Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagents for introducing deuterium, the mass-2 isotope of hydrogen, into organic compounds. Write the structure of the organic product of the following reactions, clearly showing the position of all the deuterium atoms in each:
(a)
(b)
(c)
(d)
Sample Solution (a) Sodium borodeuteride transfers deuterium to the carbonyl group of acetaldehyde, forming a C—D bond.
Hydrolysis of (CH3CHDO)4B− in H2O leads to the formation of ethanol, retaining the C—D bond formed in the preceding step while forming an O—H bond.
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