课程名称︰有机化学
课程性质︰医学系、牙医系大一必修
课程教师︰方俊民
开课学院：医学院
开课系所︰医学系
考试日期（年月日）︰2020/06/15
考试时限（分钟）：110
试题 :
本试卷总分为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.
(有附两者的结构式)
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 三者的结构式)
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
(有给三者的结构式)
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).