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 
[1,3]-C shift
[1,3]-C shift(a)
(b)
(c)
(d)
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).
Study loop for Pericyclic Reactions