Chapter 16 Aldehydes and Ketones I. Nucleophilic additions to the carbonyl group 16.1 Introduction Except for formaldehyde, the simplest aldehyde, all aldehydes have a carbonyl group, C=0 bonded on one side to a carbon and on the other side to a hydrogen. In ketones, the carbonyl group is situated between two carbon atoms. (Ar) A H—c—H R c R c R Formaldehyde Aldehydes tones 甲醛 醛
Chapter 16 Aldehydes and Ketones I. Nucleophilic additions to the carbonyl group 16.1 Introduction Except for formaldehyde, the simplest aldehyde, all aldehydes have a carbonyl group, C=O, bonded on one side to a carbon, and on the other side to a hydrogen. In ketones, the carbonyl group is situated between two carbon atoms. H C O H R C O H R C O R' (Ar) (Ar) (Ar) Formaldehyde Aldehydes Ketones 甲 醛 醛 酮
16.2 Nomenclature of aldehydes and ketones In the IUPaC system aliphatic aldehydes are named substitutively by replacing the final e of the name of the corresponding alkane with al For example H—c——HH3c—c—HCH3CH2 CHO CH3CH2CH2CHO IUPAC: Methanal Ethanal Propanal Butanal (Formaldehyde)(acetaldehyde)(propionaldehyde) 甲醛 乙醛 丙醛 丁醛
16.2 Nomenclature of aldehydes and ketones In the IUPAC system aliphatic aldehydes are named substitutively by replacing the final e of the name of the corresponding alkane with al For example H C O H H3C C O H (Formaldehyde) 甲 醛 乙 醛 Methanal Ethanal (acetaldehyde) CH3CH2CHO Propanal (propionaldehyde) CH3CH2CH2CHO Butanal 丙 醛 丁醛 IUPAC;
Aldehydes in which the-CHO group is attached to a ring system are named substitutively by adding the suffix carbaldehyde. CHO c-H C-H IUPAC; Benzenecarbaldehyde Cyclohexanecarbaldehyde 2-Naphthalenecarbaldehyde (Benzaldehyde) 苯甲醛 环己基甲醛 2-萘甲醛
Aldehydes in which the –CHO group is attached to a ring system are named substitutively by adding the suffix carbaldehyde. C O H C O H (Benzaldehyde) 苯 甲 醛 环 己 基 甲 醛 Benzenecarbaldehyde Cyclohexanecarbaldehyde 2-Naphthalenecarbaldehyde 2-萘 甲 醛 IUPAC; CHO
Aliphatic ketones are named substitutively by replacing the final e of the name of the corresponding alkane with one 12345 CH3CHE-C--CH3 CH3COCH2 CH2CH3 CH3,CH=CH2 IUPAC: 2-Butanone 2-Pentanone 4-Penten-2-one (ethyl methyl ketone)(ethyl propyl ketone) 2-丁酮 2-戊酮 4-戊烯-2-酮
Aliphatic ketones are named substitutively by replacing the final e of the name of the corresponding alkane with one C O CH3 (ethyl methyl ketone) 2-丁 酮 2-Butanone 4-Penten-2-one 4-戊 烯 -2-酮 IUPAC; CH3 CH2 CH3 COCH2 CH2 CH3 2-Pentanone (ethyl propyl ketone) CH3 COCH2 CH=CH2 1 2 3 4 5 2-戊 酮
H3—c——cH3 CH3 cotone Acetophenone Benzophenone (dimethyl ketone) (methyl phenyl ketone) (diphenyl ketone) 丙酮 苯乙酮 二苯甲酮 CHO OH H3c SO 2-Methanoylbenzoic acid 4-Ethanoylbenzenesulfonic acid (o-formylbenzoic acid (p-acetylbenzenesulfonic acid) 2-醛基苯甲酸 p-乙酰基苯磺酸
C O CH3 丙 酮 Acetone Benzophenone 二 苯 甲 酮 CH3 Acetophenone 苯 乙 酮 O CH3 O (methyl phenyl ketone) (diphenyl ketone) (dimethyl ketone) 4-Ethanoylbenzenesulfonic acid p-乙 酰 基 苯 磺 酸 2-Methanoylbenzoic acid 2-醛 基 苯 甲 酸 O OH H3 C O (p-acetylbenzenesulfonic acid) (o-formylbenzoic acid) CHO SO3 H