What functional group is not present in the antibiotic bacampicillin below? A. ester B. primary amine C. amide D. ether E. aromatic ring

Question

BlackTom AI · Accepted Answer

Identify functional groups by looking for their defining bonds and fragments: an ester is R–C(=O)–O–R', an ether is R–O–R' (no adjacent carbonyl), an amide is R–C(=O)–N–R', a primary amine is –NH2 (nitrogen bonded to one carbon and two hydrogens), and an aromatic ring is a conjugated 6‑membered ring (phenyl).

Step‑by‑step reasoning applied to bacampicillin:
1. Ester: Bacampicillin is a prodrug of ampicillin and contains an esterified side chain (the prodrug moiety is attached through a –C(=O)–O–R linkage). That C(=O)–O–R pattern is the ester functional group, so an ester is present.
2. Primary amine: The penicillin/ampicillin family has a free amino group on the side chain (the α‑amino group of the phenylglycine/benzyl side chain). That –NH2 (nitrogen bound to one carbon and two hydrogens) identifies a primary amine present in bacampicillin.
3. Amide (beta‑lactam): The core penicillin structure contains a four‑membered beta‑lactam ring, which is an amide (a C(=O)–N bond within the ring). Thus an amide functional group is present.
4. Aromatic ring: The side chain includes a phenyl (aromatic) ring attached to the ampicillin backbone, so an aromatic ring is present.
5. Ether: An ether would appear as an oxygen atom bonded to two carbon atoms (R–O–R') without a neighboring carbonyl. Scanning the structure, all oxygens are either in carbonyl‑bearing ester groups or the beta‑lactam/carboxylate environment (i.e., part of esters/acids/amides). There is no standalone R–O–R' fragment in the molecule.

Why the correct answer is correct: Because ester, primary amine, amide, and aromatic ring are all identifiable in bacampicillin, while a simple ether linkage is not present. Briefly why other choices are wrong: A (ester) — present (prodrug ester); B (primary amine) — present (–NH2 on side chain); C (amide) — present (beta‑lactam amide); E (aromatic ring) — present (phenyl ring).

Therefore the functional group not present is D (ether), which matches the provided answer.

What functional group is not present in the antibiotic bacampicillin below? A. ester B. primary amine C. amide D. ether E. aromatic ringSingle choice

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