Organic Chemistry
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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Chapter 17, Problem 17.43P
Interpretation Introduction

Interpretation: A mechanism has to be proposed for the given reaction.

Concept introduction:

Esters encompass a large family of organic compound with broad application in various fields of science and technology.

In Fischer esterification, a carboxylic acid is reacted with an alcohol in the presence of an acid catalyst, such as concentrated sulfuroc acid.

Esters can be simply represented as,

Organic Chemistry, Chapter 17, Problem 17.43P , additional homework tip  1

Fischer esterification can be represented as follows,

Organic Chemistry, Chapter 17, Problem 17.43P , additional homework tip  2

Mechanism of the reaction is the step-by-step description of the process by which reactants are changed into products.

Curved arrows show the bonds that are formed and the bonds that are broken in a reaction.

Curved arrows used to understand a reaction mechanism.

Electrophile: It is positively charged species which seeks for negative charge and hence accepts pair of electrons from negatively charged species (Nucleophiles) which results in the formation of chemical bond.

Nucleophile: It is negatively charged species which seeks for positive charge and hence donate pair of electrons to positively charged species (electrophiles) which results in the formation of chemical bond.

Acid chlorides are organic compound and they have functional group RCOCl.

Acid chlorides are most often prepared by treating a carboxylic acid with thionyl chloride.

Organic Chemistry, Chapter 17, Problem 17.43P , additional homework tip  3

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We have studied Fischer esterification, in which a carboxylic acid is reacted with an alcohol in the presence of an acid catalyst to form an ester. Suppose that you start instead with a dicarboxylic acid such as terephthalic acid and a diol such as ethylene glycol. Show how Fischer esterification in this case can lead to a macromolecule with a molecular weight several thousand times that of the starting materials. HO, OH poly(ethylene terephthalate) (РET) НО HO, 1,4-Benzenedicarboxylic acid (Terephthalic acid) 1,2-Ethanediol (Ethylene glycol) the material produced in this reaction is a high- molecular-weight polymer, which can be fabricated into Mylar films and into the textile fiber known as Dacron polyester.
Describe the acidity of different carboxylic acids and predict the products obtained when they react with strong bases.
Describe the trends in the physical properties of carboxylic acids, and contrast theirphysical properties with those of their salts.

Chapter 17 Solutions

Organic Chemistry

Ch. 17 - Write the IUPAC name of each compound, showing...Ch. 17 - Prob. 17.8PCh. 17 - Prob. 17.9PCh. 17 - Prob. 17.10PCh. 17 - Prob. 17.11PCh. 17 - Prob. 17.12PCh. 17 - Prob. 17.13PCh. 17 - On a cyclohexane ring, an axial carboxyl group has...Ch. 17 - Prob. 17.15PCh. 17 - Prob. 17.16PCh. 17 - Prob. 17.17PCh. 17 - Complete each reaction.Ch. 17 - Prob. 17.19PCh. 17 - Prob. 17.20PCh. 17 - Prob. 17.21PCh. 17 - Show the reagents and experimental conditions...Ch. 17 - Prob. 17.23PCh. 17 - Prob. 17.24PCh. 17 - Prob. 17.25PCh. 17 - In each set, assign the acid its appropriate pKa.Ch. 17 - Low-molecular-weight dicarboxylic acids normally...Ch. 17 - Complete the following acid-base reactions. (a)...Ch. 17 - Prob. 17.29PCh. 17 - Prob. 17.30PCh. 17 - Excess ascorbic acid is excreted in the urine, the...Ch. 17 - Give the expected organic product when...Ch. 17 - Show how to convert trans-3-phenyl-2-propenoic...Ch. 17 - Show how to convert 3-oxobutanoic acid...Ch. 17 - Prob. 17.35PCh. 17 - Prob. 17.36PCh. 17 - Prob. 17.37PCh. 17 - When 4-hydroxybutanoic acid is treated with an...Ch. 17 - Fischer esterification cannot be used to prepare...Ch. 17 - Draw the product formed on thermal decarboxylation...Ch. 17 - Prob. 17.41PCh. 17 - Show how cyclohexanecarboxylic acid could be...Ch. 17 - Prob. 17.43PCh. 17 - Prob. 17.44PCh. 17 - Prob. 17.45PCh. 17 - Write the products of the following sequences of...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Using your reaction roadmaps as a guide, show how...Ch. 17 - Prob. 17.51PCh. 17 - Complete the following Fischer esterification...Ch. 17 - Prob. 17.53P
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