Which of the following reagents will react with ethyl acetate to give a tertiary alcohol?Select answer from the options belowExcess MeMgBrNaOHH3O+LiAlH4
Question
Which of the following reagents will react with ethyl acetate to give a tertiary alcohol?Select answer from the options belowExcess MeMgBrNaOHH3O+LiAlH4
Solution
The reagent that will react with ethyl acetate to give a tertiary alcohol is excess MeMgBr (methylmagnesium bromide).
Here's the step-by-step reaction:
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Ethyl acetate (CH3COOCH2CH3) reacts with excess MeMgBr. The Grignard reagent (MeMgBr) attacks the carbonyl carbon of the ester (ethyl acetate), kicking off the ethoxide ion (CH3CH2O-) as a leaving group. This results in a ketone.
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The ketone then reacts with another equivalent of MeMgBr. The Grignard reagent attacks the carbonyl carbon of the ketone, resulting in a tertiary alcohol after protonation.
Please note that the other reagents (NaOH, H3O+, LiAlH4) will not give a tertiary alcohol when reacted with ethyl acetate.
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