課程名稱︰有機化學三
課程性質︰五選三必修
課程教師︰方俊民
開課學院：理學院
開課系所︰化學系
考試日期（年月日）︰2014/1/8
考試時限（分鐘）：110分鐘
是否需發放獎勵金：是
（如未明確表示，則不予發放）
試題 :
Final Examination (Orgain Chemistry III)
January 8, 2014； 化學系 203 22230
(共2頁試題)
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 的化合物結構太難畫，就沒有畫了。
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