Q18 · CSIR NET Chemistry, December 2015

Paper: CSIR NET December 2015 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium

The major structures of A and B in the following reaction sequence are $\xrightarrow[\mathrm{Me_2NH}]{\mathrm{HCHO}}$ A B
(a)A = Option (a) structure 1 of 2, ABC26OR0276 B = Option (a) structure 2 of 2, ABC26OR0276
(b)A = Option (b) structure 1 of 2, ABC26OR0276 B = Option (b) structure 2 of 2, ABC26OR0276
(c)A = Option (c) structure 1 of 2, ABC26OR0276 B = Option (c) structure 2 of 2, ABC26OR0276
(d)A = Option (d) structure 1 of 2, ABC26OR0276 B = Option (d) structure 2 of 2, ABC26OR0276
Answer
Answer: B ✓ checked by 4AB · confidence high
Explanation
Mannich reaction of N-methylpyrrole occurs at C-2 (A); MeI quaternises the amine and cyanide displaces trimethylamine to give 2-(cyanomethyl)-N-methylpyrrole (b).

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