Q22 · 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
Under review — part of this question (a structure or an option) is not clear in the source scan. 4AB is checking it against the original book; the answer shown may change.
The major structures of A and B in the following reaction sequence are 
(a)
(b)
(c)
(d)
B = 
B = Answer
Under review — not yet confirmed.
Answer: D
The source book printed C; on checking, D is correct — see the explanation.
Explanation
NaH forms the naphthoxide, which displaces chloride to give the glycidyl ether A with the epoxide configuration intact; isopropylamine then attacks the terminal epoxide carbon, so the carbinol centre is untouched — propranolol with the OH drawn as in the epoxide (d).
Study loop for Reagents, Reaction Mechanisms & Named Reactions