有机涂海洋有机化学试卷yjhxsyqmsjda

1、华中师范大学 2006华中师范大学 2006 2007 学年第一学期期末考试试卷（B卷）课程名称 有机化学 课程编号 42511400 任课教师 张爱东 题型结构命名反应问题机理结构合成总分分值883020101014100得分得分评阅人一、Write structures of the following compounds according to their names（Totally 4 problems, and each problem 2 points, 8 points）1. Naphthalene 2. Potassium 4-nitrobenzoate 3. 1,4-Dio

2、xacyclohexane 4. 2-Methyl-3-phenyl-1-butanol 得分评阅人二、Give IUPAC names to the following compounds（Totally 4 problems, and each problem 2 points, 8 points）1. 2. 4-chlorobenzenesulfonyl chloride (1R,3S)-3-methylcyclohexanol3. 4. 2-formylbenzoic acid (5E)-5-octen-3-one院（系）： 专业： 年级： 学生姓名： 学号： - 密 - 封 - 线

3、-得分得分评阅人三、Accomplish the following reactions (write stereomers when necessary)（Totally 15 spaces, and each space 2 points, 30 points）1. 2. 3. 4. 5. 6. 7. 8. 第 1 页(共 3 页)得分评阅人得分评阅人四、Answer the following questions（Totally 3 problems, 20 points）Up to now, we have learnt the influence of Substituents on

4、 Diels-Alder reactions and electrophilic substitutions of mono-substituted benzenes, and the common point is based on the electronic effects of different substituents.Please describe the favorable factors of substituents on dienes and dienophiles for Diels-Alder reactions. (4 points) Electron-releas

5、ing groups on dienes and electron-withdrawing groups on dienophiles will be favorable to the Diels-Alder reactions.Please describe the classification of substituents on benzene and their role on reactivity and orientation for further electrophilic substitutions of mono-substituted benzenes. (6 point

6、s)There are three classes of substituents on benzene. The classification and their role are listed as the following:#1, Ortho-para directors, activating effect on reactivity;#2, meta directors, deactivating effect on reactivity;#3, Orth-para directors, deactivating effect on reactivityThe simplest a

7、nd most typical aromatic heterocycles are pyridine, pyrrole, furan and thiophene. Please indicate the hybridization forms of the heteroatoms in these heterocycles and explain why these heterocycles are aromatic according to the Huckels rule. (5 points)All of the hybridization forms of heteroatoms in

8、 pyridine, pyrrole, furan and thiophene are sp2, leaving unhybridized p orbitals to participate the closed conjugation. The number of p electron of N on pyridine is 1; on pyrrole, the number is 2, as well as on furan and thiophene. Thus all the heterocycles meet the Huckel rule 4n+2 and all these he

9、terocycles are aromatic.The nucleophilic addition reaction is the most common reaction of aldehydes and ketones. Many different kinds of products can be prepared by nucleophilic additions. Please indicate what nucleophilic reagents can be employed to form cyanohydrin, imine, enamine, acetal, alkene,

10、 oxime, hydrazone and semicarbazone, respectively. (5 points)The nucleophilic reagents employed to form cyanohydrin are hydrogen cyanide. For imine, enamine, acetal, alkene, oxime, hydrazone and semicarbazone, the nucleophilic reagents are primary amine, secondary amine, alkanol, Wittig reagent, hyd

11、roxylamine, hydrazine and semicarbazine, respectively. - 密 - 封 - 线 -得分得分评阅人五、Mechanisms（Totally 2 problems, and each problem 5 points, 10 points）Write a detail mechanism for the formation of an acetal from benzaldehyde and methanol in the presence of an acid catalystProvide a reasonable mechanism fo

12、r the following reaction: 第 2 页(共 3 页)得分得分评阅人六、propose the following reactions or the structures for compoundsCompound A (C4H6) reacts with hydrogen and a platinum catalyst to yield butane. Compound A reacts with Br2 in CCl4 and aqueous KMnO4. The IR spectrum of A does not have an absorption in the

13、2200-2300 cm-1 region. On treatment with hydrogen and Ni2B (P2 catalyst), A is converted to B (C4H8). When B is treated with OsO4 and then with NaHSO3, B is converted to C (C4H10O2). Compound C cannot be resolved. Provide structures for A-C and reactions involved.Reactions omittedCompounds D and E a

14、re isomers with a molecular weight 86. D shows an IR absorption at 1730 cm-1 and a very simple 1HNMR spectrum with peaks at 9.7 (1H, singlet) and 1.2 (9H, singlet). E shows an IR peak at 1715 cm-1 and its 1HNMR spectrum has peaks at 2.4 (1H, septet, J=7Hz), 2.1 (3H, singlet), and 1.2 (6H, doublet, J=7Hz). Propose structures for D and E. (4 points) - 密 - 封 - 线 -得分得分评阅人七、Outline the needed reagents or synthesis for the following reactions or compounds（14 points）Accomplish the following transformation (4 points)With 1-butanol as your only organic starting compounds, o