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Magazine Chapter 17: Q3P (page 804)
Explain why a base can remove a proton from the -carbon of N,N-dimethylethanamide but not from the -carbon of either N-methylethanamide or ethanamide.
N,N-dimethylethanamideN-methylethanamide Ethanamide
Short Answer
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
Acidic hydrogens
Hydrogen bonded to an -carbon is more acidic than hydrogens bonded to other sp3 carbons because the base formed when a proton is removed from an-carbon is relatively stable. And, as we have seen, the more stable the base, the stronger it鈥檚 the conjugate acid.
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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