Question

Consider the reaction:
(i). `(CH_(3))_(2)CH-CH_(2)Broverset(C_(2)H_(5)OH)to(CH_(3))_(2)CH-CH_(2)-O-C_(2)H_(5)+HBr`
(ii). `(CH_(3))_(2)CH-CH_(2)Broverset(C_(2)H_(5)O^(-))to(CH_(3))_(2)CH-CH_(2)-OC_(2)H_(5)+Br^(-)`
The mechanisms of reaction (i) and (ii) are respectively.
A. `S_(N^(1)) and S_(N^(2))`
B. `S_(N^(1)) and S_(N^(1))`
C. `S_(N^(2)) and S_(N^(2))`
D. `S_(N^(2)) and S_(N^(1))`

Answer 1

Correct Answer - C
It is the correct answer. In case the reaction is to proceed by `S_(N^(1))` mechanism in branched chain alkyl halides, rearrangement of the carbocation is expected in the slow step. Since no such rearrangement is actually noticed in the products in both the reactioin, this means that they both follows `S_(N^(2))` mechanism.