Haloalkanes and HaloareneshardMCQ SINGLE

Based on the profound influence of steric hindrance, in which of the following alkyl halides is the Haloalkanes and Haloarenes Chemistry Question

Question

Based on the profound influence of steric hindrance, in which of the following alkyl halides is the classical $S_N2$ reaction rate uniquely the fastest when treated with $NaCN$ in DMF?

Answer: A

💡 Solution & Explanation

The $S_N2$ mechanism requires the nucleophile to approach the electrophilic carbon exactly from the backside of the leaving group. Steric bulk critically impedes this approach. Therefore, $S_N2$ reactivity strictly follows the order: Methyl $> 1^\circ > 2^\circ > 3^\circ$. Among the options, 1-chlorobutane is a straight-chain $1^\circ$ halide. 1-chloro-2-methylpropane is also $1^\circ$, but the bulky branching at the adjacent $\beta$ -carbon severely slows the attack. Hence, 1-chlorobutane reacts the fastest.

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