110年 - 110台灣聯合大學系統_碩士班招生考試_化學類:有機化學#104934

1. Which of the following amines is the most basic? (A) aniline (B) N-methylaniline (C) .N,N-dimethylaniline (D) piperidine (E) pyrrole

2. Physostigmine is used in the treatment of glaucoma. Within this structure, the atom indicated by is most basic, while atom is least basic.

(A) 1 (most basic), 4 (least basic) (B) 1 (most basic), 3 (least basic) (C) 2 (most basic), 4 (least basic) (D) 2 (most basic), 3 (least basic) (E) None of the above.

3. Which of the following reactive intermediates can best be described as both a nucleophile and a electrophile? (A) Carbanions (B) Carbocations (C) Carbenes (D) Free radicals (E) Alkanes.

4. Are the compounds shown below best described as? (A) Cis-trans isomers (B) Constitutional isomers (C) Not isomers (D) Geometrical isomers (E) None of the above.

複選題
5. Which of the following reagents can be used to prepare epoxide from alkenes? (A) Formic acid in water (B) Peroxyformic acid in water (C) mCPBA in methylene chloride (D) Peroxybenzoic acid in sodium hydroxide (E) Peroxyacetic acid in water

6. Which of the following configurations corresponds to the structure below? (A) (4E,52) (B) (4S, 5R) (C) (4S, 5S) (D) (4R, 5S) (E) (4R, 5R).

7. Which of the following compounds is meso? (A)(B)(C)(D)(E)

8. Rank each of the following compounds in order of increasing heat of hydrogenation. 1,2-hexadiene

A, 2-hexyne B, trans-1,4-hexadiene C, 1,5-hexadiene D, and trans-2,4-hexadiene E. (A)E＜C＜D＜B＜A (B)E＜D＜C＜B＜A (C)E＜B＜C＜D＜A (D)C＜B＜E＜A＜D (E) D＜B＜E＜A＜C

9. For same or similar molecular weight of following compounds, which one has the highest boiling point? (A) acids (B) alcohols (C) esters (D) (E) nitriles.

10. The acetoacetic ester synthesis is used to prepare? (A) alkylated acetic acid (B) substituted acetone (C) acetoacetic acid (D) malonic ester (E) none of the above.

11. Which of the following compounds are chiral?

(A) I only (B) II and III (C) III and IV (D) V only (E) I and IV.

12. Which of the following solvents could be described as polar protic? (I) ethanol, (II) acetonitrile, (III) dimethylformamide, (IV) THF, and (V) diethyl ether. (A) I only (B) II and III (C) III only (D) I and Ill (E) III and V.

13. Rank the following species in order of decreasing acid-dissociation constant (Ka): methanol (I), ethanol (I), 2-chloroethanol (III), t-butyl alcohol (IV), and phenol (V). (A) V＞IV＞III＞II＞I (B) V＞ III＞I＞II＞IV (C) III＞V＞I＞IV＞II (D) V＞I＞III＞II＞IV (E) III＞IV＞V＞II＞I.

14. Which of the following statements about the heats of combustion of acetylene, ethene, and ethane is incorrect ? (A) Acetylene is the best high-temperature flame. (B) Ethene produced the most heat per mole of gas consumed. (C) Acetylene produced the most heat per mole of products formed. (D) The oxyacetylene flame reaches temperatures as high as 2800 ℃. (E) Acetylene release the most heat per mole of gas consumed.

15. Which of the following statements about Lucas test is correct? (A) The reagent composed of HCl and Znl₂ (B) Tertiary alcohols react faster than primary alcohol (C) Primary alcohols react by the mechanism (D) Primary alcohols react faster than tertiary alcohols. (E) Tertiary alcobols react by the mechanism.

16. Which of the species below is/are more basic than acetylide?

(I) CH₃Li, (II) CH₃ONa, (III) CH；MgBr, (IV) NaOH, (V) KOH. (A)I only (B) II only (C) III only (D) I and II (E) II and IV.

17. Arrange the following compounds in order of increasing acidity (i.e., least acidic first). (A) III, I, II, V, IV (B) I, II, III, IV, V (C) V, IV, III, II, I (D) V, IV, II, I. III (E) I, IV, II, III, V

18. Which of the following compound(s) would be expected to show a sharp and strong IR absorption peak at ?

(I) CH₃C= CCH₃, (II) butane, (III) but-1-ene, (TV) CH₃CH₂C = CH, (V) butan-1-01

(A) I and III (B) III only (C) IV only (D) IV and v (E) I, IV, and V.

19. Which of the following acid derivatives has the highest IR stretching frequency for carbonyl group? (A) y-butyrolactone (B) P-propiolactam (C) 8-valerolactone (D) y-butyrolactam (E) nitrile.

20. What splitting pattern is observed in the proton NMR spectrum for the underlined hydrogens? CH₃OCH₂CH₂OCH₃ (A) Singlet (B) Doublet (C) Triplet (D) Quartet (E) Septet.

21. Please identify the product that is obtained when (R)-2-bromobutane reacts with a hydroxide ion. (A)(B)(C)(D)(E)

22. Please identify the major E2 elimination product of the following compound. t-Bu (A)(B)(C)(D)(E)

23. Which of the following compounds is less reactive toward an E2 process? And if it reacts, what is the structure of its E2 product? (A) neomenthyl chloride； (B) neomenthyl chloride； (C) menthyl chloride； (D) menthyl chloride； (E) Both compounds cannot undergo an E2 reaction.

24. Identify reagents that you could use to achieve the following transformation.

(A) Na, NH₃； H₂O (B) NaNH₂；H₂O (C) F₃CCO₂H (D) O₃； H₂O(E) disiamylborane； H₂O₂, NaOH

25. The following reaction produces one major product via an iodolactonization. Sodium bicarbonat acts as a mild base to deprotonate the carboxylic acid group. Identify the major product of this reaction. (A)(B)(C)(D)(E)

26. Identify the major product of the following reaction. (A)(B)(C)(D)(E)

27. Indicate the side product of the following transformation. (A) CO (B) CO₂ -OH (C)CO₂ (D) CH OH (E) H₂O

28. Which naturally occurring amino acid is achiral? (A) glycine (B) alanine (D) leucine (C) proline

29. Identify the major product of the following reaction. (A)(B)(C)(D)(E)

30. Identify the major product of the following reaction. (A)(B)(C)(D)(E)

31. What is the final product of this sequence of reactions? (A)(B)(C)(D)(E)

32. Which compound reacts most rapidly with CH₃ONa? (A) (B) (C) (D)(E)

33. Identify the major product of the following reaction. (A) (B)(C) (D)(E)

34. What is the final product of the following reaction sequence? (A)(B)(C)(D)(E)

35. What is the final product of this sequence of reactions? (A)(B)(C)(D)(E)

36. Identify the product of the Dieckmann condensation of the diester. (A) (B) (C) (D) (E)

37. Identify the major product of the following reaction. (A) (B) (C)(D) (E)

38. Identify a reagent that you could use to achieve the following transformation. reagent? (A) MnO₂ (B) RCO₃H (C) H₂O (D) KOH (E) Pd(OAc)₂

39. Identify the major product of the following reaction. (A)(B)(C)(D)(E)

40. Identify reagent(s) that you could use most effectively to achieve the transformation. reagent? t (A) K₂CO₃ (B) LDA (C) pyridine (D) CH₃Li (E) CH₃OTs

41. In the reaction of 1,3-butadiene with HBr if the reagents are allowed to react at 40℃, what would be the predominant product formed? (A) thermodynamic product (B) kinetic product (C) 4-bromo-1-butene (D) 3-bromo-1-butene (E) 1,4-addition product.

複選題
42. In the nitration of a 1:1 mixture of benzene and toluene, which of the following statements are correct? (A) nitrobenzene will be the major product (B) more meta- than ortho-nitrotoluene is formed (C) ortho- and para-nitrotoluenes are the major products (D) dinitrobenzene is formed (E) more ortho-nitrotoluene than nitrobenzene is formed.

複選題
43. In the formylation of benzene what reagents are needed: (A) HCOCI (B) CO/HCI (C)AlCly/CuCl (D) CH₃COCL, AlCl₃ (E) all of the above.

44. Which of the following compounds would give a positive Tollen test? Remember that the Tollen test involves mild basic aqueous conditions. (A)(B)(C)(D)(E)