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WPR II Solutions

WPR II Solutions - CADET_~ SECTION!HR~_TIME OF DEPARTURE...

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CADET_~ SECTION!HR~ __ TIME OF DEPARTURE _ DEPARTMENT OF CHEMISTRY & LIFE SCIENCE CH383,2007-2008 McMurry, Organic Chemistry, 7 th ed. WPR II, AlC Hour Chapters: 5-6, 13 26 October 2007 Experiment: 2-4 120 minutes INSTRUCTIONS 1. Do not mark on this exam or open it until "begin work" is given. 2. Solve problems in the space provided. SHOW ALL WORK. ANSWER ALL QUESTIONS. 3. Molecular model kits are permitted; however, models may only be assembled after "begin work" is given. The molecular model instruction booklet is not permitted. General and Organic Chemistry RDCs are authorized. Calculators are NOT authorized. 4. There are 11 pages in this exam. Report any illegible or missing pages to the OIC in the hallway. Write your name in the spaces provided. (TOTAL WEIGHT: 200 POINTS) DO NOT WRITE IN THIS SPACE PROBLEM MAX SCORE CUT YOUR SCORE I 80 II SO III 40 IV 30 TOTAL GRADE 200 EXTRA CREDIT 20
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--------- Name: Problem I, Fundamentals, 80 points (12) 1. What is the IUPAC name for the following compounds? a. b. / ; -' r1 , I' 1.-· I L._Ci\\ ,~ I, I I, d. c.~ - )- (I ( \ I (12) 2. Draw the following structures: a. 3-ethyl-2-methyl-2-hexene b. (E)-3-bromo-l-fluoro-2-methylpropene /" \ /r-----J // )-:::::;:':--1" / ..•. ........ - c. 3-bromo-2-methylcyc1ohexene d. 5-isopropyl-l-methy1cyc1opentene /~/ .-: i \--1 ( (/ (3) 3. ~ch of the following statement(s) about ethene is(are) incorrect? (a.; The H-C-H bond angles are approximately 109.5°. \'-\:): All of the hydrogen atoms are in the same plane. c. There are a total of five sigma bonds. d. The carbon atoms are Sp2 hybridized. CH383, AY07-08 1 WPRII, AlC Hour
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--------- Name: Problem I, Fundamentals, 80 points (continued) (3) 4. Which species below is the intermediate in the free radical addition of HBr to 1- butene? A) . B) H 3 C-CH 2 -CH 2 -CH 2 ..--~':.~- ..... C») H3C-CH2-CH-CH2Br -',-/, (12) 5. Consider the following reaction energy diagram: D B E A G Progress of rxn a. b. c. Write the letter(s) that identify any intermediate(s). -"("=-':_ '-'.' __ Write the letter(s) that identify any transition state(s). --- Is this reaction exergonic or endergonic? _ CH383, AY07-08 2 WPRII, AlC Hour
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--------- Name: Problem I, Fundamentals, 80 points (continued) (4) 6. Circle the point on the potential energy diagram that corresponds to the species below for the reaction of 2-methylpropene with hydrogen chloride. energy reaction coordinate (3) 7. Which of the following correctly depicts the mechanistic first step in the addition of HBr to 2-methylpropene? L§)CH 3 n 0 H lJr (3) 8. Which of the following is the key intermediate in the Markovnikov addition of HBr to I-butene? CH383, AY07-08 3 WPRlI, AlC Hour
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--------- Name: Problem I, Fundamentals, 80 points (continued) (3) 9. Which of the following is the most stable carbocation? CH3 .... -- - ~- i I. 6 \. /" IV. -, CH3 e 0 v. II. Oe (5 III. oe (3) 10. According to the Hammond Postulate, which of the following is correct? \ a. 1 The transition state of an exergonic reaction step will be more reactant-like '--./ that product-like. b. All transition states are more product-like that reactant-like.
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