課程名稱︰有機化學一 課程性質︰化學系必修 課程教師︰羅禮強 開課學院：理 開課系所︰化學系 考試日期（年月日）︰2011/11/17 考試時限（分鐘）：110分鐘 是否需發放獎勵金：是 （如未明確表示，則不予發放） 試題 : 1. Name the following groups; (a) -OH, (b) C=O, (c) -I, (d) -NH2, (e) -CH2CH(CH3)CH3, (f) -C6H5, (g) -CH=CH2, (h) -CH2-, and (i) -CH(CH3)2 (9 points) 2. Name the following compounds, including stereochemistry. (10 points) 紅色表示突出紙面 綠色表示沒入紙面 a) ∥ b) ／╲ ╱╲╱╲／ \╴/ / \ Br Br ︿/\ ︱ c) ╱ /＼ d) ╱╲╱╲／＼ \╱＼\ ︱ ︱ HO Cl ＣH3 e) ╱╲╱╲╱ f) ╲／╲╱ g) ∕￣￣﹨ ｜ ︱ ｜ ｜ ∕ ﹨—Ｃ—CH3 ╲╱ ︳ ︳ ｜ ︳ ︳ ＣH3 ＼ ╱ ＼／ 3. Supply the curved arrows necessary for the following reactions. (5 points) .. .. - (a) Ｏ: :Ｏ: ∥ - .. ∣ .. Ｃ + :Ｏ—H ----> H—Ｃ—Ｏ—H ╱ ╲.. '' ︱ '' H Ｏ—CH3 :Ｏ '' ''＼ CH3 (b) .. H3Ｃ Ｆ Ｏ F—Ｂ—F ∣+ ∣- ╱''╲ + ｜ ----> H3C—Ｏ—Ｂ—F H3C CH3 Ｆ　　　　　　　　 '' ︱ Ｆ 4. Compound A with the molecular formula C6H12 is optically inactive but can be resolved into enantiomers. On catalytic hydrogenation, either enantiomer of A is converted to B (C6H14) and B is optically inactive. Propose structures for A and B. (4 points) 5. Which member of the following pair, cis- and trans-1,4-dimethylcyclohexane, would you expect to be more stable? Briefly describe how you could experimentally determine the relative stability of these two compounds. (6 points) 6. You are planning to purify an impure sample of benzoic acid (C6H5CO2H) that was contaminated with toluene (C6H5CH3). Propose a strategy for purifying this sample, making use of acid-base principles, using equations to further clarify your answer. (5 points) CO2H CH3 ╱╲╱ ╱╲╱ ｜○∣ ｜○∣ ＼／ ＼／ 7. Indicate the relationship of the following pairs of structures. (6 points) a) H CH3 Br H CH3 Br ╲/╱ ╲/╱ ︳ ︳ H3C╴︳ F╴︳ /＼ /＼ F H H CH3 b) H3C CH3 H3C H ﹨╴╴/╴F \╴╴/╴Br H￣/ ﹨ F￣/ \ Br H H CH3 c) ＯH ＯH ︱ ︱ ╱╲╱╲ ╱╲╱╲ d) Cl H H H \ / \ / C＝Ｃ＝C C＝Ｃ＝C 　 　/ \ / \ H Cl Cl Cl 8. Retrosynthetic analysis for the following ether shows two plausible synthetic routes, (a) and (b), via SN2 reactions. Please provide the reagents for each route. Which one would you expect to give better yield? Explain your choice. (8 points) (a) (b) H3C-︴-O-︴—＜ 　　　　　　　 9. When a pure compound C is placed in a polarimeter, the observed rotation is +4.05° The solution was prepared by diluting 2 grams of compond C to a total volume of 50 mL, and the solution was placed into a 20 cm polarimeter cell for the measurement at 589.6 nm (the sodium D line) and 25℃. Please calculate the specific rotation for compound C and express it in a correct format. (8 points) 10. Dehydrohalogenation of meso-1,2-dibromo-1,2-diphenylethane by the action of NaOEt in EtOH yields (E)-1-bromo-1,2-diphenylerhene. Provide an explanation for the result. (5 points) 11. Write a reasonable and detailed mechanism for the following transformation: (6 points) ＯH ＣH3 ｜ CH3 concd H2SO4 ｜ ╱╲╱ ------------> ╱╲ \ /╲ heat \╴/ /￣ CH3 ╱￣╲ H3C H3C CH3 12. Predict the major product(s) of the following reactions: (12 points) (a) Ｉ (b) ｜ t-BuOK NaI(1 mol) ╱╲╱╲ ---------> ╱╲╱╲╱╲ ------------> ｜ t-BuOH Cl ︱ acetone ╲ Cl (c) (d) ╴ Cl I D╴/ \╱ MeOH (S)-2-Bromoheptane -----------> \╴/╲ ---------> MeOH CH3 - CH3 (e) Cl CH3COO (f) ╱╲╱ EtONa ｜ ----------> ｜ ｜ ---------------> ╱╲╱ CH3COOH ╲／╲ EtOH Br 13. When compond X is treated with NaOEt in EtOH, it reacts rapidly; the product is W. Under the same conditions, compound Y reacts very slowly. Explain the difference in reactivity of those two isomers. (4 points) ╴ ╱ ＼ ｜ NaOEt X Br— ┼— ----------> ╲╴／ ｜ EtOH rapidly ╱＼ ╴ ∥ ｜ ╱ ＼ ｜ NaOEt ╲／╲╱ W Y Br— ┼— ----------> ／＼ ╲╴／ ｜ EtOH slowly 14. Starting with ethyne, outline syntheses of each of the following. You may use any other needed reagents, and you need not show the synthesis of compounds prepared in earlier parts of this problem. (12 points) CH3 CH3 CH3 ╴ (a) ╴/ (b) \╴╱ (c) \ /￣ ╱￣\ — C≡C—D H3C D D --

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