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Question: Answered & Verified by Expert
Benzylamine may by alkylated as shown in the following equation?


Which of the following alkyl halides is best suited for this reaction through $\mathrm{S}_{\mathrm{N}}$ 1 mechanism?
ChemistryAmines
Options:
  • A
    $\mathrm{CH}_3 \mathrm{Br}$
  • B
    $\mathrm{C}_6 \mathrm{H}_5 \mathrm{Br}$
  • C
    $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}$
  • D
    $\mathrm{C}_2 \mathrm{H}_5 \mathrm{Br}$
Solution:
1927 Upvotes Verified Answer
The correct answer is:
$\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{Br}$
$\mathrm{S}_{\mathrm{N}} 1$ reaction involves the formation of carbocation, so, more stable carbocation will have higher reactivity towards $\mathrm{S}_{\mathrm{N}} 1$ mechanism.




As $\mathrm{C}_6 \mathrm{H}_5{ }^{+} \mathrm{CH}_2$ is the most stabilised carbocation due to resonance, hence it will be most reactive towards $\mathrm{S}_{\mathrm{N}} 1$ mechanism.

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