QuestionOrganic / Wagner–Meerwein rearrangement
The major product formed in the following reaction is:


- (a) 2,3-Dimethylnorborn-2-ene
- (b) 5,5-Dimethylnorborn-2-ene
- (c) Dimethylnorbornene isomer as drawn (C=C away from the gem position)
- (d) 3,3-Dimethylnorbornan-2-one
Answer: (a)
Protonation and loss of water at C2 next to the gem-dimethyl carbon → 1,2-methyl shift gives a tertiary cation; loss of H⁺ gives the tetrasubstituted alkene 2,3-dimethylnorborn-2-ene → (a).