有机化学A

考试科目：Organic Chemistry I.Choose a letter that designates the correct order of the assigned properties:（16%） 1. Which compound is most stable for the following compounds: ( ) -1AClClBClClCClClDClClClClClCl2. For the following compounds which has no characteristic IR absorption at 3300and 3000 cm ？( ) ABCD 3． For the following compounds which one is most reactivity in electrophilic reaction of aromatic ring? ( ) OMeAOEtBOHCNHAcDCOOCH34．For the following compounds which one is difficult in the both reaction of SN1，SN2( ) APh2CHBrBrBCPhCH2BrDPhOBr5．For the following compounds which could not undergo iodoform reaction?( ) A Ethanol B acetone C Propanal D butanone 6．The order of Acidity of (1) (2) (3) (4) is: ( )？ 1．Ethyne 2. Ethanol 3. Acetic acid 4. Phenol A 3> 4> 2> 1 B 3 > 2 > 4 > 1 C 4 > 3> 2> 1 D3 > 4> 1> 2 7. For the following compounds which is weakest base？( ) A Pyridine B Quinoline C amine D Pyrrole 第一 页，共 5 页

8．Which Grignard reagents could be prepared directly by using the following reaction of halide with Mg ? ( ) Br2BrA. HOCH2CH2Br, B. HC CCH 2 CH 2 CH C. H 3 C C CH 2 D. OCH3CH2CHCH2BrOCH3II、Predict the major product in each of the following reactions: (32%) 1． ？ 2． 3． 4． 5． 6． ？ 7． 8． 9． NBSCHO+OH3CCCH2CH3H+KOH?COCH3+HCHO+HN(CH3)2?CH3CHO+3 HCHOCa(OH)2?HCHOCa(OH)2???HBr??KOHEtOH?第二 页，共 5 页

10． OEtOHOHOONaBH4?CrO3(C5H5N)2HCl, HOH11． 12． 13． 14． 15． 16． OOHMe2COOHH2SO4OH???OO+OO?CHO+Ph3PCO2Et?III. How would you prepare the following compounds, starting with corresponding starting materials and any other reagents needed. The procedure may contain several steps. (24%) 1． 2． 3． 4． CH3 CH2ClNO2OHBrClDOOCH2OH 5． H6．

Br 第三 页，共 5 页

HBrBrBrCH2(COOC2H5)2COOHIV. Mechanism（12%） 1． 2． V. Propose the structure for the following compounds that fit the corresponding conditions(10%） 1．Propose the structure for C5H10O that fit the following 1 NMR data （1） The spectra has only two single peak. （2） δH：1.02（d，6H），2.12（s，3H），2.22（m，1H） （3） δH：1.05（t，6H），2.47（q，4H） 2. Compounds A: C6H14，when A reaction with chlorine, 3 ( B，C and D) of different monochloridescould be provided. B and Ｃ could react with Potassium t-butyl oxide respectivly, and form thesame alkene E. D could not undergo the reaction of E2 type. Please propose the structure of A，B，C，D and E. OClOHCOOCH3C=CHCH2CH2C=CHCHOCH3CH3H, H2OOHOH 第四 页，共 5 页

IV. Assign R/S configuration for the following compounds 。 （4%）。 1HC2H5CH3Br2CH3BrHHBrCH3CH34HC2H5BrC2H53H3CHH 第五页，共5页