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Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079

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Section
BuyFindarrow_forward

Organic And Biological Chemistry

7th Edition
STOKER + 1 other
ISBN: 9781305081079
Textbook Problem

What is the charge on the carboxylate ion formed when each of the acids in Problem 16-48 ionizes in water?

  1. a. Acetic acid
  2. b. Benzoic acid
  3. c. Propanoic acid
  4. d. Glutaric acid

(a)

Interpretation Introduction

Interpretation:

The charge on the carboxylate ion that is formed when acetic acid ionizes in water has to be given.

Concept Introduction:

The name of the carboxylic acid itself implies that it is acidic.  Addition of carboxylic acid to water results in ionization.  Hydrogen ion transfer occurs from carboxylic acid to water and hydronium ion is formed.  Carboxylate ion is also formed due to the loss of hydrogen ion from carboxylic acid.

Carboxylate ion is the negative ion which is formed when one or more acidic protons are lost from carboxylic acid.

Number of acidic hydrogen atoms present in the carboxylic acid can be found by identifying the number of carboxyl groups present.  Each carboxyl group gives a hydrogen atom.

The charge formed on the carboxylate ion will be equal to the negative value of the number of acidic hydrogen atoms present in the carboxylic acid.

Explanation

Carboxylic acids undergo ionization in water to form hydronium ion and carboxylate ion.  The extent of ionization in pure carboxylic acid alone is less than 5 percent.  This means that the equilibrium lies far left as shown below,

Given compound name is acetic acid.  The structure of acetic acid can be given as shown below,

(b)

Interpretation Introduction

Interpretation:

The charge on the carboxylate ion that is formed when benzoic acid ionizes in water has to be given.

Concept Introduction:

The name of the carboxylic acid itself implies that it is acidic.  Addition of carboxylic acid to water results in ionization.  Hydrogen ion transfer occurs from carboxylic acid to water and hydronium ion is formed.  Carboxylate ion is also formed due to the loss of hydrogen ion from carboxylic acid.

Carboxylate ion is the negative ion which is formed when one or more acidic protons are lost from carboxylic acid.

Number of acidic hydrogen atoms present in the carboxylic acid can be found by identifying the number of carboxyl groups present.  Each carboxyl group gives a hydrogen atom.

The charge formed on the carboxylate ion will be equal to the negative value of the number of acidic hydrogen atoms present in the carboxylic acid.

(c)

Interpretation Introduction

Interpretation:

The charge on the carboxylate ion that is formed when propanoic acid ionizes in water has to be given.

Concept Introduction:

The name of the carboxylic acid itself implies that it is acidic.  Addition of carboxylic acid to water results in ionization.  Hydrogen ion transfer occurs from carboxylic acid to water and hydronium ion is formed.  Carboxylate ion is also formed due to the loss of hydrogen ion from carboxylic acid.

Carboxylate ion is the negative ion which is formed when one or more acidic protons are lost from carboxylic acid.

Number of acidic hydrogen atoms present in the carboxylic acid can be found by identifying the number of carboxyl groups present.  Each carboxyl group gives a hydrogen atom.

The charge formed on the carboxylate ion will be equal to the negative value of the number of acidic hydrogen atoms present in the carboxylic acid.

(d)

Interpretation Introduction

Interpretation:

The charge on the carboxylate ion that is formed when glutaric acid ionizes in water has to be given.

Concept Introduction:

The name of the carboxylic acid itself implies that it is acidic.  Addition of carboxylic acid to water results in ionization.  Hydrogen ion transfer occurs from carboxylic acid to water and hydronium ion is formed.  Carboxylate ion is also formed due to the loss of hydrogen ion from carboxylic acid.

Carboxylate ion is the negative ion which is formed when one or more acidic protons are lost from carboxylic acid.

Number of acidic hydrogen atoms present in the carboxylic acid can be found by identifying the number of carboxyl groups present.  Each carboxyl group gives a hydrogen atom.

The charge formed on the carboxylate ion will be equal to the negative value of the number of acidic hydrogen atoms present in the carboxylic acid.

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