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

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

1. C, D only
2. A, B, C only
3. $\mathrm{B}, \mathrm{C}$ only
4. 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 : $1^{\circ}\gt2^{\circ}\gt3^{\circ}$

Asked in: AP EAMCET 2024 (20 May Shift 2)

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