The major product formed in the following reaction is · ABC26OR0586
Subject: Organic Chemistry · Chapter: Pericyclic Reactions · Topic: Pericyclic Reactions – General · Exam: GATE 2000-2022 · Marks: 2 · Difficulty: Medium
The major product formed in the following reaction is 
(a)
(b)
(c)
(d)
Answer
Answer: B ✓ checked by 4AB · confidence high
The source book printed no answer; this one was worked out and checked — see the explanation.
anti-7-Norbornenyl tosylate solvolyses with π-participation and retention. The book's own solution (34 Sol.) draws the product as the retention acetate (H left, OAc right) = option (b).
Explanation
The OTs group on C-7 is anti to the C=C (anti-7-norbornenyl tosylate). The π bond assists ionisation from the back side (neighbouring-group participation), giving a non-classical bishomocyclopropenyl cation. Acetic acid then attacks C-7 from the face away from the π bond, so OAc takes the position of the OTs: overall retention of configuration, giving anti-7-norbornenyl acetate (b).
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