10-21 - 10/22/2009 C C C C What is the name of the...

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Unformatted text preview: 10/22/2009 C C C C What is the name of the following alkene? What is the name of the following alkene? A. cis-9-octadecene A. B. trans-9-octadecene C. cis-8-octadecene D. trans-8-octadecene 1 A. cis-9-chloro-9-octadecene A. B. trans-9-chloro-9-octadecene C. C. none of the above 2 C C C C What is the name of the following alkene? What is the name of the following alkene? A. (9Z)-9-chloro-9-octadecene A. B. (9E)-9-chloro-9-octadecene Highest Highest priority on the same side = zusammen = (Z) Highest priority on opposite sides = entgegen = (E) 3 A. elaidic acid B. (9E)-9-chloro-9-octadecene B. C. cis-8-octadecene D. trans-8-octadecene 4 C C C C Oleic Oleic acid has a higher melting point than elaidic acid. elaidic elaidic acid oleic acid Oleic Oleic acid has a higher melting point than elaidic acid. elaidic elaidic acid oleic acid (E)-octadec-9-enoic acid A. A. Very sure this is true B. B. Somewhat sure this is true C. Maybe this is true (Z)-octadec-9-enoic acid D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false 5 mp mp = 44C, solid mp = 13C, liquid 1 10/22/2009 C C C C Oleic Oleic has a higher melting point than linolenic acid. linolenic acid oleic oleic acid Oleic Oleic has a higher melting point than linolenic acid. linolenic linolenic acid is an omega 3-fatty acid mp = -11C A. A. Very sure this is true B. B. Somewhat sure this is true C. Maybe this is true mp = 13C D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false 7 1 3 2 8 The The cell membranes of arctic reindeer have a higher proportion of lipids containing cis double bonds in their extremities, such as their legs. The The cell membranes of arctic reindeer have a higher proportion of lipids containing cis double bonds in their extremities, such as their legs. A. A. true B. false C C Oleic Oleic acid is more stable than elaidic acid. elaidic elaidic acid oleic acid A. A. Very sure this is true D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false trans trans fats B. B. Somewhat sure this is true C. Maybe this is true 2 10/22/2009 C C C C Elaidic Elaidic acid is more stable than oleic acid because of electronic effects. elaidic elaidic acid oleic acid Elaidic Elaidic acid is more stable than oleic acid because of steric effects. elaidic acid oleic acid A. A. Very sure this is true B. B. Somewhat sure this is true C. Maybe this is true D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false non non bonded interactions steric effects Catalytic hydrogenation of cis and trans 2-butene both give butane. Hydrogenation of the trans isomer releases more heat than A. True B. False the cis isomer. H C H3C C H H2 Pd/C H° = -115 kJ/mol CH3 The most stable butene isomer is 1-butene . A. True B. False H C H3C C CH3 H H2 Pd/C H° = -115 kJ/mol H C H3C C H CH3 H2 H3C CH2 CH2 CH3 Pd/C H° = -120 kJ/mol H C H3C C H CH3 H2 H3C CH2 CH2 CH3 Pd/C H° = -120 kJ/mol The most stable butene isomer is 1-butene . A. True B. False H C H3C H C C H CH3 H ° = -120 kJ/mol C CH3 H H3C H C H C H C H H How much more stable is trans 2-butene? H3C H C H3C C CH3 H H C H C H C H H H ° = -127 kJ/mol H C C H CH3 5 kJ/mol H ° = -120 kJ/mol energy H3C H ° = -115 kJ/mol energy H3C H ° = -115 kJ/mol H3C CH2 CH2 CH3 H3C CH2 CH2 CH3 3 10/22/2009 Approximately, what percent of the cis isomer would be present at equilibrium at room temperature? 10% < 90% > energy H C C H CH3 H C H3C C CH3 H H H3C H C C H C H H 1-Butene is least stable because of greater steric interactions. A. True B. False H C H3C H C C H CH3 C CH3 H H C H H3C H C C H H 7 kJ/mol 5 kJ/mol = H G ° = H ° - T S° energy H3C G° ~ H° H3C G° = -RTln Keq If Keq = 10 then the G° = 5.7 kJ/mole. If Keq ~ 105/5.7 = 7.5 H3C CH2 CH2 CH3 1-Butene is least stable because of electronic effects. Hyperconjugation is an electronic effect where electron delocalization occurs between alkyl groups attached to sp2 atoms. H C H3C C H H3C CH3 H C H C H C H H H C H H C H H C H C H H H3C H C H C H C H H Hyperconjugation is an electronic effect where electron delocalization occurs between alkyl groups attached to sp2 atoms. molecular orbital resonance model model Hyperconjugation is an electronic effect where electron delocalization occurs between alkyl groups attached to sp2 atoms. molecular orbital resonance model model energy LUMO H H3C H C C H C H H H HOMO H3C H C C H C H H 4 10/22/2009 Trans cyclohexene is more stable than cis cyclohexene. A. A. Very sure this is true B. B. Somewhat sure this is true C. Maybe this is true D. Maybe this is false E. Somewhat sure this is false F. Very sure this is false Trans cyclohexene is more stable than cis cyclohexene. H H H H Trans cyclohexene is more stable than cis cyclohexene. H H H H Are there any rings that contain trans double bonds? 28 5 ...
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