课程名称︰有机化学三 课程性质︰五选三必修 课程教师︰方俊民 开课学院：理学院 开课系所︰化学系 考试日期（年月日）︰2014/1/8 考试时限（分钟）：110分钟 是否需发放奖励金：是 （如未明确表示，则不予发放） 试题 : Final Examination (Orgain Chemistry III) January 8, 2014； 化学系 203 22230 (共2页试题) Names of chemists: (1) Emil Fischer, (2) Robert Robinson, (3) R. B. Woodward, (4) R. B. Merrifield, (5) E.J.Corey (6) William Perkin, (7) Gerhard Domagk, (8) Louis Pasteur. Structures of compounds: I.(6%) 1.Show a structure of oil derived from unsaturated fatty acid and glycerol. 2.Show a structure of phospholipid derived from saturated fatty acid, glycerol and phosphoric acid. 3.Which compound will form lipid bilayer in water? II.(9%)Acetic acid is the precursor in biosynthesis of isoprene pyrophosphate 1.Show the names for (a) and (b) reactions in the transformation of acetyl-CoA to mevalonic acid. 2.Draw the chemical structure of pyrophosphate (PP). 3.When isotope-labeled acetic acid (CH3*COOH) is used, mark the positions of the isotope carbons in isoprene pyrophosphate. III.(8%) 1.Which structure is cholesterol? 2.Who has made great contribution to the synthesis of steroids? 3.Which structure is squalene oxide? 4.Show the cationic electrocyclization of squalene oxide to give a steroid. IV.(16%) 1.Which structure is quinine? 2.Who failed to synthesize quinine from aniline derivatives, but obtained a purple dye? 3.Who succeeded in the synthesis of quinine? 4.Which structure is mauveine dye? 5.Which sturcture is an azo dye? 6.Who accidently found anti-inflammatory drug from azo dye? 7.Which structure is Cy-3, a fluorescent cyanine dye? 8.Which structure is indigo dye that is derived from oxidation of indolin-3-one? V.(18%)Refer to the structure H shown in the list. 1.Who has first assigned the structure of D-glucose? 2.Show the mechanism for interconversion between α-D-glucopyranose and its β-anomer. 3.Show the mechanism for conversion of D-fructose to D-glucose and D-mannose in alkaline solution. 4.Draw the structure of D-glucuronic acid. 5.Draw the structure of D-galactose, which is the 4-epimer of D-glucose. 6.L-Fucose is 6-deoxy-L-galactose. Draw the structure. 7.Maltose is disaccharide Glc(α1→4)Glc formed by two D-glucose molecules. Draw the structure of maltose. 8.Indicate the acetal and hemiacetal groups in maltose. 9.Draw the oxonium intermediate of glucose on formation of maltose. VI.(14%) Refer to the structures I-I shown in the list. Alanine has 1 4 isoelectric point (pI) at 6.01. 1.Among aspartic acid, serine and lysine, which compound has the pI value closest to that of alanine? Which compound has the lowest pI value? 2.Draw the zwitterionic sturctures of serine and lysine. 3.How will you protect the carboxylic group of alanine to the methyl ester derivative? 4.How wil you protect the amino group of alanine to the tert-butrl carbamate (Boc) derivative? 5.Who has devised the solid-phase synthesis of peptides? 6.How will you synthesize dipeptide L-Ala-L-Ala? VII.(8%) Refer to the structure list. 1.Which structure is D-ribose? 2.Which structure is guanine? 3.Draw the structure of guanosine, which is the β-N-glycoside formed by D-ribose and guanine. 4.Show the structure of guanine-cytosine Watson-Crick pair. VIII(4%) 1.How will you synthesize heptanal starting from bromohexane and NaCN? - 2.In the retrosynthetic analysis, what is the Umpolung synthon acted by CN IX.(5%) 1.Who has achieved a synthsis of prostaglandin PGE2 2.Indicate the strategic bonds for disconnection in the restrosynthetic analysis of PGE2. X.(12%) Synthesis of 4-chloro-1-nitro-2-propylbenzene from benzene. 1.Show the retrosynthetic analysis to explain why 4-chloro-1-nitrobenzene or 1-nitro-2-propylbenzene cannot be the possible intermediates in this synthesis. 2.Considering the possible rearrangement of primary carbocation, how will you prepare 1-chloro-3-propylbenzene from benzene? 3.How wil you complete the synthesis of 4-chloro-1-nitro-2-propylbenzene? P.S. structures of compounds 的化合物结构太难画，就没有画了。 --

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