110年 - 110 國立臺灣大學_碩士班招生考試_化學研究所化學組:有機無機#102186

選擇題 (20)

1. What is the major product of the following reaction sequence? (2 pts) (A) (B)(C) (D) (E)

2. In the following sequence of reactions, Which of butene isomers contain(s) NO deuterium? (2 pts) (A) cis-2-butene (B) trans-2-butene (C) cis-2-butene and trans-2-butene (D) 1-butene (E) None of the above

3. Which compounds are named correctly? (2 pts) (A)Ⅰ,Ⅱ,Ⅲ；(B) Ⅳ,V,VI； (C)Ⅱ,IV,V； (D)Ⅲ,IV,VI； (E)VI,I,V.

4. Which ofthe following compound(s) would undergo racemization in the presence of base? (2 pts) (A)(B) (C) (D) (E)

5. A pyranose form is a cyclic hemiacetal with a six-membered ring. Which of the following compounds cannot exist in a pyranose form? (2 pts) (A) (B) (C) (D)(E)

6. Which of the compound can produce a secondary amine with the treatment of LiAIH4 in diethyl ether followed by H₂O? (2 pts)(A) (B)(C) (D) (E)

複選題

7. Based on the low-resolution proton NMR spectrum of a particular compound shown at the right, which of the following is(are) true? (2 pts)
I. There are at least three different types of protons in this compound.
Il. There are more protons of the type cotresponding to peak 3 than the type corresponding to peak 1. III. Protons of the type corresponding to peak 2 are more
shielded than those corresponding to peak l.
(A) I only (B) II only (C) III only (D) I and II only (E) I, II, and III.

8.Which of the following is the strongest base? (2 pts)(A)(B)(C)(D)(E)

9. Which of the following is a suitable synthesis of o-methylphenol? (2 pts)(A)(B)(C)(D)(E)

10. Which is the major product of the following reaction? (2 pts)
(A)C₆H₅OH (B)(C)(D)(E)

11. The following compound has four aromatic rings. Rank them in terms of increasing reactivity toward electrophilic aromatic substitution. (2 pts)
(A)D

12. Which is the order of increasing bond stretching frequency (lowest first)? (2 pts)
I) C=N； Ⅱ) C=O； Ⅲ) C=C； IV)C=S (A) II, I, IV, III； (B) I, II, IV, Ⅲ；(C) Ⅲ, I, Ⅱ, IV； (D) TV, II, I, T； (E) Ⅲ, TV, I, Ⅱ.

13. Which diene can be used to prepare the following product by alkene metathesis? (2 pts)
(A)(B)(C)(D)(E)

14. Grignard reagent does NOT react with (2 pts) (A) I-methoxycyclohexene (B) 1-butyne (C) cyclohexanol(D) cyclohexanone (E) 2-ethyloxirane

複選題

15. On the basis of molecular orbital theory and Huckel's rule, which molecules and/or ions should be aromatic? (2 pts)
(A)I and V (B) III and VIII (C) IV, VII and IX (D)IV, VI, VII and IX (E) II and IV

16. How many of the following statement(s) about the term symbol of a d: system is(are) cortect? (3 pts)
(a) The total number of microstates of the d²system is 45.
(b) The maximum M_Lnumber is 4.
(c) The minimumM_L number is 0.
(d) The maximum M_s number is 2.
(e) The minimum M_s number is 0.
(f) ¹G₄ is a ground state.
(g) ¹S₀ has the highest energy.
(h) The ³P term can be further split into ³P₄, ³P₃, and ³P₂.
(i) The ³F term can be further split into ³F₄, ³F₃, and ³F₂.
(j) The ³F term contains 21 microstates. (A)4 (B)5 (C)6 (D)7 (E)8

17. Which of the following descriptions about the acid-base chemistry in an aqueous solution is correct? (3 pts) (A) 0. 1 M of HBr is a weaker acid than 0.15 M of H3O⁺ (B) 0.1 M of HBr has a higher pH value than 0.05 M of HI (C) 0.1 M of CH₃COOH is a stronger acid than 0.15 M of H₃O⁺ (D)0.1 M of CH COOH has a lower pH value than 0.05 M of HI (E) None of the above.

18. How many of the following point groups do NOT have an inversion center? (3 pts) (a) C_I (b) C_i, (c) C₂ (d) (e) (f) S₆ (g) S₈ (h)I_h K (i) O(j)O_h (A)4(B)5 (C)6(D)7 (E)8

19. The anion shows only a single '9F NMR peak over a wide temperature range (ignoring coupling to ). Which geometry is consistent with this data? (3 pts) (A) Trigonal bipyramidal (B) square pyramidal (C) pentagonal planar (D) cubic (E) None of the above

20. How many of the following statement(s) about characterization techniques is(are) correct? (3 pts) (a) Paramagnetic compounds can be characterized by EPR (ESR).
(b) Powder samples cannot generate diffraction patterns while using X-ray as the light source.
(c) To determine protein structures via cryoEM crystalline materials are required.
(d) Infrared spectroscopy is a useful tool to determine bond strengths of organic functional groups. (e) All NMR active compounds do not have unpaired electron(s).
(f) X-ray photoelectron spectroscopy (XPS) is a surface-se sensitive quantitative spectroscopic technique.
(g) X-ray absorption spectroscopy (XAS) can be used to determine the oxidation state of metal complexes. (A)6 (B) 5 (C) 4 (D) 3 (E) 2

申論題 (9)

第二大題:問答題(共55分)
Part II: Questions and Answers (Please provide an adequate answer to each of the following questions; Total 55 points)
21. Provide a mechanism for the following transformation. Please show all arrow pushing. (6 pts)

22. Provide a synthesis that will selectively convert S to T. Show all of the key intermediates and furnish all of the important reagents. Hint: This is not a one-step process. (8 pts)

23. Consider both regioselectivity and stereosclectivity to predict the products for the eliminations below, and draw complete mechanisms. (6 pts)

24. What are the advantages and disadvantages of the following bonding theory? (Please use specific examples to support your answers) (10 pts) (a) VSEPR Theory, (b) Valence Bond Theory, (c) Molecular Orbital Theory

25. Explain the following terms (Total 10 pts; 2 pts each): (a) turnover frequency, (b) turnover number, (c) selectivity, (d) catalyst, and (e) catalytic cycle

(a) What would you call this reaction? (1 pt)

(b) What is the d-orbital splitting diagram of complex a and complex b. (Please label each orbital) (2 pts)

(c) Provide a detailed description of the electronic structures of complex b? (You should include oxidation state, number of unpaired electrons and spin state, ctc.) (2 pts)

(d) What characterization technique(s) would you use to prove your assignment about the electronic structure of complex b in question (c). (Please include a detailed explanation in your answer) (10 pts)

110年 - 110 國立臺灣大學_碩士班招生考試_化學研究所化學組:有機無機#102186

試卷資訊

選擇題 (20)

申論題 (9)