1. AMIDES

2. Amides
In amides, an amino group replaces the –OH group of carboxylic acids O O
|| || CH3 — C — OH CH3 — C — NH2

3. Preparation of Amides
Amides are produced by reacting a carboxylic acid with ammonia or an amine (1° or 2°).
O O
 
CH3—C—OH + NH CH3—C—NH2 + H2O
O O
 
CH3—C—OH + CH3—NH CH3—C—NH—CH3
+ H2O

4. Naming Amides Amides are named as alkanamides.
In the IUPAC and common names, the –oic acid or -ic acid endings are replaced by –amide O  Methanamide (IUPAC) H—C—NH2 Formamide (common) O  Propanamide (IUPAC) CH3—CH2—C —NH2 Propionamide (common)

5. Naming Amides with N Groups
An alkyl group bonded to the N atom is named as N-alkyl in front of the amide name. O  CH3—C—NH —CH N-methylethanamide (IUPAC) N-methylacetamide (common) O CH   CH3—CH2—C —N —CH N,N-dimethylpropanamide N,N-dimethylpropionamide

6. Aromatic Amides
The amide of benzene is named benzamide.

7. Amides in Health and Medicine
Urea is the end product of protein metabolism.
Saccharin is an artificial sweetener.
Some amides such as phenobarbital, Nembutal and Seconal are barbiturates.
Acetaminophen is used to reduce fever and pain.

8. Classification of Amides
Amides are classified according to the number of carbon atoms bonded to the nitrogen atom.
O H
|| |
CH3—C—N—H Primary (1°) amide
O H
CH3—C—N—CH3 Secondary (2°) amide
O CH3
CH3 —C—N—CH3 Tertiary (3°) amide

9. Amides in Health and Medicine

10. Physical Properties of Amides
Hydrogen bonds form in primary and secondary amides, but not tertiary amides.
The melting points of primary amides are higher than secondary amides, which have higher melting points than tertiary amides.
All amides can form hydrogen bonds with water.
Amides with 1–5 carbon atoms are soluble in water.

11. Hydrogen Bonding of Amides||
CH3—C—N—H |
H Hydrogen bonding occurs
between primary amides. H

12. Reactions of Amides Amides undergo:
Acid hydrolysis to produce a carboxylic acid and ammonium salt.
Base hydrolysis to produce the salt of a carboxylic acid and an amine or ammonia.

13. Hydrolysis Reactions || CH3—C—OH + NH4+Cl- || CH3—C—NH2
acid hydrolysis O ||
CH3—C—OH + NH4+Cl- O ||
CH3—C—NH2
CH3—C—O-Na+ + NH3
HCl + H2O
NaOH
base hydrolysis