101學年度醫藥暨應用化學系碩士班考古題庫

試題第 1 頁

系所：醫藥暨應用化學系碩士班

高雄醫學大學 101 學年度研究所招生考試

_{科目：有機化學}

I. Choose one correct answer for the following questions.

【單選題】每題 2 分，共計 40 分，未作答，不給分亦不扣分，並請依序註明題號，作答於答案卷上。 1. Camphor is an example of a ___________.

(A) fused bicyclic molecule. (B) bridged bicyclic molecule. (C) fused tricyclic molecule. (D) bridged tricyclic molecule. (E) None of the above.

2. How many diastereomer(s) exist for the compound below?

H OH CO₂H H OH HO H CO2H (A) 2 (B) 4 (C) 6 (D) 8 (E) 0

3. Arrange the following bicyclic alkenes in order of increasing stability (least stable to most stable).

4. Since the two chlorine atoms add to opposite faces of the cyclohexene double bond, we say that the reaction occurs with: (A) syn stereochemistry (B) cis stereochemistry (C) anti stereochemistry (D) retention of stereochemistry (E) conversion of stereochemistry.

5. Hydroboration/oxidation of alkenes occurs with:

(A) syn stereochemistry (B) trans stereochemistry (C) anti stereochemistry (D) retention of stereochemistry (E) unpredictable stereochemistry.

6. In the reaction of an alkene with dichlorocarbene, the dichlorocarbene is the:

(A) electrophile. (B) Lewis base. (C) nucleophile. (D) both (B) and (C). (E) None of the above.

7. (S)-()-Serine:

(A) is dextrorotatory. (B) rotates plane-polarized light in a counterclockwise direction.

(C) rotates plane-polarized light in a clockwise direction. (D) is racemic. (E) is diastereomer.

8. Which of the species below is less basic than acetylide?

(A) n-BuLi (B) CH3ONa (C) CH3MgBr (D) Lithium diisopropylamide (LDA) (E) all of the above.

9. What descriptive term is applied to the type of diene represented by 2,4-hexadiene?

(A) conjugated diene (B) cumulated diene (C) isolated diene (D) alkynyl diene (E) none of the above.

10. In the proton NMR, in what region of the spectrum does one typically observe hydrogens bound to the aromatic ring? (A) 1.0-1.5 ppm (B) 2.0-3.0 ppm (C) 4.5-5.5 ppm (D) 7.0-8.0 ppm (E) 9.0-10.0 ppm.

(A) 3 < 2 < 1 (B) 1 < 2 < 3 (C) 1 < 3 < 2 (D) 2 < 3 < 1 (E) 3 < 1 < 2

試題第 2 頁

11. Which of the following undergoes S_N2 reaction with sodium methoxide most rapidly?

(A) PhBr (B) Ph₃CBr (C) PhCH₂Br (D) PhCH₂CH₂Br (E) PhCH₂CH₂CH₂Br.

12. Which of the following is the same as the tropylium ion?

(A) cycloheptatrienyl cation (B) cycloheptatrienyl anion (C) cyclopentadienyl cation (D) cyclopentadienyl anion (E) cyclopropenyl anion.

13. Rank the following groups in order of increasing activating power in electrophilic aromatic substitution reactions: -OCH₃, -O(C=O)CH₂CH₃, -CH₂CH₃, -Br.

(A) -Br < -CH₂CH₃ < -O(C=O)CH₂CH₃ < -OCH_{3 (B) -Br < -OCOCH2}CH_{3 < -CH2}CH₃ < -OCH₃ (C) -OCH₃ < -CH₂CH₃ < -O(C=O)CH₂CH₃ < -Br _{(D) -O(C=O)CH2}CH₃ < -OCH₃ < -Br < -CH₂CH₃ (E) none of the above.

14. Which of the following compounds is least reactive in the nucleophilic aromatic substitution reaction with NaOH? (A) 2,4-dinitrochlorobenzene (B) m-nitrochlorobenzene (C) o-nitrochlorobenzene

(D) p-nitrochlorobenzene (E) 3,5-dinitrochlorobenzene

15. When the carbonyl group of a neutral ketone is protonated,: (A) the resulting species becomes more electrophilic.

(B) the resulting species is activated toward nucleophilic attack.

(C) subsequent nucleophilic attack on the resulting species is said to occur under acid-catalyzed conditions. (D) the resulting species has a positive charge.

(E) all of the above.

16. Which of the following is also known as a Schiff base?

(A) an imine (B) a cyanohydrin (C) a hydrate (D) sodium hydroxide (E) an aldehyde.

17. Which of the following amines can be resolved into enantiomers?

(A) trimethylamine (B) 3-pentanamine (C) 2-pentanamine (D) dimethylammonium chloride (E) 4-(dimethylamino) pyridine.

18. Which of the following amines is most basic?

(A) aniline (B) N-ethylaniline (C) N,N-diethylaniline (D) piperidine (E) pyrrole.

19. The α-carbon atom bonded to the nitrogen of an alkylamine usually appears in what chemical shift (δ) range? (A) 5-20 (B) 30-50 (C) 80-100 (D) 120-150 (E) 180-220 ppm.

20. The methyl ester of a carboxylic acid can be synthesized directly using:

試題第 3 頁

II. Propose mechanism for the following reactions. 反應機轉，每題 5 分，共計 10 分

III. Complete the following road-map problem by drawing the structures for compounds A through T. 請依序（A 至 T）標示於於答案卷上作答，每題 2 分，共計 40 分，未作答，不給分亦不扣分。

IV. Each of the following reactions has been reported in the chemical literature and gives a predominance of a single product in synthetically acceptable yield. Give the structure of the product formed in each reaction.

試題第 1 頁

系所：醫藥暨應用化學系碩士班

高雄醫學大學 101 學年度研究所招生考試

科目：綜合化學

*可使用電子計算機

問答題：

1. (1) 何謂蛋白質 Primary 與 Secondary structure? 如何測定? (5%) (2) 何謂 Reversible enzyme inhibition? 如何測定? (5%)

2. Glycolysis 與 TCA cycle (5%) 3. Sphingolipids 與 Lipoproteins (5%) 4. mRNA synthesis 與 Processing (5%) 5. Western 與 Southern blot analysis (5%)

6. Is the function 2 2

y

x  an eigenfunction of the operator





x y x x    2 2 1

? If so, what is the eigenvalue? (5%)

7. Which of the following vibrational modes are IR active? (5%)

8. Write the Slater determinant for the ground-state configuration of Li. (5%)

9. How many types of energy level are there for polyatomic molecules? Arrange them in order of increasing energy-level spacing. (5%)

10. Consider the reaction . Assuming that only reactant A is present at t  0, what is the expected time dependence of [P] using the steady-state approximation? (5%)

11. Describe why the number of valence electon (NVE) is often equal to 18 for transition-metal organometallics and for many inorganic complexes. (10%)

12. Describe the reasons respectively why the ν(CO) frequency increases and decreases in carbonyl complexes.(10%) 13. Describe the phenomenon of s-p mixing in N2 molecule.(5%)

14. Please indicate the possible sources of (a.) random error and (b.) systematic error in chemical analyses. (5% each) 15. Assuming a aqueous solution that is 0.200 M in NH3 and 0.300 M in NH4Cl: (5% each)

(a.)

Calculate the pH of this aqueous solution.

(b.)

Calculate the pH change that takes place when a 100-mL portion of 0.0500 M NaOH(aq) is added to 400 mL of this

solution

命題教師簽章

：____________________

（簽章請勿超過虛線）

高雄醫學大學 101 學年度 研究所 招生考試

考試科目: 醫藥暨應用化學系碩

士班-「綜合化學-生物化學」

試題 第 頁

問答題：

I. (1) 何謂蛋白質 Primary 與 Secondary structure? 如何測定? (2) 何謂 Reversible enzyme inhibition? 如何測定?

II. Glycolysis 與 TCA cycle III. Sphingolipids 與 Lipoproteins IV. mRNA synthesis 與 Processing V. Western 與 Southern blot analysis

命題教師簽章

：____________________

（簽章請勿超過虛線）

高雄醫學大學 101 學年度 研究所 招生考試 考試科目: 綜合化學-物理化學

試題 第 1 頁

1. Is the function x2  y2 an eigenfunction of the operator





x y x x    2 2 1

? If so, what is the eigenvalue? (5%)

2. Which of the following vibrational modes are IR active? (5%)

3. Write the Slater determinant for the ground-state configuration of Li. (5%)

4. How many types of energy level are there for polyatomic molecules? Arrange them in order of increasing energy-level spacing. (5%)

5. Consider the reaction . Assuming that only reactant A is present at t  0, what is the expected time dependence of [P] using the steady-state approximation? (5%)

命題教師簽章

：____________________

（簽章請勿超過虛線）

高雄醫學大學 101 學年度 研究所 招生考試 考試科目: 無機化學

試題 第 1 頁

1. Describe why the number of valence electon (NVE) is often equal to 18 for transition-metal organometallics and for many inorganic complexes. (10)

2. Describe the reasons respectively why the ν(CO) frequency increases and decreases in carbonyl complexes.(10) 3. Describe the phenomenon of s-p mixing in N2 molecule.(5)

命題教師簽章

：____________________

（簽章請勿超過虛線）

高雄醫學大學 101 學年度 研究所 招生考試 考試科目: 綜合化學-分析化學

試題 第 1 頁

*可使用電子計算機

1. Please indicate the possible sources of (a.) random error and (b.) systematic error in chemical analyses.

(5pts each)

2. Assuming a aqueous solution that is 0.200 M in NH

3

and 0.300 M in NH

4

Cl: (5pts each)

(a.) Calculate the pH of this aqueous solution.

(b.) Calculate the pH change that takes place when a 100-mL portion of 0.0500 M NaOH

(aq)

is added to

400 mL of this solution