Q13 · CSIR NET Chemistry, December 2014
Paper: CSIR NET December 2014 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction is: 
1. $\mathrm{H_3O^{+}}$, $\mathrm{h\nu}$ 2. NaOH
1. $\mathrm{H_3O^{+}}$, $\mathrm{h\nu}$ 2. NaOH(a)
(b)
(c)
(d)
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
Hofmann–Löffler–Freytag: the N-chloroammonium radical abstracts the δ-hydrogen (1,5-HAT) from the angular methyl; chlorination and NaOH cyclisation give the N-methylpyrrolidine incorporating that carbon (a).
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