Q91 · CSIR-NET Chemistry, December 2015

Paper: CSIR-NET December 2015 · Subject: Organic Chemistry · Chapter: Pericyclic Reactions · Topic: Sigmatropic Shifts · Marks: 2 · Difficulty: Hard

A concerted [1, 3]-sigmatropic rearrangement took place in the reaction shown below. The structure of the resulting product is Question structure 1 of 5, ABC26OR1041 Question structure 2 of 5, ABC26OR1041 Question structure 3 of 5, ABC26OR1041 Question structure 4 of 5, ABC26OR1041 Question structure 5 of 5, ABC26OR1041
(a)Option (a) structure, ABC26OR1041
(b)Option (b) structure, ABC26OR1041
(c)Option (c) structure, ABC26OR1041
(d)Option (d) structure, ABC26OR1041
Answer
Answer: C ✓ checked by 4AB · confidence medium
Explanation
A thermal suprafacial [1,3]-C shift must go with inversion at the migrating carbon. The OAc/D-bearing carbon is inverted, giving the norbornenyl acetate (c) (source key c).

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