The most stable product of the following reac | vedclass

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(C) The reaction proceeds in two steps:$1$. The reaction of the secondary alcohol with $p$-toluenesulfonyl chloride $(TsCl)$ in the presence of pyridi

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Vedclass · Answer

(C) The reaction proceeds in two steps:$1$. The reaction of the secondary alcohol with $p$-toluenesulfonyl chloride $(TsCl)$ in the presence of pyridine converts the $-OH$ group into a good leaving group,the tosylate $(-OTs)$ group,with retention of configuration at the chiral center.$2$. The subsequent reaction with $NaCN$ in $DMF$ is an $S_N2$ reaction. The nucleophile $CN^{-}$ attacks the chiral carbon from the side opposite to the $-OTs$ group,resulting in an inversion of configuration at that center.Starting with the given stereoisomer,the $-OH$ is on a wedge. After forming the $-OTs$ group (still on a wedge),the $S_N2$ attack by $CN^{-}$ forces it to the dashed position (inversion). Thus,the correct product has the $CN$ group on a dash while the other chiral center remains unchanged.

The most stable product of the following reaction is:

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