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Question

(A) The reaction involves the nucleophilic addition of $HS-CH_2-CH_2-OH$ to acrylonitrile $(CH_2=CH-CN)$.Thiols $(R-SH)$ are better nucleophiles than

Vedclass · Accepted Answer

$HO-CH_2-CH_2-S-CH_2-CH_2-CN$

Vedclass · Answer

(A) The reaction involves the nucleophilic addition of $HS-CH_2-CH_2-OH$ to acrylonitrile $(CH_2=CH-CN)$.Thiols $(R-SH)$ are better nucleophiles than alcohols $(R-OH)$ because sulfur is larger,more polarizable,and less electronegative than oxygen.Therefore,the sulfur atom of $HS-CH_2-CH_2-OH$ attacks the $\beta$-carbon of the electron-deficient double bond in acrylonitrile via a Michael addition mechanism.The reaction proceeds as follows: $CH_2=CH-CN + HS-CH_2-CH_2-OH \rightarrow HO-CH_2-CH_2-S-CH_2-CH_2-CN$.Thus,the major product is $HO-CH_2-CH_2-S-CH_2-CH_2-CN$.

The major product for the following reaction is:

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