7 Questions for Exam 3 - Organic Chemistry II, Spring 2003 | CHEM 241, Exams of Organic Chemistry

Download 7 Questions for Exam 3 - Organic Chemistry II, Spring 2003 | CHEM 241 and more Exams Organic Chemistry in PDF only on Docsity! 1 of 8 Chemistry 243-Exam 3 Spring 2003 Instructor Manoso April 11, 2003 Name Circle Bridget Jessica your section number 8114 Bill 8117 8141 Mark 8155 Problem 1 2 3 4 5 6 7 TOTAL (CHEM243): 8115 Monique 8142 8135 Grade of of of of of of of of 8127 Me 8137 Possible 20 20 18 24 12 20 36 150 8134 8147 8154 Write out and sign the University Honor Pledge in the space below: ("I pledge on my honor that I have not given or received any unauthorized assistance on this examination"): 2 of 8 Question 1: Acidity. (20 points) Question 1a. Circle the most acidic proton in each the following molecules, and give its pKa . (8 points) H O CH3 CH3 H O ex O O H H pKa = pKa = pKa = Question 1b. Rank the following molecules in order of decreasing acidity (increasing pKa). (12 points) AH O B D Most Acidic Least Acidic Question 2: Give IUPAC names for the following compounds (20 points). O H CN 5 of 8 Question 5: Prepare the following compound using either an acetoacetic ester synthesis or a malonic ester synthesis. Show all intermediate structures and reagents, but DO NOT SHOW MECHANISMS. You must use either diethyl malonate (EtO2C(CH2)CO2Et), or ethyl acetoacetate (EtO2C(CH2)COMe), and any organic compound that has six carbons or fewer, plus any needed solvents or inorganic reagents. (12 points) 6 of 8 Question 6: (20 points) Shown below are two reactions (a - b). Choose one and draw a clear arrow-pushing mechanism. Again, answer only one; cross out the question that you choose not to answer. If you answer both, only question a will be graded. a) Draw a clear, arrow pushing mechanism for the following transformation. (20 points) i NaOH ~J ^ H 20 7 of 8 b) Draw a clear, arrow pushing mechanism for the following transformation. (20 points) H+ —————>- H 2O