1、深圳大学期末考试试卷O/C Closed-exam C/D paper CNumber Class Name Organic Chemistry credit命题人(签字) 审题人(签字) 年 月 日Number 一 二 三 四 五 六 七 八 九 十 BASICTotal Add.Value评卷人This paper includes Section A and Section B. Section A is basic problems, and all the value is 100 points. Section B is an additional question and val
2、ues 30 points.Section A1. Nomenclature and write structures. This part has 10 items, each item values 1 point. If having stereochemistry properties, please show it correctly. Put your answer under corresponding question.CH2Ph1. 2.H3CClCH3 ClHCHOOCH33.H3COOCH3 4. CO2MeCO2eCH32PhCH2_学院 专业 姓名 学号 座号( 密
3、封 线 内 不 答 题 )密封线线5. THF 6. p-hydroxybenzoic acid7. t-tert-butanol 8. (S)-2-bromopropanal9. bicyclo【3.2.0】heptane 10. benzyl methyl ether2. Choice and ordering. This part includes 15 questions and each one values 1 point. Only one answer is correct about the choice question and for ordering items, yo
4、u must give a correct place for each compound in the same group. Put your answer on the bracket behind. 1Major product of chlorination of isopentane is（ ）.A B C DCl ClCl Cl2The reaction product of 2-hexyne with Na/NH3(l) is（ ）.A B C D3In the reaction of nitration, which compound can give the most ra
5、pid reaction?（ ）.A B C DCH3 CH3CH3 CH3CH3 H3CCH3CH34What is the major product by elimination reaction of following amine(TM) withi. H2O2/ii. （ ）.PhMeHPhe2N HPhMePh HPhPhMePhPhHMeTMA B C5Which compound has no chirality（ ）.OCl Br CH3OHO3COA B C DCH36The stability order of following carbocations in des
6、cending order is（ ） 。A ClC+HCH2CH3 B C+H2CH2CH2CH3C CF3C+HCH2CH3 D CH3OC+HCH2CH2CH37Basicity order of following compounds in descending order is（ ）.N NH2A B C DNH2 CH2N28Acidity of following compounds in descending order is（ ）.FCO2H CO2H CO2HCO2HA B C DBr l9In the reaction with HX, reactivity order
7、of following alkenes in descending order is（ ）.A CH2=CH2 B CH3CH=CH2 C BrCH=CH2 D CH3OCH=CH210Which compound has the smallest reactivity in the following compounds under the condition of SN1or SN2（ ）？A PhCH2Br B C Et3C-Br DBrr11Which compound has no aromaticity ? （ ）A B C DO12When reacting with ZnCl
8、2/HCl(c), reactivity of following alcohols in descending order is（ ）.A CH3CH2CHOHCH3 B CH3CH2OH C CH3OH D PhCH2OH13About the aldol condensation , which group of compounds can take place in good yield?（ ）A CH3CHO + CH3CH2CHO B C2H5CHO + C2H5CHOC HCHO + HCHO D PhCHO + PhCHO14. The reaction product of
9、following compound TM with HCl is（ ）CH3HClCH3HHO CH3ClCH3Hl CH3HlCH3l CH3HOCH3OA B CTM15Which compound can give white deposit with saturated NaHSO3（ ）COH3 CH2OCH3 CH2OCH23 COH2C3A B C D3. Give the major product(s) for the following reactions. If involving stereochemistry, you must use stereochemical
10、 formula to express. This part has 15 questions , 2 points for each and the total is 30 points. Write your answers behind the arrows.i. CH3MgIi. 3+O1. OCH32. + CH3CH2OHFCH23 3AcONacH3. ClCl ClCl K4MnO4OH-, 4.KOHEt5.CH3OTsDH6. OHBrHBri.O3i. H2/Zn7.8. BrBrCH3ONaBr2NaOHCH2CH3OClHNH39.CHO OH-10. + CH32C
11、HO1. i. CH3I(e)i. Ag2O(wet)i. NHCH3i. HCO2Et/tONai. EtNa/MeI12.O13. CONEt2LiAlH(OR)34. Mechanism problem. This part has just one question and the value is 5 points. Make sure to use an appropriate arrow to show moving direction of electrons and if not, you will lose a half point !CH3H3CPhH+ CH3H3C5.
12、 Syntheses. Besides pointed materials, any alcohols and alkenes needed may be used, and you can use any inorganic reagents. The part has 4 items and 5 points for each. The total value is 20 points.1Show how the following compound may be synthesized from compounds containing five or fewer carbons. O2
13、. Outline a synthesis of following compound from toluene as material(Note: Drect chlorination is unacceptable).H3C Cl3Design a synthesis of the diol below from ethyne as only carbon source.CH23HOCH23O4. Synthesize the following ketone from ethanol as only organic carbon source.O6. Structural determi
14、nation. This part contains 2 items and 5 points for each and total value is 10 points. You must give your reason for the structures determined. If you just give structures and have no deriving process, you will just lose a half .1. Propose a structure that is consistent with each set of data (Charac
15、teristic infrared absorption is given as well.)(a) C4H8O3 1HNMRdata IR datatcm-1(broad peak) and 1715 cm-1qss（points）(b) C7H8O 1HNMRdata IR datascm-1(broad peak) 4.58(2H, s)7.28(5H, m)（2 points）2Compound A has the formula C8H12 and is optically active. It reacts with hydrogen in the presence of plat
16、inum metal to give B, which has the formula C8H18 and is optically inactive. Careful hydrogenation of A using H2 and a poisoned palladium catalyst gives C, which has the formula C8H14 and is optically active. Compound A reacts with sodium in ammonia to give D, which also has the formula C8H14 and is
17、 optically inactive. What are compounds A through D?7. Suggest a qualitative chemical test that could be used to distinguish between the following pairs of isomeric compounds. Indicate what you would do and see.1. A o-methylphenol B o-methybenzoic acid C o-methylbenzaldehyde D o-methylacetophenone2A
18、 butene B cyclobutane C methylcyclopropane D butyneSection BAdditional question. This part includes two subjects. The total value is 30 points. 1. Optically active (2R,3S)-3-chloro-2-butanol is allowed with sodium hydroxide in ethanol to give an optically active oxirane , which is treated with potas
19、sium hydroxide in water to obtain 2,3-butanediol. What is the stereostructure of the diol ? What can you say about its optical rotation? (Total: 20 points)2. Syntheses. (5 points for each question. Total: 10points)(1) Show how you would make the following compound by using the acetoacetic ester and phenyl vinyl ketone as materials.O(2) Using as your starting compounds benzaldehyde, acetone, diethyl malonate and any needed inorganic reagents, show how you might synthesize the compound shown below.OC6H5C6H5CO
