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Chapter 17: Q3P (page 804)

Explain why a base can remove a proton from the α-carbon of N,N-dimethylethanamide but not from the -carbon of either N-methylethanamide or ethanamide.

N,N-dimethylethanamideN-methylethanamide Ethanamide

Short Answer

Expert verified

Due to the lack of N-H bond in N, N-dimethyl ethanamide, a base can remove a proton from the alpha carbon of N, N-dimethyl ethanamine.

Step by step solution

01

Acidic hydrogens

Hydrogen bonded to an α-carbon is more acidic than hydrogens bonded to other sp3 carbons because the base formed when a proton is removed from anα-carbon is relatively stable. And, as we have seen, the more stable the base, the stronger it’s the conjugate acid.

02

Removal of a proton by a base

The nitrogen atom is much more electronegative than carbon, nitrogen accepts a negative charge. Hence, the base can remove protons of nitrogen from N-methyl ethanamide and ethanamide.

Removal of proton

Whereas due to the lack of N-H bond in N, N-dimethyl ethanamide, a base can remove a proton from the alpha carbon of N, N-dimethyl ethanamine. The formed carbanion is a resonance stabilized anion.

Removal of proton

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