Acetaldehyde () is subjected to reduction utilizing sodium borodeuteride () as the reducing agent, followed by a workup/hydrolysis using standard light water (). How many individual deuterium () atoms

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?

Prashant Kotian · Accepted Answer

Correct answer: 1. The reagent acts as a nucleophilic source of deuteride ions (), which attack the electrophilic carbonyl carbon, forming a bond and an alkoxide intermediate (). During the subsequent aqueous workup, the alkoxide oxygen abstracts a standard proton () from the solvent. The final product is , containing exactly 1 deuterium atom.

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