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Amines and Amides

Amines and Amides. Chapter 16. Nitrogen. Fourth most common atom in living systems. Important component of the structure of nucleic acids, DNA, and RNA Essential to the structure and function of proteins – enzymes and antibodies. Amine Structure.

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Amines and Amides

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  1. Amines and Amides Chapter 16

  2. Nitrogen • Fourth most common atom in living systems. • Important component of the structure of nucleic acids, DNA, and RNA • Essential to the structure and function of proteins – enzymes and antibodies

  3. Amine Structure • Characterized by the presence of an amino group (-NH2) • One or more of the hydrogen atoms can be replaced by an organic group.

  4. Amines • Organic derivatives of ammonia and, like ammonia, they are basic. • Amines are classified according to the number of alkyl groups attached to the nitrogen.

  5. Classification of Amines • Primary (1°) – one hydrogen replaced • Secondary (2°) – two hydrogens replaced • Tertiary (3°) – three hydrogens replaced

  6. Properties of Amines • Because nitrogen is more electronegative than hydrogen, the N-H bond is polar. • Hydrogen bonding can occur between amines and water. • Primary and secondary amines have higher boiling points than tertiary amines because tertiary amines cannot form hydrogen bonds. • Small amines (six or fewer carbons) are soluble in water.

  7. Naming Amines - IUPAC • Least common system used • Parent chain is longest continuous chain to which the amine group is attached. • Use a number to indicate the position of the alkane. • Add the prefix “amino” to the name of the alkane. • If a substituent is present on the nitrogen, it is designated by the prefix N-alkyl.

  8. Naming Amines - IUPAC aminomethane aminoethane N-methylaminomethane N-methylaminoethane N,N-dimethylaminomethane

  9. Naming Amines – CA system • CA system – Chemical Abstracts system • The final –e of the parent name is dropped and the suffix –amine is added. • For secondary and tertiary amines, the prefix N-alkyl is added to the parent compound.

  10. Naming Amines – CA system methanamine ethanamine N-methylmethanamine N-methylethanamine N,N-dimethylmethanamine

  11. Aromatic Amines Aniline or benzenamine o-toluidine p-toluidine m-toluidine

  12. Other Common Name Amines methylamine ethylamine dimethylamine ethylmethylamine trimethylamine

  13. Amides • Products formed in a reaction between a carboxylic acid and an amine. • Contains two portions: the carbonyl group from a carboxylic acid and the amino group from the amine Amide Bond

  14. Properties of Amides • Most are solids at room temperature • Very high boiling points – hydrogen bonding between N-H bond of one amide and the C=O group of the second amide • Simpler ones are quite soluble in water • Unlike amines, amides are NOT bases

  15. Naming Amides - IUPAC • Replace the –oic acid from the carboxylic acid with the ending –amide. • Substituents on the nitrogen are placed as prefixes and are indicated by N- followed by the name of the substituent.

  16. Examples Ethanamide Acetamide Propanamide N-methylpropanamide

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