The amide shown is reduced with an excess of lithium aluminium hydride, followed by aqueous work-up. Which of the following is formed?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: B

N,N-Dimethylethanamide is reduced by lithium aluminium hydride with C=O being converted to CH2 (the oxygen leaves as an aluminate from the tetrahedral intermediate to give an iminium ion that is reduced). The product is the tertiary amine N,N-dimethylethanamine. Cleavage of the C-N bond to give an alcohol, as occurs with esters, does not happen.

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