Treating cyclohexanone with N-bromosuccinimide in the presence of carbon tetrachloride gives A. A on treatment with aqueous KOH gives B. Deduce the structures of A and B.
A is 2-bromocyclohexanone and B is potassium cyclopentane carboxylate.
- In the first step, why did the bromine atom get attached to the second position? The carbonyl group, being electron withdrawing, should direct the incoming electrophile away from it.
- In the second step, I am quite sure that the product mentioned is a result of Favorskii rearrangement. But there is also a possibility for the hydroxide ion to substitute bromine. Is this possible? If yes, why is the substituted product not a major product? If not, why?