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105 年 - 105 學士後西醫:有機化學#78642 

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1.

1. Rank the following monomers in order of increasing reactivity toward cationic polymerization (least reactive to most reactive). 5d56501126536.jpg
(A) III, IV, I, II
(B) II, I, IV, III
(C) I, II, IV, III
(D) IV, III, I, II
(E) I, II, III, IV



2.

2. What product would be obtained for the following reaction? 5d56502e7c5bd.jpg
(A) CH3(CH2)3C≡CCH2OH
(B) CH3(CH2)3C≡CCHO
(C) CH3(CH2)3C≡CH
(D) CH3(CH2)3C≡CNMe2
(E) None of the above.



3.

3. Which two have the same molecular geometry? 5d565055bb30d.jpg
(A) I, II
(B) III, IV
(C) I, V
(D) II, V
(E) IV, V



4.

4. Which nitrogen(s) have more basic? 5d56506faf306.jpg
(A) I
(B) II
(C) III
(D) I, II, and III are acidic
(E) None of the above.



5.

5. Rank the acidity of the following compounds. 5d5650850cfa1.jpg
(A) I > IV > III > II
(B) I > III > IV > II
(C) IV > II > I > III
(D) II > I > IV > III
(E) None of the above.



6.

6. What is the order of increasing acidity for the following compounds? 5d56509da577a.jpg
(A) IV < I < II < III
(B) III < II < I < IV
(C) III < II < IV < I
(D) IV < II < I < III
(E) I < IV < II < III



7.7. Which of these substances contains both covalent and ionic bonds?
(A) HN3
(B) NH4Cl
(C) H2O2
(D) XeF2
(E) PCl5


8.

8. Choose the correct product of the following reaction? 5d5650d018f4c.jpg
(A) 5d5650e18cfb4.jpg
(B) 5d5650f3550d7.jpg
(C) 5d5651075455b.jpg
(D) 5d56511828508.jpg
(E) 5d565128440ee.jpg



9.

9. How many monochloro substituted products C6H13Cl you might obtain by reaction of 2-methylpentane with Cl2? 5d565149f1a17.jpg
(A) 1
(B) 2
(C) 3
(D) 4
(E) 5



10.

10. There are some isomers of 4-t-butylcyclhexane-1,3-diol. Which isomer reacts readily with acetone and an acid catalyst to form an acetal, but other stereoisomers do not react?
(A) 5d56516d71846.jpg
(B) 5d56517d3b251.jpg
(C) 5d5651917330e.jpg
(D) 5d5651a02f583.jpg
(E) 5d5651bbbb264.jpg



11.11. Which of the following correctly describes a molecule that is achiral?
(A) Non-superimposability of the molecule on its mirror image
(B) Superimposability of the molecule on its mirror image
(C) Contains a carbon atom with four different substituents
(D) Does not have a plane of symmetry
(E) Both {B} and {D}.


12.

12. Which of the following pairs are enantiomers? 5d5651fd9ef83.jpg
(A) II, IV
(B) I, III
(C) I, II, III
(D) I, II, V
(E) I, III, V



13.

13. Consider the two energy diagrams Fig. I and Fig. II given below. 5d56523a1b734.jpg Which of the following is correct with respect to these diagrams?
(A) Fig. I represents an SN2 reaction
(B) Fig. II represents an SN1 reaction
(C) Fig. II represents an SN2 reaction
(D) Fig. I represents an SN1 reaction
(E) Both {C} and {D}.



14.

14. Find the energy cost of a 1,3-diaxial interaction for the following compounds, which has most 1,3-diaxial interaction energy? Assume the following 1,3-diaxial strains. 5d5653e9a6614.jpg
(A) Isopropylcyclohexane
(B) Fluorocyclohexane
(C) Cyclohexanecarbonitrile
(D) cis-1-Chloro-2-methylcyclohexane
(E) trans-1-Chloro-2-methylcyclohexane.



15.

15. Which of the following species is the least nucleophilic?
(A) Me3CO 5d5654085789b.jpg
(B) H2O
(C) Me3N
(D) BF3
(E) 5d56541e2f229.jpgCN



16.

16. What is the correct structure for α-D-glucopyranose?
(A) 5d56543817dcd.jpg
(B) 5d56544906d9a.jpg
(C) 5d565459156c7.jpg
(D) 5d56546b87928.jpg
(E) 5d56547c458b9.jpg



17.

17. Which of the following is a correct representation of the amino acid below? 5d56549cefb50.jpg
(A) Isoleucine
(B) Ile
(C) I
(D) All of these represent this amino acid
(E) Either {A},{B}, or {C}represent this amino acid.



18.18. In humans, most steroids function as:
(A) Enzymes
(B) Hormones
(C) Nucleic acids
(D) Proteins
(E) Saccharides.


19.

19. What is the IUPAC name of the following compound? 5d5654ed0016e.jpg
(A) (2S,4R)-Dimethylpentanal
(B) (2S,4S)-Dimethylpentanal
(C) (R)-2,4-Dimethylpentanal
(D) (S)-2,4-Dimethylpentanal
(E) (2R,4R)-Dimethlypentanal.



20.

20. How many E configuration are there in the following compounds? 5d565508eb00e.jpg
(A) 1
(B) 2
(C) 3
(D) 4
(E) 5



21.21. If silver nitrate is converted into silver nanoparticles, the most possible process for such a conversion is?
(A) Exposure to oxygen
(B) Exposure to heat
(C) Exposure to water
(D) Exposure to alcohol compound
(E) Exposure to acid compound.


22.22. A compound with the following molecular formula contains two double bonds. What is the correct subscript for H in the formula? C10H?ClN2O
(A) 19
(B) 22
(C) 18
(D) 20
(E) 21


23.23. When butane undergoes free radical bromination, the product mixture contains 98% 2-bromobutane and 2% 1-bromobutane. How many times more susceptible to hydrogen atom abstraction is a secondary hydrogen in butane than is a primary hydrogen?
(A) 100
(B) 73.5
(C) 50
(D) 8.7
(E) 1.5


24.24. Which of the following is not a property of a protecting group?
(A) Change the reactivity of a functional group
(B) Inert to reaction conditions
(C) Becomes a permanent part of the product
(D) Alters the mechanism of the desired reaction
(E) All of these are properties of a protecting group.


25.

25. Which of the following carbonyl groups exhibits the highest wavenumber in infrared spectroscopy?
(A) 5d5655286b1e2.jpg
(B) 5d5655391412d.jpg
(C) 5d56554824b11.jpg
(D) 5d565557a7995.jpg
(E) 5d565568114b2.jpg



26.

26. Compound X has the molecular formula C10H12O. The IR spectrum of X has a strong band near 1710 cm-1. Compound X forms a phenylhydrazone, but gives a negative Tollens’ test and a positive iodoform test. What is the structure of the compound X?
(A) 5d5655924ca85.jpg
(B) 5d5655a808a02.jpg
(C) 5d5655b9c0cb5.jpg
(D) 5d5655cce36a4.jpg
(E) 5d5655dd2dbff.jpg



27.27. For the mass spectrum of compound Y, we found 3 lines in the molecular ion region (M+ , M+ +2, M+ +4), shows the peak heights in the ratio of 9 : 6 : 1. What would the compound Y be?
(A) cis-1,2-Dichlorocyclohexane
(B) 2-Chloropentane
(C) cis-1,2-Dibromocyclohexane
(D) Bromobenzene
(E) 1,2-Dibromopentane.


28.28. Which of the following would not produce nuclear magnetic resonance?
(A) 2 H
(B) 14N
(C) 16O
(D) 19F
(E) 11


29.

29. Which compounds have 3 signals in the 13C NMR spectrum? 5d56563222f56.jpg
(A) I, II
(B) III, IV
(C) I, II, III
(D) I, III, IV
(E) I, II, III, IV



30.

30. Using a 300 MHz 1 H NMR instrument, if a H shows a triplet at δ 4.02, 4.00, 3.98 ppm, please calculate it’s coupling constant. And where will this triplet peak shows up at a 600 MHz 1 H NMR instrument?
(A) 6 Hz; δ: 4.01, 4.00, 3.99 ppm
(B) 6 Hz;δ: 4.02, 4.00, 3.98 ppm
(C) 6 Hz; δ: δ: 4.00, 3.98, 3.96 ppm
(D) 2 Hz; δ: 4.02, 4.00, 3.98 ppm
(E) 2 Hz; δ: 4.00, 3.98, 3.96 ppm.



31.

31. Consider the reaction below, how many pairs of electrons are involved in this pericyclic reaction? 5d56569526ea6.jpg
(A) 2
(B) 4
(C) 8
(D) 16
(E) 10



32.32. Which of the following reaction types are pericyclic reactions?
(A) Diels-Alder reaction
(B) Cope rearrangement
(C) Claisen rearrangement
(D) Stork reaction
(E) All except {D}are pericyclic reactions.


33.

33. What is the order of decreasing reactivity towards nucleophilic acyl substitution for the carboxylic acid derivatives? (most reactive first) 5d5656c6cce62.jpg
(A) I, III, II, IV
(B) II, III, I, IV
(C) III, II, I, IV
(D) IV, I, III, II
(E) IV, III, I, II



34.

34. Consider the elimination reaction: 2-bromohexane was treated with sodium methoxide in methanol. The product(s) of the reaction is(are):
(A) 5d5656e7bc749.jpg
(B) 5d5656fd1cccb.jpg
(C) An equimolar mixture of {A} and{B}
(D) A mixture of the major product {A}with the minor product {B}
(E) A mixture of the major product{B} with the minor product{A}.



35.

35. To answer the following question, consider the reaction below: 5d56578183284.jpg The dehydration of alcohol by reaction with POCl3 in pyridine is an example of:
(A) E1 process
(B) SN1 process
(C) E2 process
(D) SN2 process
(E) None of above.



36.

36. Which is addition reaction in the following reactions?
(A) 5d5657b74ee3f.jpg
(B) 5d5657c658668.jpg 
(C) 5d5657e022e54.jpg
(D) 5d56580aa4ec2.jpg
(E) 5d56583b466dd.jpg



37.

37. Which of the following substrates will not form a Grignard reagent when treated with Mg/diethyl ether?
(A) 5d565854bfd17.jpg
(B) 5d565862f0771.jpg
(C) 5d56587301378.jpg
(D) 5d5658849d1e0.jpg
(E) 5d565897a82e6.jpg



38.

38. Which is the name reaction in the following reaction? 5d5658b55520e.jpg
(A) Mannich reaction
(B) McMurry reaction
(C) Wolff-Kishner reaction
(D) Dess-Martin reaction
(E) Dieckmann reaction.



39.

39. What is the major product of the following reaction? 5d5658cb85c88.jpg
(A) 5d5658dc41bae.jpg
(B) 5d5658f05ef36.jpg
(C) 5d565900dd437.jpg
(D) 5d565913804c8.jpg
(E) 5d56592629f47.jpg



40.

40. Predict the structure of the expected product for the following reaction. 5d5659656e647.jpg
(A) 5d5659729afff.jpg
(B) 5d56598318ae3.jpg
(C) 5d56599374c2f.jpg
(D) 5d5659a506e09.jpg
(E) 5d5659b5c16e6.jpg



41.

41. What product would be obtained from the following reaction? 5d5659d62eebd.jpg
(A) 5d5659e75afe5.jpg
(B) 5d5659fe43d57.jpg
(C) 5d565a1a4a809.jpg
(D) 5d565a2f77a78.jpg
(E) 5d565a42dff6d.jpg



42.

42. Which structure for the compound A (formula C5H8O) that fit the following proton NMR data? Chemical shift δ: 1.55 (singlet, 6H), 2.27 (broad singlet, 1H), 2.46 (singlet, 1H) ppm.
(A) 5d565a63e2cf6.jpg
(B) 5d565a75e43aa.jpg
(C) 5d565a869d83a.jpg
(D) 5d565a95d5ff0.jpg
(E) 5d565aa40e8ec.jpg



43.

43. Which of the following reactions is often called olefin metathesis?
(A) 5d565aca012e6.jpg
(B) 5d565ada655fd.jpg
(C) 5d565af116b9a.jpg
(D) 5d565b0594744.jpg
(E) 5d565b19c8439.jpg



44.

44. For the reaction shown below, the resulting stereochemistry of the expected product is best described as: 5d565b411302d.jpg
(A) (R, E)
(B) (S, E)
(C) (R, Z)
(D) (S, Z)
(E) only (S). 



45.

45. How would you prepare the following carbonyl compound from a nitrile? 5d565b577e2af.jpg
(A) 1) EtMgBr; 2) NaOH, H2O
(B) 1) EtMgBr; 2) LiAlH4; 3) H3O 5d565b79970a9.jpg
(C) 1) EtMgBr; 2) H2O
(D) 2) EtMgBr; 2) CO2; 3) H3O 5d565b97be3c4.jpg
(E) 1) EtMgBr; 2) PCC



46.

46. Which one is the reactant of the following reaction? 5d565bb5c49e7.jpg
(A) 5d565bc66fd2b.jpg
(B) 5d565be139bfe.jpg
(C) 5d565bf18a637.jpg
(D) 5d565c020f163.jpg
(E) 5d565c120ba87.jpg



47.

47. Which is the best reagent for following reaction? 5d565c2f51ac5.jpg
(A) PCC
(B) Jones reagent
(C) MnO2
(D) Ag2O
(E) KMnO4



48.48. An epoxide compound may undergo the ring-opening reaction with water to generate
(A) Triol
(B) Peroxide
(C) Glycol
(D) Glycol ether
(E) Ethylene oxide.


49.

49. Show how you might use an annulation reaction to synthesize the following compound. Draw the structure of final product. 5d565c567c2ed.jpg
(A) 5d565c6b7cd3d.jpg
(B) 5d565c7ddcac4.jpg
(C) 5d565cad66712.jpg
(D) 5d565cc47a18b.jpg
(E) 5d565cd79ac35.jpg



50.50. Which of the following ethers can’t be prepared by a Williamson ether synthesis?
(A) t-Butyl phenyl ether
(B) Isopropyl methyl ether
(C) Anisole
(D) t-Butyl methyl ether
(E) None of the above.


51.

51. Which of the following reagents is suitable for the following transformation? 5d565d061dd87.jpg
(A) I
(B) II
(C) III
(D) I, II
(E) II, III



52.

52. What product would be obtained from the following reaction? 5d565d1d7f536.jpg
(A) 5d565d3b849e9.jpg
(B) 5d565d4e1ee01.jpg
(C) 5d565d5d1ff46.jpg
(D) 5d565d6d56045.jpg
(E) 5d565d7f56d21.jpg



53.

53. What is the product of this reaction? 5d565e22861ac.jpg
(A) 5d565e32ad201.jpg
(B) 5d565e44ac743.jpg
(C) 5d565e57b5324.jpg
(D) 5d565e6a88047.jpg
(E) 5d565e7c9e98f.jpg



54.

54. What is the major product would you obtain for the following reaction? 5d565ea01f9b3.jpg
(A) 5d565eb362d22.jpg 
(B) 5d565ed4e76b4.jpg
(C) 5d565ee73818c.jpg
(D) 5d565ef9f0f3b.jpg
(E) None of the above.



55.

55. Provide the structure of the major organic product in the reaction shown below. 5d565f1069493.jpg
(A) 5d565f22d2168.jpg
(B) 5d565f341f851.jpg
(C) 5d565f44e1913.jpg
(D) 5d565f60dcfb5.jpg
(E) 5d565f78319b8.jpg



56.

56. What product would be obtained for the following reaction? 5d565f96941df.jpg
(A) 5d565fa76c4df.jpg
(B) 5d565fb95cea6.jpg
(C) 5d565fcb06fe5.jpg
(D) 5d565fde59618.jpg
(E) 5d565ff2c5c15.jpg



57.

57. Please predict the product of the following reaction. 5d56601b205cc.jpg
(A) 5d566029d2a55.jpg
(B) 5d56603e4a3e9.jpg
(C) 5d56604e1c0c6.jpg
(D) 5d56606540eaf.jpg
(E) 5d566076096f3.jpg



58.

58. Mescaline is a hallucinogenic alkaloid isolated from peyote cactus. Synthesize mescaline from 3,4,5-trimethoxytoluene. Show all reagents toward the target compound. 5d56609380e1e.jpg
(A) 1) NBS; 2) NaCN; 3) LiAlH4
(B) 1) n-BuLi; 2) BrCH2NH2
(C) 1) Br2; 2) LiCH2CN
(D) 1) light; 2) BrCH2NH2
(E) 1) NBS; 2) LiCH2NH2



59.

59. Which set of reagents will best convert 2,2-dimethylpropan-1-ol to 4,4-dimethylpentan-2-ol?
(A) 1) HCl, ZnCl2; 2) 2 eq. Mg; 3) CH2O; H3O 5d5660f35f1a2.jpg
(B) 1) SOCl2; 2) 2 eq. Mg; 3) MeCHO; H3O 5d5661214ee7e.jpg
(C) 1) SOCl2; 2) 2eq. Mg; 3) CH2O; H3O 5d56613b98fc5.jpg
(D) 1) HCl, ZnCl2; 2) 1 eq. Mg; 3) CH2O; H3O 5d56615b08cf8.jpg
(E) 1) HCl; 2) 1 eq. Mg; 3) MeCHO; H3O  5d5661754a39a.jpg



60.

60. Compound A can make Br2/CCl4 become colorless. What is the structure of compound B? 5d5661acbbd12.jpg 
(A) 5d5661c291007.jpg
(B) 5d5661d66a66b.jpg
(C) 5d5661e8870e3.jpg
(D) 5d5661fcd4eac.jpg
(E) 5d566219d5fa9.jpg 



61.

61. The reaction of Cl2 with a methyl radical has a positive ∆H°. Which of these drawings is the best representation of the transition state of this reaction?
(A) 5d56624aa24f5.jpg
(B) 5d566268c7a76.jpg
(C) 5d5662771edf5.jpg
(D) 5d56628acced3.jpg
(E) 5d5662a1e15f2.jpg



62.

62. Which structure corresponds to the trimer of Me2C=CH2 formed under condition of cationic polymerization?
(A) 5d5662c964ba2.jpg
(B) 5d5662dde959a.jpg
(C) 5d5663063d6ec.jpg
(D) 5d56631cb2c50.jpg
(E) 5d56632f5b193.jpg



63.

63. Remove a proton from the following structure to create the most reactive (least stable) carbanion.
(A) 5d5663557df2b.jpg
(B) 5d56636553c06.jpg
(C) 5d56637da8864.jpg
(D) 5d5663cc68d58.jpg
(E) 5d5663e3c42cd.jpg



64.

64. The carbon marked by a dot (•) is 13C isotope. Which structure below shows the correct position of the 13C in the product for the carbocation rearrangement shown above? 5d5664120ade7.jpg
(A) 5d56642a23ad7.jpg
(B) 5d566450bcb30.jpg
(C) 5d56646344a4f.jpg
(D) 5d56647d6325c.jpg
(E) 5d56649279af2.jpg



65.

65. Choose substituents X and Y (listed in order below) for the following compound so as to make a Z isomer. 5d5664b7995a8.jpg
(A) 5d5664e943c75.jpg
(B) 5d5664faa4941.jpg
(C) 5d5665101acc6.jpg
(D) 5d566552360a4.jpg
(E) 5d56656c96b95.jpg



66.66. Rank the degree of unsaturation in each of the following compounds. I. Cholesterol , C27H46O II. DDT, C14H9Cl5 III. Prostaglandin E1, C20H34O5 IV. Caffeine , C8H10N4O2
(A) I > III > II > IV
(B) II > IV > I > III
(C) I > II > III > IV
(D) II > IV > III > I
(E) I > IV > II > III


67.

67. This cyclic carbocation has two sets of degenerate pi-molecular orbitals. Choose the correct order MO, s energies for this system? 5d5665d67a6ad.jpg
(A) V = I < IV < III = II
(B) V < IV = II < I = III
(C) III = II < I = IV < V
(D) III = IV < II < I = V
(E) V < I = IV < II = III



68.

68. What product would be obtained for the following reaction? 5d5665f61ed06.jpg.
(A) 5d566615cb413.jpg
(B) 5d566626da4e1.jpg
(C) 5d566638a046a.jpg
(D) 5d56664a5a76a.jpg
(E)None of the above



69.

69. When 1-methyl-1-cyclohexene is respectively treated with the following reagent set, which will give the same product? 5d5666762b417.jpg
(A) II, V
(B) III, IV
(C) II, III, V
(D) I, V
(E) I, III



70.

70. Predict the outcome of the following sequence of reactions. 5d56668d9cb32.jpg
(A) 5d5666a42e099.jpg
(B) 5d5666b618d12.jpg
(C) 5d5666c817f9a.jpg
(D) 5d5666da01f7c.jpg
(E) 5d5666eb6f6d2.jpg



71.

71. The following substrate is a starting material in the synthesis of compounds having opioid activity. Show all products that would result from the reaction below. 5d56670ac397c.jpg
(A) I, II, III
(B) I, III, IV
(C) I, III, V
(D) II, III, IV
(E) II, IV, V



72.

72. Predict the structure of the hydrolysis product. 5d56672427555.jpg
(A) 5d566736a7631.jpg
(B) 5d56674821cc3.jpg
(C) 5d56675d06df6.jpg
(D) 5d566774f1fd7.jpg
(E) 5d566787cba1a.jpg



73.

73. In order to synthesize the final product shown below, predict when should a protecting group be added and when should it be removed? 5d5667a9c9384.jpg
(A) The hydroxyl group should be protected before step I and removed after step I
(B) The hydroxyl group should be protected before step I and removed after step II
(C) The hydroxyl group should be protected before step I and removed after step III
(D) The hydroxyl group should be protected before step II and removed after step III
(E) There is no need for a protecting group in this synthesis.



74.

74. Which of the following Diels-Alder reactions has the largest reaction rate constant?
(A) 5d5667c3e33d3.jpg
(B) 5d5667d12fbdb.jpg
(C) 5d5667e7a89be.jpg
(D) 5d5667f99ddc9.jpg
(E) 5d56680b9dc72.jpg



75.

75. What is the product of this reaction? ? 5d56682b6f2f0.jpg
(A) 5d566839f1bd5.jpg
(B) 5d56684f8f55b.jpg
(C) 5d566860af2e5.jpg
(D) 5d5668724d974.jpg
(E) 5d5668825c390.jpg



76.

76. What is the major product obtained from the following reaction sequence? 5d56689e87139.jpg
(A) 5d5668b03e029.jpg
(B) 5d5668c290438.jpg
(C) 5d5668d330398.jpg
(D) 5d5668e4a3887.jpg
(E) 5d5668f4b29ba.jpg



77.

77. What is the major product of the following reaction? 5d566914176b2.jpg
(A) 5d5669264cefa.jpg
(B) 5d566936cc60d.jpg
(C) 5d566947f30f1.jpg
(D) 5d56695be4ca5.jpg
(E) 5d56696bbebb8.jpg



78.

78. Which of the following reactions is called Gabriel synthesis?
(A) 5d566988e3ee4.jpg
(B) 5d566999eec33.jpg
(C) 5d5669af4783b.jpg
(D) 5d5669c8ec1fd.jpg
(E) None of the above.



79.

79. What is the major product of the following triene to undergo the intramolecular Diels-Alder reaction? 5d5669ebf1cb1.jpg
(A) 5d5669ff25551.jpg
(B) 5d566a0f779d7.jpg
(C) 5d566a22b0879.jpg 
(D) 5d566a3a76591.jpg
(E) 5d566a4a42fb6.jpg



80.

80. The following reaction involves an intramolecular Michael reaction followed by an intramolecular aldol reaction. What is the major product of this reaction? 5d566a6e00d8e.jpg
(A) 5d566a80266aa.jpg
(B) 5d566a92d1aea.jpg
(C) 5d566acd766a8.jpg
(D) 5d566ae82a619.jpg
(E) 5d566b02d7b9a.jpg



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23.〈陋室銘〉與〈座右銘〉相比較,下列敘述何者有誤? (A)「銘」是文體之一,主要用途是記訓誡或頌功德 (B)陋室銘在激勵後輩子孫,座右銘用來...

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105 年 - 105 學士後西醫:有機化學#78642-阿摩線上測驗

105 年 - 105 學士後西醫:有機化學#78642