RuCt&0号 Organic Chemistry,6th Edition R L.G.Wade,Jr. Chapter 18 Ketones and Aldehydes Jo Blackburn Richland College,Dallas,TX Dallas County Community College District ©2006，Prentice Hall
Chapter 18 Ketones and Aldehydes Jo Blackburn Richland College, Dallas, TX Dallas County Community College District © 2006, Prentice Hall Organic Chemistry, 6th Edition L. G. Wade, Jr
RC-0 Carbonyl Compounds R TABLE 18-1 Some Common Classes of Carbonyl Compounds Class General Formula Class General Formula ketones R-C-R aldehydes carboxylic acids R-C-OH acid chlorides 0 esters R-C-O-R amides Copyright 2005 Pearson Prentice Hall,Inc. => Chapter 18
Chapter 18 2 Carbonyl Compounds =>
Carbonyl Structure R Carbon is sp2 hybridized. C=O bond is shorter,stronger,and more polar than C=C bond in alkenes. 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) Copyright2005 Pearson Prentice Hall,Inc. 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. =>
RC-0 IUPAC Names R for Ketones Replace -e with -one.Indicate the position of the carbonyl with a number. Number the chain so that carbonyl carbon has the lowest number. For cyclic ketones the carbonyl carbon is assigned the number 1. Chapter 18
Chapter 18 4 IUPAC Names for Ketones • Replace -e with -one. Indicate the position of the carbonyl with a number. • Number the chain so that carbonyl carbon has the lowest number. • For cyclic ketones the carbonyl carbon is assigned the number 1. =>
RC-0 R Examples CH-CH CH3 3-methyl-2-butanone Br 3-methylbutan-2-one 3-bromocyclohexanone 0 cus-E-CH-cton CH3 4-hydroxy-3-methyl-2-butanone 4-hydroxy-3-methylbutan-2-one 三> Chapter 18 6
Chapter 18 5 Examples CH3 C O CH CH3 CH3 O Br CH3 C O CH CH3 CH2OH 3-methyl-2-butanone 3-methylbutan-2-one 3-bromocyclohexanone 4-hydroxy-3-methyl-2-butanone 4-hydroxy-3-methylbutan-2-one =>