B xleftarrow{CH_3OH/CH_3ONa} text{Epoxide} xr | vedclass

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Question

(A) In acidic medium,the nucleophile $(H_2O^{18})$ attacks the more substituted carbon of the epoxide (isobutylene oxide) due to the stability of the

Vedclass · Accepted Answer

$CH_3-C(CH_3)(^{18}OH)-CH_2-OH$,$CH_3-C(CH_3)(OH)-CH_2-OCH_3$

Vedclass · Answer

(A) In acidic medium,the nucleophile $(H_2O^{18})$ attacks the more substituted carbon of the epoxide (isobutylene oxide) due to the stability of the carbocation-like transition state. Thus,$A$ is $CH_3-C(CH_3)(^{18}OH)-CH_2-OH$.In basic medium,the nucleophile $(CH_3O^{-})$ attacks the less substituted carbon due to steric hindrance. Thus,$B$ is $CH_3-C(CH_3)(OH)-CH_2-OCH_3$.

$B \xleftarrow{CH_3OH/CH_3ONa} \text{Epoxide} \xrightarrow{H_2O^{18}/H^{+}} A$. $A$ and $B$ are:

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