Which of the following is an excellent substrate for $S_{N} 1$ reaction?

R - C H_{2} - X

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A r - C H_{2} - X

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C H_{2} = C H - C H_{2} - X

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C H_{2} = C H - X

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Solution

The correct option is D $A r - C H_{2} - X$
$S N^{1}$ mechanism proceeds through carbocation formation, as stability of carbocation increases, reaction favors $S N^{1}$ mechanism. Benzylic carbocation is most stable due to more resonating structures and allylic carbocations are more stable than aliphatic carbocation due to resonance so order of stability of carbocations is benzyl > allyl > $3^{0} > 2^{0} > 1^{0}$ .

( $3^{0}$ carbocation are more stable than others or stability order of carbocations is $3^{0} > 2^{0} > 1^{0}$ so order of alkyl halides towards $S N^{1}$ reaction is $3^{0} > 2^{0} > 1^{0}$ .)

So order of reactivity for $S N^{1}$ mechanism is benzyl > allyl > $3^{0} > 2^{0} > 1^{0}$ .

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