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Chapter 16 Carboxylic Acids and
Esters
16.1
Carboxylic Acids
General, Organic, and Biological Chemistry
Copyright © 2010 Pearson Education, Inc.
1
Carboxylic Acids
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
General, Organic, and Biological Chemistry
Copyright © 2010 Pearson Education, Inc.
2
Some Typical Carboxylic Acids
General, Organic, and Biological Chemistry
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3
Guide to Naming Carboxylic
Acids
General, Organic, and Biological Chemistry
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Example of Writing IUPAC
Names for Carboxylic Acids
To write the IUPAC names of a carboxylic acid
STEP 1 Replace the e in the alkane name with oic
acid.
CH4
Methane
HCOOH
Methanoic acid
CH3—CH3 Ethane
CH3—COOH Ethanoic acid
STEP 2 Locate and name substituents, counting
from the carboxyl carbon as carbon 1.
General, Organic, and Biological Chemistry
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Common Names for Simple
Carboxylic Acids
The common names of simple carboxylic acids
 are formic acid (1C), acetic acid (2C), propionic acid
(3C), and butyric acid (4C).
 Examples:
HCOOH
CH3—COOH
Methanoic acid
Ethanoic acid
(formic acid)
(acetic acid)
General, Organic, and Biological Chemistry
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Common Names for Carboxylic
Acids
The common names of carboxylic acids
 use letters , , or  to indicate locations of
substituents
3-Methylbutanoic acid
(-methylbutryic acid)
General, Organic, and Biological Chemistry
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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
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8
Common Carboxylic Acids
Methanoic acid (formic acid)
Ethanoic acid (acetic acid)
General, Organic, and Biological Chemistry
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9
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
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Aromatic Carboxylic Acids
(continued)
General, Organic, and Biological Chemistry
Copyright © 2010 Pearson Education, Inc.
11
Learning Check
Give the IUPAC and common names for each of the
following:
A.
B.
C.
General, Organic, and Biological Chemistry
Copyright © 2010 Pearson Education, Inc.
12
Solution
Give the IUPAC and common names for each of the
following:
A.
Ethanoic acid (acetic acid)
B.
2-Methylpropanoic acid
(-methylpropionic acid)
C.
2-Bromobenzoic acid
(o-bromobenzoic acid)
General, Organic, and Biological Chemistry
Copyright © 2010 Pearson Education, Inc.
13
Learning Check
Give the IUPAC and common names for the following:
A.
B.
O
C
OH
C.
Br
General, Organic, and Biological Chemistry
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Solution
A.
Propanoic acid
(propionic acid)
B.
3-Methylbutanoic acid
(-methylbutyric acid)
C.
3-Bromobenzoic acid
(m-bromobenzoic acid)
General, Organic, and Biological Chemistry
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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.
16
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.
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Solution
What alcohol would be used to prepare the following:
[O]
[O]
1. Butanol
butanal
butanoic acid
[O]
2. 1-Propanol
General, Organic, and Biological Chemistry
[O]
propanal
propanoic acid
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