Chemical Exam: Filling Missing Parts in Organic Compounds Reactions, Exams of Organic Chemistry

Download Chemical Exam: Filling Missing Parts in Organic Compounds Reactions and more Exams Organic Chemistry in PDF only on Docsity! 2. (20 points) Fill in the missing starting material, reagent or product. a. b. c. Name ___key_____________ d. This is an open-book, open notes exam. Please show your work in detail. Exam #4 Friday, December 14, 2007 Chem 331 ? O ? ? H2 Pd cat poioned H OH OH H2N NH2 NaH H ? O 1. (20 points) Deduce the structure of B, and fill in the missing reagent(s). You do not need to show mechanisms. 1H NMR: 5.56, ddd, J = 15.2, 6.8, 5.1 Hz, 1H 5.34, ddd, J= 15.2, 7.2, 5.2, Hz, 1H 3.73, s, 6H 3.41, t, J = 7.6 Hz, 1H 2.58, m. 2H 1.9 - 2.1, m, 2H 0.94, t, J = 7.1 Hz, 3H B C10H16O4 13C NMR: 169.2, s (2) 135.5, d 123.9, d 52.4, q (2) 52.0,d 31.9, t 25.6, t 13.8, q A CO2CH3 CO2CH3Br CO2CH3 CO2CH3H Bu3SnH AIBN MgCl OH H H2SO4 Hg cat 4. (20 points) Deduce the structure of F, and draw an arrow-pushing mechanism for the transformation. 1H NMR: 6.26 d, J = 12.9 Hz, 1H 5.84-5.69 m, 1H 5.04-4.95 m, 2H 4.73 dd, J = 12.9, 8.4 Hz, 1H 3.85-3.73 m, 4H 2.2 bs, 1H (exchanges) 1.9 - 2.1 m, 3H 1.00 d, J = 6.6 Hz, 3H 13C NMR: 144.9, d 137.1, d 115.7, t 110.6, d 70.1, t 61.4, t 42.3, t 32.7, d 21.2, q F C9H16O2 E O O MgCl 3. (20 points) Outline a synthesis of D from C. You may use any piece that contributes three or fewer carbons to the final product. Absolute configuration is not important, but relative configuration is. CH3O Br C CH3O D OH H3C H BuLi; I H3C H2 Pd cat poisoned H3C MCPBA H3C O CH3O Br Mg; H3C O CH3O OH OHO Note the CH3 doublet at 1.00 The alkene couplings and chemical shift are also diagnostic