1. Amines and Amides Amines Reactions of Amines Amides
Reactions of Amides

2. Amines Organic compounds of nitrogen N
Classified as primary, secondary, tertiary
CH CH3
 
CH3—NH2 CH3—NH CH3—N — CH3
1° 2° °

3. Naming Amines IUPAC aminoalkane Common alkylamine
CH3CH2NH CH3—NH —CH3
aminoethane N-methylaminomethane
(ethylamine) (dimethylamine)
NH2 |
CH3CHCH3
2-aminopropane Aniline N-methylaniline
(isopropylamine)

4. Practice Naming
Give the common name and classify as primary, secondary or tertiary:
CH3NHCH2CH3
CH3 |
B. CH3CH2NCH3

5. Solution A. CH3NHCH2CH3 N-methylaminoethane (ethylmethylamine), 2° CH3|
CH3CH2NCH3
N,N-dimethylaminoethane (ethyldimethylamine), 3°

6. Reactions of Amines Act as weak bases in water
CH3NH H2O CH3NH OH–
methylammonium hydroxide
Neutralization with acid gives ammonium salt
CH3NH HCl CH3NH3+ Cl–
methylammonium chloride

7. Alkaloids Physiologically active nitrogen-containing compounds
Obtained from plants
Used as anesthetics, antidepressants, and stimulants
Many are addictive

8. Nicotine

9. Caffeine

10. Procaine

11. Practice Write a structural formula for 1-aminopentane
B. 1,3-diaminocyclohexane

12. Solution A. 1-aminopentane CH3CH2CH2CH2CH2-NH2
B. 1,3-diaminocyclohexane

13. More naming practice
Draw:
N-methyl-N-propyl-2-aminobutane

14. Solution

15. Properties of Amines
When organisms decompose, large and complex molecules such as proteins are broken down into simpler amines.
Amines often have an unpleasant odour, such as rotting fish.
Putrescine (1,4-diaminobutane) and Cadavarine (1,5-diaminopentane) are amines produced by bacteria when animal tissue decomposes.

16. Properties cntd
Amines have higher melting and boiling points than comparable hydrocarbons as they are more polar.
Amines with 1-5 carbons are soluble in water. When N-H bonds are present (primary or secondary amines), hydrogen bonding can occur with water.
The N-H bond is not as polar as the O-H bond in alcohols.

17. Preparing Amines
Preparing a Primary Amine (ammonia reacts with an alkyl halide)

18. Secondary Amines
Preparing a Secondary Amine (primary amine reacts with alkyl halide)

19. Tertiary Amines
Preparing a Tertiary Amine (secondary amine reacts with alkyl halide)

20. Amides
Derivatives of carboxylic acids where an amino (-NH2) group replaces the –OH group. (CON)
O O
 
CH3 — C—OH CH3 — C—NH2
carboxylic acid amide
acetic acid ethanamide

21. Naming Amides Alkanamide from acid name O  methanamide (IUPAC)
HC–NH2 formamide (common)
 propanamide (IUPAC)
CH3CH2C–NH2 propionamide(common)

22. Naming Amides with N-Groups
CH3C–NHCH3 N-methylethanamide (IUPAC)
N-methylacetamide (common)
CH3CH2C–N(CH3)2
N,N-dimethylpropanamide
N,N-dimethylpropionamide

23. Aromatic Amides

24. Practice Name the following amides: O  A. CH3CH2CH2C–NH2
B. CH3C–N(CH2CH3)2

25. Solution  A. CH3CH2CH2C–NH2 butanamide; butryamide (common)
B. CH3C–N(CH2CH3)2
N,N-diethylethanamide;
N,N-diethylacetamide

26. Practice
Draw the structures of
A. Pentanamide
B. N-methylbutanamide

27. Solution A. Pentanamide O  CH3CH2CH2CH2C–NH2 B. N-methylbutanamide
CH3CH2CH2C–NHCH3

28. Preparing Amides Carboxylic Acid + Ammonia
Carboxylic Acid with Primary or Secondary Amine

29. Reactions of Amides Amides undergo acid hydrolysis base hydrolysis
carboxylic acid salt of carboxylic acid
ammonium salt and an amine or ammonia

30. Reactions of Amides acid hydrolysis O  O HCl + H2O CH3COH + NH4+Cl–
CH3CNH O
NaOH 
CH3CO– Na+ + NH3
base hydrolysis

31. Practice Write the products of the hydrolysis of
N- ethylpropanamide with NaOH.

32. Solution CH3CH2CO– Na+ + CH3CH2NH2
Hydrolysis of N-ethylpropanamide with NaOH gives the following products. O 
CH3CH2CO– Na+ + CH3CH2NH2

33. Properties of Amides
Amides are weak bases and generally insoluble in water. Smaller amides are slightly soluble in water due to hydrogen bonding with NH group of amide and OH group of water.
Amides whose N atoms are bonding to two H atoms have higher melting and boiling points than those with more alkyl groups attached due to more hydrogen bonding.
Amide functional groups (CON) are an important linkage in proteins.