《有机化学》课程PPT教学课件（Official PPT of Organic Chemistry 6th LG Wade by Prentice Hall，L. G. Wade, Jr.）Chapter 19 Amines

Organic Chemistry,6th Edition L.G.Wade,Jr. Chapter 19 Amines Jo Blackburn Richland College,Dallas,TX Dallas County Community College District ©2006，Prentice Hall

Chapter 19 Amines Jo Blackburn Richland College, Dallas, TX Dallas County Community College District © 2006, Prentice Hall Organic Chemistry, 6th Edition L. G. Wade, Jr

Introduction Organic derivatives of ammonia. Many are biologically active. CH2一CH-COOH OH :NH2 HO CH2 HO CH-CH2-N CH2 CH3 HO HN HO H dopamine epinephrine L-tryptophan a neurotransmitter an adrenal hormone an amino acid 0 CH2OH CH2CH2NH2 HO CH2OH OH H一) H:C > piperazine nicotinic acid pyridoxine histamine kills intestinal worms niacin,a vitamin vitamin B6 dilates blood vessels Copyright 2005 Pearson Prentice Hall,Inc

Chapter 19 2 Introduction • Organic derivatives of ammonia. • Many are biologically active. =>

Biological Activity Neurotransmitters:dopamine Bioregulators:epinephrine ·Vitamins:niacin,.Bs Alkaloids:nicotine,morphine,cocaine 。Amino acids > Chapter 19 3

Chapter 19 3 Biological Activity • Neurotransmitters: dopamine • Bioregulators: epinephrine • Vitamins: niacin, B6 • Alkaloids: nicotine, morphine, cocaine • Amino acids =>

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 4

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. =>

Classify: CH3 CH3 CH3 Br CH3 C-NH2 CH3CH2-N-CH2CH3 CH3 CH3 三> Chapter 19 5

Chapter 19 5 Classify: N H CH3 C CH3 CH3 NH2 N CH3 CH3 CH3CH2 N CH3 CH2CH3 + Br _ =>

Common Names Name the alkyl or aryl groups bonded to nitrogen,then add suffix-amine. (CH:CH2)2NCH3 diethylmethylamine N(CH3)2 cyclohexyldimethylamine H diphenylamine => Chapter 19 6

Chapter 19 6 Common Names Name the alkyl or aryl groups bonded to nitrogen, then add suffix -amine. diethylmethylamine cyclohexyldimethylamine diphenylamine =>

Amine as Substituent 。 On a molecule with a higher priority functional group,the amine is named as a substituent. NH-CH-CH-CHCOOH OH NHCHs y-aminobutyric acid or 4-aminobutanoic acid 2-methylaminophenol => Chapter 19

Chapter 19 7 Amine as Substituent • On a molecule with a higher priority functional group, the amine is named as a substituent. NH2 CH2 CH2 CH2 COOH NHCH3 OH -aminobutyric acid or 4-aminobutanoic acid 2-methylaminophenol =>

Aromatic Amines Amino group is bonded to a benzene ring. Parent compound is called aniline. NH2 N(CH2CH3)2 NH2 CH3 N,N-diethylaniline 4-methylaniline aniline or p-toluidine => Chapter 19 8

Chapter 19 8 Aromatic Amines Amino group is bonded to a benzene ring. Parent compound is called aniline. =>

Heterocyclic Amines The nitrogen is assigned the number 1. H H CH3 aziridine pyrrole pyrrolidine pyridine 2-methylpyridine => Chapter 19 9

Chapter 19 9 Heterocyclic Amines The nitrogen is assigned the number 1. =>

IUPAC Names Name is based on longest carbon chain. -e of alkane is replaced with -amine. Substituents on nitrogen have N-prefix. Br N(CH3)2 NH2CHCH2CHCHCH3 CH3CH2CHCH2CH2CH3 3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine => Chapter 19 10

Chapter 19 10 IUPAC Names • Name is based on longest carbon chain. • -e of alkane is replaced with -amine. • Substituents on nitrogen have N- prefix. NH2 CH2 CH2 CHCH2 CH3 Br CH3 CH2 CHCH2 CH2 CH3 N(CH3 ) 2 3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine =>