7. Compound X is an antibacterial drug of the sulfonamide group, and was widely used in the mid-20th century as one of the earliest antimicrobial drugs. X is synthesized through the following sequence of reactions. Draw structures of A-C and X, and show mechanism for the reaction C to X. NO2 NO2 1) NaNO2, H*, H20 H202 NH3 B H2 NaSH > X ZrCl4 Pd 2) O=$=0 H2N `NH2 NH2

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter22: Carbonyl Alpha-substitution Reactions
Section22.SE: Something Extra
Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...
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7. Compound X is an antibacterial drug of the sulfonamide group, and was widely used in
the mid-20th century as one of the earliest antimicrobial drugs. X is synthesized through
the following sequence of reactions. Draw structures of A-C and X, and show mechanism
for the reaction C to X.
NO2
NO2
1) NaNO2, H*, H20
H202
NH3
B
H2
NaSH
> X
ZrCl4
Pd
2)
O=S=0
H2N
`NH2
NH2
Transcribed Image Text:7. Compound X is an antibacterial drug of the sulfonamide group, and was widely used in the mid-20th century as one of the earliest antimicrobial drugs. X is synthesized through the following sequence of reactions. Draw structures of A-C and X, and show mechanism for the reaction C to X. NO2 NO2 1) NaNO2, H*, H20 H202 NH3 B H2 NaSH > X ZrCl4 Pd 2) O=S=0 H2N `NH2 NH2
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