The product of which of the following reactions undergo hydrolysis by $\mathrm{S}_{\mathrm{N}} 1$ mechanism?

• A

  C, D only
• B

  A, B, C only
• Correct answer
  C

  $\mathrm{B}, \mathrm{C}$ only
• D

  A, D only

Solution

So only (B) and (C) formed stable benzylic carbocation so it will undergo hydrolysis by $\mathrm{S}_{\mathrm{N}} 1$ mechanism. $\mathrm{S}_{\mathrm{N}} 1$ reactivity order : benzylic $\gt3^{\circ}\gt2^{\circ}\gt1^{\circ}$ $\mathrm{S}_{\mathrm{N}} 2$ reactivity order : $1^{\circ}\gt2^{\circ}\gt3^{\circ}$

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