Chapter 19 - Wade(1)

Chapter 19 - Wade(1) - Chapter 19 Amines Dr David P Brown...

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Unformatted text preview: Chapter 19 Amines Dr. David P. Brown Department of Chemistry Introduction to General and Organic Chemistry III Chapter 19 2 Introduction • Organic derivatives of ammonia • Many are biologically active. => Chapter 19 3 Biological Activity • Neurotransmitters: dopamine • Bioregulators: epinephrine • Vitamins: niacin, B 6 • Alkaloids: nicotine, morphine, cocaine • Amino acids => Chapter 19 4 Classes of Amines • Primary (1 ° ): one C-N bond, 2 N-H bonds. • Secondary (2 ° ): two C-N bonds, 1 N-H bond. • Tertiary (3 ° ): three C-N bonds, no N-H bond. • Quaternary (4 ° ): four C-N bonds, nitrogen has a + formal charge. => Chapter 19 5 Classify: N H CH 3 C CH 3 CH 3 NH 2 N CH 3 CH 3 CH 3 CH 2 N CH 3 CH 2 CH 3 + Br _ => Chapter 19 6 Common Names Name the alkyl or aryl groups bonded to nitrogen, then add suffix - amine . (CH 3 CH 2 ) 2 NCH 3 NHCH 3 NH Diethylmethylamine Cyclopentylmethylamine Diphenylamine => Chapter 19 7 Amine as Substituent • On a molecule with a higher priority functional group the amine is named as a substituent. NH 2 CH 2 CH 2 CH 2 COOH NHCH 3 OH γ-aminobutyric acid or 4-aminobutanoic acid 2-methylaminophenol => Chapter 19 8 IUPAC Names • Name is based on longest carbon chain. •- e of alkane is replaced with - amine . • Substituents on nitrogen have N- prefix. NH 2 CH 2 CH 2 CHCH 2 CH 3 Br CH 3 CH 2 CHCH 2 CH 2 CH 3 N(CH 3 ) 2 3-bromo-1-pentanamine N , N-dimethyl-3-hexanamine => Chapter 19 9 Aromatic Amines Amino group is bonded to a benzene ring. Parent compound is called aniline. NH 2 aniline N CH 3 CH 3 N , N-dimethylaniline => NH 2 H 3 C 4-methylaniline or p-toluidine Chapter 19 10 Heterocyclic Amines The nitrogen is assigned the number 1. => N H N H N H N N CH 3 aziridine Pyrrole Pyrrolidine Pyridine 2-methylpyridine Chapter 19 11 Structure of Amines Nitrogen is sp 3 hybridized with a lone pair of electrons in an sp 3 orbital....
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Chapter 19 - Wade(1) - Chapter 19 Amines Dr David P Brown...

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