ORGANIC CHEMISTRY W/OWL
ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
Question
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Chapter 24.8, Problem 16P
Interpretation Introduction

Interpretation:

Using benzene and any other necessary amines how to synthesize sulfathiazole is to be shown.

Concept introduction:

The steps involved in the synthesis of sulfathiazole from benzene are i) Nitration of benzene ii) Reduction of nitrobenzene iii) Acetylation of the amino group iv) Chlorosulfonation of the anilide v) Treatment with 2-aminothiazole vi) Hydrolysis of the anilide to an amine.

To Show:

How to synthesize sulfathiazole starting from benzene and using any other necessary amines.

Answer:

The synthesis of sulfathiazole starting from benzene and using any other necessary amines is given below.

ORGANIC CHEMISTRY W/OWL, Chapter 24.8, Problem 16P , additional homework tip  1

Explanation:

Nitration of benzene with Conc. HNO3 and Conc. H2SO4 yields nitrobenzene which on reduction with H2/Pt in ethanol gives aniline. Acetylation of aniline with acetic anhydride produces acetanilide. Chlorosulfonation of acetanilide leads to the formation of a p-chlorosulfonate as anilide group is orthp and para directing. Treatment of chlorosulfonate with 2-aminothiazole yields N-acetylsulfothiazole. Hydrolysis of N-acetylsulfothiazole yields sulfathiazole.

Conclusion:

The synthesis of sulfathiazole starting from benzene and using 2-aminothiazole is given below.

ORGANIC CHEMISTRY W/OWL, Chapter 24.8, Problem 16P , additional homework tip  2

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Chapter 24 Solutions

ORGANIC CHEMISTRY W/OWL

Ch. 24.6 - Prob. 11PCh. 24.6 - Prob. 12PCh. 24.6 - Prob. 13PCh. 24.7 - Prob. 14PCh. 24.7 - Prob. 15PCh. 24.8 - Prob. 16PCh. 24.8 - Propose syntheses of the following compounds from...Ch. 24.8 - How would you prepare the following compounds from...Ch. 24.8 - Prob. 19PCh. 24.9 - Draw an orbital picture of thiazole. Assume that...Ch. 24.9 - Prob. 21PCh. 24.9 - Prob. 22PCh. 24.9 - Which nitrogen atom in the hallucinogenic indole...Ch. 24.9 - Prob. 24PCh. 24.10 - Prob. 25PCh. 24.SE - Name the following amines, and identify each as...Ch. 24.SE - The following compound contains three nitrogen...Ch. 24.SE - Name the following amine, including R, S...Ch. 24.SE - Prob. 29VCCh. 24.SE - Predict the product(s) for each reaction below and...Ch. 24.SE - Predict the product(s) and provide the complete...Ch. 24.SE - Prob. 32MPCh. 24.SE - Predict the product(s) and provide the mechanism...Ch. 24.SE - The diazotization of aniline first involves the...Ch. 24.SE - Prob. 35MPCh. 24.SE - Prob. 36MPCh. 24.SE - Prob. 37MPCh. 24.SE - Prob. 38MPCh. 24.SE - Choline, a component of the phospholipids in cell...Ch. 24.SE - Prob. 40MPCh. 24.SE - -Amino acids can be prepared by the Strecker...Ch. 24.SE - Prob. 42MPCh. 24.SE - Prob. 43MPCh. 24.SE - Prob. 44MPCh. 24.SE - Propose a mechanism for the following reaction:Ch. 24.SE - Prob. 46MPCh. 24.SE - Name the following compounds:Ch. 24.SE - Prob. 48APCh. 24.SE - Prob. 49APCh. 24.SE - Prob. 50APCh. 24.SE - Histamine, whose release in the body triggers...Ch. 24.SE - Prob. 52APCh. 24.SE - Prob. 53APCh. 24.SE - Prob. 54APCh. 24.SE - Prob. 55APCh. 24.SE - Prob. 56APCh. 24.SE - Prob. 57APCh. 24.SE - Prob. 58APCh. 24.SE - Prob. 59APCh. 24.SE - Prob. 60APCh. 24.SE - Show the products from reaction of p-bromoaniline...Ch. 24.SE - Prob. 62APCh. 24.SE - How would you prepare the following compounds from...Ch. 24.SE - Prob. 64APCh. 24.SE - Phenacetin, a substance formerly used in...Ch. 24.SE - Prob. 66APCh. 24.SE - Draw the structure of the amine that produced the...Ch. 24.SE - Fill in the missing reagents a-e in the following...Ch. 24.SE - Prob. 69APCh. 24.SE - Prob. 70APCh. 24.SE - Deduce the structure of the compound with formula...Ch. 24.SE - Prob. 72APCh. 24.SE - Prob. 73APCh. 24.SE - Prob. 74APCh. 24.SE - Prob. 75APCh. 24.SE - Prob. 76APCh. 24.SE - Propose a structure for the product with formula...Ch. 24.SE - Prob. 78APCh. 24.SE - Prob. 79APCh. 24.SE - Prob. 80APCh. 24.SE - Prob. 81APCh. 24.SE - Prob. 82APCh. 24.SE - Prob. 83APCh. 24.SE - Prob. 84AP
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