Q20 · CSIR-NET Chemistry, December 2016

Paper: CSIR-NET December 2016 · Subject: Organic Chemistry · Chapter: Reagents, Reaction Mechanisms & Named Reactions · Topic: Named Reactions · 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.
Products of the following reaction is: Question structure 1 of 2, ABC26OR0321 Question structure 2 of 2, ABC26OR0321
(a)Option (a) structure, ABC26OR0321
(b)Option (b) structure 1 of 2, ABC26OR0321 Option (b) structure 2 of 2, ABC26OR0321
(c)Option (c) structure 1 of 2, ABC26OR0321 Option (c) structure 2 of 2, ABC26OR0321
(d)Option (d) structure 1 of 2, ABC26OR0321 Option (d) structure 2 of 2, ABC26OR0321
Answer
Under review — not yet confirmed.
Answer: C
Explanation
BF₃ activates the alcohol and the indole alkylates intramolecularly. Attack at C-3 gives a spiroindolenine that rearranges (1,2-shift) to C-2, so the label ends up at either carbon: the two tetrahydrocarbazoles of (c).

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