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Exam II Answer Key

Exam II Answer Key - NAME[Qt/ISLVaV Keg Midterm Examination...

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Unformatted text preview: NAME [Qt/ISLVaV Keg: Midterm Examination II CHM 231 Spring, 2008 Dr. Gust Time limit: 50 minutes Total points = 100 Answer on Pearson machine-grading sheets by marking response A, B, C, D or E. BE SURE T O ENTER YOUR LAST AND FIRST NAMES, AND YOUR 10-DIGIT ASU ID NUMBER ON THE FORM. DO NOT SUPPLY YOUR BIRTH DATE. THE QUESTIONS BELOW ARE EACH WORTH 3 POINTS Consider the reaction coordinate diagram shown below for the following reaction in which reactants A and B yield products D and E. A+B—>D+E Energy Reaction coordinate 1. Is the overall reaction endothermic or exothermic? (A) Endothermic Exothermic 2. Are the reactants A & B more stable or less stable than the products D & E? (A) More stable ‘ess stable 3. Which of the three energies indicated with vertical lines represents the overall heat of reaction, AH? (A) E1 (B) E2 @ E3 NAME 4. This is a two—step reaction that occurs by way of an intermediate. Which is the intermediate? (A) structure A (B) structure F @ structure C (D) structure G 5. Which step of the reaction has the largest activation energy? (A) step 1 (El) step 2 (E2) (C) step 3 (E3) 6. What is the transition state for the first step of the reaction? (A) structure A (B) structure C @ structure F (D) structure G For questions 7 — [0, consider the cyclobutane molecules below. Hydrogen atoms are not shown. Cl Cl C! CI CI CI Cl CI Cl CI a b c d e 7. Which pair of molecules above are enantiomers? Aa&b Ba&d Cb&c @b&e Ea&e 8. Which pair of molecules above are constitutional isomers? A a&b .a&d c [3&0 D a&c E a&e 9. Which pair of molecules above are homomers (the same compound)? A a&b B a&d @b&c D a&c E a&e 10. Which molecule(s) above are achiral? .a&d B onlyd C [9&0 D d&e E a&e NAME For questions I 1 — J 5, consider the alkenes shown below. 11. 12. 13. 14. 15. 16. A B C D Which of the alkenes above has the most stable double bond? (19 B C D E Which of the alkenes above could be prepared by dehydrohalogenation of 1-bromo—1- methylcyclohexane? @ B C D E Which of the alkenes above would yield a primary alkyl bromide upon reaction with HBr? A B C D 633 Two of the alkenes above would give tertiary carbocations upon treatment with HBr. One of these is A. What is the other? A C D E Which of the alkenes above would give an achiral molecule upon treatment with Brz? A C D E What is the major product of the following reaction? E None of these MOH + SOCI2 —» 17. l8. 19. 20. 21. 22. NAME What is the major product of the following reaction? y‘“ H20204 ——-> 5 (EH 53 EM A ® 0 D Which alkyl halide will react most rapidly with hydroxide ion by an 8N2 mechanism? w {Fr/m WWBr 0 (9 A B Which molecules in question 18 are achiral? A (A&B) @(B&D) C (C&D) D (A&D) If reaction of compound C in question 18 with hydroxide ion to give an alcohol happened with inversion of configuration, by which mechanism would the reaction have occurred? SNl 8N2 El E2 A C D Markovnikov’s rule states that when H-X adds to a double bond, hydrogen becomes attached to the carbon that already has the most hydrogen atoms attached. @True B False All chiral molecules have non-superposable mirror images. @ True B False NAME From the group of structures below, choose the major organic product of each of the reactions in problems 23 — 26. N02 NH2 01 0 CH3 OCH3 SO3H 2 f 3 j 4 5 N02 1 CH3 CH3 6 O $03H N02 N02 :er02 © Q 8 © NH2 7 303H 9 10 11 CH3 CH3 0:0” CH3 CHZNOZ 12 N02 HO/CQO 14 15 16 23. AICI E) + CH3Br ——>3 A B ((3 D E 12 5 15 10 16 24. CH3 00 AICI3 + CH3C\ —> Cl A B @ D E 5 6 10 12 25. H2804 + HNO3 ———-> 100 °C 26. 27. 28. 29. NAME No2 E: + H2804 ———> ABC®E 6 ll 7 8 16 Which of the following compounds is not aromatic? © 1/ l ‘ \ N~ O O H A B @ D E Which reagent would you use to carry out the following reaction preparatively? COM—+0” A Cr03 +H2804 B H2CI‘O4 @PCC D KMnO4 What reagents would you use to carry out the following conversion? A H2CIO3 peroxyacetic acid, followed by H20 C 0304 followed by NaH803 in water D H20 with an acid catalyst E PCC 30. 31. 32. 33. 34. NAME What is the most likely product of the following reaction? OH O +HzCrO4 —> H A an alkene B an aldehyde @a ketone D a carboxylic acid In their normal state, hair proteins contain disulfides. @ True B False No molecule may have more than one enantiomer. @True B False The reaction of primary alcohols with HBr always occurs by the SNZ mechanism. @ True B False (one point) Which compound below is an alcohol? 0 OH 0 <5 0 <f> D A B ...
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