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Chapter 17: Aldehydes and Ketones: Nucleophilic Addition to the Carbonyl Group 17.1: Nomenclature (please read) 17.2: Structure and Bonding: Carbonyl groups have a significant dipole moment ;17.3: Physical Properties (please read) 17.4: Sources of Aldehydes and Ketones (Table 17.1, p. 708) 1a. Oxidation of 1° and 2° alcohols (15.10) 1b. From carboxylic acids 1c. Ketones from aldehydes ;;17.5: Reactions of Aldehydes and Ketones: A Review and a Preview;Reduction to 1° and 2° alcohols (15.2) 3. Addition of Grignard Reagents (14.6-14.7);17.6: Principles of Nucleophilic Addition: Hydration of Aldehydes and Ketones Water can reversibly add to the carbonyl carbon of aldehydes and ketones to give 1,1-diols (geminal or gem-diols);Acid-catalyzed mechanism (Fig. 17.2): protonated carbonyl is a better electrophile;17.7: Cyanohydrin Formation Addition of H-CN adds to the aldehydes and unhindered ketones. (related to the hydration reaction) The equilibrium favors cyanohydrin formation Mechanism of cyanohydron fromation (Fig. 17.3);17.8: Acetal Formation Acetals are geminal diethers- structurally related to hydrates, which are geminal diols. ;Mechanism of acetal (ketal) formation is acid-catalyzed (Fig 17.4);Dioxolanes and dioxanes: cyclic acetal (ketals) from 1,2- and 1,3-diols;17.9: Acetals (Ketals) as Protecting Groups Protecting group: Temporarily convert a functional group that is incompatible with a set of reaction conditions into a new functional group (with the protecting group) that is compatible with the reaction. The protecting group is then removed giving the original functional group (deprotection). ;The reaction cannot be done directly, as shown. Why? ;Mechanism of imine formation (Fig. 17.5):;17.11: Reaction with Secondary Amines: Enamines;17.12: The Wittig Reaction 1979 Nobel Prize in Chemistry: Georg Wittig (Wittig Reaction) and H.C. Brown (Hydroboration) The synthesis of an alkene from the reaction of an aldehyde or ketone and