Q11 · CSIR-NET Chemistry, June 2012

Paper: CSIR-NET June 2012 · 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 structure of the tricyclic compound formed in the following two step sequence is
(a)Option (a) structure 1 of 2, ABC26OR0198 Option (a) structure 2 of 2, ABC26OR0198
(b)Option (b) structure 1 of 7, ABC26OR0198 Option (b) structure 2 of 7, ABC26OR0198 Option (b) structure 3 of 7, ABC26OR0198 Option (b) structure 4 of 7, ABC26OR0198 Option (b) structure 5 of 7, ABC26OR0198 Option (b) structure 6 of 7, ABC26OR0198 Option (b) structure 7 of 7, ABC26OR0198
(c)Option (c) structure, ABC26OR0198
(d)Option (d) structure, ABC26OR0198
Answer
Under review — not yet confirmed.
Answer: D
Explanation
NBS (2 eq) brominates both benzylic methyls to the bis(bromomethyl) compound; aqueous NaOH converts it (via the benzylic alcohol) into the cyclic ether, the 1,3-dihydrofuro-fused tricyclic (d).

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