[理学]有机化学二复习要点2013.pptVIP

用中文或英文系统命名法命名下列化合物或根据名称写出结构式。注意R,S以及Z,E命名（本题共8小题，每小题1分，共8分） 简略回答问题。（本题共8小题，每小题3分，共24分） 完成反应写出主要产物。（本题共12小题，每小题2分，共24分） 用化学方法区别各组化合物。（本题共12分） 推测化合物的结构。（本题共2小题，每小题6分，共12分） 以指定原料合成化合物（本题共4小题，每小题5分，共20分） Chap 19 Synthesis Review Oxidation 2? alcohol + Na2Cr2O7 ? ketone 1? alcohol + PCC ? aldehyde Ozonolysis of alkenes. Synthesis Review (2) Friedel-Crafts acylation Acid chloride/AlCl3 + benzene ? ketone CO + HCl + AlCl3/CuCl + benzene ? benzaldehyde (Gatterman-Koch) Hydration of terminal alkyne Use HgSO4, H2SO4, H2O for methyl ketone Use Sia2BH followed by H2O2 in NaOH for aldehyde. Ketones from 1,3-Dithiane After the first alkylation, remove the second H+, react with another primary alkyl halide, then hydrolyze. Aldehydes from Acid Chlorides Use a mild reducing agent to prevent reduction to primary alcohol. 19-9 Addition of Alcohol Formation of Imines亚胺 Nucleophilic addition of ammonia or primary amine, followed by elimination of water molecule. C=O becomes C=N-R Phosphorus Ylides磷叶立德 Prepared from triphenylphosphine and an unhindered alkyl halide.三苯基膦和卤代烃反应合成季磷盐 Butyllithium then abstracts a hydrogen from the carbon attached to phosphorus. Mechanism for Wittig The negative C on ylide attacks the positive C of carbonyl to form a betaine. Oxygen combines with phosphine to form the phosphine oxide. Tollens Test Tollens试剂 Add ammonia solution to AgNO3 solution until precipitate dissolves.银氨溶液 Aldehyde reaction forms a silver mirror. 19-15 Reduction Reagents Sodium borohydride, NaBH4, reduces C=O, but not C=C. Lithium aluminum hydride, LiAlH4, much stronger, difficult to handle. Hydrogen gas with catalyst also reduces the C=C bond. Clemmensen Reduction Wolff-Kisher Reduction Form hydrazone, then heat with strong base like KOH or potassium t-butoxide. Use a high-boiling solvent: ethylene glycol, diethylene glycol, or DMSO. Synthesis of Amine Reductive Amination Acylation-Reduction Direct Alkylation Gabriel Synthesis Azide Reduction N3 Nitrile Reduction Hofmann Rearrang