Q4 · CSIR NET Chemistry, June 2014
Paper: CSIR NET June 2014 · Subject: Organic Chemistry · Chapter: Photochemical Reactions · Topic: Photocycloaddition · Marks: 2 · Difficulty: Medium
The major product formed in the following photochemical reaction is

(a)

(b)

(c)

(d)

Answer
Answer: A ✓ checked by 4AB · confidence medium
Explanation
1,2,4-Tri-tert-butylbenzene relieves its ortho strain by photochemical valence isomerisation to the Dewar benzene in which one t-Bu sits at a bridgehead and the other two on separate double bonds, with the cis bridgehead H (a).
Study loop for Photochemical Reactions