predict the product: .H1) NaBH4, EtOН2) H*

Answered: 1) NaBH4, EtOH 2) H*

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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predict the product:

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Action of sodium borohydride on the substrate: Reduction of aldehyde to primary alcohol

1. The substrate consists of an ester and an aldehyde group. The carbon atom of carbonyl group of aldehyde group is more positive and is highly reactive towards the substitution by hydride ion (nucleophile) from NaBH₄

NaBH₄ $\to N a^{+} B {H_{4}}^{-}$

$B {H_{4}}^{-} \to B H_{3} + H^{-}$

H^- acts as a nucleophile.

Whereas, the carbon atom of carbonyl group of ester is less positive as it undergoes resonance with the oxygen atom of the alkoxy group (propoxy group here). This makes the attack of H^- difficult and reduction of ester by NaBH₄ difficult.

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