Question

How many products are expected and what are the mechanisms involved in the following reaction?

• A. Only $S_{N}2-1\text{Product}$
• B. Only $E_2-2\text{Products}$
• C. $S_{N}2-1\text{Product}\text{and}{E}_2-2\text{Products}$
• D. Only $E_2-1\text{Product}$

Answer 1

The correct option is C $S_{N}2-1\text{Product}\text{and}{E}_2-2\text{Products}$

The given substrate is secondary alkyl halide.
${}^{-}OH$ is a strong base/nucleophile so it can undergo both E2 and $S_{N}2$ reaction.
In chair form of cyclohexane derivative, $Br$ has two hydrogens at anti-periplanar position which on elimination give two products (one is Saytzeff and other is Hofmann).

In $S_{N}2$ reaction, the ${}^{-}OH$ group will attact the carbon bearing leaving group at equitorial position to give a product with inverted configuration.