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Which of the following halogen compound gives a rearranged product when reaction proceeds by S_N1 pathway ?

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${CH}_{2} = CH - {CH}_{2} - Cl$

${({CH}_{3})}_{3} C - Br$

${({CH}_{3})}_{2} CH - {CH}_{2} - Br$

${({CH}_{3})}_{2} CH - Cl$

answer is C.

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Detailed Solution

$(3) {({CH}_{3})}_{2} CH - \overset{+}{C} H_{2} \overset{1, 2 H^{-} shift}{⇌} {({CH}_{3})}_{3} \overset{+}{C}; Thus {({CH}_{3})}_{3} C - OH is formed .$

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