西北农林科技大学：《有机化学 Organic chemistry》课程教学课件（2012）Chapter 19 Ketones and Aldehydes

Organic Chemistry,6th Edition L.G.Wade,Jr. Chapter 19 Aldehydes and Ketones

Chapter 19 Aldehydes and Ketones Organic Chemistry, 6th Edition L. G. Wade, Jr

自成不精大好 Content 院 Carbonyl Structure Properties Preparation >Functional group transformations >Carbon-carbon bond formation >C-C Bond cleavage Reactions of Aldehydes and Ketones ●C=O ●o-H,-C

Content Carbonyl Structure & Properties Preparation Functional group transformations Carbon-carbon bond formation C-C Bond cleavage Reactions of Aldehydes and Ketones C=O -H, - C

Some Common Functional Groups alcohol C-OH alkane C-C ether C-O-C C-H alkene C=C aldehyde C-H alkyne CEC ketone C-H carbonyl acid aromatic groups OH ester amine amide

Some Common Functional Groups: Some Common Functional Groups: C C C H alkane alkene C C C H alkyne C C C H aromatic alcohol C OH ether COC C O H aldehyde C O ketone C O OH acid C O ester O C O N amide N amine carbonyl groups

Carbonyl Compounds TABLE 18-1 Some Common Classes of Carbonyl Compounds Class General Formula Class General Formula ketones R R aldehydes R carboxylic acids OH acid chlorides esters -OR amides Copyright 2005 Pearson Prentice Hall,Inc

Carbonyl Compounds

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. Examples CH: Br 4-hydroxy-3-methyl-2-butanone 3-bromocyclohexanone 4-hydroxy-3-methylbutan-2-one

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. O Br CH 3 C O CH CH 3 CH 2OH 3-bromocyclohexanone 4-hydroxy-3-methyl-2-butanone 4-hydroxy-3-methylbutan-2-one Examples

Naming Aldehydes IUPAC:Replace -e with -al The aldehyde carbon is number 1. If -CHO is attached to a ring,use the suffix -carbaldehyde. CHO Example 2-cyclopentenecarbaldehyde cyclopent-2-en-1-carbaldehyde

Naming Aldehydes IUPAC: Replace - e with -al. The aldehyde carbon is number 1. If -CHO is attached to a ring, use the suffix -carbaldehyde. Example CHO 2-cyclopentenecarbaldehyde cyclopent-2-en-1-carbaldehyde

Name as Substituent On a molecule with a higher priority functional group,C=O is oxo-and -CHO is formyl. Aldehyde priority is higher than ketone. COOH CHO 3-methyl-4-oxopentanal 3-formylbenzoic acid

Name as Substituent On a molecule with a higher priority functional group, C=O is oxo- and -CHO is formyl. Aldehyde priority is higher than ketone. CH 3 C CH CH 3 CH 2 C H O O COOH CHO 3-methyl-4-oxopentanal 3-formylbenzoic acid

Common Names ■for Ketones Named as alkyl attachments to -C=O. OUse Greek letters instead of numbers. 0 0 CH3一C一CH-CH3 CH;CH-C-CH-CH3 CH3 Br CH: methyl isopropyl ketone a-bromoethyl isopropyl ketone Historical Common Names CH; acetone acetophenone benzophenone

Common Names for Ketones Named as alkyl attachments to -C=O. Use Greek letters instead of numbers. Historical Common Names CH 3 C O CH CH 3 CH 3 CH 3CH C O CH CH 3 CH 3 Br methyl isopropyl ketone bromoethyl isopropyl ketone CH 3 C O CH 3 C CH 3 O C O acetone acetophenone benzophenone

Aldehyde Common Names Use the common name of the acid. Drop -ic acid and add -aldehyde. 1 C:formic acid,formaldehyde 2 C's:acetic acid,acetaldehyde 3 C's:propionic acid,propionaldehyde 4 C's:butyric acid,butyraldehyde. Br B-bromobutyraldehyde 3-bromobutanal

Aldehyde Common Names Use the common name of the acid. Drop -ic acid and add -aldehyde. 1 C: formic acid, formaldehyde 2 C’s: acetic acid, acetaldehyde 3 C’s: propionic acid, propionaldehyde 4 C’s: butyric acid, butyraldehyde. CH 3 CH Br CH 2 C H O -bromobutyraldehyde 3-bromobutanal

Sec 1 Structure Properties Nature of the Carbonyl Group Carbon is sp2 hybridized. C=O bond is shorter,stronger, and more polar than C=C bond in alkenes. The carbonyl group is planar with bond angles of 120 length energy ketone C=0 bond 1.23A 745 kJ/mol (178 kcal/mol alkene C=C bond 1.34A 611 kJ/mol (146 kcal/mol) Copyright 2005 Pearson Prentice Hall,Inc

Sec 1 Structure & Properties Carbon is sp2 hybridized. C=O bond is shorter, stronger, and more polar than C=C bond in alkenes.  The carbonyl group is planar with bond angles of 120