115年 - 115 國立中興大學_學士後醫學系公費生招生考試試題：化學科#138024

1. What is the bond order of the carbon-carbon bonds in benzene?(A)2(B) 1.5(C) 3(D)0.5(E) 1

2. 1-Methylcyclopentanol is classified as ________. (A) an enol (B) a secondary alcohol (C) a tertiary alcohol (D) a phenol (E) a primary alcohol

3. The Hofmann elimination proceeds via a(n) ________ pathway. (A)E1 (B) E2 (C) S_N2 (D)S_N1 (E) none of the above

4. Which of the following yields a primary alcohol upon reduction? (A) a ketone (B) an alkene (C) an amine (D) an aldehyde (E) an ether

5. The following two reactions are important in the blast furnace production of iron metal from iron ore (Fe₂O₃):

Using these balanced reactions, how many moles of O2 are required for the production of 2.51 kg of Fe? (Molecular weight of Fe = 55.85 g/mol) (A)33.7 moles (B) 15.0 moles (C) 135 moles (D)44.9 moles (E) 1.88 moles

6. Esters and amides are most easily made by nucleophilic acyl substitution reactions on ________. (A) acid chlorides (B) carboxylic acids (C) acid anhydrides (D) carboxylates (E) alcohols

7. Which of the following is also an acceptable name for 3-nitrophenol? (A)3-cresol (B) hydroquinone (C) m-nitrophenol (D)p-nitrophenol (E) o-nitrophenol

8. Consider the fermentation reaction of glucose:

A 1.00-mole sample of C₆H₁₂O₆ was placed in a vat with 100 g of yeast. If 48.6 grams of C₂H₅OH was obtained, what was the percent yield of C₂H₅OH? (A)52.7 % (B) 26.4 % (C) 100 % (D)48.6 % (E) None of these

9. Which of the following solvents could be described as polar and protic? (A)18-crown-6 (B) ethanol (C) acetone (D)dimethylformamide (E) acetonitrile

10. In which of the following compounds does N have its maximum oxidation state? (A)NH₃ (B) N₂O (C) N₂ (D)NaNO₃ (E) HN₃

11. The RNA backbone is linked through a phosphate group. What type of bonding occurs between two consecutive nucleotides in RNA? (A)Ester (B) Amide (C) Hydrogen (D)Ionic (E) Hydrophobic

12. How many peaks appear in the proton spin decoupled ¹³C NMR spectrum of the compound below?
(A)2 (B) 3 (C) 4 (D)5 (E) 6

13. UV spectroscopy measures the energy required to promote an electron from the ________ molecular orbital to the ________ molecular orbital. (A)lowest occupied, highest unoccupied (B) lowest occupied, lowest unoccupied (C) highest occupied, highest unoccupied (D)highest occupied, lowest unoccupied (E) None of the above

14. When pent-1-ene is treated with mercury(II) acetate in methanol and the resulting product is reacted with NaBH4, what is the primary organic compound which results? (A)3-ethoxypentane (B) 1-methoxypentane (C) 2-ethoxypentane (D)2-methoxypentane (E) 1-ethoxypentane

15. Provide an acceptable name for the compound below.
(A)1,3-diphenyl-3-oxypropane (B) phenoxyphenylmethane (C) diphenyl ether (D)dibenzyl ether (E) dibenzyl acetal

16. How would you perform the following transformation?
(A)LiAlH₄ (B) 1. SOCl₂ / 2. LiAlH(O-t-Bu)₃ (C) NaBH₄ (D)1. DIBAL-H / 2. H₂O (E) 1. LiAlH₄ / 2. concentrated KMO₄

17. What is the best way to perform the transformation shown below?
(A) 1. NaCN / 2. H₃O⁺ (B) 1. Mg / 2. CO / 3. H₃O⁺ (C) concentrated KMnO₄ (D) 1. NaN₃ / 2. H₃O⁺ (E) Both A and B would work

18. Which of the following molecules has a characteristic stretch at 3300 cm^-1? (A)(CH₃)₂CHCO₂CH₃ (B) (CH₃)2CHCH₂N(CH₃)₂ (C) (CH₃)₃CH (D)(CH₃)₂CHCH=CH₂ (E) (CH₃)₂CHC≡CH

19. What type of carbon environment does not generate a signal in the DEPT-90 spectrum and gives a positive peak in the DEPT-135 spectrum? (A)methine (B) methylene (C) quaternary (D)methyl (E) carbonyl

20. An NMR spectrometer that operates at a frequency of 60 MHz for ¹³C NMR spectra, operates at what frequency for ¹ H NMR spectra? (A)60 MHz (B) 15 MHz (C) 120 MHz (D)240 MHz (E) 30 MHz

21. If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of the mixture? (A)100 (B) 75 (C) 3 (D)50 (E) 25

22. Consider the constitutional isomers 2-methylbut-1-ene, 2-methylbut-2-ene, and 3-methylbut-1-ene. When each of these alkenes is subjected to catalytic hydrogenation (H2, Pt), a single product results. Which of the following best describes the structural relationship among these products? (A)The products are diastereomers. (B) The products are identical. (C) The products are constitutional isomers. (D)The products are enantiomers. (E) The products are cis-trans isomers.

23. How many elements of unsaturation are implied by the molecular formula C₈H₁₁N? (A)0 (B) 1 (C) 2 (D)3 (E) 4

24. Which of the following terms best describes the stereochemical relationship of the two compounds shown below in Fischer notation?
(A)Diastereomers (B) cis/trans – isomers (C) enantiomers (D) constitutional isomers (E) meso - same structure

25. Which line-angle formula corresponds to the chair conformation shown below? (A)(B) (C) (D)

26. Predict the major organic product from the following reaction.

(A)2° amide (B) ester (C) carboxylic acid (D)nitrile (E) aldehyde

27. Show how you would perform the following synthesis. (A)1. mCPBA / 2. Potassium dichromate (B) OsO₄ (C) KMnO₄, cold. Basic (D)1. O₃ / 2. (CH₃)₂S (E) H₂O₂

28. Identify the correct name for the following structure.
(A)4-hydroxy-7,N-dimethylcyclohept-6-enamine (B) 5-hydroxy-2,N-dimethylcyclohept-2-enamine (C) 4-methyl-5-(methylamino)cyclohept-3-enol (D)5-methyl-4-(methylamino)cyclohept-5-enol (E) 4-methyl-5-(methylamino)cyclohept-3-en-1-one

29. Which of the following structures is aromatic? (A) (B) (C) (D) (E)

30. Acid chlorides can be prepared from carboxylic acids by treatment with ________. (A)(COCl)₂ (B) SOCl₂ (C) KCl (D)Both A and B (E) Both B and C

31. By what mechanism does cyclohexanol react when treated in sulfuric acid and what compound results? (A)E2; methoxycyclohexane (B) E1; cyclohexene (C) S_N1; methoxycyclohexane (D)E2; cyclohexene (E) E1; methoxycyclohexane

32. Which of the following is transition metal? (A)Sodium (B) Potassium (C) Copper (D)Silicon

33. What is the major organic product that results when 1-heptyne is treated with 2 equivalents of HBr? (A)2,2-dibromoheptane (B) 1,2-dibromoheptane (C) 2,3-dibromo-1-heptene (D)2,3-dibromo-2-heptene (E) 1,1-dibromoheptane

34. Provide the reagents necessary to complete the following transformation.
(A) 1. CH₃CO₃H / 2. H⁺ , H₂O (B) H₂O, H₂SO₄ (C) CH₃CO₃H (D) OsO₄, H₂O₂ (E) 1. BH₃∙THF / 2. H₂O₂, HO^-

35. Which of the following additions to alkenes occur(s) specifically in an syn fashion? (A) addition of H₂ (B) hydroboration (C) dihydroxylation using OsO₄, H₂O₂ (D) addition of HCl (E) A, B and C

36. What is the correct name for the structure of coordination number 6? (A)Tetrahedral (B) Octahedral (C) Square planar (D)Linea

37. Which of the following has the highest melting temperature? (A)H₂O (B) CO₂ (C) LiF (D)C₆₀

38. What is the oxidation number of manganese in K4[Mn(CN)6]? (A)2+ (B) 3+ (C) 4+ (D)6+

39. Which of the following metal ions has a d⁸ electron configuration? (A) Ni²⁺ (B) Zn²⁺ (C) Cr³⁺ (D) Cu⁺

40. Which of the following is polar molecule? (A)H₂ (B) He (C)CO₂ (D)H₂O

41. Using the following data reactions:

calculate the energy of an H-Br bond. (A) 728 kJ (B) 261 kJ (C) 364 kJ (D) 522 kJ (E) 182 kJ

42. What type of structure does the XeOF₂ molecule have? (A) Trigonal pyramid (B) Tetrahedral (C) T-shaped (D) Trigonal planar (E) Bent

43. How many electrons are involved in π bonding in benzene, C6H6? (A) 3 (B) 12 (C) 18 (D) 6 (E) 10

44. An element with the electron configuration [Xe] 6s²4f¹⁴5d⁷ would belong to which class on the periodic table? (A) transition elements (B) halogens (C) rare earth elements (D) alkaline earth elements

45. For the reaction 4FeCl₂(aq) + 3O₂(g) → 2Fe₂O₃(s) + _4Cl2(g), what volume of a 0.620 M solution of FeCl₂ is required to react completely with 7.26 ×10²¹ molecules of O₂? (A) 6.45 × 10³ mL (B) 9.97 mL (C) 14.6 mL (D) 25.9 mL (E) 5.61 mL

46. The calibration points for the linear Reaumur scale are the usual melting point of ice and boiling point of water, which are assigned the values 0°R and 80°R, respectively. The boiling point of benzene is 80.1°F. What is this temperature in °R? (A)160.1°R (B) 49.8 °R (C) 26.7 °R (D)212.2 °R (E) 21.4 °R

47. Relative abundance is the unit along the y-axis in a mass spectrum. What are the units on the x-axis? (A)mass (m) (B) frequency (ν) (C) molecular weight (amu) (D)mass/charge (m/z) (E) boiling point (b.p.)

48. Consider the reaction 3A + B + C → D + E where the rate law is defined as

An experiment is carried out where [B]₀ = [C]₀ = 1.00 M and [A]₀ = 1.00 × 10^–4 M. After 3.00 minutes, [A] = 3.26 × 10^–5 M and= 3.067 × 10⁴ . The value of k is : (A)6.23 × 10^–3 L³ /mol³ ·s (B) 3.26 × 10^–5 L³ /mol³ ·s (C) 1.15 × 10² L³ /mol³ ·s (D)1.00 × 10⁸ L³ /mol³ ·s (E) None of these

49. The relationship between 1 and 2 is: ________.
(A) constitutional isomers (B)same compound (C) enantiomers (D)diastereomers (E) none of above

50. The relationship between 1 and 2 is: ________.
(A) constitutional isomers (B)same compound (C) diastereomers (D) enantiomers (E) none of above