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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

Classify each of the following substances as (1) a salt of a monocarboxylic acid or (2) a salt of a dicarboxylic acid.

a. Sodium formate

b. Potassium pentanedioate

c. Calcium oxalate

d. Magnesium propanoate

(a)

Interpretation Introduction

Interpretation:

The given substance has to be classified as salt of monocarboxylic acid or a salt of dicarboxylic acid.

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.  Similar to carboxylic acid it reacts with strong base to form carboxylic acid salt and water.

If the negative ion contains two carboxylate groups in it then it is a dicarboxylate.  The parent acid of this has to be dicarboxylic acid.  If the negative ion contains one carboxylate group in it then it is a monocarboxylate.  The parent acid of this has to be monocarboxylic acid.

This can also be found from the name of the salt given.  If the IUPAC name contains suffix “-ate” alone means it is a salt of monocarboxylic acid.  If the IUPAC name contains prefix “di-” that is preceded by “-ate” in the ending means it is a salt dicarboxylic acid.

Explanation

Given compound name is sodium formate.  The structure of sodium formate can be given as shown below,

From the name of the given salt, the name ends with suffix “-ate” that does not have the prefix “di-”...

(b)

Interpretation Introduction

Interpretation:

The given substance has to be classified as salt of monocarboxylic acid or a salt of dicarboxylic acid.

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.  Similar to carboxylic acid it reacts with strong base to form carboxylic acid salt and water.

If the negative ion contains two carboxylate groups in it then it is a dicarboxylate.  The parent acid of this has to be dicarboxylic acid.  If the negative ion contains one carboxylate group in it then it is a monocarboxylate.  The parent acid of this has to be monocarboxylic acid.

This can also be found from the name of the salt given.  If the IUPAC name contains suffix “-ate” alone means it is a salt of monocarboxylic acid.  If the IUPAC name contains prefix “di-” that is preceded by “-ate” in the ending means it is a salt dicarboxylic acid.

(c)

Interpretation Introduction

Interpretation:

The given substance has to be classified as salt of monocarboxylic acid or a salt of dicarboxylic acid.

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.  Similar to carboxylic acid it reacts with strong base to form carboxylic acid salt and water.

If the negative ion contains two carboxylate groups in it then it is a dicarboxylate.  The parent acid of this has to be dicarboxylic acid.  If the negative ion contains one carboxylate group in it then it is a monocarboxylate.  The parent acid of this has to be monocarboxylic acid.

This can also be found from the name of the salt given.  If the IUPAC name contains suffix “-ate” alone means it is a salt of monocarboxylic acid.  If the IUPAC name contains prefix “di-” that is preceded by “-ate” in the ending means it is a salt dicarboxylic acid.

(d)

Interpretation Introduction

Interpretation:

The given substance has to be classified as salt of monocarboxylic acid or a salt of dicarboxylic acid.

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.  Similar to carboxylic acid it reacts with strong base to form carboxylic acid salt and water.

If the negative ion contains two carboxylate groups in it then it is a dicarboxylate.  The parent acid of this has to be dicarboxylic acid.  If the negative ion contains one carboxylate group in it then it is a monocarboxylate.  The parent acid of this has to be monocarboxylic acid.

This can also be found from the name of the salt given.  If the IUPAC name contains suffix “-ate” alone means it is a salt of monocarboxylic acid.  If the IUPAC name contains prefix “di-” that is preceded by “-ate” in the ending means it is a salt dicarboxylic acid.

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