C6H5-CH2-NH2+RX→C6H5-CH2-NH-RWhich of the following alkyl halides is best suited for this reaction by SN1 mechanism?

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$C_{6} H_{5} - {CH}_{2} - {NH}_{2} + RX \to C_{6} H_{5} - {CH}_{2} - NH - R$

Which of the following alkyl halides is best suited for this reaction by ${SN}_{1}$ mechanism?

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${CH}_{3} - Br$

$C_{6} H_{5} - Br$

$C_{2} H_{5} - Br$

$C_{6} H_{5} - {CH}_{2} - Br$

answer is C.

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Detailed Solution

$C_{6} H_{5} - {CH}_{2} - Br$ is best suited for this reaction through a ${SN}^{1}$ mechanism as the carbocation(benzyl carbocation) formed in the reaction is resonance stabilized. The benzyl carbocation formed is $C_{6} H_{5} - {CH}_{2}^{+}$ . Reactivity in these reactions depends upon the stability of the carbocation intermediate.