Acetaldehyde () is subjected to reduction utilizing sodium borodeuteride () as the reducing agent, f — Alcohols Phenols and Ethers Chemistry Question
Question
Acetaldehyde ($CH_3CHO$) is subjected to reduction utilizing sodium borodeuteride ($NaBD_4$) as the reducing agent, followed by a workup/hydrolysis using standard light water ($H_2O$). How many individual deuterium ($D$) atoms will be covalently incorporated into the final alcohol molecule?
Answer: 1
💡 Solution & Explanation
The $NaBD_4$ reagent acts as a nucleophilic source of deuteride ions ($D^-$), which attack the electrophilic carbonyl carbon, forming a $C-D$ bond and an alkoxide intermediate ($CH_3-CH(D)-O^-$). During the subsequent aqueous workup, the alkoxide oxygen abstracts a standard proton ($H^+$) from the $H_2O$ solvent. The final product is $CH_3CH(D)OH$, containing exactly 1 deuterium atom.
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