华东理工大学2006–2007学年第一学期
《 有机化学 》课程期末考试试卷 B 2007.2.26
开课学院：理优05 专业： 考试形式：一页开卷，所需时间：120分钟
考生姓名： 学号： 班级： 任课教师：荣国斌
题序 一 二 三 四 五 六 七 八 总 分
得分
评卷人
可用中文或英文回答一~七各题（共六页，八大题）：
一.
(1) Write the structure of all the alkenes that can be hydrogenated to form 2-methylpentane.(6 points)
(2) Assign E/Z configurations to each of the following alkenes: (4 points)
(3) Assign R and S designation to the following compounds: (4 points)
(4) Place the following radicals in decreasing order of stability: (4 points)
CH3CH2•C(CH3)2 •CH2CH2CH(CH3)2 CH3•CHCH(CH3)2
1 2 3
(5) For each of the following compounds,give the number of H’s with distinct NMR signals,and their relative δ values in decreasing order. (6 points)
CaH3OC(CbH3)3 CaH3CbH2CO2cH
1 2
二．
(1) Give the product from the hydroboration-oxidation of 1-methylcyclopentene and classify the mode of addition.(6 points)
(2) Give the structures of the products of the following reactions[s:2]4 points)
(3) Write the structure for the products from reductive ozonolysis of 1,2-dimethylcyclohexene. (2points)
(4) Prepare (a) PhCHDCH3 (b) p-DC6H4CH2CH3 from PhCH2CH3. (8 points)
三. Account for the formation of both 2-bromo-3,3-dimethylbutane and 2-bromo-2,3-dimethylbutane from the reaction of HBr with 3,3-dimethyl-1-butene.(10 points)
四. The synthetic sequences shown below are unlikely to occur as written. Tell what is wrong with each, and predict the true product: (6 points)
（1）
（2）
五. Indicate the products in each following transformation case. (10 points)
(1)
(2)
(3)
(4)
(5)
六. Using acetylene and any alkyl halides as starting materials, synthesize the following compounds 1 and 2 respectively. More than one step may be required. Show all reagents and all intermediate compounds in your synthetic scheme.（10 points）
七. In an abandoned laboratory has been found a flammable liquid, 1, in a bottle bearing only the label “Compound 1: C7H12”. Compound 1 reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO4, gives the dicarboxylic acid 3. Another bottle from the same laboratory is labeled “Compound 2 (isomer of 1).” Compound 2 also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone 4 after treatment with acidic KMnO4. Give the structures for 1 and 2 (10 points)
八. Translate the following message to Chinese: (10 points)
Hydroxylation of an alkene—the addition of an –OH group to each of the alkene carbons—can be carried out by reaction of the alkene with potassium permanganate, KMnO4, in basic solution. Since oxygen is added to the alkene during the reaction, we call this an oxidation. The reaction occurs with synstereochemistry and yields a 1,2-dialcohol, or diol, product(also called a glycol). For example, cyclohexene gives cis-1,2-cyclohexanediol in 37% yields.
When oxidation of the alkene is carried out with KMnO4 in either neutral or acidic solution, cleavage of the double bond occurs and carbonyl-containing products are obtained. If the double bond is tetrasubstituted, the two carbonyl-containing products are ketones; if a hydrogen is present on the double bond, one of the carbonyl-containing products is a carboxylic acid; and if two hydrogens are present on one carbon, CO2 is formed.
《 有机化学 》课程期末考试试卷 B 2007.2.26
开课学院：理优05 专业： 考试形式：一页开卷，所需时间：120分钟
考生姓名： 学号： 班级： 任课教师：荣国斌
题序 一 二 三 四 五 六 七 八 总 分
得分
评卷人
可用中文或英文回答一~七各题（共六页，八大题）：
一.
(1) Write the structure of all the alkenes that can be hydrogenated to form 2-methylpentane.(6 points)
(2) Assign E/Z configurations to each of the following alkenes: (4 points)
(3) Assign R and S designation to the following compounds: (4 points)
(4) Place the following radicals in decreasing order of stability: (4 points)
CH3CH2•C(CH3)2 •CH2CH2CH(CH3)2 CH3•CHCH(CH3)2
1 2 3
(5) For each of the following compounds,give the number of H’s with distinct NMR signals,and their relative δ values in decreasing order. (6 points)
CaH3OC(CbH3)3 CaH3CbH2CO2cH
1 2
二．
(1) Give the product from the hydroboration-oxidation of 1-methylcyclopentene and classify the mode of addition.(6 points)
(2) Give the structures of the products of the following reactions[s:2]4 points)
(3) Write the structure for the products from reductive ozonolysis of 1,2-dimethylcyclohexene. (2points)
(4) Prepare (a) PhCHDCH3 (b) p-DC6H4CH2CH3 from PhCH2CH3. (8 points)
三. Account for the formation of both 2-bromo-3,3-dimethylbutane and 2-bromo-2,3-dimethylbutane from the reaction of HBr with 3,3-dimethyl-1-butene.(10 points)
四. The synthetic sequences shown below are unlikely to occur as written. Tell what is wrong with each, and predict the true product: (6 points)
（1）
（2）
五. Indicate the products in each following transformation case. (10 points)
(1)
(2)
(3)
(4)
(5)
六. Using acetylene and any alkyl halides as starting materials, synthesize the following compounds 1 and 2 respectively. More than one step may be required. Show all reagents and all intermediate compounds in your synthetic scheme.（10 points）
七. In an abandoned laboratory has been found a flammable liquid, 1, in a bottle bearing only the label “Compound 1: C7H12”. Compound 1 reacts with 1 mol equiv of hydrogen and, after treatment with acidic KMnO4, gives the dicarboxylic acid 3. Another bottle from the same laboratory is labeled “Compound 2 (isomer of 1).” Compound 2 also reacts with 1 mol equiv of hydrogen, but yields cyclohexanone 4 after treatment with acidic KMnO4. Give the structures for 1 and 2 (10 points)
八. Translate the following message to Chinese: (10 points)
Hydroxylation of an alkene—the addition of an –OH group to each of the alkene carbons—can be carried out by reaction of the alkene with potassium permanganate, KMnO4, in basic solution. Since oxygen is added to the alkene during the reaction, we call this an oxidation. The reaction occurs with synstereochemistry and yields a 1,2-dialcohol, or diol, product(also called a glycol). For example, cyclohexene gives cis-1,2-cyclohexanediol in 37% yields.
When oxidation of the alkene is carried out with KMnO4 in either neutral or acidic solution, cleavage of the double bond occurs and carbonyl-containing products are obtained. If the double bond is tetrasubstituted, the two carbonyl-containing products are ketones; if a hydrogen is present on the double bond, one of the carbonyl-containing products is a carboxylic acid; and if two hydrogens are present on one carbon, CO2 is formed.
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