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CHEM 2211 FALL 2010 TEST 1 - CHEMISTRY 2211 EXAM 1 SCORE...

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Unformatted text preview: CHEMISTRY 2211 EXAM 1 September 15, 2010 SCORE 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!! 1, l. (6 pts) Consider the following compounds: 2 o Cis-1-ethyl-2-methylcyclohexane o Trans-1-ethyl-2-methylcyclohexane 3_ Which of these two compounds is the most stable overall? 4. grams — "C'Fkyl-1~WL\7' C7¢(ol/‘L>(Ar\<_ 5. . . _ , 6. Draw the most the most stable chair conformation of the compound you indicated in the box above: 7. 8. 9. 1 0. Total: KJ/mol Name: 2. (10 pts) Looking down the Carbon 3 — Carbon 4 bond of 3-chloro—4-ethylhexane, provide the following: Draw all three staggered conformations, circle the least stable conformer and calculate its total strain energy: Total strain energy for the least stable conformer: "L1 J“ " L' + '4' 1 = 7'0 6| Draw all three eclipsed conformations, circle the most stable conformer and calculate its total strain energy: (1143041 0’3““7. Name: 2. (10 pts) Looking down the Carbon 3 —- Carbon 4 bond of 3—chloro-4—ethylhexane, provide the following: Draw all three staggered conformations, circle the least stable conformer and calculate its total strain energy: Draw all three eclipsed conformations, circle the most stable conformer and calculate its total strain energy: Name: 3. (12 pts) Identify the functional groups found in the following compounds. Clearly circle all of the atoms/ rou s of atoms necessa to identi each s ecific functional rou . Label each group that you have circled with the appropriate functional group name: \ Name: 4. (10 pts) Provide appropriate IUPAC names for each of the structures shown below: of / I“ Buy, — ‘Z,§’di"~cH‘7’ — ‘1 - O'WkflP’DPHB Gyo’o Mfr-“4C. j g/g'biokkz"lt"1- dH‘a—O‘I‘L‘z’ OGhfiaL, ‘Tans—l—isom - —MH\/ a 11 mow 7mg - army -{- (I—mLA7ICLL7|\ CyclaLV—fhmc, C do n) d (.th .0; '- Cycle pnfyl CycloOC/‘Fafvc. Name: 5. (10 pts) Provide the appropriate skeletal structure for each of the IUPAC names given below: 3,4,6-Triethyloctane: 3,4-diethyl—3-fluoro-2,5-dimethylhexane: Name: 1-tert-butyl-3—Isobutyl—S-propylcyclohexane: 3-is0propyl-5,6-dimethylnonane: 51w”; 1,1 -, '5- EH7. , 1, g, u _ ,Hfiwhfl “to/1‘44, Name: 6. (6 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. Ring Flip Total Strain Energy: Name: 7. (12 points) Draw skeletal structures of six constitutional isomers sharing the molecular formula C3H60: Name: 8. (10 points) Indicate whether the following pairs of compounds are constitutional isomers, stereoisomers, conformational isomers, or identical to one another: Name: 9. (12 points) Compare the torsional, angle, and steric strain of each pair of compounds (A and B) shown below. Indicate which compound in each pair has the largest amount of each specific type of strain by writing the appropriate letter (A or B) into the corresponding box. If a particular type of strain is not present in a pair or that type of strain is identical for both compounds, leave the corresponding box blank. Strain Energies Torsional Angle Steric CH3 A B CH3 CH3 A B 10 [OD TIHNSHITTHNEEIZI m a Name: 10. (12 pts) Several constitutional isomers of C6H100 are given below. Match these structures with the IR spectra provided. Draw the appropriate structure corresponding to each spectrum in the boxes provided. In addition, you must label the peaks in each spectrum that correspond to the identifying functional groups. 6 W0” 6 NR 0 O s (3 pb /\/\OH /\/O\/\ awake, 2839- 2934 C .. H HHVENUHIEfllfll c=c—H me‘i C'H 11 lOD TIHHSHETTHNCEIZI m u dflflU 3000 2000 "EVENUHEERIfll Name: 1500 12 500 [OD TR HHSHITTINEEI 5H 01 D C;—:c,— H IIH‘IFENUI'II ERI -|l Name: 13 100 nmsmrrnuczm 8 who 5000 20m lawman 'll Name: 1500 1000 14 SIO ...
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