課程名稱︰有機化學 課程性質︰醫學系必修 課程教師︰陸天堯 開課學院： 開課系所︰ 考試日期（年月日）︰2011/06/23 考試時限（分鐘）：110 是否需發放獎勵金：是 感謝 （如未明確表示，則不予發放） 試題 : 上接 PART2 #1E1q6vFP 18. Which of the following compounds would be consistent with 1H NMR spectrum shown below? (Ratio of peak areas; a:b:c:d:e=2:2:2:3:3) (補註: Number of splitting; a=2, b=2, c=4, d=1, e=3) ┌───────────────────────────────────┐ │ │ｄ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ │ ｅ │ │ │ │ │ │ │ │ │ ａ ｂ ｃ │　 │ │ │ │ │ │ │ ││ │ │ │ │ │ ││ │ │ │ │ ├──-┴┴───────────────────┴-┴───┴─────┤ ├-------┬-------┬-------┬-------┬-------┬-------┬-------┬-------┤ ８ ７　 　　６ 　　　５　 　　４　 　　３　 　　２　 　　１　 　　０ (A) propylbenzene (B) 1-ethyl-4-methylbenzene (C) isopropylbenzene (D) 1,3,5-trimethylbenzene (E) 1,2,5-trimethylbenzene (本來應該是結構圖的 @.@ 可是畫起來真的太累了 Orz) 19. Which of the following compounds shows four peaks in the 13C NMR spectrum? (A) 1,4-diethylbenzene (B) 1,3-diethylbenzene (C) 1,2-diethylbenzene (D) butylbenzene (E) 1-methyl-4-propylbenzene 20. Which of the molecule below has a significant absorption band in the IR spectrum at 3400 cm^(-1) (strong and broad)? (A) CH3CO2CH2CH3 (B) CH3C≡CCH2CH3 (C) CH3CH2CH2CHO (D) (CH3)3N (E) CH3CH2CH2OH 21. 此題為IR spectrum和1H NMR spectrum混合的考題...沒能畫了... 22. Which of the following protons (indicated with subscripts a-e) would have the largest pKa value? Ｏ　Ｏ Hd ∥ ∥ 　　　 ╲╱╲╱╲╱╲╱╲ ∣○∣ ╱╲ ∣ Ha ╱╲╱ H Hc Hb He (A) Ha (B) Hb (C) Hc (D) Hd (E) He 23. How many of the following reactions would give indicated product? Ｏ NH2 ∥ NH2 I ╱╲╱ ╱╲ 1. HCl, H2O ╱╲╱ ∣○∣ 　　 Cl HNO3, H2SO4 2. HO- ∣○∣ ╲╱ ────＞ ──────＞ ──────＞ ╱╲╱ O2N ╱╲╱╲ ╱╲╱╲ II ∥ ＋ NH2CH3 ────＞ ∥ Ｏ Ｎ　 　　　　　 　　　　　　　　　　　　　　　　　 ╲ Ｏ HＮCH3 ∥ ∣ III ╱╲　　　　　　　　　　　　 Ni/Al ╱╲ 　 ∣○∣ ＋ NH2CH3 ────＞ ────＞ ∣○∣ ╲╱ ╲╱ Ｏ Ｏ IV ∥ HCl ∥ + - ╱╲ ╱ ＋ H2O ────＞ ╱╲ ＋ (CH3)2NH2Cl Ｎ OH ∣ ＮCH2CH3 Ｏ V ∥ HCl ∥ + - ╱╲ ＋ H2O ────＞ ╱╲ ＋ CH3CH2NH3Cl OH (A) 1 (B) 2 (C) 3 (D) 4 (E) 5 24. Which of the following benzaldehydes would react with aniline to give an imine most rapidly? (A) 4-methoxybenzenecarbaldehyde (B) 4-nitrobenzenecarbaldehyde (C) 4-fluorobenzenecarbaldehyde (D) 4-chlorobenzenecarbaldehyde (E) 4-methylbenzenecarbaldehyde 25. Which of the following statements concerning acid catalyzed hydrolysis of ethyl acetate is FALSE? Ｏ Ｏ ∥ H+ ∥ ╱╲ ＋ H2O ────＞ ╱╲ ＋ CH3CH2OH H3C OCH2CH3 H3C OH (A) A tetrahedral intermediate is involved in the overall reaction. 18 18 (B) When H2 O is used, the product acetic acid would contain all the O isotope. (C) In the first step, protonation on the carbonyl oxygen would occur. (D) The hydrolysis of an ester can also be carried out with aqueous base (e.g. NaOH in H2O). 18 18 (E) When the oxygen of the carbonyl group is labeled with O, the O would be found in alcohol. ~~~~ THE END ~~~~ --

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