Which of the following reagents will react with ethyl acetate to give a tertiary alcohol?Select answer from the options belowExcess MeMgBrH3O+NaOHLiAlH4Save for LaterSubmit Answer
Question
Which of the following reagents will react with ethyl acetate to give a tertiary alcohol?Select answer from the options belowExcess MeMgBrH3O+NaOHLiAlH4Save for LaterSubmit Answer
Solution
The reagent that will react with ethyl acetate to give a tertiary alcohol is Excess MeMgBr followed by H3O+.
Here's the step-by-step reaction:
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Ethyl acetate reacts with excess MeMgBr (Grignard reagent) in a nucleophilic addition-elimination reaction. The Grignard reagent attacks the carbonyl carbon of the ester, kicking off the ethoxide ion.
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This results in a tertiary alkoxide intermediate.
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The reaction is then quenched with H3O+ (acidic water) to protonate the alkoxide, forming a tertiary alcohol.
The other reagents listed (NaOH and LiAlH4) will not result in a tertiary alcohol when reacted with ethyl acetate. NaOH will not react with esters under normal conditions, and LiAlH4 will reduce the ester to a primary alcohol, not a tertiary alcohol.
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