[試題] 101上羅禮強有機化學一期末考

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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：理學院開課系所︰化學系考試日期（年月日）︰2013/01/10 考試時限（分鐘）：130 是否需發放獎勵金：是（如未明確表示，則不予發放）試題 : ==試題中以紅色表示凸出紙面,以黃色表示沉入紙面.== 試題開始 You might need the following DH' values (in kJ/mole) for the calculation ┌───────┬───────┬───────┬───────┐ │ H-H 436 │ H-Cl 432 │ CH3-Br 293 │ CH3CH2-H 421 │ ├───────┼───────┼───────┼───────┘ │ Cl-Cl 243 │ H-Br 366 │CH3CH2-Cl 354 │ ├───────┼───────┼───────┤ │ Br-Br 193 │ CH3-Cl 352 │CH3CH2-Br 294 │ └───────┴───────┴───────┘ 1. How many signals would each compound give in its 'H NMR spectrum? (5 points) (a) (b) (c) H H (d) (e) ＿/ ＼＿ \/ ／＼／〝／ |＼／＼ △ ／＼ ║ │Ｏ│ │ O OCH3 / \ 　　Ｂr　　Ｂr /\　　　　＼／ Cl H 2. Explain in detail how you could distinguish between the following sets of compounds using NMR spectroscopy. (8 points) (a) (b) O O HO HO ║ ║ ╱\╲ \ ／Ｏ ╱\╲ \ ／Ｏ／＼／＼＼／＼／ HO \ ╲\╱ \ HO \ ╲\╱ \ O O \ \ \ \ HO \ ╱\╲ \ OCH3 HO \ ╱\╲ \ ＼\╱ \ ╲\╱ ＼\╱ \ ╲\ HO HO | OCH3 (chair form) 3. Carry out a splitting tree analysis for the following system and show how mamy peaks the signal from (b) would be split into if Jab = 4Hz and Jbc = 6Hz. (5 points) (a)(b)(c) CH3CH2CH2Z 4. Calculate the heat of reaction, △H',for the following reactions: (6 points) (a) H2 + Cl2 → 2HCl (b) CH3CH3 + Cl2 → CH3CH2Cl + HCl 5. Consider the chlorination of (R)-2-chloropentane at C4. (6 points) (a) Write structural formula for the products, showing three dimentions at all chirality centers. Give each its proper (R,S) designation. (b) What is the stereoisometric relationship between these products? Which of these are optically active? (c) What other dichloropentanes would be obtained by chlorination of (R)-2-chloropentane? Which of these are optically active? 6. Provide the reagents necessary for the following synthetic transformations. Most than one step may be required. You need not repeat steps already carried out. (12 points) (a) (b) (c) │ │ ＿o │ ─→ ─┼─D │ → ─┼─OH ／＼ ─→ ／＼/ ／＼ │ ／＼ │ \＿/ \＿/ 7. Starting with the compounds indicated in each part and using any other needed reagents, outline syntheses of each of the following compounds. More than one step may be required. (16 points) (a) (b) H CH3 ＼＿／ CH3CH3 ─→ ／＼ H-C≡C-H ─→ ／—＼ N3 3HC H (c) (d) Cl OH ＿＿ ╱＼╱ ╱＼／＿／＼＿OH ─→＿／＼＿CN ｜ ∣ ─→ ∣ ｜＼＿／＼＿／＼／＼╱＼Br 8. The halogenatom of an alkyl halide can be replaced by the hydrogen atom bonded to tin in tributyltin hydride (Bu3SnH). The process is a radical reaction, and it can be initiated by AIBN. AIBN decomposes to form nitrogen gas and two isobutyronitrile radicals, which initiate the reaction. Write a mechanism for the reaction. (8 points) ╭────────────────╮ │ │ │ │ │＿N＝N CN │ ╱＼╱＼ AIBN ╱＼╱ │ ／\ \／ AIBN │ │Ｏ∣ I + Bu3SnH ──→ ∣Ｏ｜ │ CN │＼ │ ＼╱ ＼╱ │ │ │ ╰────────────────╯ 9. Treating 3- methyl-2-butanol with HBr yields 2-bromo-2-methylbutane as the sole pruduct. Propose mechanism that explains the course of the reaction. (6 points) 10. Write structures for products A,B,C and D,showing sterochemistry.(6 points) ／＼／＼／＼／　　 K Br │Ｏ│ │ ───→ Ａ　────→ B ＼／ OH (-H2) │ TsCl │ pyridine│ ↓ ／＼ OH C ────→ D K2CO3 13 11. Interpret the following C-NMR spectrum of a compound C5H10Br2: elucidate 13 the structure and assign all the C resonance. DEPT experiments indicate that all the three signals are CH2. (6 points) ││ ││ ││ │ ╨────────────────┴┴─┴──────── ─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬─┬── 75 70 65 60 55 50 45 40 35 30 25 20 15 10 5 ppm 12. Propose a mechanism for the following reactions. (12 points) O CH3 (a) OH Br2 ／＼／ //＼／＼／ ─────→ \＿ /\ Ph (b) O H3C Ph ║ CH3 HO \／ H2SO4 ／＼／ \／＼ ─────→ │ │＼／＼ OH ＼／ Ph \＿/ 13. Show how each of the following transformations could be accomplished. (4 points) O ／＼ O O (a) ║ (b) ╱╱ ＼ ║ ║ ／＼／＼ ─→ ／＼／＼ \ / ─→ ／＼／＼／＼ \＿/ OH \＿/ H \＿＿/ H H 14. Deduce the structure of compound E(C10H12O) based on the following NMR spectra. Explain your answers. (8 points) ┌───────────────────────────────────┐ │ │ │ │ │ │ │ (6H,d) │ │ │ │ ║ │ │ ║ │ │ ║ │ │ ║ │ │(1H,s) (2H,d) ║ │ │ 　 ║ │ ││ (2H,d) ║ │ ││ (1H,m) ║ │ ││ ║║ ║ │ ├┴───────╨╨──────────────╨──────╨───┤ -┬-------------┬-------------┬------------┬------------┬-----------┤ 10 ８　６　　　４　　　　２　　　　　　 (δ≒135,C) (δ≒130,CH) (δ≒37,CH) (δ≒127,CH) (δ≒23,CH3) (δ≒171,C) (δ≒155,C)││ │ ││ │ │ │ │││ ││ │ │ │││ ││ │ │ │││ ││ ───┴─────┴─┴┴┴─────────────┴┴─── ──┬──┬──┬──┬──┬──┬──┬──┬──┬──┬── 200 180 160 140 120 100 80 60 40 20 ppm 試題結束. -- ※ 發信站: 批踢踢實業坊(ptt.cc) ◆ From: 140.112.249.121

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firepeter

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