EdExam2 - Jentz Edward 810186982 “Ill mmmmuuumnummmummumm...

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Unformatted text preview: Jentz, Edward 810186982 “Ill mmmmuuumnummmummumm CHEMISTRY 2211 EXAM 2 July 1, 2009 SCO Be sure to read each question carefully. Partial credit will be assigned where appmpn'ate. ’ To receive full credit you must answer the question completely. Relax and good luckll I. ‘(f’ 1. (10 pts) Provide the proper IUPAC names for the following compounds in the spaces provided below: 2. ll. 12. i i r r w W- «aim l3. \ l Total: _/{l Br HZN N Ho F >— 3. (6 pts) Identify the following reactions as addition, elimination, substitution, or rearrangement in the box provided to right of each equation: Br W OCHS ' + CHsoH ——> + HBr —‘ r_ I A"? '- 5 5; x.- c’“ <’ 4. (10 points) Looking down the Carbon 2 — Carhon 3 bond of 2—bromo-3-ethylpentane, provide the following: i' r_ Draw all three staggered conformations, circle the mflo'IS't stable conformer and calculate its total strain energy: Draw all three eclipsed conformations, circle the least stable conformer and calculate its total strain energy: 4. Lf. If. w: I“? IV 5. (10 pt) Calculate the heat of formation (AHD) for the following reaction using the’ appropriate bond dissociation energies found in the tables provided with your test. In order to receive full credit, vou must show all of your work: + '—>' + - .74 / I "f ‘20 a “r {mf— k {2/ in I" {ah I on? a]; (“b/.- ZO L 5 v ’1 I k ,l (J: _ JL Reaciant bond dissociation energy A Calculate the AGO for this reaction ifthe change in entropy is ASD = 0.033 KJ/(K-mol) at a temperature of 315K. Show your work: 7’7 i _ $61.46!] “ 6. (10 pts) Draw a reaction energy diagram that corresponds to the following criteria: i. The first step is slow and has a negative AH" ii. The second step is the slowest of the three and endothermic iii. The third step is fast and has a negative AG" iv. The reaction’s overall ch > 1 Clearly label each individual step’s activation energy and transition state as well as the AGB of the overall reaction. Make sure that your labeling is neat and clear: Energy Reaction Prog ress —_—~—~——> "‘1' \ A --—\ l t 1 l 7. (10 pts) Draw the two possible chair conformations of the following compound. Your structures must adhere to the indicated numberin scheme. Calculate the total strain energy of each conformation and circle the most stable conformer. f HacHZC‘ CH(CH3)2 nIIUJ Ring Flip Total Strain Energy: Draw the most stable chair conformation of trans-l—bromo—4-tert—hutylcyclohexanc in the box provided below: /' -'-_ r. f f3 8. (4 pts) Calculate the degrees ofunsaturation in the following molecular formulas: C4lH81BrCIFN202 7 0163-71 —J“_— fig» - - an ClgstBr3C1F203 :g remark: 29414-7934 7 . \- Li 9. (10 pts) Draw an appropriate reaction mechanism for each of the propagation steps of the following radical reaction: \A + 02 H._fl.__+ \A/O 4. HQ] Monoc hlorin ation of isop enta ne Provide the appropriate reactants and products in the boxes provided below. You must also provide the appropriate arrows to clearly account for all electron movement. Propagation: 10. (6 pts) Draw structures for the major product(s) of the following reactions. [Hint— think regiochcmistry]: HBr —-———’- Ether, 25°C HCi Ether, 25°C dfl HBr ——-—-—’- Ether, 25°C 11. (4 pts) Draw the structurc(s) of the appropriate starting material(s) that will produce only the indicated product under the provided reaction conditions: HBr —————+—> Ether, 25°C Br 55w :‘ a if“ ‘6 12. (6 pts) Provide a complete, detailed and stepwise mechanism for the following reaction. In order to receive full credit ’011 must show all electron movement and rovide all of the intermediates for this reaction: Br HBr " ' " ' Ethafi"2"530—_' ' " "' "" 13. (8 pts) Indicate whether the following pairs of compounds are constitutional isomers, stereoisomcrs, conformational isomers, or identical to one another: CHO OHC _1_‘7 7 F ‘ I WOMG HaC 3, " "CHO CHO CH(CH3)2 CH(CH3)2 % OCHa OCHS CHa 01—13 H Br HGC (3H;J Hac H Br H We H CH2CH3 CH2CH3 ‘ Cl C: 10 Table 5.3 Some Bond Dissociafion Energies, D MPW : 2007 Thomson Higher Educafion I 1] a 3 li- . . Ben {Mlmnl} i Bond thJmuI) Bond 1mm!) Hwy. 436- E (ca-1313c»! 209' Csz—CHS . 3.55 H-g-F 5.70 chzca—H 444 (CH332CH—CH3 351 3243' 4'32 H3C=CH+CI 368 (make—ca; 339' H—Br 366, H2C=C.HCH2--.-H 361 Hzc=c:H—CH3 I 405 8—4. 298 HZC=CHCH2HCI 239 H20=CHCH2*CH3 310 . 5 _ . 035;; 2.43 - a HZC'=C_H§ 511 Bar-13: 193. g 464 _ c213. . I“; .151 . -' 427. car” 438 § . c1 ' 2. . cage—ct as”: g- 405- . _ pay-men; cHa.-_BI 2'93 3 332 CH3“? 234 - - CHz—H (21432—024 330 O 368 O- . j . ' . 1|: ., 368 Carma-'12 335 ; CH3C”H B 209.7 Thomson Higher Education , (5H ~44 4:20 . - m. . 3:" - . - CH? C; HO—‘H 4.93 chs—«c: 338 293 . . - HO—OH 2.13 csz—a: 235 - . CH e 222 - *3" , ., :2. 5 . ' ' -‘--' mas—H 373 glaroa 3310 337 _ . 2. ._ - _ - : C2H50—~H 435 (CHQZCHJ-AH 401 - ' ' (c9 '1 -c:+-CI 339 - . cg . El . 3% 2 .2 .. ' I I I Cch—CHQ 322 tcnawch—a: 27.4 469 i {CH3)3C'-—H .390 - i CH3CH20wCflg 33; {CH313C—CI 330 Hc-ach-i 552 g NH'g—H 449 {CH3)3C~— Br 263 (ma—CHa 3'76 1 ann "518' .3 Table 4.1 Energy Costs for Interactions in Alkane Conformers H -- H Eclipsed H -- CH3 Eclipsed “ H -- CHZCH3 Eclipsed H -- Br Eclipsed H —- Cl Eclipsed H —- CN Eclipsed CH3 —- CH3 Eclipsed CH3 —- CHZCHa Eclipsed CHZCHa -- CH20H3 Eclipsed Br —— Br Eclipsed Cl —— CI Eclipsed CN —- CN Eclipsed CH3 —- CI Eclipsed Br —— Br Gauche CH3 -- Br Gauche CHZCHg -- Br Gauche CI -- Cl Gauche “ CN -- CN Gauche CI -- CN Gauche CH3 -- CN Gauche CH3 —— CH3 Gauche CH3 -- (2Hch3 Gauche CH3 -- CI Gauche CH2CH3 -- CI Gauche Table 4.2 Steric Strain in Monosubstituted Cycloalkanes Q 0 I -_ — — SEEM—runsfim $55,: étzfi treat; >F_.m_Em—=U..u:5mm 23:33 h... Sigh. Esteban 2: ~_:, 3.. 2: mm .3 am 5E 35 an“. E: n. .5“. n. 5.... a. 5“. a. E. B mm mm 3 a... N... E a a: 3 fl 8 n. a new :5 mu.an n. 23.5 n. 5.3.. n. mama...— n. «NE— T 535 E ‘23 7 Ga: n. .dea .3 mmEmc ESE 5 $359“ 9: Eu; umn: an =3, me 30% ESE? £52m ho wEmEBm Eu ESE? ucm mmEm: BEES?» 2:... a: 965m 95 S. mEmEEw E— Tmflv E mucmwmfi 9.: $550.. w‘mvm 7%.: T ~.s.m7mn.m 7 mm TWw Tum.” _.. v: 2;. = $93 map 2: a n E 5a.. .52 no “$43.5. 32;: wk =._ Br 2:. 5 3 “can. .25 22.2.3 3 E. E E and“ .3202 :oEEou E Baum EOE 9: .o EmnEsc mmmE Em mmmszEmu E EwnEE mmmE "202 m: E. 5.30.. o 08.? u 02 co “.0me 9m wwmmmE SEEN 95mqu :93. II mme 2E0? mEEw coszxO umfiflmm [I vl 355mm 2: .6 298. 2.8%.”. ...
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This note was uploaded on 02/13/2011 for the course PHYS 2211 taught by Professor Jackson during the Spring '11 term at UGA.

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EdExam2 - Jentz Edward 810186982 “Ill mmmmuuumnummmummumm...

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