华东理工大学2004—2005学年第二学期《有机化学》期终试卷(A)(理优03级).docxVIP

华东理工大学 2004— 2005 学年第二学期 《有机化学》 期终试卷 (A)( 理优 03 级 ) 班级 _________ 姓名 _________ 学号 __________ 成绩 _________ 2005.4.29 (用英文或中文回答下列六大题 ) Order the following compounds in each set with respect to increasing acidity and explain why?（10 points） CO2H CO2H OCH3 OH 1 2 CO2H HO2C 1 2 Predict the reagent or product of the following reactions:（ 20 points）： 1) PhCH 2CHO  OH -  ? 2) CHO- ? CH 3CH 2CO2C2H5 3) O + HCHO + Me2NH 1 4) 1) BH 3 ? 2) H 2O2/OH- 5) O O 1) O NaOC 2H 5 + N 1 2 + 2) H3O C2H5OH H 6) CH3 NaNO2/HCl 1) NH2 2) 1 HBF4 7) CH3 Cl O + CO2OH 1 3. For following compound, Give :1）Chinese name (the R/S designation of each chiral center should be concerned) of IUPAC；2）equilibrating chair conformation and indicate which one is the most stable； 3） the product from the reaction with strong base by E2 process（.12 points） Br CH3 1) Give three methods for converting a ketone group to methylene group 2) How would you prepare the following two compounds from the starting material given?（33 points） D CH3 CH3 HC CH OH H H Three compounds 1 (C4H6), 2 (C4H6O),3 (C4 H6O) have been prepared by the routs shown below. Suggest structures for these isomers (15 points) CO2OH NaNH2 Cl LiI Cl ButOH 1 2 重排 3 1； 1H NMR: 5.35(2H,s) ，1.0(4H,s)； 13C NMR: 3different signals 2；IR: no strong peaks outside fingerprint; 1H NMR: 3.0(2H, s) ， 0.85(4H, t) 3；IR: 1770 cm-1 , 1H NMR: 3.02(4H, t, J=5H Z), 1.98(2H, m, J=5HZ) Propose a mechanism for the following reaction（10 points）： CH3 + OH