β-lactam rings, as a resistance mechanism against these antibiotics. Therefore, β-lactams are
sometimes given with β-lactamase inhibitors to increase their efficacy.
MCAT Concept Check 9.2:
Before you move on, assess your understanding of the material with these questions.
Rank the following molecules by decreasing reactivity to OR–: acetamide, acetic
anhydride, and ethyl acetate.
2.
3.
What is responsible for the increased rate of hydrolysis in β-lactams?
What properties account for the differences in reactivity seen between anhydrides, esters,
and amides with nucleophiles?
