1. 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 1

2. 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. 2

3. 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 CH 4 Methane HCOOH Methanoic acid CH 3 —CH 3 Ethane CH 3 —COOH Ethanoic acid substituents are numbered from the carboxyl carbon 1 CH 3 O CH 3 —CH—CH 2 —C—OH 4 3 2 1 3-methylbutanoic acid 3

4. 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 4

5. 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 H  C  OH Ethanoic acid (acetic acid) O CH 3  C  OH 5

6. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc. Naming Carboxylic Acids 6

7. 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 1Identify the carbon chain containing the carboxyl group and replace the -e in the alkane name with -oic acid. Pentanoic acid 7

8. 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 8

9. 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 9

10. 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. 10

11. 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 11

12. 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. CH 3  CH 2  COOH B. CH 3 | CH 3  CH  CH 2  COOHC. 12

13. 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. CH 3  CH 2  COOH propionoic acid B. CH 3 | CH 3  CH  CH 2  COOHC. 3-methylbutanoic acid 3-bromobenzoic acid 13