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)
1. Order the following compounds in each set with respect to increasing acidity and
explain why?（10 points）
?
CO2HOCH312CO2HOH?
CO2H1
HO2C22. Predict the reagent or product of the following reactions:（20 points）：
1)
PhCH2CHOOH-?
2)
CH3CH2CO2C2H5
?C2H5O-3)
O
1+HCHO+Me2NH4)
1)BH3-2)H2O2 / OH?
5)
O
O+
6)
CH3NH2NH11)O22)H3O+NaOC2H5C2H5OH
1)NaNO2/HCl2)HBF41
7)
CH3OCl+CO2OH13. 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
CH34. 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）
DCH3CH3HCCHHHOH
5. Three compounds 1 (C4H6), 2 (C4H6O),3 (C4H6O) have been prepared by the
routs shown below. Suggest structures for these isomers (15 points)
CO2OH
Cl1
NaNH2ButOH1Cl 13
2LiI重排31；H NMR: 5.35(2H,s)，1.0(4H,s)；
C 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=5HZ), 1.98(2H, m, J=5HZ)
6. Propose a mechanism for the following reaction（10 points）：
CH3H+OH
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)
