Sodium borodeuteride (NaBD4) and lithium aluminum deuteride (LiAlD4) are convenient reagen...

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 formating an O-H bond.