Chem 3331 Spring 2003 Exam # 2: Organic Chemistry Exam Questions and Answers, Exams of Organic Chemistry

Download Chem 3331 Spring 2003 Exam # 2: Organic Chemistry Exam Questions and Answers and more Exams Organic Chemistry in PDF only on Docsity! Chem 3331 Spring 2003 Exam # 2 Page Name____________________________ Second 2-Hour Exam By printing your name below, you pledge that "On my honor, as a University of Colorado at Boulder student, I have neither given nor received unauthorized assistance on this work." Name Recitation TA’s Name:___________________ Recitation Day and Time: ___________________ Points: Problem # Max. Points Your Score 1 10 2 10 3 30 4 30 5 20 BONUS 5 _________ TOTAL (out of 100) General Instructions: • You have 2 hours to complete the exam • Please write your name on the top of each page • Use the back of pages for scratch paper • Don’t cheat! Chem 3331 Spring 2003 Exam # 2 Page Name____________________________ Question # 1 10 pts total Circle the correct answer (2 pts each): a) Osmium tetraoxide is a cheap, non-toxic substance. . TRUE FALSE b) Cuprates are useful for epoxide opening because they are more basic TRUE FALSE than Grignard reagents. c) LAH is a useful reagent for the reduction of esters to aldehydes. TRUE FALSE d) Carbenes are reactive species that contain a carbon atom with TRUE FALSE 7 valence electrons. e) Catalysis works by reducing the activation barrier to a reaction. TRUE FALSE f) Condensation of a primary or secondary amine with a ketone gives TRUE FALSE an imine. g) Oxidation can involve the removal of O from an organic compound. TRUE FALSE h) Jones oxidation is a useful method for the oxidation of primary alcohols TRUE FALSE to aldehydes. i) Epoxides are more reactive than regular ethers because of angle strain. TRUE FALSE j) A catalyst affects the equilibrium position of a reaction. TRUE FALSE Chem 3331 Spring 2003 Exam # 2 Page Name____________________________ f) HO OH HIO4 4pt g) NaCN H2SO4O H O 4pt h) O LiAlH4 3pt i) O O MgBr O 3pt Chem 3331 Spring 2003 Exam # 2 Page Name____________________________ Question # 4 30 pts total How would you synthesize the following molecules using organic reagents containing less than 7 carbons, and any inorganic reagents you choose. Please pay attention to stereochemistry where it is shown! For partial credit show retrosynthesis and/or the products of each step if your synthesis requires more than one step. a) 9 pt OMe O Ph b) 4 pt H O O Chem 3331 Spring 2003 Exam # 2 Page Name____________________________ c) 9 pt N d) 8 pt H HO CN