CNGNGE JOHN MCMURRY CHAPTER 18 Amines and Heterocycles T H I R D E DIT ION Organic Chemistry with Biological Applications
CHAPTER 18 Amines and Heterocycles
Amines and Heterocycles Amines are organic derivatives of ammonia Amines contain a nitrogen atom with a lone pair of electrons Amines are basic and nucleophilic Amines occur widely in both plants and animals H3C CO2CH3 CH3 CH3 Trimethylamine Nicotine Cocaine angage Learring Al Rights Resorved
Amines are organic derivatives of ammonia ▪ Amines contain a nitrogen atom with a lone pair of electrons ▪ Amines are basic and nucleophilic ▪ Amines occur widely in both plants and animals Amines and Heterocycles
18-1 Naming Amines Amines can be either alkyl-substituted(alkylamines)or aryl-substituted (arylamines) Amines are classified depending on the number of organic substituents attached to nitrogen: ·Primary(RNH2) One organic substituent such as methylamine (CH3NH2) ·Secondary(RzNH) Two organic substituents such as dimethylamine [(CHa)2NH] 。Tertiary(RgN) Three organic substituents such as trimethylamine [(CHa)aN] CH3 CH3 CH3 H3C-C-OH H3C-N H3C-C-NH2 CH3 CH3 CH3 tert-Butyl alcohol Trimethylamine tert-Butylamine (a tertiary alcohol) (a tertiary amine) (a primary amine)
Amines can be either alkyl-substituted (alkylamines) or aryl-substituted (arylamines) ▪ Amines are classified depending on the number of organic substituents attached to nitrogen: ▪ Primary (RNH2 ) ▪ One organic substituent such as methylamine (CH3NH2 ) ▪ Secondary (R2NH) ▪ Two organic substituents such as dimethylamine [(CH3 )2NH] ▪ Tertiary (R3N) ▪ Three organic substituents such as trimethylamine [(CH3 )3N] 18-1 Naming Amines
Naming Amines Quaternary ammonium salts Nitrogen containing compounds with four organic(R)groups attached to the nitrogen atom Nitrogen carries a formal positive charge R R一 -R X A quaternary ammonium salt R
Quaternary ammonium salts ▪ Nitrogen containing compounds with four organic (R) groups attached to the nitrogen atom ▪ Nitrogen carries a formal positive charge Naming Amines
Naming Amines Primary amines are named in the IUPAC system in several ways For simple amines the CH3 suffix-amine is added H3C-C-NH2 to the name of the alkyl CH3 tert-Butylamine Cyclohexylamine Aniline substituent Aniline is an aryl amine The suffix-amine can by used in place of the final -e in the name of the NH2 parent compound H2NCH2CH2CH2CH2NH2 H3C 4,4-Dimethylcyclohexanamine Butane-1,4-diamine
Primary amines are named in the IUPAC system in several ways ▪ For simple amines the suffix –amine is added to the name of the alkyl substituent ▪ Aniline is an aryl amine ▪ The suffix –amine can by used in place of the final –e in the name of the parent compound Naming Amines