Chapter 14 Carboxylic Acids Esters Amines and Amides

Chapter 14 Carboxylic Acids, Esters, Amines, and Amides 1 14. 1 Carboxylic Acids Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Carboxylic Acids 2 A carboxylic acid contains a carboxyl group, which consists of a hydroxyl group OH attached to the carbon in a carbonyl group. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

IUPAC Names for Carboxylic Acids 3 In the IUPAC names of carboxylic acids, • the -e in the alkane name is replaced with -oic acid CH 4 CH 3—CH 3 • Methane Ethane HCOOH Methanoic acid 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 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Common Carboxylic Acids 5 Methanoic acid (formic acid) O H C OH Ethanoic acid (acetic acid) O CH 3 C OH 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 7 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Naming Carboxylic Acids 8 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Aromatic Carboxylic Acids 9 Benzoic acid • is the simplest aromatic carboxylic acid • locates substituents by numbering the ring from carbon 1 in the carboxyl group Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alpha Hydroxy Acids (AHAs) 10 Alpha hydroxy acids (AHAs) are naturally occurring carboxylic acids with a hydroxyl group ( OH) on the carbon adjacent to the carboxyl group. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Alpha Hydroxy Acids (AHAs) 11 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 Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Learning Check 12 Give the IUPAC names of each compound. A. CH 3 CH 2 COOH B. CH 3 | CH 3 CH CH 2 COOH C. Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.

Solution 13 Give the IUPAC names of each compound. A. CH 3 CH 2 COOH propionoic acid B. CH 3 | CH 3 CH CH 2 COOH 3 -methylbutanoic acid C. 3 -bromobenzoic acid Chemistry: An Introduction to General, Organic, and Biological Chemistry, Eleventh Edition Copyright © 2012 by Pearson Education, Inc.