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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3o3219

2,2-Dimethyloxirane is opened under different conditions. Which statements are correct?

AWith $CH X_{3} OH$ and $H X_{2} SO X_{4}$ the main product is $CH X_{3} O - C (CH X_{3}) X_{2} - CH X_{2} OH$
BWith $CH X_{3} ONa$ in $CH X_{3} OH$ the main product is $HO - C (CH X_{3}) X_{2} - CH X_{2} OCH X_{3}$
CWith $LiAlH X_{4}$ followed by water the product is $(CH X_{3}) X_{3} C - OH$
DWith $LiAlH X_{4}$ followed by water the product is $(CH X_{3}) X_{2} CH - CH X_{2} OH$

Answer: A, B, C

Under acidic conditions the more substituted carbon is attacked, giving the tertiary ether and primary alcohol. Methoxide and hydride are strong nucleophiles and attack the unhindered

CH X_{2}

carbon. Hydride at

CH X_{2}

gives

(CH X_{3}) X_{2} C (O -) - CH X_{3}

, i.e. tert-butyl alcohol, and not isobutyl alcohol.

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