QuestionOrganic / benzyne mechanism
The major product(s) formed in the following reaction is/are:


- (a) o-Toluidine only
- (b) 2-Bromo-3-methylaniline
- (c) m-Toluidine only
- (d) o-Toluidine + m-toluidine
Answer: (a)
NaNH₂/liq. NH₃ on o-bromotoluene goes by elimination–addition (benzyne): 3-methylbenzyne forms and NH₂⁻ adds to either end. Strictly this gives a mixture of o- and m-toluidine (option d). UPSC's key holds (a).