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Which reagent can be reacted with phenylmagnesium bromide to obtain 2-phenylethanol?

1. Formaldehyde
2. Acetaldehyde
3. Acetone
4. Ethylene oxide

Correct answer: Ethylene oxide

Solution

Phenylmagnesium bromide opens the strained ring of ethylene oxide to give, after workup, PhCH2CH2OH (2-phenylethanol). Adding two carbons requires the epoxide; aldehydes/ketones would give different alcohols.

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