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)?

Identify the most stable conjugate base in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer.

(f)

Identify the most acidic proton in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer. [Always start by drawing the conjugate base.]

(b)

Identify the most acidic proton in each pair. Tell which structural features you analyzed and why you weighted them as you did in picking one answer. [Always start by drawing the conjugate base.]

(d)

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

(a)

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?

Which is the most stable base in each pair?

(c) NH₃ vs. H₂O

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.