103年 - 103 國立成功大學_碩土班招生考試試題_化學系：有機化學#123767

1. How many ¹H NMR peaks would trans-1,2-dibromocyclopropane give? (A) 1 (B) 2 (C) 3 (D) 4

2. Arrange the following nitrogen containing compounds in the order of increasing basicity.
(A) A＜B＜E＜C＜D (B) C＜B＜E＜A＜D (C)B＜A＜C＜D＜E (D)D＜A＜B＜C＜E (5) C＜E＜B＜A＜D

3. Arrange the following compounds in the order of increasing acidity.
(A) A＜B＜E＜C＜D (B) E＜A＜B＜C＜D (C)B＜A＜D＜C＜E (D) B＜A＜E＜D＜C (5) C＜E＜B＜A＜D

4. A compound with the molecular formula C₁₀H₁₃Br gave the following ¹H NMR spectrum δ 1.6 (s, 6H), 3.1 (s, 2H), 7.2 (m, 5H). The most likely structure for this compound is (A) C₆H₅CH₂CBr(CH₃)₂ (B) C₆H₅CH₂CH₂CHBrCH₃ (C) C₆H₅C(CH₃)BrCH₂CH₃ (D) C₆H₅CHBrCH(CH₃)₂

5. What is the IUPAC name of the following compound?
(A)4-bromo 6-chloro-3-methylphenol (B)4-bromo-2-chloro-5-methylphenol (C)2-chloro-4-bromo-5-methylphenol (D)2-bromo-5-hydroxy-4-chlorotoluene

6. What is the IUPAC name of the following compound?
(A) 5-ethyl-3-methyl-1-heptene (B) 4-ethyl-2-vinylhexane (C) 3-ethyl-5-methyl-6-heptene (D) 3-ethyl-5-vinylhexane

7. What is the IUPAC name of the alkyl group?
(A) 1-propyl-4,4-dimethylpentyl (B) 4,4-dimethyl-1-propylpentyl (C) 2,2-dimethyloctyl (D) 3,3-dimethyl-1-butyl)-butyl

8. What is the major product for the addition of Cl₂ to cis-2-butene?(A) 2-chlorobutane (B) meso-2,3-dichlorobutane (C) racemic mixture of (2R,3R) and (2S,3S)-2,3-dichlorobutane(D) 1,2-dichlorobutane

9. Which statement is true for a chiral molecule?(A) The molecule has an enantiomer.(B) The molecule has a superimposable mirror image.(C) The molecule may be a meso compound.(D) The molecule is optical active.

10. Which of the following compounds can undergo Diels-Alder reaction with maleic anhydride?(A)(B)(C)(D)(E)

1. Which of the following compounds should be stabilized by resonance to a greater extent? Please account for your answer.

2. Draw the most stable conformation of the following compounds.

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