Question

The reduction of ethyl acetoacetate with sodium borohydride is show below.  Explain why the product of the reaction does not have two alcohol functional groups.  

QH NaBH4 ethanol, 0°C

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Answer #1

Simple answer to this question is that NaBH4 is mild reducing agent it only reduces aldehydes and ketones . Given compound is having both ester and ketone functional group so Use of NaBh4 only reduces keton part not the ester one. Instead if we have used LiAlH4 ( lithium aluminium hydride ) it reduces both ester as well as ketone because it is a powerful reducing agent .

Mechanism .

Nat H =B-H c3 H H O བ བ་ PRODUCT

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