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Chapter 16 Carboxylic Acids and Esters

16.1Carboxylic Acids

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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

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Some Typical Carboxylic Acids

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Guide to Naming Carboxylic Acids

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To write the IUPAC names of a carboxylic acidSTEP 1 Replace the e in the alkane name with oic

acid. CH4 Methane HCOOH Methanoic acidCH3—CH3 Ethane CH3—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

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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)

Common Names for Simple Carboxylic Acids

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3-Methylbutanoic acid (-methylbutryic acid)

Common Names for Carboxylic AcidsThe common names of carboxylic acids use letters , , or to indicate locations of

substituents

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Alpha Hydroxy Acids

Alpha hydroxy acids (AHAs)occur naturally in fruit, milk, and sugarcaneare used in skin care products

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Methanoic acid (formic acid)

Ethanoic acid (acetic acid)

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Common Carboxylic Acids

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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 substituentsortho (o) 1, 2 locationmeta (m) 1, 3 location para (p) 1, 4 location

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Aromatic Carboxylic Acids (continued)

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Give the IUPAC and common names for each of the following:A.

B.

C.

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Learning Check

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Give the IUPAC and common names for each of the following:A.

B.

C.

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Solution

2-Bromobenzoic acid(o-bromobenzoic acid)

2-Methylpropanoic acid(-methylpropionic acid)

Ethanoic acid (acetic acid)

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Learning Check

Give the IUPAC and common names for the following:A.

B.

C.

OHC

O

Br

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Solution

Propanoic acid(propionic acid)

3-Methylbutanoic acid(-methylbutyric acid)

3-Bromobenzoic acid(m-bromobenzoic acid)

A.

B.

C.

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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)

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Learning Check

What alcohol would be used to prepare the following:

1. Butanoic acid

2. Propanoic acid

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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