Q11 · CSIR NET Chemistry, June 2018

Paper: CSIR NET June 2018 · Subject: Organic Chemistry · Chapter: Pericyclic Reactions · Topic: Pericyclic Reactions – General · Marks: 2 · Difficulty: Medium

The structure of the intermediate $A$ and the major product $B$, formed in the following reaction are Question structure 1 of 6, ABC26OR0154 Question structure 2 of 6, ABC26OR0154 Question structure 3 of 6, ABC26OR0154 Question structure 4 of 6, ABC26OR0154 Question structure 5 of 6, ABC26OR0154 Question structure 6 of 6, ABC26OR0154
(a)Option (a) structure 1 of 4, ABC26OR0154 Option (a) structure 2 of 4, ABC26OR0154 Option (a) structure 3 of 4, ABC26OR0154 Option (a) structure 4 of 4, ABC26OR0154
(b)Option (b) structure 1 of 4, ABC26OR0154 Option (b) structure 2 of 4, ABC26OR0154 Option (b) structure 3 of 4, ABC26OR0154 Option (b) structure 4 of 4, ABC26OR0154
(c)A = Option (c) structure 1 of 3, ABC26OR0154 Option (c) structure 2 of 3, ABC26OR0154 Option (c) structure 3 of 3, ABC26OR0154
(d)Option (d) structure, ABC26OR0154
Answer
Answer: A ✓ checked by 4AB · confidence high
Explanation
Heating the enediyne triggers the Bergman cyclisation to the 1,4-didehydrobenzene (p-benzyne) diradical A; Bu₃SnD donates a deuterium atom to each radical centre, giving the 1,4-dideuterio arene B.

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