1. Ch. 14: Carboxylic Acids, Esters, Amines and Amides
Chem 20
El Camino College

2. Carboxylic Acids, Esters, Amines

3. Naming Carboxylic Acids
Name the longest carbon chain containing the carboxyl group.
Use the suffix “oic acid”
# the chain to give the carboxyl gp the lowest #
Give the location and name of other substituents in alphabetical order, using numbers, hyphens, and commas between numbers

4. Un-Numbered 13.3

5. Name These propanoic acid methanoic acid (formic acid) ethanoic acid
(acetic acid)
3-methylpentanoic acid

6. Benzoic Acid
Benzoic acid is an important carboxylic acid

7. Carboxylic Acid Properties
Carboxylic acids are extremely polar
They have higher boiling pts than alcohols, ketones, and aldehydes of similar mass
propanal, bp = 49 oC
1-propanol, bp = 97 oC
acetic acid, bp = 118 oC
Carboxylic acids with 4 C or less are water soluble

8. Figure 13.1

9. Un-Numbered 13.5

10. Esterification
Carboxylic acids react with alcohols in the presence of heat and acid (H+) to form esters and water
The OH comes off the carboxylic acid, and the H comes off the alcohol
A new bond forms to make the ester

11. Draw the Ester Product

12. Naming Esters
Name the the part that came from an alcohol (directly connected to an oxygen) first, use “yl”
Then name the part that came from a carboxylic acid, use the “oate” suffix

13. Properties of Esters
The scents of many flowers and fruits are esters

14. Types of Amines
Amines are classified as primary (1o), secondary (2o), or tertiary (3o)
In 1o amines, the N is attached to 1 carbon
In 2o amines, the N is attached to 2 carbons
In 3o amines, the N is attached to 3 carbons

15. Naming of Amines
Name the carbon attachments in alphabetical order, use the word “amine”
Use di- and tri- for identical substituents

16. Properties of Amines Amines tend to be bad-smelling compounds
Amines are polar, they have relatively high boiling points
Small amines are water soluble.

17. Un-Numbered 13.9

18. Un-Numbered 13.10

19. Un-Numbered 13.11

20. Amide
Amides are derivative of carboxylic acids, in which a nitrogen group replaces the hydroxyl group. Amide is formed when a salt of carboxylic with ammonia or amine is heated; a molecule of water is eliminated.
Amide can be hydrolyzed back to carboxylic acid and ammonium salt in acidic solution, or to a salt of carboxylic acid and ammonia or amine in basic solution.