※ [本文转录自 NTU-Exam 看板] 作者: fruitman (WIN) 站内: NTU-Exam 标题: [试题] 93上刘绪宗有机化学第一次期中考 时间: Thu Dec 2 14:15:13 2004 Organic Chemistry 1st Exam. Oct 21, 2004 1.Nomenclature. Give the correct IUPAC name or structure for the following.(20) (A) │ (B) ╴ (C) ／╲╱╲╱╲╱╲╱ Br▃／ ＼﹍╱ ／＼╴／＼ ｜ ╲╴／ \╴/ ╲／ ／╲ (D) ／＼ (E) ｜＼ (F) ╱╲╱╲ ／￣￣＼ ｜ ＼ ｜ ｜ ＼╴╴／ ／￣｜￣￣╲ ◤╲╱╲╱◥F ／ ｜ ╲ ￣￣￣ ╲ ／ ＼ ／ (G) trans-Decalin (H) 5,8-bis(1-methylethyl)dedecane (I) 6-(2-chloro-2,3,3-trimethylbutyl)undecane 2.Sulfuryl chloride(SO2Cl2) can be substituted the chlorine gas for the chlorination of methane with the formation of SO2 as by product(equation below). hν CH4 + SO2Cl2 ────→ CH3Cl + SO2 + HCl Propose a reaction pathway leading to the formation of CH3Cl.(8) 3.Please draw all possible staggered and eclipsed conformations(in Newman projection) with respect to C3-C4 of 2,2,4-trimethylpentane. Arrange the relative stability of these conformers in order.(16) 4.Please arrange the relative stability of radical species in order. Please explain why?(6) ╱╲‧ ／╲‧ ‧CH3 │ ∣ ∣ ─┤‧ ╲╱ │ 5.For the photochemical halogenations of A, which of the following reagent would give the mono-substituted product in the highest selectivity? Please draw the structure of the resulting product.(5) ＼／＼／ ｜ ╱╲ F2 , Cl2 , Br2 , I2 A 6.Find the isoprene units in each of the following molecules.(5) ╲╱ ╴ ╴ ＼﹍／￣＼▂ ／＼／￣╲╴／￣＼╴／＼ ／ ＼╴／ ｜ ∥ ／￣ ／￣ OH ◢ ╲／╲ HO Methanol Vitamin A 7.Draw the most stable conformation of trans-1-chloro-4-isopropylcyclohexane; then flip the ring and redraw the chair conformer. Accordingly, estimate the energy difference between the two chair conformation isomers. Calculate the ratio of the two at 300K. (10) 8.Draw the Newman projection of methylcyclohexane showing the methyl group being at axial position. (5) 9.Characterize the following species as either Nucleophile or electrophile. (5) H+ , NH3 , AlCl3 , Li+ , CN- . 10.Draw all resonance structures of nitrate. (6) [Lewis structure] 11.What are the "angle strain" and "torsional strain" in cyclopropane? (8) 12.Give three possible products from the pyrolysis of octane. Showing the pathways leading to these products. (6) --

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