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exam2.05.2 - E CHEMISTRY 2211 EXAM II Be Sure to read each...

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Unformatted text preview: E CHEMISTRY 2211 EXAM II OCTOBER 05, 2005 Be Sure to read each question carefully. Partial credit will be assigned where appropriate. To receive full credit you must answer the question completely. Relax and good luck!! ttl: C 1. (8 pts) Provide proper IUPAC names for each of the following compounds: \\.r’Z:::>””Br «E +r0n5-l‘ Greene) ‘7)"6HA I a- mu '5,"l*l>i~eHn \ w) Lo“ Aimi’k \ och/u, _7 Br CiS"l-— 5wmov¥b~flme+k IC cl clean & 3 H —-*E0h7kflmblk ’ +kflxd 10. ll. l2. 13. Total: SCORE 2. (8 pts) Convert each of the following IUPAC names into an appropriate structure: 3-Bromo-4-ethy1—2,5~dimethylheptane: Gr trans—1-Ethy1-2-methylcycloheptane: //’”‘x\ cmzcu3 “Hue“ 3 2-tert-Butyl- 1 -chloro—4—ethyl-4-methy1hexane: C 1 L0 -Methylpropy1)-3-(2-methylpropyl)cyclohexane: l0 0 Ci §/+rzfig 3. (8 pts) Examine the following IUPAC names carefully. Each name is, in some Way, inherently incorrect. Provide corrected names for each of the compounds in the spaces provided below: 2-Bromo-4-sec—buty1-5-ethylhexane: Q~ @mmc—* Li~9cc,—bm l~§~ Mel—WI Who-e. ‘71» $rb~ro — 9‘ — ruling ~ L4 ~(l»r\-D¢Jr{n7.lprog>y\) What 1—(1-methylhexyl)cyclopentane: ' 2* can; We” mes-(a, 1-Chloro-4-ethyl-3-isopropylcycloheptane: L‘l-Clalo-r‘o-—l—€L1Lin-|‘Z'i$° m C“ I 14‘?th L1- aware » )- etw w 2— (holiday! any) wet-ma cis-l , 1 -Dimethylcyclohexane: 4. (8 pts) Provide the requested conformers of the compound 2,3-Dimethylbutane. Draw your Newman projections looking down the Carbon 2 - Carbon 3 bond: Draw a Newman projection of the most stable eclipsed conformer . d calculate its total torsional strain (you must show all your wor : H043 ; x (0.0 LJ/mt : IZM‘VMJ How/M ch / Draw a Newman projection of the least stable Sta; cred conforme and calculate its total steric strain (you must show all your work): CPI-5 5. (10 pts) Identify the functional groups found in the following compound: 6. (4 pts) Draw the Newman projection of 1-bromo-2-ehloroethane that corresponds to the conformer with the largest net dipole. Briefly explain your answer: (Ecol All or 4% Congerw 9 (eroicg (Cfif-tcihh) . (L- (Zr/c—cll) H / _ H \H H . (an: PDIA'i'té ’f‘ “HILL gem r Mfwfiré *T; 70“ drill-0 FL“— 3&0“,va (Ll-Roi‘iéfi ,4- ‘—ADD N 'fl’w ’aryLSJ... Caanr-nur Sgt Dr. Habe’A —-—* Pfi’KI‘at-L Mi‘ dr‘Polc, 7. (9 pts) Draw both of the possible chair conformations of trans-l-ethyl-S— isopropylcyclohexane. Calculate the total steric strain energy of each conformation and circle the most stable conformer (you must show all of your work): ’1‘ 9:5 Energy Calculations: ' Energy Calculations: 2 a X H.0k‘5/A” :— Q X, Lilo RSIAOI a: ‘ bi' "A! L - r1 2 [/3 bi“Xfa-‘ dIfiRJ—ACH‘AS ; L? “X! Had-H0 S Total Steric Strain Energy: Total Steric StrainEnergy: Claw ~ M another: 8. (10 pts) Indicate whether the following pairs of compounds are constitutional isomers, cis/trans isomers, conformers, the same compound, or not isomers of one TSOWS Cl CI H3C CH3 CFC +~r2m§ F—Sofl-ud‘g Br Br I; H i; CH3 H a H ; H"”CH3 ; (Wet-I H3O OH H3C 9. (9 pts) Draw both of the possible chair conformations of trans-1,2- dimethylcyclohexane. Calculate the total steric strain energy of each conformation and circle the most stable conformer (you must show all of your work): Energy Calculations: Ll 7L 3r<6 14:74,“ 3 H (,"S bits-JANA. TnWAd‘HOAS_ Total Steric Strain Energy: _ -Total’StériC‘Slrain Energy: I)? a kj/A¢}\ ‘33 k'X/mapi ‘ 10. (6 pts) Draw the most stable chair conformation of the compound shown below. Calculate the total strain energy for this conformation (show all of your work): ll COZH ‘ CH3 43ch 1—1 % “3 "‘ Ll tow CH3 Com! 11. (10 pts) Draw , two possible chair conformers for cis-l-isopropyl-4— methylcyclohexane. Calculate the percent composition of each conformer in the equilibrium mixture at 298K. For full credit you must clearly show all of your , work. (R = 8.315 J/K ' mol) CHLLH333 («H-5 c CJH :3 ”5% fl [9,; fl/Hu \' H3, 3 Moms structure structure BLLLI 0/0 (0s6(479 %‘ composition % composition show work: 3K -—* [Count CHM”, h, tboe’T/MJ] A5 I: a: 2 kjyfi-iol ’7- L k-S/flqol I... ' 1‘0 kj/n-Ill g b (O £0033“; kj/K’MOB (aqgk) ln K IHK : -.o_l(¢b‘b 'K: 0-5914 M 0.3,», ——-—4-— l ,UW :m ("also _==” 059W: \ (SJHX '00 “w; 4?»: - 12. (10 pts) Identify the following reactions as additions, eliminations, substitutions, or rearrangements: CHSCHzBr + NaCN -—.__. CH3CH20N (+ NaBr) gmbsgfi‘mfi acid catalyst OH -----——-—-—-—1-— (+ H20) 5 ”HENRI-3H9“ O Q + . heat Wk - W I flarclldfi'am O . -—--—-—_—_.__._.._ ' ' N02 0 + OZN — N02 h ht 0/ (+ HNOZ) SuL-H“: 1“ £0“ i i | | i ...
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