Carbonyl compounds.ppt

Chapter 10 Aldehydes and Ketones Text 1: p 774-835 Text 2: p 311-348 10.1 Nomenclature of aldehydes and ketones IUPAC names common names aldehydes: alkane — alkanal ---ic acid—---aldehyde ketones: alkane — alkanone alkyl alkyl ketone 10.4 Synthesis of aldehydes and ketones 1. Nucleophilic addition to the carbon-oxygen double bond (3) The addition of hydrogen cyanide (HCN) (2) The addition of alcohols to aldehydes and ketones: Formation of Acetals(缩醛（酮）) 3). Nitrogen as nucleophilic atom(氮为亲核性原子) (1) Formation of imines (亚胺) and enamine (烯胺) 4). Sulfur as nucleophilic atom硫为亲核原子 The Wolff-Kishner reduction吉日聂尔-沃尔夫-黄鸣龙反应 (2) Oxidation of aldehydes and ketones the Baeyer-Villiger oxidation（拜尔-魏林格氧化） Assignments Assignment Text 1: 18-35, 37, 50, 60, 66 Text 2: 12, 14, 19 Cyanohydrins 腈醇, α-羟基腈 Cyanohydrins are useful intermediates in organic synthesis. β-amino alcohol β-氨基醇 α-hydroxy acid α-羟基酸 α,β-unsaturated acid α,β-不饱和酸 For example 2). Oxygen as nucleophilic atom (氧为亲核性原子) (1) The addition of water to aldehydes and ketones:  formation of hydrates(水合物) Hydrate ( a gem-diol)同碳二醇 How about the mechanisms ? Catalysis: acid or base Reversible reaction 可逆反应 unstable hemiacetal 半缩醛(酮) acetal 缩醛(酮) Catalysis: acid Reversible reaction 可逆反应 Old use: acetal 缩醛 ketal 缩酮 IUPAC: acetal Mechanism Hemiacetal 半缩醛(酮) acetal 缩醛(酮) Base (-OH) can not catalyze the acetal formation. Why? SN1 Cyclic acetals (环状缩酮) often have more favorable equilibrium constants than acyclic acetals. For example Use of acetals as protecting groups （保护基）. Example 1 Example 2 Example 3 NH2—H ammonia 氨 NH2—R amine 胺 NH2—OH hydroxylamine 羟氨 NH2—NH2 hydrazine 肼 NH2—NHCONH2 semicarbazine 氨基脲 carbinolamine 醇胺 Imine 亚胺 Shiff base 西佛碱 Catalysis: acid Reversible reaction 可逆反应