6. The structure shown below is amoxicillin, one of the most commonly prescribed
ID: 1034688 • Letter: 6
Question
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 ?-lactam, which is the center of the molecule on the left. Bacterial resistance to penicillins, including amoxicillin, involves an enzyme called ?-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? aid less a L> atto acc NH2 HO ??Explanation / Answer
6. For amoxycillin,
a. The functional group that is the amide are easily attacked by the nucleophilic bases such as water, wherein, water attacks the carbonyl center and cleavage of the C-N bond occurs to release the strain of the ring. Four membered rings are highly strained due to the change in their tetrahedral bond angle from 109.5 o This is thus a favoured process.
b. This ring is more starined due to the presence of carbonyl oxygen and nitrogen in the rign. The N try to maintain th geometry to tetrahedral whereas, the carbonyl carbon try to form the planar geometry. Thereby inducing more strain to the already strained four membered ring.
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