Exam II Answer Key_1

Exam II Answer Key_1 - NAME ANIWEK Ff?" Midterm...

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Unformatted text preview: NAME ANIWEK Ff?" Midterm Examination 1] CHM 231 Spring, 2007 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 TO ENTER YOUR LAST AND FIRST NAMES, AND YOUR lU-DIGIT ASU ID NUMBER ON THE FORM. DO NOT SUPPLY YOUR BIRTH DATE. THE QUESTIONS BELOW ARE EACH WOR'I‘l-I 3 POINTS 1. What is the major product from reaction of [lBr with the alkene shown below? CQI-Br (n'fl (HHH CQ-Br 3' H CH3 3' 1FCHg 3 H CH3 H“ BrH HB Br H ® B C D For qtte.S'tim't.5' 2 5. consider the ht-‘dmt'w'htms shot-1"}? below-1 a b c d e 3. Which pair ofalkanes above are enantiomers‘? @nditb B ud’w! C {Edi-c D 37626 F. audit.” .1. Which pair ot'alkanes above are constitutional isomers? A 0&5) B ad’sd C 562:“ D adéc @udfie NAME 4. Which pair ot‘alkanes above are homomers (the same compound}? A 0&3) B {1&(3 ©b&c D (1&6 E 9&9 5. Which alkane(s) abOve are achira]? A a d} b B only (2' C 25 di- c @ d & e E a div 8 For questions 6 — 1’ I. consider the (liken-ex shown bdrm-n A B C D E None of these 6. Which ot‘the alkenes abOve has the most stable double bond? A B C @ E 7. Which of the alkenes above could be prepared by dchydrohalogenation ofE-methyI-S- bromohexane'? A B C @ a 8. Which otithe alkenes above would yield a primary alkyl bromide upon reaction with I-lBr‘? A B C D ® 0, Which of the alkenes above could exist in (’ffi' and trans forms? B C D E 10. Two of the alkencs above would give secondary carbocations upon treatment with HBr. One ofthese is A. What is the other? A B © 0 E NAME 11. Which of the alkenes abowe would be most likely to give a mixture of two major addition products upon treatment with l-"lBr‘? <9 12. What is [he most likely mechanism for the tollowing reaction? I 08H + H0] —-- C + H20 @ so B 3N2 C E] D [-32 E Markovnikov addition 13. What is [he most likely product oflhe tollowing reaction? OH + HZCrO4 —h- A an alkene B an aldehyde @ a kelone D an ether 14. Oxidation ofa thiol by 02 gives a disulfide. @ 'l‘rue B False 15. B—Cadinene is present in the essential oils ofjuniper and cedar trees. How many Stereocemers are present in [i-eadinene. whose structure is shown below? Id D4 ‘J’U - J @ How many stereoisomers are possible for [S-eadinene (see structure in question 15}? @8 16. A1 BE C4 [)6 Lu NAME 1?. Compound a. shown below. may be converted to compound I) by using a sequence of two reactions. i and if. Which ofthc reagents below would you use for the first reaction, I"? qscg/ b A NaBr B Br; ©HBr D CI-lgCHgO'" Nar E CH3Br 18. In the transfomtation in problem 1?. which of the reagents below would you use for the second reaction”? A NaBr B Br2 (.‘ llBr ®CH3CHgU Na‘ E CHgBr 19. What is the major product ofthe following reaction? MOH + socsl2 —. H A C O D 20. A molecule may have at most one enantiomer. ®True B False 21. Which alkyl halide will react most rapidly with methanol by an le mechanism? Br Br 11% \IM YKA W3 A c D 22. Which alkyl halide in question 2] will react most rapidly with hydroxide ion by an SN} mechanism to give an alcohol? A B C NAME In answering problems 23 w 26, consider the structures shown below. Cl: H H : H H : Cl Cl C! H H Cl CI a b c 23 Which of the molecules above has a (1'3 structure? A a @ b C c D mmc ofthe above 24. Which of the molecules above isfare achiral‘? A (t .1.) C c D u&c 25. Which ot‘the molecules above have stereocenters? A 0an a B w'tt’_1'b C only ct cf: 6 @ah’ 3 molecules 36. Which of the molecules above could form a solution that rotates the plane ot‘plane- polarized light?I A Gab-'0 B only!) ©(miy u or t" D at’t’3mnt'ccttfes E noneofrheJ 2?. Primary alcohols are more easily dehydrated to alkenes than tertiary alcohols. A True (l3 False 28. Most cthers (other than epoxidcs) are relatively ttttreactive. @True B False 29. Xaitsev"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. A True False UI NAME 30. The SINZ reaction occurs with inversion ofconfiguration at the carbon bearing the leaving group. @True B False 31. Molecules with two or more stereocenters are always chiral. A True CB) False 32. Only chiral molecules can have enantiomers. (19 True 13 False 333. Which reagent would you use to carry out the following reaction preparatively‘? O OH ___.... H A CrO; + H3804 B HgCr04 ©PCC D KMnm 34. {one point) Vladimir Markovnikov is best known as the father ofAnna Nicole Smith's SOIL A True @False ...
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This note was uploaded on 04/27/2009 for the course CHM 231 taught by Professor Gust during the Spring '09 term at Arizona.

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Exam II Answer Key_1 - NAME ANIWEK Ff?" Midterm...

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