General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.1 Chapter 16 Carboxylic Acids and Esters 16.1 Carboxylic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.2 A carboxylic acid  contains a carboxyl group, which is a carbonyl group (C═O) attached to a hydroxyl group (—OH)  has the carboxyl group on carbon 1 Carboxylic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.3 Some Typical Carboxylic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Guide to Naming Carboxylic Acids 4

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.5 To write the IUPAC names of a carboxylic acid STEP 1 Replace the e in the alkane name with oic acid. CH 4 Methane HCOOH Methanoic acid CH 3 —CH 3 Ethane CH 3 —COOH Ethanoic acid STEP 2 Locate and name substituents, counting from the carboxyl carbon as carbon 1. Example of Writing IUPAC Names for Carboxylic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.6 The common names of simple carboxylic acids  are formic acid (1C), acetic acid (2C), propionic acid (3C), and butyric acid (4C).  Examples: HCOOH CH 3 —COOH Methanoic acid Ethanoic acid (formic acid)(acetic acid) Common Names for Simple Carboxylic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.7 3-Methylbutanoic acid (  -methylbutryic acid) Common Names for Carboxylic Acids The common names of carboxylic acids  use letters , , or  to indicate locations of substituents

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.8 Alpha Hydroxy Acids Alpha hydroxy acids (AHAs)  occur naturally in fruit, milk, and sugarcane  are used in skin care products

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Methanoic acid (formic acid) Ethanoic acid (acetic acid) 9 Common Carboxylic Acids

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.10 Aromatic Carboxylic Acids Benzoic acid  is the aromatic carboxylic acid  locates substituents by assigning 1 to the carbon attached to the carboxyl group  has common names that assign prefixes ortho-, meta-, and para- for 2 substituents ortho (o)1, 2 location meta (m) 1, 3 location para (p) 1, 4 location

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.11 Aromatic Carboxylic Acids (continued)

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Give the IUPAC and common names for each of the following: A. B. C. 12 Learning Check

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc. Give the IUPAC and common names for each of the following: A. B. C. 13 Solution 2-Bromobenzoic acid (o-bromobenzoic acid) 2-Methylpropanoic acid (  -methylpropionic acid) Ethanoic acid (acetic acid)

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.14 Learning Check Give the IUPAC and common names for the following: A. B. C.

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.15 Solution Propanoic acid (propionic acid) 3-Methylbutanoic acid (  -methylbutyric acid) 3-Bromobenzoic acid (m-bromobenzoic acid) A. B. C.

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.16 Preparation of Carboxylic Acids Carboxylic acids are prepared  by oxidizing primary alcohols or aldehydes  from the oxidation of ethanol, which produces ethanoic acid (acetic acid)

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.17 Learning Check What alcohol would be used to prepare the following: 1. Butanoic acid 2. Propanoic acid

General, Organic, and Biological Chemistry Copyright © 2010 Pearson Education, Inc.18 Solution What alcohol would be used to prepare the following: [O] [O] 1. Butanol butanal butanoic acid [O] [O] 2. 1-Propanol propanal propanoic acid