WPR III Solutions

WPR III Solutions - CADET _ _ _ _ _ _SECTIONIHR TIME OF...

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CADET ______SECTIONIHR TIME OF DEPARTURE _ DEPARTMENT OF CHEMISTRY & LIFE SCIENCE CH383, AY 08-1 McMurry, Organic Chemistry, t h ed. WPR III, AlC Hour Chapters 7-9, Experiment 5 20 November 2007 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. Calculators are not authorized. RDCs are authorized. 4. There are 13 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 40 II 60 III IV 30 V EXTRA CREDIT 20 TOTAL GRADE 200
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Name: Problem I, Fundamentals, 40 Points (8) 1. Name the following compounds: a. b. Br LI_ ", . . c-H.I 1 ) f l, r '''.-'.,_· '/'1-' -I ',r i"'C' t'r - -. . ..... , v' d'"" !J' "\. -r / n / I (8) 2. Draw the correct structure for: (E)-5-methyl-5-hepten-l-yne 6,6,6-trichloro-2-hexyne ( I (3) 3. is produced when 1 equivalent ofHBr is added to l-hexyne in the presence of peroxides. (E)-2-bromo-2-hexene Cf) A mixture of E and Z isomers of l-bromo-hexene c. 2-bromo-l-hexene d. (E)-l-bromo-l-hexene e. (Z)-l-bromo-l-hexene (3) 4. Which of the following statement(s) correctly describe(s) the general reactivity of alkynes? Unlike alkenes, alkynes fail to undergo electrophilic addition reactions. b:, Alkanes are generally more reactive than alkynes. CS) An alkyne is an electron-rich molecule and therefore reacts as a nucleophile. d. The IT bonds of alkynes are higher in energy than the n bonds and are thus more reactive. Alkynes reacts as electrophiles, whereas alkenes reacts as nucleophiles. CH383, AY 08-1 WPRIII, AlC Hour
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--------- Name: Problem I, continued (3) 5. Which of the following tenn~besH:les€riht(~ the pair of compounds shown: enantiomers, diastereomers, tfthe same compound? Cl ~ (3) 6. Which of the following is the best synthesis of2, 2-dibromobutane: Br2 2HBr a. .. ... ~ CCl 4 @~ Br2 d. b. ~ peroxides'" ~ H 2 O (3) 7. In the Fischer projection below, what are the configurations of the two asymmetric centers? '::="\ (t.)2R,3R '-l{ 2R,3S c. 2S,3R H+H3 d. 2S,3S HTo H e. Cannot be determined from structure CH 2 CH 2 0H (3) 8. Which of the following is a meso compound? trans-I, 4-dimethylcyclohexane @ cis-I, 3-dimethylcyclohexane c. 3-dimethylcyclohexane d. cis-I, 4-dimethylcyclohexane e. 2-dimethylcyclohexane CH383, AY 08-1 2 WPRIII, AlC Hour
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--------- Name: Problem II, Reactions, 60 Points (20) 1. Complete four of the following five boxes for the following tree of reactions by giving the major products and put an "X" in the box you do NOT want graded: H2~+ P~:1 CH 3 3 6=:CH 2 1. BH 3 2. oIr ,H2~,H20 CH383, AY 08-1 4 WPRIII, AlC Hour
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--------- --- -- Name: Problem II, continued (20) 2. Complete four ofthe following five reactions with the correct reactant. Indicate stereochemistry as appropriate. Cross out the reaction you do not want graded by placing a large "X" through the entire reaction. a. b.
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WPR III Solutions - CADET _ _ _ _ _ _SECTIONIHR TIME OF...

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