6. The structure shown below is amoxicillin, one of the most commonly prescribed penicillin-type antibiotics in use today. The structure on the right is a ß-lactam, which is the center of the molecule on the left. Bacterial resistance to penicillins, including amoxicillin, involves an enzyme called B- lactamase, which exploits two of the principles we have covered thusfar: functional group reactivity and ring strain. Using the simplified structure on the right, explain a. Why the functional group might attract a nucleophile/Lewis base (such as water)? b. Why this particular 4-membered ring is much more strained than cyclobutane? NH₂ H HO OH

6. The structure shown below is amoxicillin, one of the most commonly prescribed penicillin-type antibiotics in use today. The structure on the right is a ß-lactam, which is the center of the molecule on the left. Bacterial resistance to penicillins, including amoxicillin, involves an enzyme called B- lactamase, which exploits two of the principles we have covered thusfar: functional group reactivity and ring strain. Using the simplified structure on the right, explain a. Why the functional group might attract a nucleophile/Lewis base (such as water)? b. Why this particular 4-membered ring is much more strained than cyclobutane? NH₂ H HO OH

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter4: Polar Bonds, Polar Reactions

Section: Chapter Questions

Problem 16E: Organic chemistry is a bit like cooking. Later in this course we will study “recipes” for...

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