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Chapter 19 slides - Chapter 19 Amines Introduction Organic...

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Chapter 19 Amines
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Chapter 19 2 Introduction • Organic derivatives of ammonia • Many are biologically active. =>
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Chapter 19 3 Biological Activity • Neurotransmitters: dopamine • Bioregulators: epinephrine • Vitamins: niacin, B 6 • Alkaloids: nicotine, morphine, cocaine • Amino acids =>
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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. =>
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Chapter 19 5 Classify: N H CH 3 C 3 3 NH 2 N 3 3 3 2 N 3 2 3 + Br _ => Primary (be careful – alkyl group is tertiary but amine is primary!!) Quaternary Secondary Tertiary
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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 =>
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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 2 2 COOH NHCH 3 OH γ -aminobutyric acid or 4-aminobutanoic acid 2-methylaminophenol =>
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Chapter 19 8 IUPAC Names • Name is based on longest carbon chain. •- e of alkane is replaced with - amine . • Substituents on nitrogen have N -pref ix. NH 2 CH 2 2 CHCH 2 3 Br 3 2 CHCH 2 2 3 N(CH 3 ) 2 3-bromo-1-pentanamine N , N -dimethyl-3-hexanamine =>
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Chapter 19 9 Aromatic Amines Amino group is bonded to a benzene ring. Parent compound is called aniline. NH 2 aniline N CH 3 3 N , N -dimethylaniline => 2 H 3 C 4-methylaniline or p -toluidine
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Chapter 19 10 Heterocyclic Amines The nitrogen is assigned the number 1. => N H N H N H N NC H 3 aziridine Pyrrole Pyrrolidine Pyridine 2-methylpyridine
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Chapter 19 11 Structure of Amines Nitrogen is sp 3 hybridized with a lone pair of electrons in an sp 3 orbital. => Less than 109.5 ° -why?
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Chapter 19 12 Chirality of Amines Nitrogen may have 3 different groups and a lone pair, but enantiomers cannot be isolated due to inversion around N. =>
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Chapter 19 13 Chiral Amines • Amines with chiral carbon: 2-butanamine. • Quaternary ammonium salts with four different groups bonded to nitrogen. • Amines in which the nitrogen is restricted in rotation so it cannot interconvert. =>
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Chapter 19 14 Boiling Points • N-H less polar than O-H. • Weaker hydrogen bonding. • Tertiary amines cannot hydrogen bond. =>
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Chapter 19 15 Solubility and Odor • Small amines (<6 C) soluble in water. • All amines accept hydrogen bonds from water and alcohol.
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This note was uploaded on 04/08/2008 for the course CHEM 224 taught by Professor Pearson during the Spring '08 term at Case Western.

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Chapter 19 slides - Chapter 19 Amines Introduction Organic...

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