中原大学九十学年度硕士班入学招生考试.doc

中原大學九十學年度碩士班入學招生考試 4月28日第2節 化學系誠實是我們珍視的美德，我們喜愛拒絕作弊，堅守正直的你！科目： 有 機 化 學（共4頁 第1頁）I. Supply the missing compounds in the following equations. Show stereochemistry where appropriate. If more than one organic product results, give only the major product. (34%) (a)(b)(c)(d)(e)(f)(g)(h)(i)(j)(k)(l)(m)(n)II. Synthesis： (20%) 1.Trans-2-penene from HCCH2.3.from alcohols of three carbons. 4.and any other reagents. III. Give a mechanism for the following： (12%) 1.R2CNNH2 + HO- R2CH2 + N2 2.CH3CHCH2 + HBr CH3CH2CH2Br IV. Answer the following question： (16%) 1. Arrange the following compounds in order of decreasing heat of hydrogenation. 2. List the following compounds in order of decreasing reactivity toward CH3O- in an SN2 reaction carried out in CH3OH : CH3F, CH3Cl, CH3Br, CH3I, CH3OSO2CF3, 14CH3OH. 3. Arrange the following in order of reactivity toward acid-catalyzed dehydration: 1-pentanol, 2-methyl-2butanol, 3-methyl-2-butanol V. Spectroscopy: (10%)Give a structure consistent with each of the following sets o proton NMR data: (a)C10H12 a.multiplet0.65, 2Hb.multiplet 0.81, 2Hc.singlet1.37, 3Hd.singlet7.17, 5H(b)C4H7BrO2a.triplet1.30, 3Hb. singlet 3.77, 2Hc.quartet4.23, 2H(8%) (a) On catalytic hydrogenation, compound A, C5H8, gave cis-1, 2-dimethylcyclopropane. On this basis, three isomeric structures were considered possible for A. What were they? (b) Absence of infrared absorption at 890 cm- made one of the structures unlikely. Which one was it? (c) The NMR spectrum of A showed signals at 2.22 and 1.04 with intensity ratio 3:1. Which of the three structures in (a)is consistent with this? (d) The base peak in he mass spectrum was found at m/e 67. W