When methoxyethane () is treated with a single equivalent of cold, dilute hydroiodic acid (), the cleavage follows an mechanism. What are the resulting products?

Question

When methoxyethane ($CH_3-O-CH_2CH_3$) is treated with a single equivalent of cold, dilute hydroiodic acid ($HI$), the cleavage follows an $S_N2$ mechanism. What are the resulting products?

Prashant Kotian · Accepted Answer

Correct answer: B. In cold/dilute conditions with primary or secondary alkyl groups, the cleavage follows . The bulky iodide nucleophile () prefers to attack the least sterically hindered carbon atom. Thus, it attacks the methyl group, forming methyl iodide and leaving the larger fragment as ethanol.

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