上海工程技术大学有机化学一复习要点2012解析.ppt

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6小题，每小题2分，共12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2小题，每小题6分，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4分，共16分） 7-5 Preparation of RX Free radical halogenation (Chapter 4) produces mixtures, not good lab synthesis unless: all H’s are equivalent, or halogenation is highly selective. Free radical allylic halogenation produces alkyl halide with double bond on the neighboring carbon.  HX Addition to Alkene Uses for SN2 Reactions Synthesis of other classes of compounds. Halogen exchange reaction.卤素交换反应 7-9 SN2: Nucleophilic Strength Stronger nucleophiles react faster. Strong bases are strong nucleophiles, but not all strong nucleophiles are basic. Trends in Nuc. Strength Of a conjugate acid-base pair, the base is stronger: OH- H2O, NH2- NH3 Decreases left to right on Periodic Table. More electronegative atoms less likely to form new bond: OH- F-, NH3 H2O 同一周期，从左到右亲核性降低 Increases down Periodic Table, as size and polarizability increase: I- Br- Cl- 同一族从上到下亲核性增大  Solvent Effects (2) Polar aprotic solvents (no O-H or N-H) do not form hydrogen bonds with nucleophile极性非质子性溶剂 Examples: Homework 7-31,7-37,7-39,7-40 Structure for C6H7N? If you prefer to use a formula, the element of unsaturation is Alkene SynthesisOverview E2 dehydrohalogenation (-HX) E1 dehydrohalogenation (-HX) Dehalogenation of vicinal dibromides (-X2) Dehydration of alcohols (-H2O)  Homework 8-2,8-24 Indirect Hydration 间接水合 Oxymercuration-Demercuration Markovnikov product formed Anti addition of H-OH No rearrangements Hydroboration Anti-Markovnikov product formed Syn addition of H-OH  Predict the Product Test for Unsaturation Add Br2 in CCl4 (dark, red-brown color) to an alkene in the presence of light. The color quickly disappears as the bromine adds to the double bond. “Decolorizing bromine” is the chemical test for the presence of a double bond.  9-9 Formation of Halohydrin卤