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Fall 2007 Test 1 - Organic Chemistry 227 Test 1 fa112007...

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Unformatted text preview: Organic Chemistry 227 Test 1 fa112007 name K94 Score = o nscan " 83/16 + essay = HCl (2591550311 (CHwéH (CHJhCWéH (“3919.6112 1930+ HNOJ CF3C02H "HF Hfico3 CH3C02H CH3C0CH200CH3 Nl-L. ‘- CJJSOH Hm} CH3NH3 * [1'20 CH3CH20H (CI-13);,C0H CI—lfiCOCl-IL‘ HCECH H2 NH; CHZHCHz CH3CH3 69* 83/16+ I“? = 19.2 25 35 38 50 L99 Nomenclature: 1 point each. Name the following, com nounds. Common names are acce ted. 1-bromo-2-chloro-3- fluorocyclohexane 4,5-dibromo-4,5-dichloro-6,6-difluoro-3,3-diiodo- 4-tert-butyl-5-neo_oentyldodecane 2,2—dimethyloctane Nomenclature: 1 noint each. Draw the followiIL com nounds. Dash or bond line is fine. isopentane 2—methylbutane 2-bromo-1,4— dimethylc clohe stane 3,3-diethyl-2,2,4,4-tetran1ethylpentane 2 ,4-diisopropyl-1,1 ,3 ,3 -tetramethylcyclobutane “Lt UOAC. “(0“ Afipeax “foul “ya/51,77) w ‘ 5 km em” *1“- ' f Good times with spectroscopyfl points - a" or "one! A compound has a molecular formula of C4H190 and the spectra below. What is its structure? I .... —l’l _c,——-C 0 l’ ‘3 ‘P: (Ms M Draw structure in box above. IR spectrum: U30 Tllflfi-HITTMCEIZI a! I: dllDU 3000 ZUDI lllllll L000 IFI'I'ENUHI ERI -I I Meow 0d Low“ l3C NMR spectrum: C 70 6'0 5'0 4'0 30 20 10 0 PPM Good times with spectroscopyfl points - a" or “one! A compound has a molecular formula of C4H100 and the spectra below. What is its structure? __(l_~c~—L--c-—o-H '4 D W l“ l“ Sl‘Je l H . H H 1‘1 Draw structure in box above. IR spectrum: [00 new“) A \ (ALMA D l Illlflfl anon lilltl LOW IIR'I'ENUHI ERI -II 13C NMR Spectrum: lp, I 39“ l‘lb 60 50 I 40 so 20 I 10 ' 0 PPM 1. Stanley Miller would have most likely said “ 1'! ® I mixed methane and ammonia and water; zapped it with electricity; and I got amino acids. B. Don’t tase me bro. C. I use the volume of the gases to calculate the number of molecules present. D. My combustion experiments led to my theory that organic compounds contain C, H, and O. B. By combining one theory with another I was able to determine molecular formulae. 2. Kekulé dreamed of A. floating balloons of hydrogen and oxygen B. collecting C02 gas from burning wood C. electrons 37 years before their discovery @ a snake biting its tail E. Lavoisier’s beheading 3. The molecules below are @identica] B. not isomers C. constitutional isomers D. aconjugate acidfbase pair F o F Br CI 0 Cl Br R1\ 1?" F F 1! 4. The VSEPR model of H20 has the same shape as the VSEPR model of b A. NH4+ B. H30 (2. CH3‘ @NHz' E. 13H3 5. The formal charge on C in CN‘ is @ A.-2 (9—1 on D.+1®E_+2 :CE N: 6. In ethane A H—C—C = D Cg A. 88 13.104 @1095 D120 E. 180 7. Atomic orbitals are hybridized to create molecular orbitals A. in order to decrease pKa’s B. because the math is simpler C. because electronegative elements are involved D. so that bonds can be broken easier (9 so that correct bonding geometry can be achieved 8. pK.=__.—1eg (K...) B. sin (— K.) C. 14.0— K. 91 1). 50.0- Ka E. (K.+32)*1.3 9. All of the molecules below are identical except _. @2,2,3,3,4—pentamethylhexane Q/ ? 10. There are _ 2° carbons in the molecule on the right. A.2 3.3 c.4 13.? lb 11. Cyclobutane bends away from planar A. to become achiral B. to become chiral C. to decrease angle strain C5) to decrease torsional strain E E. to become more spherical 12. Which reaction below is most likely to take place as written? A. CH3C02Na + CH3OH —><—> CH3COZH + CH30Na 2:16. :5 B. CH30Na + H2 —*-- CH3OH + NaH 35 no C. CH4 + CH3CH20Li i» CH3Li + CHZCHZOH also >< til. D. HCECH + KOH——i- HCECK + H20 75 ./ ® HCECNa + H20 —- HCECH + NaOH ((9 LS E Consider the conformations of compound Y shown below for questions 13 - 15. CH3 CH3 CH3 HCH3 H films H H H H H H H H H H CH3 CH3 I II III 13. The lowest energy (most 14. The best name for stable) conformation is compound Y is A. I A. l-methyl-Z-methylethane @ II B. dimethylpropane C. 111 C. 2-methylbutane E D. IV D. neobutane E. V @butane E 16. Which graph is the most accurate for CF3(CH2),,CO;_H? pKa pKa 5- 5 3-— .A 3 2— 2 IV 1 S. Conformation I is best described as A. cationic B. anti C. staggered D. eclipsed ® gauche ...
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