Chem 3331 Exam 2, Spring 2004: Organic Chemistry Problem Set, Exams of Organic Chemistry

Download Chem 3331 Exam 2, Spring 2004: Organic Chemistry Problem Set and more Exams Organic Chemistry in PDF only on Docsity! Chem 3331 Exam 2 Spring 2004 Tarek Sammakia page 1 Second Hour Exam Name: Recitation instructor's name: Recitation day and time: Page Possible points Score 2 24 3 21 4 27 5 28 TOTAL 100 You have 2 hours to complete the exam. Please don't cheat! Chem 3331 Exam 2, 2004 Name page 2 1) Provide the products of the following reactions. If no reaction would occur, then write NR. Draw all possible stereoisomers (i.e., draw dashed and bold lines as needed) and indicate if they would be produced in equal or unequal amounts. There is an appropriate aqueous work up for each reaction (3 points each). A) OH OOH H2SO4 (1%) -H2O B) O EtOH / NaOEt ∆OMe H O C) OMe Me MCPBA (1 equiv) OCH3 D) OEt O O NaOEt (1 equiv) /EtOH MeI (1 equiv) E) O Br2 (1 equiv) F) H O (Ph)3P Me Br - Li (1 equiv) 2) Complete the short syntheses shown below in one or two steps using organic reagents of 7 carbons or less and any inorganic reagents you wish. Be sure to indicate the number of equivalents of your reagents! If your synthesis requires more than one step, you must write the product of each step. Note that all chiral compounds are racemic mixtures. You do not have to include aqueous work up conditions in your syntheses (3 points each). A) C N OH O