The reaction of with $\mathrm{CH}_{3} \mathrm{OH}$ in (i) acid $\mathrm{H}^{+}$, and (ii) base…

The reaction of with $\mathrm{CH}_{3} \mathrm{OH}$ in (i) acid $\mathrm{H}^{+}$, and (ii) base $\mathrm{CH}_{3} \mathrm{O}^{-}$, respectively, give
  1. $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}\left(\mathrm{OCH}_{3}ight) \mathrm{CH}_{2} \mathrm{OH}$ and $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{CH}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{OCH}_{3}$
  2. $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}\left(\mathrm{OCH}_{3}ight) \mathrm{CH}_{2} \mathrm{OH}$ and $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}\left(\mathrm{OCH}_{3}ight) \mathrm{CH}_{2} \mathrm{OH}$
  3. $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}\left(\mathrm{OCH}_{3}ight) \mathrm{CH}_{2} \mathrm{OCH}_{3}$ and $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{OH}$
  4. $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}(\mathrm{OH}) \mathrm{CH}_{2} \mathrm{OH}$ and $\left(\mathrm{CH}_{3}ight)_{2} \mathrm{C}\left(\mathrm{OCH}_{3}ight) \mathrm{CH}_{2} \mathrm{OCH}_{3}$

Solution

There occurs cleavage of ether linkage in oxiranes (cyclic three membered ring including oxygen). In acidcatalyzed reaction, nucleophile ${ }^{-} \mathrm{OCH}_{3}$ from $\mathrm{CH}_{3} \mathrm{OH}$ attaches to the more substituted carbon where as in basecatalyzed reaction, it is attached to the less substituted carbon. .

Asked in: JEE-TOPICTESTS-CHEMISTRY

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