Amide A, -valerolactam, is a typical amide with a conjugate-acid pK a of 0.8. The two cyclictertiary
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Amide A, δ-valerolactam, is a typical amide with a conjugate-acid pKa of 0.8. The two cyclic tertiary amines B and C also have typical conjugate-acid pKa values. In contrast, the conjugate-acid pKa of amide D is unusually high for an amide, and it hydrolyzes much more rapidly than other amides. Draw the structure of the conjugate acid of amide D, and suggest a reason for both its unusual pKa and its rapid hydrolysis.
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The data show that the conjugateacid pK values of a bicyclic tertiary amine C which is the same as a...View the full answer
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