Chemistry Exam 3: Structure, Reactions, and Mechanisms in Chemistry 220a, Exams of Organic Chemistry

Download Chemistry Exam 3: Structure, Reactions, and Mechanisms in Chemistry 220a and more Exams Organic Chemistry in PDF only on Docsity! EXAM 3 CHEMISTRY 220a Friday, November 4, 2005 NAME (print): _______________________________________________________________ TA:_____________________ Section Day:_________________ Section Time:__________ No Calculators! Take a few moments to look over the exam. Answer each question on the exam paper. Important clues and structures are in bold. Do all preliminary drawing or computations on the work sheets at the end of the exam. The work sheets will not be graded. The exam is 55 minutes. STOP writing and hand in your exam when you are asked to do so. REMEMBER: Neatness is to your advantage. 1. (20 pts) Structure ______ 2. (30 pts) Reactions (5 of 6) ______ 3. (25 pts) Potpourri ______ 4. (25 pts) Mechanisms (do 1 of 4) ______ ___________________________________________ Total (100 pts) 1. Structure: (20 pts) Treatment of compound A, C10H20, with O3 and then dimethyl sulfide provides a single, branched-chain ketone B. Exposure of A to bromine water affords (±)-C, which, when treated with aqueous NaOH, produces meso-epoxide D. What are the structures A-D? Explain and illustrate. 2. Reactions: (30 pts) Complete 5 of 6 of the following questions. Specify the structures in each one with a brief rationale for your choice. Pay attention to stereochemistry, optical activity, etc. where they apply. . If you do six questions, cross out the one that you do not want graded. …continued next page 2. continued.