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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 below:

  • Excess MeMgBr
  • NaOH
  • H3O+
  • LiAlH4
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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:

  1. 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.

  2. 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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