Unformatted text preview: Name_________________________ Section and TA_________________________ 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 ____/12 Total ____/100 Name_________________________ Section and TA_________________________ 1. For this problem, circle the correct answer. (24 pts) a) Which is less po lar? C H C F 3 3 C F C F 3 3 b) Which is more acidic? O NH2 NH 2 c) Which is more soluble in water? H 3C OH O H d) Which has the higher bo iling point? e) Which has the smaller heat of combust ion? f) Which is has the higher pKa? OH N OH g) Which is less basic? NH H C 3 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 more soluble in water? O Name_________________________ Section and TA_________________________ j) Which is more polar? N H 3 B F3 k) Which will react faster with HI? H3 C OH H C 3 H O l) Which is more stable? B r B r B r B r 2. Oseltamivir (drawn below) is an ant iviral drug that is used to treat influenza. (10 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 an X, and the secondmost negatively charged atom with a Y. (10 pts) H C N O H C N O Y More stable X less stable Name_________________________ Section and TA_________________________ 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 H O B r CH 3 O H PBr 3 CH 3 B r 5. Draw Newman pro ject ions (down the bond between carbons 2 and 3) of all staggered conformations of 2,3dibro mobutane. 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 Name_________________________ Section and TA_________________________ 6. Name these co mpounds according to IUPAC rules (12 pts): B r Cl HO 4ethyl3,5dimethylheptane 2bromo3chlorobicyclo[2.2.1]heptane 2tertbutylcyclopentano 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) cis1,2dipropylcyclohexane trans4tbutylcyclohexanol transbicyclo[4.2.0]octane OH Name_________________________ Section and TA_________________________ ...
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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