question_answer

Identify the compound in the following pair that reacts with sodium iodide in acetone at a faster rate towards \[{{S}_{{{N}^{2}}}}\] mechanism. 1-Chlorohexane or cyclohexyl chloride:

Answer:

\[\underset{\text{1-Chlorohexane}\,\,\text{(}{{\text{1}}^{\text{o}}}\text{)}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}Cl}}\,\] 1-Chlorohexane is a primary alkyl halide and is expected to be more reactive towards \[{{S}_{{{N}^{2}}}}\] reactions as compared to cyclohexyl chloride which is secondary in nature. This is because of less steric hindrance present in primary alkyl halide.