines are usually formed from amides, imides, halides, nitro compounds, etc. They exhibit hydrogen bonding which influences their physical properties. In alkyl amines, a combination of electron releasing, steric and H-bonding factors influence the stability of the substituted ammonium cations in protic polar solvents and thus affect the basic nature of amines. Alkyl amines are found to be stronger bases than ammonia. Amines being basic in nature, react with acids to form salts. Aryldiazonium salts, undergo replacement of the diazonium group with a variety of nucleophiles to produce aryl halides, cyanides, phenols and arenes.
Which of the following amine(s) show(s) positive carbamylamine test? 