Q14 · CSIR NET Chemistry, June 2015
Paper: CSIR NET June 2015 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Reagents, Reaction Mechanisms & Named Reactions – General · Marks: 2 · Difficulty: Medium
The major product formed in following reaction sequence is 
1. (i) $\mathrm{SOCl_2}$, (ii) $\mathrm{NaN_3}$, MeOH 
1. (i) $\mathrm{SOCl_2}$, (ii) $\mathrm{NaN_3}$, MeOH (a)
(b)
(c)
(d)
Answer
Answer: C ✓ checked by 4AB · confidence medium
Explanation
The acyl azide gives the isocyanate by Curtius rearrangement, and MeOH traps it as the carbamate. tBuOK then opens the camphor ketone (retro-Claisen-type), and H₃O⁺ closes the cis-fused bicyclic γ-lactam acid (c, as in the source key).
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