Question

For the given pair of compounds, compare which compound is better $S_{N}2$ substrate.

2,2-dimethyl 1-chlorobutane, 2-chlorobutane

• A. 2,2-dimethyl 1-chlorobutane
• B. 2-chlorobutane
• C. Both show $S_{N}1$
• D. Both of them show similar reactivity

Answer 1

The correct option is B 2-chlorobutane

Due to probability of rearranged more stable $3^o$ carbocation, 2,2-dimethyl1chlorobutane follows $S{N}^1$ mechanism while 2chlorobutane follows $S{N}^2$.