99學年度藥學研究所博士班考古題庫

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藥學系博士班

高雄醫學大學 99 學年度 研究所 招生考試

儀器分析

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1. Define: (30%)

(a) absorptivity

(b) wavenumber

(c) fluorescence

(d) phosphorescence

(e) coupling constants

(f) chemical shift

(g) base peak in mass spectrometry

(h) molecular ion peak in mass spectrometry

(i) tandem mass spectrometry

(j) retention time

2. Describe van Deemter equation. (10%)

3. Describe the components of a fluorometer. (10%)

4. Describe Beer’s Law. (10%)

5. What is an internal standard and why is it used? (10%)

6. Describe the components of a mass spectrometer. (10%)

7. For a normal-phase separation, predict the order of elution of n-hexane,

n-hexanol, benzene. (10%)

8. Which electronic molecular energy levels are most used for absorption

spectrometry? (10%)

高雄醫學大學 99 學年度 牙研究所 招生考試

藥學系博士班

有機化學

共 1 頁

Show all possible products, indicate which is expected to be the major product, and explain why. (15%)

2. Draw structures of compounds A – E, formed by reactions in the sequence resulting in the overall conversion of benzene into naphthalene. (20%) O O O + AlCl3 A (C₁₀H₁₀O₃) Zn/Hg B (C₁₀H₁₂O₂) HCl 1. SOCl₂ C (C₁₀H₁₀O) 2. AlCl₃ Zn/Hg D (C₁₀H₁₂) HCl Br₂ E (C₁₀H₁₁Br) peroxides

3. Propose structures that are consistent with each set of peaks: (20%) (a) C8H10, 1.25 ppm (t, 3H), 2.68 ppm (q, 2H), 7.23 ppm (m, 5H);

(b) C7H8O, 2.43 ppm (s, 1H), 4.58 ppm (s, 2H), 7.28 ppm (m, 5H); IR peak at 3350 cm-1;

(c) C3H6O2, 1.27 ppm (t, 3H), 2.66 ppm (q, 2H), 10.95 ppm (s, 1H); IR peaks at 1715 cm-1 and 3500 – 3000 cm-1; (d) C5H10O, 1.10 ppm (d, 6H), 2.10 ppm (s, 3H), 2.50 ppm (m, 1H); IR peak at 1720 cm-1;

(e) C8H9Br, 2.00 ppm (d, 3H), 5.15 ppm (q, 1H), 7.35 ppm (m, 5H)

4. Show the reactions and reagents necessary to accomplish each of the following syntheses. (30%) (a) cyclohexane to cyclohexylacetylene

(b) 1-butene to 3-methyl-1-pentyne (c) ethylene to 2-pentyne

(d) nitrobenzene to m-bromophenol (e) toluene to benzylamine

(f) benzene to phenol

(g) toluene to p-nitrobenzoic acid

(h) cyclohexene to trans-1,2-cyclohexanediol (i) ethyl bromide to 1-bromobutane

(j) CH3OCH2CH2Br to CH3O(CH2)4OH

5. Three compounds, A, B, and C, have the same molecular formula, C5H8. All three compounds decolorize Br2 / CCl4. Both

A and B produce pentane when reacted with excess H2 / Pt. Under the same conditions, C absorbs one equivalent of H2. (a) Reaction of A with hot KMnO4 gave CH3CH2CH2COOH, while similar treatment of B produced CH3CH2COOH. What are structures of A and B? (10%)