Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Question
Chapter 7, Problem 7.7P
Interpretation Introduction
Interpretation:
Number of stereoisomers possible for enanthotoxin has to be given.
Concept introduction:
Chiral centre:
A chiral molecule/ion is non-superimposable on its mirror image.
Expert Solution & Answer
Explanation of Solution
There is one tetrahedral chiral centre (marked with an
) and three double bonds that can show cis-trans isomerism, so there are 24 or 16 possible stereoisomers.
Hence, the totally 16 isomer is possible.
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A diuretic is a compound that causes increased urination and thereby reduces fluid volume in the body. An important use of diuretics in clinical medicine is in the reduction of the fluid buildup, particularly in the lungs, that is associated with congestive heart failure. It is also used as an antihypertensive (i.e., to reduce blood pressure). Furosemide, an exceptionally potent diuretic, is prescribed under 30 or more trade names, the best known of which is Lasix. The synthesis of furosemide begins with treatment of 2,4-dichlorobenzoic acid with chlorosulfonic acid in a reaction called chlorosulfonation. The product of this reaction is then treated with ammonia followed by heating with furfurylamine.
Q. Propose a mechanism for the chlorosulfonation reaction in Step (1).
A diuretic is a compound that causes increased urination and thereby reduces fluid volume in the body. An important use of diuretics in clinical medicine is in the reduction of the fluid buildup, particularly in the lungs, that is associated with congestive heart failure. It is also used as an antihypertensive (i.e., to reduce blood pressure). Furosemide, an exceptionally potent diuretic, is prescribed under 30 or more trade names, the best known of which is Lasix. The synthesis of furosemide begins with treatment of 2,4-dichlorobenzoic acid with chlorosulfonic acid in a reaction called chlorosulfonation. The product of this reaction is then treated with ammonia followed by heating with furfurylamine.
Q. Propose a mechanism for Step (3).
A diuretic is a compound that causes increased urination and thereby reduces fluid volume in the body. An important use of diuretics in clinical medicine is in the reduction of the fluid buildup, particularly in the lungs, that is associated with congestive heart failure. It is also used as an antihypertensive (i.e., to reduce blood pressure). Furosemide, an exceptionally potent diuretic, is prescribed under 30 or more trade names, the best known of which is Lasix. The synthesis of furosemide begins with treatment of 2,4-dichlorobenzoic acid with chlorosulfonic acid in a reaction called chlorosulfonation. The product of this reaction is then treated with ammonia followed by heating with furfurylamine.
Q. Is furosemide chiral? If so, which of the possible stereoisomers are formed in this synthesis?
Chapter 7 Solutions
Organic Chemistry
Ch. 7.2 - Write the IUPAC name of each compound.Ch. 7.2 - Write the common name of each alkyne.Ch. 7.5 - Prob. 7.3PCh. 7.7 - Draw a structural formula for a hydrocarbon with...Ch. 7.7 - Hydration of 2-pentyne gives a mixture of two...Ch. 7.9 - Prob. 7.6PCh. 7 - Prob. 7.7PCh. 7 - Show how to prepare each alkyne from the given...Ch. 7 - Prob. 7.9PCh. 7 - Complete each acid-base reaction and predict...
Ch. 7 - Draw structural formulas for the major product(s)...Ch. 7 - Draw the structural formula of the enol formed in...Ch. 7 - Prob. 7.13PCh. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Show reagents and experimental conditions you...Ch. 7 - Show reagents and experimental conditions you...Ch. 7 - Show how to convert 1-butyne to each of these...Ch. 7 - Prob. 7.19PCh. 7 - Show reagents and experimental conditions to bring...Ch. 7 - Show reagents to bring about each conversion.Ch. 7 - Propose a synthesis for (Z)-9-tricosene...Ch. 7 - Propose a synthesis of each compound starting from...Ch. 7 - Show how to prepare each compound from 1-heptene....Ch. 7 - Prob. 7.25PCh. 7 - Prob. 7.26PCh. 7 - Following is the structural formula of the...Ch. 7 - The standard procedure for synthesizing a compound...Ch. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Using your reaction roadmap as a guide, show how...Ch. 7 - Prob. 7.35P
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