Organic Chemistry,7th Edition L.G.Wade,Jr. Chapter 18 Ketones and Aldehydes Copyright 2010 Pearson Education,Inc
Chapter 18 Copyright © 2010 Pearson Education, Inc. Organic Chemistry, 7th Edition L. G. Wade, Jr. Ketones and Aldehydes
Carbonyl Compounds TABLE 18-1 Common Classes of Carbonyl Compounds Class General Formula Class General Formula ketones R-C-R aldehydes R-C-H carboxylic acids C-OH acid chlorides R-C-CI esters R-C-O-R amides R NH Copyright2010 Pearson Prentice Hall,Inc. Chapter 18 2
Chapter 18 2 Carbonyl Compounds
Carbonyl Structure length energy ketone C=O bond 1.23A 745 kJ/mol (178 kcal/mol alkene C=C bond 1.34A 611 kJ/mol (146 kcal/mol) Copyright 2010 Pearson Prentice Hall,Inc. Carbon is sp2 hybridized. C-O bond is shorter,stronger,and more polar than C=C bond in alkenes. Chapter 18 3
Chapter 18 3 Carbonyl Structure ▪ Carbon is sp2 hybridized. ▪ C═O bond is shorter, stronger, and more polar than C═C bond in alkenes
Ketone Nomenclature 3 4 in-chom 2 2 CH3 CH3 3-methyl-2-butanone 4-hydroxy-3-methyl-2-butanone -Number the chain so that carbonyl carbon has the lowest number. Replace the alkane -e with -one. Chapter 18 4
Chapter 18 4 Ketone Nomenclature ▪ Number the chain so that carbonyl carbon has the lowest number. ▪ Replace the alkane -e with -one. 3-methyl-2-butanone 4-hydroxy-3-methyl-2-butanone CH3 C O CH CH3 CH3 CH3 C O CH CH3 CH2OH 1 2 3 4 1 2 3 4
Ketone Nomenclature (Continued) 3-bromocyclohexanone 3 Br For cyclic ketones,the carbonyl carbon is assigned the number 1. Chapter 18 5
Chapter 18 5 Ketone Nomenclature (Continued) ▪ For cyclic ketones, the carbonyl carbon is assigned the number 1. 3-bromocyclohexanone O Br 1 3