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Unformatted text preview: Chem 237 Exam 1 Key October 27, 2006 Instructions: You will have 50 minutes to complete as many problems as possible. Where provided, write your answers in the boxes. Your answers will not be graded unless they are in the proper box. Problem 1 2 3 4 5 6 7 Points ____/24 ____/10 ____/10 ____/20 ____/12 ____/12 ____/10 Total ____/100 1. For this problem, circle the correct answer. (24 pts) a) Which is more polar? C H C F3 3 C F3 C F 3 b) Which has a higher pKa? O NH2 NH 2 c) Which is more soluble in water? H 3C OH O H d) Which has the lower boiling point ? e) Which has the greater heat of co mbust ion? f) Which is more acidic? OH N OH g) Which is more basic? NH H3C NH 2 NH 2 h) Which has the higher bo iling point? C H O C H 3 3 C H S C H 3 3 i) Which is less so luble in water? O j) Which is more polar? N H 3 B F3 H 3C OH H O k) Which will react faster with HBr? H3C l) Which is more stable? B r B r Br Br 2. Oseltamivir (drawn below) is an ant iviral drug that is used to treat influenza. (9 pts) a. Identify the hybridizat ion of the atoms indicated by the arrows. b. Mark the most acidic site in this mo lecule with an A, and the most basic site wit h a B. sp3 O H C 3 sp3 A H
N O B H N 2 O O CH 3 sp2 sp2 sp3 3. Draw the most important resonance structures for nitrile oxide, HCNO. Rank them in order of stabilit y. Label the most negatively charged atom wit h a 1, and the secondmost negatively charged atom with a 2. (10 pts) H C N O H C N O 2 More stable 1 less stable 4. Fill in the boxes with the appropriate reagents and/or products. Remember that boxes over the arrow may contain any reagent, but all other boxes must contain only organic compounds. (20 pts) Cl Cl2 Cl HBr or PBr 3 O H B r CH3 CH 3 SOCl2 OH Cl 5. Draw Newman pro ject ions (down the bond between carbons 2 and 3) of all staggered conformations of 2,3dichlorobutane. Identify the most stable conformer by circling it. (12 pts) Me H Cl Me Cl H Me Cl Cl Me H H Cl Cl H Me Me H these last two are identical most stable = 1 6. Name these co mpounds according to IUPAC rules (12pts): OH Br Cl 4ethyl3,5dimethylheptane 2bromo3chlorobicyclo[2.2.2]octane 3tertbutylcyclopentano l 7. Draw a clear 3dimensio nal representation of the most stable conformat ion of each of the fo llo wing co mpounds (12 pts) cis4tbutylcyclohexanol cisbicyclo[4.2.0]octane trans1,2dipropylcyclohexane OH ...
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This note was uploaded on 10/27/2010 for the course CHEM 237 taught by Professor Andersen during the Fall '08 term at University of Washington.
- Fall '08