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TS EAMCET · Chemistry · General Organic Chemistry

Which one of the following is more readily hydrolysed by \(\mathrm{S}_{\mathrm{N}} 1\) mechanism?

  1. A \(\left(\mathrm{C}_6 \mathrm{H}_5\right)_2 \mathrm{C}\left(\mathrm{CH}_3\right) \mathrm{Br}\)
  2. B \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}\)
  3. C \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}\left(\mathrm{CH}_3\right) \mathrm{Br}\)
  4. D \(\left(\mathrm{C}_6 \mathrm{H}_5\right)_2 \mathrm{CHBr}\)
Verified Solution

Answer & Solution

Correct Answer

(A) \(\left(\mathrm{C}_6 \mathrm{H}_5\right)_2 \mathrm{C}\left(\mathrm{CH}_3\right) \mathrm{Br}\)

Step-by-step Solution

Detailed explanation

The order of reactivity of halides towards \(\mathrm{S}_{\mathrm{N}} 1\) reaction is \(\text { benzyl }>\text { allyl }>3^{\circ}>2^{\circ}>1^{\circ}>\mathrm{Me}\) Therefore, the order of hydrolysis by \(\mathrm{S}_{\mathrm{N}} 1\) mechanism is