2005 ochemexam 2

2005 ochemexam 2 - CHEM 2211 Exam#2 July 5 2005 Name...

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Unformatted text preview: CHEM 2211 Exam #2 July 5, 2005 Name: Afifiwff K6: Instructions: Answer the following questions as clearly and concisely as you can. Remember the structure drawing fonnalisrns of organic chemistry; ambiguously drawn structures and those showing improper valency will not receive credit. You will be allotted 9i} minutes to complete the test. You may use a molecular model set and a calculator to help you. but the use of notes, hooks, and other materials is not permitted. Show your work to receive partial and full credit. The administration of this exam is governed by the policies on academic honesty and integrity outlined in the University of Georgia’s Academic Honesty Policy. Please assert that you have complied with the letter and spirit of these guidelines in taicittg this exam: On my honor, I have neither given not received any unauthorized aid on this exam. Further, I have not observed others giving or receiving unauthorized aid on this exam. Signature: Date: Pageleffl l. Examine-the following IUPAC‘. nemeeentl indicate whether the}; are eerteet er ~ incorrect (first blank]. If ineerr'eet, provide the eerreei IUPAC name in the eeeenti blank. [f correct, simply write. “MA” in the second blank. {12 pts) I a) LEthyi—firieebulyieetane Tn ear-reek 32,"? rbimHniihH-Er-ojflnpfiewb ‘ b) I—Ethyl—3-{3—me_thylhexylkyelepentane | In earr Lair- 3 r l' "Evil-k1; .3 hi. —'5*—rmLJ-“iw the“ e] 3-Ethyl-2;5,T-tiimethyieetene Carraglr- We | 2'. Prefide preper IUPAC names for the following eempeuntis: {9 pie) Lyn-u" ‘ CM -— I- {Le-Amewlpmwij— LP H-Nihy-‘ibhyixl fiI-rfleL'I—q'ii'I-n-L @t‘ W Cig- |.- In: re —L’f— ("H-o ifieelohpfifit W W Ci-valgmrlx) [1,;‘1- dimihfiewpym {rel-e11 — 1:1 .'?r+emLh5,1 fiefifl - — T {CHaiaCClICHflgGHEGHEGHg M CH3 Lie-S II 3 i 3 i 4‘1 F {15' Pagefidffl 3. Rank thafoiluwing mmpounds in min of incmfismg boiling paint [I = Iqwesr, 3 = highest) {5 pts] 13) O 0 g T hflllimibf— Lc'rJL-J" A ;~ —-$—~ T Emlwp Farm-\- 4, Calculate the dagrw ofunsaturatinn (If the fQIIDWing-mnlccuiar fumlas: [fl pts] :1) CSHISND 3 HI? Hra. = “I: 5 3H: 11) CISHHBHNOZ *5- H'fl "H'L'L = Hip = E”; Q a} CmHIs — 14;;th _ 'HH _L RH: Page 3 of E 5. Identify the: following examples; by labeling thegm awarding tn their reaction type (elimination; subslimtic-n, addifiun, rearrangamem}. (3 pts} 3} {I31 GH30H=GH3 + H-GJ _,, HSGCH-CHE A'tgt'll-I'HD'W 3:} CHSCHECHz—Gl + 90H ._... GHgfiHEGHg—OH + eel Sub‘H-a-hfian 6] “m x —i|- / m. flflrkrran than-1'." d) GE )fi/fl++HCI E :1. Mlfifilfipfi Page 4-13f S E, Stimulate Kw, fat the: manochlmination pf methane (110° = 1-26.55 klfmn] and R = 8.315 JfiCmfiI and T = 293K). Show all yam" work. {5 pts) 101.55% L413 | .3”? at E : I'Gb‘ETSD I/mrl ‘3 j 2-: IKE : 0.0DBII‘F Mal ”CE LC. 'a’H-I‘I FIE-5953 KT/ km] EDI; ESTES} Gym-w. mtg-5‘; Eff-n55 _—-_—-——b '; fr: Kc? _( “5/ )E --.)F— llfi Kea- amillfi . J .m zeal/r; ($.th 334%} (mix) R " _. _ _" {ml-{Li ‘ Jfi Fi— J Wit ‘ :1. H m" l K43“ 3.11 my” 1'. Calculate the heat 'ut‘fnrmafion BAH?) for the following-reaction using the appmpriatcbund djmciatian ensrgies found in the tables pmfidfid with yum- test: {6 pm] W3 CH3 HEG-QH + Bra __3.. Haflfitiifir + HBr CH3 CH3 Show all 3011: wurk. @H‘HL"H 3°19 “TIMI (CHg1crEF its: Hymn fir—Br H3 1%.: Hug! E- Lfl‘ta ML--"'l.|'I-"'b- n1| AH: 5 gggkjfml (”*LhnH) - b1”? K'Effml meihmfi: J.) — Lhdl “5-5/1“ Di H 15 this reaction cxafltetmié or efldfltl'lemflc? LP— 555 bJ-‘lmurmi C..- Page 5 of 8 3. Draw a reaction energy diagram fl'lat e'errespends ten the following-criteria: I. First step is fast and endothermic IE. Senend step is slow and fill-I“ is negative “ fiH' = 'fits" : III. Third-stag is fast and exethennie IV. The-reaenen’s overall Ken} 1 = hath“ = Ewell-Emu}; Be sure ti} clearly label each step's individual aefivafien enm-‘gy. as well as the energ}I change 0f the everall reaction. Also label the reactants, products, intermediatefs}. and transit'rgn state(s). {11 pts} Effinwm'c-r fee—fiL'J‘Wpr-s Phi?) mtg; "—"'——-5- Haw many transitinn states are present in this reaction? ‘3 Page 6 of B 9. Draw bath chair eunfermatiens for each [If the fellewirlg eempeunde. Calculate the total steriestr‘ain energy fer each eenferrnatien (shew all your work}. {12 pts) Energy Calculations: Energy Caiemattene: H >< ens/+1 éiex-n'l ”I 3“ “11/an term-M TWHH'“ : Lr ,c 33 Kighfll ‘2 Total elem: Strain Energy: r ‘3. :2 KTJM I Energy Calculations: Energy Galeulatlens: ,1 y: [Cfi‘j‘i/ H Auuqfi Q ,1; Lair-1 / H all «and A x are LEE/Ann =2 5:} r 1.3 mean - TetaE Stark: Strain Energy: P Total aren't: Strain Energy: [Ea-E‘wa‘fi 'S-% #:3an Page; T if 3' III). me the CumplEIc reaction mechanism for the following radical reaction: ma-Ciz—a- \/l\+HG‘r Monochlorinatidn .fif nmana Bf: sure to :31:me label each {If the Steps. asapciatcfi with the: maclifln. [.11 pls) Tn-Lih'l‘iofi. '. {ED-L1 '———-"I Eli-1' Ema-”‘5 4511911 fl av 4r? ___.~, Cr-flf-i _/1 DI W (s. L] _____*-p i fl- W4}? ._=.. éhhfil M Page 3 of'S 11. Looking down the C2483 bond of Esmefliylpentane, draw the following: (8 pts} a] All three of the possible staggered Newman projections. Chris the most stable eenfonitation: h) All three of the possible eclipsed Newman projections. Eirete the least mmmafion: 12. Ammonia resets with aeetyl chloride togive aeetarnitie according to the following mention-scheme: {6 pts) .94) o- n -: NHs . Cor i H 30'. Z:AMHE II + w ‘ C. + tut-t4 GI _ Add the appropriate arrows to the reaction scheme shown above to eompiete this polar reaction mechanism. ...
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