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Shweta Thakur posted an Question
May 04, 2020 • 21:02 pm 30 points
  • IIT JAM
  • Chemistry (CY)

Sir if the ester carbonyl carbon is always prone to nucleophilic attack then why ester get reduced to alcohop

sir if the ester carbonyl carbon is always prone to nucleophilic attack then why ester get reduced to alcohop

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    Lingareddy 1 Best Answer

    common conditions esters converted into alcohols

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    Lingareddy 1

    Nucleophilic Acyl Substitution then NucleophilicAddition .Carboxylic esters are reduced give 2 alcohols, one from the alcohol portion of the ester and a 1o alcohol from the reduction of the carboxylate portion. Esters are less reactive towards Nu than aldehydes or ketones. They can only be reduced by LiAlH4 but NOT by the less reactive NaBH4 The reaction requires that 2 hydrides (H-) be added to the carbonyl group of the ester The mechanism is an example of the reactive system type. The reaction proceeds via a aldehyde intermediate which then reacts with the second equivalent of the hydride reagent Since the aldehyde is more reactive than the ester, the reaction is not normally used as a preparation of aldehydes .

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