Which of the following alkyl halides is hydrolysed by ${\mathrm{S}}_{\mathrm{N}}1$ mechanism?

• A

  $\mathrm{C}{\mathrm{H}}_3\mathrm{C}\mathrm{l}$
• B

  $\mathrm{C}{\mathrm{H}}_3\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{l}$
• C

  $\mathrm{C}{\mathrm{H}}_3\mathrm{C}{\mathrm{H}}_2\mathrm{C}{\mathrm{H}}_2\mathrm{C}\mathrm{l}$
• Correct answer
  D

  ${\left(\mathrm{C}{\mathrm{H}}_3\right)}_3\mathrm{C}\mathrm{C}\mathrm{l}$

Solution

${\mathrm{S}}_{\mathrm{N}}1$ reaction is favoured by stability of carbocation i.e. tertiary > secondary > primary.

Hence, the correct answer is option: 'D'.