Answered: Sodium triacetoxyborohydride,…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter3: Organic Compounds: Alkanes And Their Stereochemistry

Section3.SE: Something Extra

Problem 50AP: Formaldehyde, H2C=O, is known to all biologists because of its usefulness as a tissue preservative....

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Sodium triacetoxyborohydride, NaBH(OAc)3, is a mild reducing agent that reduces aldehydes
much more quickly than ketones. It can be used to reduce aldehydes in the presence of ketones,
such as in the following reaction:
CH3 C CH2
O O
C H CH3 C CH2
O
CH2
OH
NaBH(OAc)3
CH3COOH
(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.
(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

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