厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）Chapter 16 Aldehydes and Ketones I：NucleophilicAddition to the Carbonyl Group（16.1-16.5）Introduction

r 1 hydes and I: Nucleophilic dition to the Carbonyl

Chapter 16 Aldehydes and Ketones I: Nucleophilic Addition to the Carbonyl Group

ORGANIC CHEMISTRY Chapter 16 16. 1 Introduction Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 16.1 Introduction

ORGANIC CHEMISTRY Chapter 16 o Aldehydes and ketones contain an acyl group bonded either to hydrogen or to another carbon 120 O RC Acyl group酰基 Carbonyl group羰基 H R H R R RCHO RCOR Formaldehyde General formulas General formulas for an aldehydes for a ketones Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 Aldehydes and ketones contain an acyl group bonded either to hydrogen or to another carbon. C O δ+ δ− sp2 Carbonyl group 羰基 120 RC 120 O Acyl group 酰基 O C H H O C R H O C R R Formaldehyde General formulas for an aldehydes General formulas for a ketones RCHO RCOR

ORGANIC CHEMISTRY Chapter 16 16.2 Nomenclature of Aldehydes and Ketones Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 16.2 Nomenclature of Aldehydes and Ketones

ORGANIC CHEMISTRY Chapter 16 o Aldehydes are named by replacing the terminal - e of the corresponding alkane name with -al o The longest chain selected as the base name must contain the-CHO group, and the -CHo carbon is al ways numbered as carbon 1 H-C-H CH3-c-h Ch2 CHb-C-H Methanal Ethanal Propanal (Formaldehyde) (Acetaldehyde)(Propionaldehyde) CICHoCHCHoCH-C-H CkHsCHo-C-H 5-Chloropentanal Phenylethanol (Phenylacetaldehyde Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 Aldehydes are named by replacing the terminal –e of the corresponding alkane name with –al. The longest chain selected as the base name must contain the –CHO group, and the –CHO carbon is always numbered as carbon 1. O H C H O CH3 C H O CH3CH2 C H Methanal (Formaldehyde) Ethanal (Acetaldehyde) Propanal (Propionaldehyde) O ClCH2CH2CH2CH2 C H 5-Chloropentanal O C6H5CH2 C H Phenylethanal (Phenylacetaldehyde)

ORGANIC CHEMISTRY Chapter 16 o For more complex aldehyde in which the-CHO group is attached to a ring the suffix-carbaldehyde is used CHO CHO Benzenecarbaldehyde Cyclohexanecarbaldehyde ( benzaldehyde)苯甲醛 环己烷甲醛 CHO 2- naphthalenecarbaldehyde2-萘甲醛 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 For more complex aldehyde in which the –CHO group is attached to a ring, the suffix -carbaldehyde is used. CHO CHO CHO Benzenecarbaldehyde Cyclohexanecarbaldehyde 2-naphthalenecarbaldehyde (benzaldehyde) 环己烷甲醛 2-萘甲醛 苯甲醛

ORGANIC CHEMISTRY Chapter 16 o Ketones are named by replacing the terminal -e of the corresponding alkane name with -one o The chain selected for the base name is the longest one that contains the ketone group, and the numbering begins at the end nearer the carbonyl carbon CH3 CH CH2-C-CH2 CH3 3- Hexanone3-已酮 (common name: Ethyl propyl ketone) CH3CH=CHCH2 CCH3 CH CHoCCHoCCH 4- Hexen-2-one4-己烯-2-酮2,4- Hexanedione2,4-已二酮 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 Ketones are named by replacing the terminal –e of the corresponding alkane name with –one. The chain selected for the base name is the longest one that contains the ketone group, and the numbering begins at the end nearer the carbonyl carbon. CH3CH2CH2 C CH2CH3 O 3-Hexanone 3-己酮 CH3CH CHCH2CCH3 O CH3CH2CCH2CCH3 O O 4-Hexen-2-one 4-己烯-2-酮 2,4-Hexanedione 2,4-己二酮 (common name: Ethyl propyl ketone)

ORGANIC CHEMISTRY Chapter 16 g Some ketones have common names that are retained in the IUPAC system CHa-C-CH C-CH Acetone丙酮 Acetophenone苯乙酮 Benzophenone二苯甲酮 propanone 1-phenylethanone diphenylmethane (dimethyl ketone)(methyl phenyl ketone)(diphenyl ketone) o When RCo-group are named as substituents, they are called alkanoyl or acyl groups O R-C HC ChC Acyl Formyl Acetyl B enzo 酰基甲酰基乙酰基苯甲酰基 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 Some ketones have common names that are retained in the IUPAC system. CH3 C CH3 O 丙酮 propanone Acetone C CH3 O Acetophenone 苯乙酮 C O Benzophenone 二苯甲酮 1-phenylethanone diphenylmethanone (dimethyl ketone) (methyl phenyl ketone) (diphenyl ketone) When RCO- group are named as substituents, they are called alkanoyl or acyl groups. HC O CH3C O R C O C O 酰基 甲酰基 乙酰基 Acyl Formyl Acetyl Benzoyl 苯甲酰基

o If another functional groups or a-CHo are present ORGANIC CHEMISTRY Chapter 16 and the doubly bonded oxygen must be considered a substituent, the prefix oxo-is used CH3 CH2-C-CH2CHo CH2 CH,C-CH,CH,CO,H 3-Oxopentanal 4-0xohexanoic acid 3-氧代戊醛 4-氧代已酸 CHO 2'-Oxocyclohexanecarbaldehyde 2-氧代环己烷甲醛 Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 If another functional groups or a –CHO are present and the doubly bonded oxygen must be considered a substituent, the prefix oxo- is used. CHO O 2'-氧代环己烷甲醛 2'-Oxocyclohexanecarbaldehyde CH3CH2 C CH2CHO O 3-氧代戊醛 3-Oxopentanal CH3CH2 C CH2CH2CO2H O 4-Oxohexanoic acid 4-氧代己酸

ORGANIC CHEMISTRY Chapter 16 16.3 Physical Properties Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 16 16.3 Physical Properties