Reduction of acetone with NaBH4 yields which product?

Master NCEA Level 3 Organic Chemistry Reaction Schemes. Prepare with multiple choice questions, complete with hints and detailed explanations. Ace your exam with our comprehensive tools!

Multiple Choice

Reduction of acetone with NaBH4 yields which product?

NaBH4 reduces carbonyl groups to alcohols by delivering a hydride to the carbonyl carbon, and after workup the oxygen is protonated to form the alcohol. Acetone has two methyl groups around the carbonyl carbon, so when the C=O is reduced you get a secondary alcohol with the same carbon skeleton: CH3-CHOH-CH3, known as isopropanol. The other listed alcohols would come from reducing different carbonyl compounds (for example, reducing acetaldehyde gives ethanol, reducing formaldehyde gives methanol, reducing propanal gives propanol), not from acetone. So the product of reducing acetone with NaBH4 is isopropanol.

NaBH4 reduces carbonyl groups to alcohols by delivering a hydride to the carbonyl carbon, and after workup the oxygen is protonated to form the alcohol. Acetone has two methyl groups around the carbonyl carbon, so when the C=O is reduced you get a secondary alcohol with the same carbon skeleton: CH3-CHOH-CH3, known as isopropanol. The other listed alcohols would come from reducing different carbonyl compounds (for example, reducing acetaldehyde gives ethanol, reducing formaldehyde gives methanol, reducing propanal gives propanol), not from acetone. So the product of reducing acetone with NaBH4 is isopropanol.

More practice questions