Organic Chemistry,7th Edition L.G.Wade,Jr. H CH2CH3 Chapter 19 Amines Copyright 2010 Pearson Education,Inc
Chapter 19 Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7th Edition L. G. Wade, Jr. Amines
Biologically Active Amines CH3 O CH-CH2NH2 CH3 -OCH3 O-C-Ph CH3O OCH3 CH OCH3 OH OH H cocaine nicotine mescaline morphine in coca leaves in tobacco in peyote cactus in opium poppies Copyright2010 Pearson Prentice Hall,Inc. The alkaloids are an important group of biologically active amines,mostly synthesized by plants to protect them from being eaten by insects and other animals. Many drugs of addiction are classified as alkaloids. Chapter 19 2
Chapter 19 2 Biologically Active Amines ▪ The alkaloids are an important group of biologically active amines, mostly synthesized by plants to protect them from being eaten by insects and other animals. ▪ Many drugs of addiction are classified as alkaloids
Biological Activity of Amines Dopamine is a neurotransmitter. -Epinephrine is a bioregulator. -Niacin,Vitamin B6,is an amine. -Alkaloids:nicotine,morphine,cocaine Amino acids Chapter 19 3
Chapter 19 3 Biological Activity of Amines ▪ Dopamine is a neurotransmitter. ▪ Epinephrine is a bioregulator. ▪ Niacin, Vitamin B6 , is an amine. ▪ Alkaloids: nicotine, morphine, cocaine ▪ Amino acids
Classes of Amines Primary (19:Has one alkyl group bonded to the nitrogen(RNH2) -Secondary (2:Has two alkyl groups bonded to the nitrogen(R2NH). Tertiary (39:Has three alkyl groups bonded to the nitrogen (R3N). -Quaternary (49:Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(RN). Chapter 19
Chapter 19 4 Classes of Amines ▪ Primary (1): Has one alkyl group bonded to the nitrogen (RNH2 ). ▪ Secondary (2): Has two alkyl groups bonded to the nitrogen (R2NH). ▪ Tertiary (3): Has three alkyl groups bonded to the nitrogen (R3N). ▪ Quaternary (4): Has four alkyl groups bonded to the nitrogen and the nitrogen bears a positive charge(R4N + )
Examples of Amines -NH2 N CH3 Primary Secondary Tertiary (1) (2) (3) Chapter 19 5
Chapter 19 5 Examples of Amines NH2 N H N CH3 Primary (1º) Secondary (2º) Tertiary (3º)
Common Names CH3 CH3CH2NH2 (CH3CHCH2CH2)2NH (CH3CH2)2NCH3 (CH3CH2CH2CH2)4N+-CI ethylamine diisopentylamine diethylmethylamine tetrabutylammonium chloride CH2NH2 N(CH3)2 cyclohexyldimethylamine benzylamine diphenylamine Copyright 2010 Pearson Prentice Hall,Inc. Chapter 19 6
Chapter 19 6 Common Names
Amine as Substituent H OH H OH y CH2CH2CH2一COOH H2N 3-aminocyclopentene y-aminobutyric acid trans-3-aminocyclohexanol p-aminobenzoic acid(PABA) (cyclopent-2-en-I-amine) (4-aminobutanoie acid) Copyright2010 Pearson Prentice Hall,Inc. On a molecule with a higher priority functional group,the amine is named as a substituent. Chapter 19 7
Chapter 19 7 Amine as Substituent ▪ On a molecule with a higher priority functional group, the amine is named as a substituent
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 NH2CH2CH2CHCH2CH3 CH3CH2CHCH2CH2CH3 3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine Chapter 19 8
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. 3-bromo-1-pentanamine N,N-dimethyl-3-hexanamine NH2CH2CH2CHCH2CH3 Br CH3CH2CHCH2CH2CH3 N(CH3)2
Aromatic Amines NH2 NH2 N(CH2CH3)2 NH2 CH2CH3 CH aniline 2-ethylaniline N,N-diethylaniline 4-methylaniline or o-ethylaniline or p-toluidine Copyright 2010 Pearson Prentice Hall,Inc. In aromatic amines,the amino group is bonded to a benzene ring. Parent compound is called aniline. Chapter 19 9
Chapter 19 9 Aromatic Amines ▪ In aromatic amines, the amino group is bonded to a benzene ring. ▪ Parent compound is called aniline
Heterocyclic Amines When naming a cyclic amine the nitrogen is assigned position number 1. H— H CH3 H aziridine pyrrole pyrrolidine 1-methylpyrrolidine imidazole indole (N-methylpyrrolidine) CH3 H pyridine 2-methylpyridine piperidine pyrimidine purine Copyright2010 Pearson Prentice Hall,Inc. Chapter 19 10
Chapter 19 10 Heterocyclic Amines When naming a cyclic amine the nitrogen is assigned position number 1