Carboxylic Acids, Esters,

Amines, and Amides

Chemistry 100
 Carboxylic Acid
Contains a carboxyl group, which consists of a hydroxyl group OH attached to
the carbon in a carbonyl group
Are weak acids or COOH

IUPAC name, drop the -e in the alkane name is replaced with -oic acid
*Carboxyl C is always Carbon 1 in a carboxylic acid
Physical Properties of Carboxylic Acids
Carboxylic acids are strongly polar because they have two polar bonds
hydroxyl (OH) and carbonyl (C=O)

Solubility
• 1-5 C atoms are very soluble in water
due to their ability to form H bonds with water molecules
• as the number of carbons increases, the solubility of the carboxylic acid in
water is reduced
 Acidity of Carboxylic Acids
Carboxylic acids are weak acids
• Ionize in water to produce carboxylate ions and hydronium ions
• Can lose a proton because two oxygen atoms in carboxylate ion stabilize
negative charge
 Neutralization of Carboxylic Acids
• Weak acids - Ionize in water to produce carboxylate ions and hydronium ions

Neutralization of a Carboxylic acid with a strong base will produce a salt

CH3—COOH + NaOH CH3—COO– Na+ + H 2O

Ethanoic Acid Carboxylate Salt - ionic

• Solids at room temperature, High melting points, Usually soluble in water

 Esters
Carboxylic acid reacts with alcohol to produce an ester and water.
The main chain of an ester comes from the carboxylic acid, while the alkyl
group in an ester comes from the alcohol.

Esterification
 Naming Esters
The IUPAC name of an ester consists of two words derived from the name of the
alcohol and the carboxylic acid in that ester
1. The first word indicates the alkyl group from the alcohol
2. The second word is the carbon chain of the carboxylic acid with –ate ending
drop -ic acid and add –ate
Study Check 1
Give the IUPAC names of each compound.
A. CH3 B. O
|
OH
CH3CHCH2COOH

Br

C. O
||
CH3—CH2—C—O—CH2—CH2—CH2—CH3
Study Check 1 Answers
Names of the compounds
A. . CH3 3-methylbutanoic acid
|
O
CH3CHCH2COOH
OH

B. 3-bromobenzoic acid
Br
O
||
C. CH3—CH2—C—O—CH2—CH2—CH2—CH3 butylpropanoate
 Hydrolysis of Esters
Ester reacts with water to produce a carboxylic acid and an alcohol
• Acid Hydrolysis
O O
 H+ 
H—C—O—CH2—CH3 + H2O H—C—OH + H—O—CH2—CH3
carboxylic acid alcohol

O
• Base Hydrolysis NaOH 
Saponification H—C—O-Na+ + H—O—CH2—CH3
carboxylate salt alcohol
 Amines Naming and Classifying
Derivatives of ammonia, NH3 replace one or more H with alkyl or aromatic groups
Common Names: named as alkyl amines
• list the names of the alkyl groups bonded to the N atom in alphabetical order in
front of amine

Classification:
 Solubility of Amines in Water
Amines – polar N-H bond
• with 1-6 carbon atoms are soluble in water
• form hydrogen bonds with the polar O-H bond in water
 Study Check 2
Name and classify the following amines. Which of the following compounds
would be the most soluble in water?

A. CH3
|
CH3—N—CH2—CH2—CH2—CH2—CH3

B. CH3—NH—CH2—CH3
Study Check 2 Answers
A. CH3
|
CH3—N—CH2—CH2—CH2—CH2—CH3 dimethylpentylamine, 3

B. CH3—NH—CH2—CH3 ethylmethylamine, 2

Ethylmethylamine would be more soluble in water.

Amines React as Bases in Water

Like ammonia, amines are weak bases in water.

Ammonium Salts

Neutralization Forms Amine Salts

 Amides
Derivatives of carboxylic acids in which a nitrogen group (–NH2) replaces the –OH
group.
O O

CH3—C—OH CH3—C—NH2
Preparation of Amides

Reacting a Carboxylic Acid with ammonia or a 1 or 2 amine with heat.

 Naming Amides
IUPAC naming -oic acid from the carboxylic acid ending is replaced with –amide
O
propanamide
CH3—CH2—C—NH2

An alkyl group attached to the nitrogen of an amide is named with the prefix N-,
followed by the alkyl name.
O
N-ethylpropanamide
CH3—CH2 —C—NH—CH2—CH3
Study Check 3

Name the following compounds.

A. O

CH3 —C—NH2

B. O

CH3—CH2—CH2—CH2 —C—NH—CH3
Study Check Answers 3

A. O

CH3 —C—NH2 ethanamide

B. O

CH3—CH2—CH2—CH2 —C—NH—CH3
N-methylpentanamide
Solubility of Amides

One to five carbon atoms are soluble in water because they can form
hydrogen bonds with water molecules.
Hydrogen bonding effects are diminished when molecules have more than
five carbon atoms, therefore reducing solubility.
 Hydrolysis of Amides
Acid hydrolysis to produce a carboxylic acid and an ammonium salt

Base hydrolysis to produce the salt of a carboxylic acid and an amine or ammonia
 Study Check 4
Give the products of the following reaction if the hydrolysis is catalyzed by HCl
(acid ) or NaOH (base).

Acid hydrolysis

O HCl
||
CH3—C—NH2 + H 2O
NaOH

Base hydrolysis
Study Check 4 Answers
acid hydrolysis
O

O CH3—C—OH + NH4+Cl–
HCl salt
CH3—C—NH2 + H2 O

NaOH O

CH3—C—O– Na+ + NH3

salt
base hydrolysis