chapter 14 carboxylic acids, esters, amines, and amides

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides

14.1 Carboxylic Acids

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Carboxylic Acids

A carboxylic acid contains a carboxyl group, which consists of a hydroxyl group OH attached to the carbon in a carbonyl group.

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

IUPAC Names for Carboxylic Acids

In the IUPAC names of carboxylic acids, • the -e in the alkane name is replaced with -oic acid

CH4 Methane HCOOH Methanoic acid CH3—CH3 Ethane CH3—COOH Ethanoic acid

• substituents are numbered from the carboxyl carbon 1

CH3 O

CH3—CH—CH2—C—OH 4 3 2 1

3-methylbutanoic acid

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Common and IUPAC Names of Some Carboxylic Acids

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Common Carboxylic Acids

Methanoic acid (formic acid) O

HCOH

Ethanoic acid (acetic acid) O

CH3COH

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Carboxylic Acids 6

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Carboxylic Acids

Give the IUPAC name for the

following carboxylic acid.

Step 1 Identify the carbon chain containing the carboxyl group and replace the -e in the alkane name with

-oic acid. Pentanoic acid

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OH

O

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Carboxylic Acids

Give the IUPAC name for the

following carboxylic acid.

Step 2 Give the location and name of each substituent on

the main chain by counting the carboxyl carbon as

1. 2-methylpentanoic acid

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OH

O

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Aromatic Carboxylic Acids

Benzoic acid• is the simplest aromatic carboxylic acid• locates substituents by numbering the ring from carbon

1 in the carboxyl group

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alpha Hydroxy Acids (AHAs)

Alpha hydroxy acids (AHAs) are naturally occurring carboxylic acids with a hydroxyl group (OH) on the carbon adjacent to the carboxyl group.

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alpha Hydroxy Acids (AHAs)

Alpha hydroxy acids (AHAs)• are used to remove acne scars and age spots• were used by Cleopatra, Queen of Egypt, who bathed in

sour milk, which contains lactic acid, an AHA

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Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check

Give the IUPAC names of each compound.

A. CH3CH2COOH

B. CH3

| CH3CHCH2COOH C.

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OH

O

Br

Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution

Give the IUPAC names of each compound.

A. CH3CH2COOH

propionoic acid

B. CH3

| CH3CHCH2COOH C.

3-methylbutanoic acid 3-bromobenzoic acid

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OH

O

Br