Organic Chemistry CHE230-001 EXAM 2 Page 1 of 4 Cover Sheet! EXAM2 CHEM230-001 FALL 2003 PRINT your name legibly on the line below. _____________________________________________________Organic Chemistry CHE230-001 EXAM 2 Page 2 of 4 Name: ______________________ Student ID No:____________ First: You are allowed to have a writing utensil, a calculator and molecular model set at your seat. Please put away all other materials. Second: Place your student identification on your desk. A proctor will come around to check everyone’s ID. Is your name and number on your test? Third: Quickly read through the entire exam. Your goal, as always, is to score as many points as possible. Do not waste time on problems that you can’t do if there are easy questions to do first. Fourth: It is critically important that your answers be written in a clear, unambiguous manner. Answers in which your intentions are unclear will not receive credit. SHOW YOUR WORK! Fifth: READ THE INSTRUCTIONS FOR EACH PROBLEM. answer each question Problem Number Points possible Score 1a. 10 _____ 1b. 05 _____ 1c. 10 _____ 1d. 10 _____ 2. 45 _____ 3. 10 _____ 4. 10 _____ Total 100 _____Organic Chemistry CHE230-001 EXAM 2 Page 3 of 4 1) OSOOCF3HpKa = -12 Given the pKa of the acid to the left, answer the following questions. a. (10 pts.) Draw two possible elimination products of molecule 1A. OSOOCF3elimination+1AH40 °C in acetic acid b. (5 pts.) Does molecule 1B eliminate at the same rate as molecule 1A? Briefly justify your answer. Credit will only be given if you provide a reason for your answer. ______________________________________ ______________________________________ ______________________________________ ______________________________________ c. (10 pts.) Draw product 1cb of the reaction below, it has ten 13C NMR signals. Pay attention to stereochemistry! d. (10 pts.) In 1ca, the carbon atom bonded to CH3 is stereogenic. What is its absolute configuration in terms of R or S? _______ What is the absolute stereochemistry of the other stereogenic carbon atom in 1ca? _______ OSOOCF3H1BOSOOCF3CCH3CONthis is thesolvent1caLi-30 °C 1cbOrganic Chemistry CHE230-001 EXAM 2 Page 4 of 4 2) (45 pts.) Fill in the blank(s) with any or all of the following letters. a. (5 pts.) ________________ are isomers. b. (5 pts.) ________________ is (are) meso molecule(s). c. (5 pts.) ________________ are achiral. d. (5 pts.) ______________ are stereoisomers. e. (5 pts.) ______________ are enantiomers. f. (5 pts.) ______________ are diastereomers (select only one pair). g. (5 pts.) ______________ has (have) axial and equatorial groups. h. (5 pts.) ______________ has (have) two groups in equatorial positions. i. (5 pts.) _____________ are molecules with identical properties. 3) The year is 3050 AD. The namuh are aliens from another planet. We humans are their enantiomers on the biochemical level. 3a (5 pts.) A human offers a numah three mind-altering substances. Ecstasy, mescaline and psilocybin. She is considering two and avoiding one; which one? _______ Why? ______________________________________________________________ 3b (5 pts.) You are lucky enough to date a gorgeous Numah. The relationship deepens and you marry. The loving is good, but can you have children? _____, Why or why not? ________________________________________________________________________ ______________________________________________________________ 4) (10 pts.) Draw the structure of product 4B. Hints: 1) Product 4B has only three 13C signals. 2) Even though 4A is chiral, 4B is not. 3) The first step in this reaction is proton transfer. 4) In 4B DU = 1. 2A 2B 2C 2D
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