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COMEDK · Chemistry · 25. Haloalkanes and Haloarenes

Which one of the following will undergo Nucleophilic substitution, by \(\mathrm{S}_{\mathrm{N}}{ }^1\) mechanism, fastest?

  1. A \(\mathrm{Br}-\mathrm{CH}_2-\mathrm{CH}=\mathrm{CH}_2\)
  2. B \(\mathrm{C}_6 \mathrm{H}_5 \mathrm{Br}\)
  3. C \(\mathrm{C}_6 \mathrm{H}_{11} \mathrm{Br}\)
  4. D \(\mathrm{CH}_3-\mathrm{CH}=\mathrm{CHBr}\)
Verified Solution

Answer & Solution

Correct Answer

(A) \(\mathrm{Br}-\mathrm{CH}_2-\mathrm{CH}=\mathrm{CH}_2\)

Step-by-step Solution

Detailed explanation

The rate of \(\mathrm{S}_{\mathrm{N}}1\) reaction depends on the stability of the carbocation intermediate formed after the departure of the leaving group. For option (1), \(\mathrm{Br}-\mathrm{CH}_2-\mathrm{CH}=\mathrm{CH}_2\) forms the allyl carbocation…