課程名稱︰有機化學 課程性質︰醫學系、牙醫系大一必修 課程教師︰方俊民 開課學院：醫學院 開課系所︰醫學系 考試日期（年月日）︰2020/06/15 考試時限（分鐘）：110 試題 : 本試卷總分為120分 I. Simple Choice (54%) 1. Alkaloid is a natural (A) acid (B) amine (C) ester (D) ketone 2. The compound 2-methylpropylamine is a (A) primary amine (B) secondary amine (C) (C) tertiary amine (D) quaternary amine 3. Which compound has the highest basicity？ (A) aniline (B) acetamide (C) acetonitrile (D) ethylamine 4. The reaction of N-methylpyrrole with Br2 mainly obtain (A) 2-bromo-N-methylpyrrole (B) 3-bromo-N-methylpyrrole (C) N-(bromomethyl)pyrrole (D) 2-3-dibromo-N-methylpyrrole 5. Which compound can act as both general acid and general base? (A) pyrrole (B) indole (C) imidazole (D) pyridine 6. An electromagnetic wave of 2000cm^(-1) wavenumber correspond to energy of (A) 1.4 (B) 5.7 (C) 14 (D) 57 kcal/mol 7. A compound shows magenta(red) color , so it will show the UV-vis absorption max at (A) 267 (B) 497 (C) 667 (D) 867 nm 8. The absorption at 2200 cm^(-1) in IR spectrum correspond to which functional group? (A) C三N (B) C=C (C) C=O (D) C=N 9. How many carbon signals of m-dichlorobenzene will appear in the 13C NMR spectrum? (A) 1 (B) 2 (C) 3 (D) 4 10.A compound has UV molar absorptivity 13260 L/(mol˙cm). A sample is measured in a cell with 1 cm pathlength to show A=0.40. The concentration of this compound is (A) 3mM (B) 30mM (C) 3uM (D) 30uM 11.beta-D-Glucopyranose and alpha-D-Glucopyranose are (A) enantiomers (B) tautomers (C) conformers (D) anomers 12.Peptide bond is (A) amide (B) ester (C) hydrogen (D) carbonyl bond 13.Kinase is an enzyme for (A) oxidation of alcohol (B) transfer of phosphate group (C) hydrolysis of ester (D) hydrolysis of protein 14.Glutamic acid is abbreviated as (A) D (B) E (C) F (D) G 15.The only secondary amino acid is (A) arginine (B) histidine (C) lysine (D) proline 16.Which amino acid contains a mercapto group? (A) lysine (B) serine (C) cysteine (D) methionine 17.Which amino acid is the most basic? (A) arginine (B) histidine (C) lysine (D) proline 18.Which compound contains a chromophore with absorption max at 280 nm? (A) histidine (B) tyrosine (C) tryptophan (D) phenylalanine 19.Protein can be purified by electrophoresis based on (A) pI value (B) size (C) charge (D) binding 20.What reagent is used in Edman degradayion of peptide? (A) trypsin (B) chymotrypsin (C) phenyl isothiocyanate (D) dicyclohexyl carbodiimide 21.Edman degradation of tetrapeptide gly-lys-phe-asp will give (A) gly (B) gly-lys (C) phe-asp (D) lys-phe-asp 22.Trypsin digestion of pentapeptide met-arg-tyr-asp-val will give (A) met (B) met-arg (C) asp-val (D) val 23.Ninhydrin is used to analyze (A) lipid (B) carbohydrate (C) amino acid (D) nucleic acid 24.Who has great contribution to development of solid-state peptide synthesis? (A) R. B. Merryfield (B) V. Grignard (C) E. Fischer (D) F. Sanger 25.Which compound belongs to steroid? (A) cholesterol (B) triacylglycerol (C) morphine (D) phosphatidylcholine 26.Which compound will form bilayer vesicle in water? (A) oleic acid (B) fatty acid (C) phosphatidic acid (D) bile acid 27.The DNA from sea urchins contains 32% A and 18% G. What is the approximate percentage of T? (A) 18% (B) 32% (C) 50% (D) 68% II. (12%) Show the designated reactants (1-4) and reagents for synthesis of benzylamine: (1) an amide (2) a nitrile (3) an azide (4) an aldehyde III. (12%) The 1H NMR spectrum (300MHz) of ethyl acetate shows three signals at delta 4.12 , 2.04 , 1.26 using TMS as the internal reference (delta=0) 1. How many hertz is the delta=4.12 signal away from TMS? 2. Which chemical shift (delta) can be assigned to the CH2 protons? 3. Draw the spliting pattern of the CH2 signal. Indicate the value of coupling constant (J). 4. When the 1H NMR spectrum of the same sample is recorded on a 600 MHz NMR spectrometer , will the delta and J value of ethyl acetate change or not? Give reasons for your answer. 5. Which carbon atom will show the largest chemical shift in the 13C NMR spectrum of ethyl acetate? IV. (12%) The Fischer projections of D-glucose and D-fructose are shown. (有附兩者的結構式) 1. Which stereocenter is responsible for the definition of D-sugar? 2. Which stereocenter in D-glucose has (S)-configuration? 3. What reagent is used to test if glucose is a reducing sugar? 4. Draw the Haworth formula of beta-glucopyranose. 5. Draw the chair conformation of methyl alpha-glucopyranoside. 6. D-glucose and D-fructose are interconvertible in dilute acid. Propose the mechanism, V. (10%) Chemical synthesis of dipeptide Ala-Gly: (有附 L-Alanine , L-Glycine , Ala-Gly 三者的結構式) 1. Glycine is protected as the methyl ester. How will you prepare glycine methyl ester (Gly-CH3)? 2. Alanine is treated with di-tert-butyl bicarbonate to give the tert-butyl carnamate (Boc-Ala). Show the chemical structure of Boc-Ala product. 3. Dicyclohexylcarbodiimide (DCC) is used for the coupling reaction of Boc-Ala and Gly-CH3 to give Boc-Ala-Gly-CH3. Show the structure of DCC. 4. What reagent is used to remove the Boc group from Boc-Ala-Gly-CH3? 5. What reagent is used to remove the methyl group from Ala-Gly-CH3? VI. (20%) Given the structures of compounds 1-3: 1:beta-D-Ribofuranose 2:Adenine 3:Thymine (有給三者的結構式) 1. Draw the Fischer projection of D-ribose. 2. Draw the product for the reaction of compound(1) with excess acetic anhydride in pyridine. 3. Draw the product for the reduction of compound(1) with NaBH4. 4. Draw the structure of beta-D-2-deoxyribofuraose. 5. Draw the structure of 2'-deoxyadenosine , which is formed from compound(2) and 2-deoxyribofuranose. 6. Draw the structure of Uracil , which occurs in RNA instead of compound(3). 7. Draw the structure of adenosine 5'-phosphate (AMP). 8. Draw the structure of cyclic AMP (cAMP). 9. Draw the structure if adenosine 5'-triphosphate (ATP). 10.Draw the hydrogen-bonded pair of compound(2) and compound(3). --

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