112年 - [非官方正解]112 國立中山大學碩士暨碩士專班招生考試_化學系碩士班:有機化學及無機化學#119263

2. Rank the following molecules in order of increasing relative rate of S_N1solvolysis with methanol and heat (slowest to fastest reacting).(A) 3＜2＜4＜5＜1 (B) 2＜3＜4＜1＜5 (C) 5＜4＜3＜2＜1 (D) 2＜3＜4＜5＜1 (E) l＜2＜5＜4＜3

4. Rank the following compounds in order of increasing reactivity towards chlorination with CI₂/AICI₃ (slowest reacting to fastest). (A) 3＜4＜2＜1＜5(B) 2＜4＜1＜3＜5 (C) 4＜2＜1＜3＜5 (D) 2＜4＜5＜1＜3 (E) 2＜4＜1＜5＜3

5. Which of the following structures, if flat, would be classified as antiaromatic? (A)(B)(C)(D)(E)

9. Predict the major product fbr the following reaction. (A)(B)(C)(D)(E)

11. Which one of these alkene would be likely to experience a carbocation rearrangement when treated with aqueous acid? (A)(B)(C)(D)(E) None of these would undergo a rearrangement

12. What is the complete systematic IUPAC name for the following compound?(A) (S)-4-ethyl-4-isopropoxycyclopent-2-en-1 -one(B) (R)-4-ethyl-4-isopropoxycyclopent-2-en-l -one (C) (S)-3-ethyl-3-isopropoxycyclopent-4-en-l-one (D)(R)-3-ethyl-3-isopropoxycyclopent-4-en-l-one (E) (R)- 4-isopropoxy-4-ethyl-cyclopent-2-en-l-one

13. Which of the following is the best Michael acceptor? (A)(B) (C)(D)(E)

14. Provide the major organic product of the reaction below. (A) (B)(C)(D) (E)

15. Provide the structure of the major organic product of the reaction below. (A)(B) (C)(D)(E)

16. Provide the structure of the major organic product in the reaction below. (A)(B)(C)(D)(E)

17. Which position of the molecule shown below is most likely to undergo a Friedel-Craft acylation? (A)(B)(C)(D)(E)

18. What would be the resulting product when (3R, 4S)-3,4-dimethylhexa-1,5-diene (shown below) is heated? (A) (±)-3,4-dimethyl-1,5-hexadiene(B) (3S,4R)-3,4-dimethylhexa-1,5-diene (C) (2E, 6E)-octa-2,6-diene(D) (2Z, 6Z)-octa-2,6-diene(E)(2Z, 6E)-octa-2,6-diene

22. How many π bonds does an O₂ molecule have?(A)0(B)1(C)2(D)3(E)4

30. In H2O, the wave functionrepresents the group orbital that is highest in energy, where c c2, and c3 are normalized coefficients, c¹ + c² + c³ = (A)0(B)1 (C) 2(D)3(E)4

32. The magnetic moment (in μB)of [Co(H₂O)₆]³⁺ = (A)0 (B) 1.4 (C) 1.7(D)2 (E)none of the above

36. Wliich of the following is true for tetrahedral [FeCI₄]^-? (A) it is diamagnetic (B) its magnetic moment = 1.7 μB (C) there are MLCT bands in its UV-vis spectrum(D) its spin multiplicity = 4 (E) d-d transitions are spin forbidden

a)

b)

c)

d)

2. Design a synthesis of Compound G from Compound F (more than one step is required)? (4%)

(a)

(b)