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?

CH3Br C2H5Br C6H5CH2Br None of the above

C6H5CH2Br

Since C6H5CH2Br on ionization gives a resonance stabilized benzyl carbocation (C6H5CH2+) therefore, C6H5CH2Br is best suited for SN1 reaction.