
Concept explainers
Several compounds have been found to inhibit β-lactamase, and drugs based on these compounds can be taken in combination with penicillins and cephalosporins to restore their effectiveness when resistance is known to be a problem. The commonly prescribed formulation called Augmentin is a combination of the β-lactamase inhibitor shown below with amoxicillin (shown above). It is used to treat childhood ear infections when resistance is suspected, and many kids know it as the white liquid that tastes like bananas. Which of the statements below are true statements?
- 1. The stereochemistry of the fusion between the four-and five-membered rings in the inhibitor and amoxicillin are different.
- 2. The inhibitor possesses enol ether and allylic alcohol functional groups while the antibiotic possesses a phenol and a secondary amide functional group.
- 3. Neither the inhibitor nor the antibiotic contains strained rings.
- 4. Both 1 and 2 are true.

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Chapter 18 Solutions
Organic Chemistry, Loose-leaf Version
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