有机化学课件10 Aldehydes and Ketones教学教材.pptVIP

* Chapter 10 Aldehydes and Ketones In this and next chapters, we will discuss the most important functional group in organic chemistry — the carbonyl group, C=O. Carbonyl compounds are everywhere in nature. Most biologically important molecules contain carbonyl-groups, as do many pharmaceutical agents and many of the synthetic chemicals that touch our everyday lives. Biochemistry is carbonyl chemistry. Almost all metabolic processes used by all living organisms involve one or more of four fundamental carbonyl-group reactions we will discuss in this and next chapters. The digestion and metabolic breakdown of all the major classes of food molecules—fats, carbohydrates, and proteins — take place by nucleophilic addition reaction, nucleophilic acyl substitutions, ? substitution, and carbonyl condensations. Similarly, hormones and other crucial biological molecules are built up from smaller precursors by the same carbonyl-group reactions. * * 2s 2p sp2 hybridization 2p 2p C O H H used for p bond used for s bonds * 9.1 Structure of Carbonyl Groups Electronegativity: C=2.5, O=3.5 Carbon-carbon double bond Carbon-oxygen double bond ： ： * Electronegativity: C=2.5, O=3.5 Electrophilic carbonyl reacts with bases and nucleophiles Nucleophilic oxygen reacts with acids and electrophiles ? ? + _ * Enamines formation and synthetic applications * Beckmann Reaction * 9.4 Nucleophilic Addition — Oxygen Nucleophiles Acetal formation application — Protecting groups * Umpolung,极性反转 * 9.5 Keto – Enol Tautomerism — Carbonyl Alpha Substitution Reactions and Condensations * 9.6.1 Reactions of Enols – Alpha Halogenations of Aldehydes and Ketones * X=Cl, Br, I R’=Alkyl X=Cl, Br, I R’=H Haloform Reactions * 9.6.2 Reactions of Enolate Ions – Aldol Reactions * 9.7 The Important Reactions Related to Aldehydes and Ketones 9.7.1 Cannizzaro Reaction (歧化反应) * Benzoin condensation Umpolung:极性反转 * ? * 9.7.2 Baeyer – Villiger Reaction * As to R1 and R2 ： H 3o 2o cyclohexyl