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Carboxylic Acids Esters, Amines and Amides

Carboxylic Acids Esters, Amines and Amides. Amines Reactions of Amines Amides Reactions of Amides. Amines. Organic compounds of nitrogen N Classified as primary, secondary, tertiary CH 3 CH 3   CH 3 — N H 2 CH 3 — N H CH 3 — N — CH 3

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Carboxylic Acids Esters, Amines and Amides

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  1. Carboxylic Acids Esters, Amines and Amides Amines Reactions of Amines Amides Reactions of Amides

  2. Amines • Organic compounds of nitrogen N • Classified as primary, secondary, tertiary CH3 CH3   CH3—NH2 CH3—NH CH3—N — CH3 1° 2° 3°

  3. Naming Amines IUPAC aminoalkane Common alkylamine CH3CH2NH2 CH3—NH —CH3 aminoethane N-methylaminomethane (ethylamine) (dimethylamine) NH2 | CH3CHCH3 2-aminopropane Aniline N-methylaniline (isopropylamine)

  4. Learning Check AM1 Give the common name and classify: A. CH3NHCH2CH3 CH3 | B. CH3CH2NCH3

  5. Solution AM1 A. CH3NHCH2CH3 ethylmethylamine, 2° CH3 | • CH3CH2NCH3 ethyldimethylamine, 3°

  6. Reactions of Amines • Act as weak bases in water CH3NH2 + H2O CH3NH3+ + OH– methylammonium hydroxide • Neutralization with acid gives ammonium salt CH3NH2 + 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. Leaning Check AM2 Write a structural formula for • 2-aminopentane B. 1,3-diaminocyclohexane

  12. Solution AM2 A.1-aminopentane CH3CH2CH2CH2CH2-NH2 B. 1,3-diaminocyclohexane

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

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

  15. Naming Amides with N-Groups O  CH3C–NHCH3N-methylethanamide (IUPAC) N-methylacetamide (common) O  CH3CH2C–N(CH3)2 N,N-dimethylpropanamide N,N-dimethylpropionamide

  16. Aromatic Amides

  17. Learning Check AM3 Name the following amides: O  A. CH3CH2CH2C–NH2 O  B. CH3C–N(CH2CH3)2

  18. Solution AM3 O  A. CH3CH2CH2C–NH2 butanamide; butryamide (common) O  B. CH3C–N(CH2CH3)2 N,N-diethylethanamide; N,N-diethylacetamide

  19. Learning Check AM4 Draw the structures of A. Pentanamide B. N-methylbutyramide

  20. Solution AM4 A. Pentanamide O  CH3CH2CH2CH2C–NH2 B. N-methylbutyramide O  CH3CH2CH2C–NHCH3

  21. Reactions of Amides Amides undergo acid hydrolysisbase hydrolysis carboxylic acid salt of carboxylic acid ammonium salt and an amine or ammonia

  22. Reactions of Amides acid hydrolysis O  O HCl + H2O CH3COH + NH4+Cl–  CH3CNH2 O NaOH  CH3CO– Na+ + NH3 base hydrolysis

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

  24. Solution AM5 Hydrolysis of N-ethylpropanamide with NaOH gives the following products. O  CH3CH2CO– Na+ + CH3CH2NH2

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