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）︰2012/1/12 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. Please name the following species or groups. (9 points) (a) (b) (c) (d) (e) 　　　　　　 Br OH　　　　　　　　　　　　　　　　　HO OH + ｜　｜ - 　　　　　　　　｜　｜ —Ｃ— —Ｃ—Ｃ— —Ｃ≡Ｃ: —ＣＨ2— —Ｃ—Ｃ— ｜ ｜ ｜　　　　　　　　　　　　　　　　　｜　∣ (f) + —Ｏ— ︱ 2. Please name the following compounds. (12 points) (a) (b) (c) (d) Ｏ ∥ ╱＼／＼ H3C—Ｓ—Cl ∣Ｏ｜ OH SOCl2 CH2N2 ∥ ＼／ Ｏ (e) (f) (g) (h) OCH3 ｜ ｜ ◥ OsO4 (CH3CH2CH2)3B ／＼ ╱╲ ╱╲╱╲╱╲ O 3. Predict the intermediates and final product(s) obtained when (2R,3R)- 2-bromo-3-methylpentane is subjected to the following sequence of reactions, briefly explaining your rationale. Provide regiochemical and stereochemical details as relevant. NaOC2H5/C2H5OH, heat; (b) BH3, THF; (c)H2O2, OH-. (6 points) 4. Draw Fischer projection formula(s) of the major product(s) pf the reaction between (E)-3-hexene and aqueous Br2. (4 points) 5. Draw Fischer projection formula(s) of the major product(s) of the reaction between (Z)-2-butene and cold, alkaline KMnO4. (4 points) 1 13 6. Provide the predicted H-and C-NMR spectra for the following compounds. Provide explanation for your answers. (20 points) (a) (b) Ｏ ╲╱╲╱ ╲ CH3CH2CH2Br ∥ Ｏ 7. Provide a mechanistic explanation for the following observation: The same major product is obtained when 2-ethyl-1-hexene and 3-methyl-2-heptene are allowed to react with HCl. (5 points) 13 8. Explain why the signal of CDCl3 appears as a triplet in a C-NMR spectrum. (4 points) 9. Complete the following reaction sequence: indicate regiochemical/ stereochemical details as relevant. (6 points) i) Br2, hv ii) C2H5ONa/C2H5OH, heat 1,1,2-trimethylcyclohexane -----------------------------> ？ iii) Ozonolysis 10. Draw bond-line formula (including stereochemistry) of all monochloro derivatives that might be formed when 2,3-dimethylbutane is allowed to react with Cl2 under UV irradiation. (4 points) 13 11. Interpret the following C-NMR spectrum of a compound C5H10Br2: elucidate 13 the structure and assign all the C resonances. 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. Write structural formulas for the following compounds. (6 points) 1 C5H10O: H-NMR δ2.50 (m,1H), 2.10(s,3H), 1.10(d,6H);IR:strong peak near 1720 cm-1. (s:singlet, d:doublet, t:triplet, q:quartet, m:multiplet) 13. Provide a reasonable synthetic strategy for the synthesis of the following compound. You may use any compounds containing THREE carbons or fewer as the starting material. (8 points) ╱╲ + enantiomer ◢￣￣◣╱╲ 14. Write a radical chain reaction mechanism for the following reaction. (6 points) Ｏ ∥ Br Br ╱＼╱╲ ╱ heat ╱＼╱ ｜ ∣ Ｏ ------> ∣ ｜ + CO2 ＼╱ ＼╱ --

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