Please explain the Chemistry behind the synthesis process of Sulfonamides.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section: Chapter Questions
Problem 20.48P
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Please explain the Chemistry behind the synthesis process of Sulfonamides.

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Eulfenamide
FAITH M. POLICARPIO
(ELECTRON-FLOW MECHANISM)
• BENZENE TO NITROBENZENE
NO2
NO2
NO2
NO2
(HNO3/
HeS04)
ON
-
NO2
-H*
• NITROBENZE TO ANILINE
DH
+2e,t2H*.
(Sn/ HCI)
-Heo.
+2e, 2H+
Sn/HCI
HO-
+2e, +2H
-H20
H.
• ANILINE TO ACETANILIDE
CHS
NH2
HzN
NHCOCH3
CHSCOOH
CH3
C.
-CH3COOH
+ CHs
• ACETANILIDE TO 4-ACETAMEDOBENZENE SULFONYL CHLORIDE
NHCOCH3
NHCOCHS
CISOSH
H*
-H20
OH
OH
NHCOCHS
NHCOCH3
NHCOCH3
NHCOCH3
H
SO,CI
•4-ACETAMEDO BENZENE SULTONYL CHLORIDE TO 4-ACETAMEDO BENZENE SUL FONAMIDE
NHCOCH3
NHCOCH3
NHCOCH,
NH3
H-
-CI
NH2
ŠO NH,
• 4-ACETAMEDO BENZENESULFONAMIDE TO SULFONAMIDE
O OH
C:
HO:
HN-
CH3
HN-
CH3
HN-
CH3
OH
H°
Hzö
H20/HCI
„H.
ŠO, NH2
SO, NH2
SO̟NH
NH2
i> -H*
ii>+H*
+ CH,COOH
SO-NH2
Transcribed Image Text:Eulfenamide FAITH M. POLICARPIO (ELECTRON-FLOW MECHANISM) • BENZENE TO NITROBENZENE NO2 NO2 NO2 NO2 (HNO3/ HeS04) ON - NO2 -H* • NITROBENZE TO ANILINE DH +2e,t2H*. (Sn/ HCI) -Heo. +2e, 2H+ Sn/HCI HO- +2e, +2H -H20 H. • ANILINE TO ACETANILIDE CHS NH2 HzN NHCOCH3 CHSCOOH CH3 C. -CH3COOH + CHs • ACETANILIDE TO 4-ACETAMEDOBENZENE SULFONYL CHLORIDE NHCOCH3 NHCOCHS CISOSH H* -H20 OH OH NHCOCHS NHCOCH3 NHCOCH3 NHCOCH3 H SO,CI •4-ACETAMEDO BENZENE SULTONYL CHLORIDE TO 4-ACETAMEDO BENZENE SUL FONAMIDE NHCOCH3 NHCOCH3 NHCOCH, NH3 H- -CI NH2 ŠO NH, • 4-ACETAMEDO BENZENESULFONAMIDE TO SULFONAMIDE O OH C: HO: HN- CH3 HN- CH3 HN- CH3 OH H° Hzö H20/HCI „H. ŠO, NH2 SO, NH2 SO̟NH NH2 i> -H* ii>+H* + CH,COOH SO-NH2
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