MolSynapsequestion bank

MolSynapse / Question bank / Organic Reaction Mechanisms III: Nucleophilic Substitution / Reactions of ethers and epoxides

NEET levelSingle correct optionDifficulty 1 of 3o3172

Ethyl methyl ether ( $CH X_{3} - O - CH X_{2} CH X_{3}$ ) reacts with one equivalent of cold concentrated HI. The major products arise by SN2 attack of iodide on the less hindered carbon and are

A $CH X_{3} CH X_{2} - I$ and $CH X_{3} - OH$
B $CH X_{2} = CH X_{2}$ and $CH X_{3} - OH$
C $CH X_{3} - I$ and $CH X_{3} CH X_{2} - I$
D $CH X_{3} - I$ and $CH X_{3} CH X_{2} - OH$

Answer: D

The protonated ether is attacked by

I X^{-}

at the less hindered methyl carbon (SN2). This breaks the

CH X_{3} - O

bond and leaves ethanol with the ethyl group. With only one equivalent of HI the alcohol is not converted further.

Practice Organic Reaction Mechanisms III: Nucleophilic Substitution More on Reactions of ethers and epoxides

Previous questionNext question

More questions on Reactions of ethers and epoxides