Practice Problem 3

The discovery of penicillin in 1928 marked the beginning of what has been called the "golden age of chemotherapy," in which previously life-threatening bacterial infections were transformed into little more than a source of discomfort. For those who are allergic to penicillin, a variety of antibiotics, including tetracycline, are available. Identify the numerous functional groups in the tetracycline molecule.



This compound contains an aromatic ring fused to three six-membered cycloalkane rings. It is also an alcohol (with five OH groups), a ketone (with C=O groups at the bottom of the second and fourth rings), an amine (the N(CH3)2 substituent at the top of the fourth ring), and an amide (the CONH2 group at the bottom right-hand corner of the fourth ring.)