Which is the most stable base in each pair?
(c) NH₃ vs. H₂O

Which acid in each pair would you expect to more readily donate a proton to a basic compound?

(a)

Why is the pK_a value of protonated hydroxylamine (6.0) so much lower than the value of a protonated primary amine such as protonated methylamine (10.7)?

In light of your answers to Assessments 24.54 and 24.55, rank the following based on the rate of protonation of the alkene (1 = most basic, 6 = least basic). [Ignore the fact that the alkene may not be the most basic site in the molecule.]

Consider the following drugs used to treat the indicated diseases. Would you expect the activity of these drugs to be impacted by a patient taking other medicines for acid reflux disease?

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

Citrus fruits are rich in citric acid, a compound with three COOH groups. Explain the following:

a. The first pK_a (for the COOH group in the center of the molecule) is lower than the pK_a of acetic acid.

Which of the following amino acid side chains can help remove a proton from the α-carbon of an aldehyde?

Rank the following compounds from easiest to hardest at removing a proton from its methyl substituent: