Sodium triacetoxyborohydride , is a mild reducing agent

QUESTION:

Sodium triacetoxyborohydride, \(\mathrm{NaBH}(\mathrm{OAC})_{3}\), 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:

\(\mathrm{CH}_{3}-\mathrm{C}-\mathrm{CH}_{2}-\mathrm{C}-\mathrm{H}\)

\(\frac{\mathrm{NaBH}(O A C)_{3}}{\mathrm{CH}_{3} \mathrm{COOH}}\)

\(C H_{3}-C-C H_{2}-C H_{2}\)

(a) Draw a complete Lewis structure for sodium triacetoxyborohydride.

(b) Propose a mechanism for the reduction of an aldehyde by sodium triacetoxyborohydride.

Equation transcription:

Text transcription:

{NaBH}({OAC}){3}

{CH}{3}-{C}-{CH}{2}-{C}-{H}

frac{{NaBH}(O A C){3}}{{CH}{3} {COOH}}

C H{3}-C-C H{2}-C H{2}