In which of the following S_N1 reactions will | vedclass

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(C) The correct answer is $(C)$.In option $(C)$,the reaction proceeds via an $S_N1$ mechanism.The alcohol $Ph-C(CH_3)_2-CH_2-OH$ reacts with Lucas rea

Vedclass · Accepted Answer

$Ph-C(CH_3)_2-CH_2-OH \xrightarrow{HCl/ZnCl_2} 	ext{Product}$

Vedclass · Answer

(C) The correct answer is $(C)$.In option $(C)$,the reaction proceeds via an $S_N1$ mechanism.The alcohol $Ph-C(CH_3)_2-CH_2-OH$ reacts with Lucas reagent $(HCl/ZnCl_2)$ to form a primary carbocation $Ph-C(CH_3)_2-CH_2^+$.This carbocation undergoes a $1,2$-methyl shift to form a more stable tertiary benzylic carbocation $Ph-C^+(CH_3)-CH_2-CH_3$.Since this carbocation is planar,the nucleophile $Cl^-$ can attack from either side with equal probability,resulting in the formation of a racemic mixture of $2$-chloro-$2$-phenylbutane as the major product.

Column-$I$ (Reagents)	Column-$II$ (Products)
$A$. $HCl + ZnCl_2$	$i$. $CH_3CH=CHCH_3$
$B$. $HBr$	$ii$. $CH_3CH_2CH_2CH_2Cl$
$C$. $SOCl_2$	$iii$. $CH_3CH_2CH_2CH_2Br$
$D$. $H_2SO_4, \Delta$	$iv$. $CH_3CH_2CH_2CH_2Cl$

In which of the following $S_N1$ reactions will a racemic mixture form as the major product?

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