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

2. 2 Amines Organic compounds of nitrogen N Classified as primary, secondary, tertiary CH 3 CH 3  CH 3 —NH 2 CH 3 —NH CH 3 —N — CH 3 1° 2° 3°

3. 3 Naming Amines IUPAC aminoalkane Common alkylamine CH 3 CH 2 NH 2 CH 3 —NH —CH 3 aminoethane N-methylaminomethane (ethylamine) (dimethylamine) NH 2 | CH 3 CHCH 3 2-aminopropane AnilineN-methylaniline (isopropylamine)

4. 4 Learning Check AM1 Give the common name and classify: A. CH 3 NHCH 2 CH 3 CH 3 | B.CH 3 CH 2 NCH 3

5. 5 Solution AM1 A.CH 3 NHCH 2 CH 3 ethylmethylamine, 2° CH 3 | B.CH 3 CH 2 NCH 3 ethyldimethylamine, 3°

6. 6 Alkaloids Physiologically active nitrogen-containing compounds Obtained from plants Used as anesthetics, antidepressants, and stimulants Many are addictive

7. 7 Nicotine

8. 8 Caffeine

9. 9 Procaine

10. “Medicinal” Amine Salts Cocaine HClCocaine (Free base)

11. 11

12. 12 Leaning Check AM2 Write a structural formula for A. 2-aminopentane B. 1,3-diaminocyclohexane

13. 13 Solution AM2 A. 1-aminopentane CH 3 CH 2 CH 2 CH 2 CH 2 -NH 2 B. 1,3-diaminocyclohexane

14. 14 Reactions of Amines Act as weak bases in water CH 3 NH 2 + H 2 O CH 3 NH 3 + + OH – methylammonium hydroxide Neutralization with acid gives ammonium salt CH 3 NH 2 + HClCH 3 NH 3 + Cl – methylammonium chloride

15. 15 Amides Derivatives of carboxylic acids where an amino (-NH 2 ) group replaces the –OH group. O O   CH 3 — C—OH CH 3 — C—NH 2 carboxylic acid amide acetic acidacetamide

16. 16 Naming Amides Alkanamidefrom acid name O  methanamide (IUPAC) HC–NH 2 formamide (common) O  propanamide (IUPAC) CH 3 CH 2 C–NH 2 propionamide(common)

17. 17 Naming Amides with N-Groups O  CH 3 C–NHCH 3 N-methylethanamide (IUPAC) N-methylacetamide (common) O  CH 3 CH 2 C–N(CH 3 ) 2 N,N-dimethylpropanamide N,N-dimethylpropionamide

18. 18 Aromatic Amides

19. 19 Learning Check AM3 Name the following amides: O  A. CH 3 CH 2 CH 2 C–NH 2 O  B. CH 3 C–N(CH 2 CH 3 ) 2

20. 20 Solution AM3 O  A. CH 3 CH 2 CH 2 C–NH 2 butanamide O  B.CH 3 C–N(CH 2 CH 3 ) 2 N,N-diethylethanamide;

21. 21 Learning Check AM4 Draw the structures of A.Pentanamide B.N-methylbutanamide

22. 22 Solution AM4 A.Pentanamide O  CH 3 CH 2 CH 2 CH 2 C–NH 2 B.N-methylbutanamide O  CH 3 CH 2 CH 2 C–NHCH 3

23. 23 Reactions of Amides Amides undergo acid hydrolysis base hydrolysis carboxylic acid salt of carboxylic acid ammonium salt and an amine or ammonia

24. 24 Reactions of Amides acid hydrolysis O  O HCl + H 2 O CH 3 COH + NH 4 + Cl –  CH 3 CNH 2 O NaOH  CH 3 CO – Na + + NH 3 base hydrolysis

25. 25 Learning Check AM5 Write the products of the hydrolysis of N- ethylpropanamide with NaOH.

26. 26 Solution AM5 Hydrolysis of N-ethylpropanamide with NaOH gives the following products. O  CH 3 CH 2 CO – Na + + CH 3 CH 2 NH 2