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5. Benzylamine may be alkylated as shown in the following equation : C6H5CH2NH2 + R—X → C6H5CH2NHR Which of the following alkyl halides is best suited for this reaction through SN1 mechanism? (i) CH3Br (ii) C6H5Br (iii) C6H5CH2Br (iv) C2H5 Br

Solution:

Option (iii) is the answer.

Reason:

 is best suited for this reaction through  mechanism as the carbocation  formed is resonance stabilized.