CHEM2211Exam3Key - CHEMISTRY 22] 1 Em“ 3 November 7.,...

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Unformatted text preview: CHEMISTRY 22] 1 Em“ 3 November 7., am}? He sure to read each question eaml‘ully. This test must be taken in pen. Tests taken in pencil will not be graded. Partial ererlit will be assigned 1a‘here appropriate. To receive full ereilil you must answer the question completely. Relax and good laekll :t: E l. [12 pts} Draw a reaction energy diagram that eel-responds to the following criteria: i. The first step is the slowest and has a positive oG" ii. The second step is fast and exergenie {-flb") E iii. The third step is slower than the second step has a negative M3" 5 iv. The reaetien‘s overall Km 3* 1 l:- flb" eel-rally Clearly label eaeh individual step‘s activation energy and transition state as well as eaeh reaetien intermediate position. Make sure that your labeling is neat and clear: 1as.L_ _ _ . — _. ._,_._-—I-'_ NAME 1"“. SCURE INJ Lil lit. Total: 1. {E points} What starting alkene {A — D] and reagents would you choose to make the specific isomer of 1,2-dirnethyleyelol1exanol shown below as the onlt- product? Provide the letter corresponding to the appropriate starting material in the hozs provided on the left and indicate the proper reagents in the box above the arrow. Hint - be mindful of the stereoehemistry. “CH2 @CH3 (it: H; CH3 ; 1 “fing o H 3 :3 H3 oH2 A B C D Storting Material B 3. (l [1' pts} Provide skeletal structures for fire isomers that conform to the molecular formula (331140: 4. U 2 paints} There are twe sequences of reactions that allow fur the eunversian ui' nerbernene (a bieyeiie aikene) tn trans~2,3-nerhnrnanediel [a glyeel). Draw the appropriate strueiures [If each intermediate and preside the reagents required te achieve eaeh transfurmatinn. Reagents Intermediate :4. Reagents ECG}. H3D+ H. OH gr D nememene MCPB'A’ 0H ‘ H H trans-2,3-nerbernanediol {'“Id “5"- _ Reagents '5‘" $91-$4- Mflfi 4-" 59"“; '5'!- fE-‘Akd firm-H mam X2. , “10 Reagents Sufufirfl LumblflI—Hfl/‘IS Pofll'bk. cm #5 L.“ 'ir'l 9H. tl-iw fi-Lr‘g-ofi, 1914'.— 4-1'M? mH-‘F' Lari. +r-Anvl: 4" print. anH-W 5. [1' pts} Rank the fellewing alkenes frnm least [1] to most {4) stable. Write the number in the space provided. i _1_ i #9._ flank the fellewing eal'hneatieus frem least (1] to meet {3} stable. Write the number in tlie spate previtletl. fir g5 E} ii; (i. {5 pts] Brew structures for all el'the possible Jar-mittens] ef the fellewing reeetiene: HG HESUdu H20 I I' + THF, sate \ . 1- “"x 3’ xxx/1 KDH W e —h. CH3CH20H + NV Br K T affix-'1'? '2, {3:19}- EwL—L loft: a 14 (ul- 5“]: 4 _ _ T. (14 pts] 111 the boxes provided, draw the mechanisms illustrating the formation of both of the products [A and B) of this reaction, rimming every intermediate, and osiog'curved arrow formalism to show the flow of electrons. HINT: The first two steps are the some for both mechanisms. H213 Br CH3 $6443 _ Har CH3 CH3 CH3 ' Br .6. a Mechanism formin Productfi: Mechanism fermionr Product B: I...“ E. { 8 pie} Provide the preper IUPAC names fer the following eempeunde in the spaces previded: (53"L‘1—4'm - -drMLL1—5r -H-nener‘lL 0;" " 2/1 -' iFNbr-“nyll - 1'f-IfI--+'~-ra.a.i'...},| eiky13~ 'I-Pwal - l‘l' Ffierumt "‘ HE 9. [4 pts} Assign the apprflpriale EIZ etereechemistry,F tn the elkenes provided belew: HDHEC CDzH HO CNL HCIHC CHa' 'HENch CHEBr' >=< >=< k0” >=< _DHC C020H3I H300 CHENHZ IHSCQHEC Hzc=eH em El ll]. {2|} pts} Complete the following reaction schemes by adding the appropriate starting meteriaL reagenqs) aodfor prodoetls}. Make sure to indicate the proper l'egioehemistry anti storeoehemislry when oeeeSsary: M ii ———p.. + Hall H D C} 2 equivalents of H2 Lexi ———hr— Pro2 1 DH DR- ‘Hé E! ngl— Ill-(a +FJ-fi'i 3T2 — ‘x .- or CH3CHEDH M QCHlfiH CH3 1.30304 0'“ DH “xx ———P— 2.3NeH303.H20 Raf-J '5 PP'HHJI dflwfi In! (H: Pain-Ha “Fr F ...
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This note was uploaded on 03/20/2008 for the course CHEM 2212 taught by Professor Habbard during the Spring '08 term at University of Georgia Athens.

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CHEM2211Exam3Key - CHEMISTRY 22] 1 Em“ 3 November 7.,...

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