Problems 729
- Sulfonamides, the first antibiotics, were introduced clinically in 1934 (Sections 25.8 and 30.4). Show how a sulfonamide can be
prepared from benzene.
- a. How could aspirin be synthesized, starting with benzene?
b. Ibuprofen is the active ingredient in pain relievers such as Advil Motrin and Nuprin How could ibuprofen be synthesized,
starting with benzene?
- The following compound has been found to be an inhibitor of penicillinase. The enzyme can be reactivated by hydroxylamine
Propose a mechanism to account for the inhibition and for the reactivation.
- For each of the following reactions, propose a mechanism that will account for the formation of the product:
a.
b.
- Show how Novocain®, a painkiller used frequently by dentists (Section 30.3), can be prepared from benzene.
- Catalytic antibodies catalyze a reaction by binding to the transition state, thereby stabilizing it. As a result, the energy of activation
is lowered and the reaction goes faster. The synthesis of the antibody is carried out in the presence of a transition state analog—a
NCH 2 CH 2 OC
CH 3 CH 2
CH 3 CH 2
NH 2
O
Novocain
OH
O ONO 2
H 3 C S
CH 3 O− Na+
NO 2 O
O O− Na+
H 3 C S
NO 2
NO 2
HO
NHCO 2 CH 3
CO 2 CH 3
N
HCl
O O
CH 2 CNHCH 2 PO
COO−
O−
(NH 2 OH).
O
COH
OCCH 3
O
aspirin
O
CH 3 CHCH 2 CHCOH
CH 3 CH 3
ibuprofen
®, ®, ®.
H 2 N SNHR
O
O
a sulfonamide
