09-30 - 9/30/2009 Cis-1,3-dimethylcyclohexane is more...

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Unformatted text preview: 9/30/2009 Cis-1,3-dimethylcyclohexane is more stable than trans-1,3-dimethylcyclohexane. Cis-1,3-dimethylcyclohexane is more stable than trans-1,3-dimethylcyclohexane. 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 H CH3 H CH3 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 cis 1 2 How can alkanes and cycloalkanes be prepared? How can alkanes and cycloalkanes be prepared? catalytic hydrogenation catalytic hydrogenation C C HH catalyst catalyst (Pd/C) (Pd/C) H C H C HH C C HH catalyst catalyst (Pd/C) (Pd/C) H C H C syn or cis addition of H2. or 3 4 How can alkanes and cycloalkanes be prepared? How can alkanes and cycloalkanes be prepared? catalytic hydrogenation catalytic hydrogenation C C HH catalyst catalyst (Pd/C) (Pd/C) H C H C C C HH catalyst catalyst (Pd/C) (Pd/C) H C H C H H H H H H H H catalyst catalyst (Pd/C) (Pd/C) 5 6 1 9/30/2009 What is the product of the following reaction? 13C Nuclear Nuclear Magnetic Resonance Spectroscopy? HH 1 mole catalyst catalyst (Pd/C) (Pd/C) H H H H H H H H catalyst catalyst (Pd/C) (Pd/C) Nuclear Nuclear Magnetic Resonance Spectroscopy Instrument 13 13C pure chemical compound C5H10O H H H H H * E * H A B C D * 7 X 8 Give the structure of C5H10O. O. Give the structure of C5H10O. O. Each chemically different carbon atom in a structure structure results in one absorption The position of a carbon atom absorption depends depends upon its chemical environment pure pure chemical compound C5H10O Each chemically different carbon atom in a structure structure results in one absorption The position of a carbon atom absorption depends depends upon its chemical environment O H O pure pure chemical compound C5H10O O O * * A B O C D * E * * X 9 * X 10 Propose a synthesis of the following compound from reactants containing 4 carbons or less. H H C C Br OH C C C OH H PCC Br C C O Br C H2 Pd/C OH 1. Li C H C H C Br 2. C O 3. H2O C C OH C C PCC OH 11 2 9/30/2009 Acid/Base: Use the curved arrow formalism to show the bond making and bond breaking in the following reactions. Acid/Base: Use the curved arrow formalism to show the bond making and bond breaking in the following reactions. Li H Li Br Br H 1. Li + Br O H An unknown compound has the formula C5H10O and the following ir spectrum. What structural information do you know about the unknown? C-H -C-H =C-H O-H (s) CO2H CC C=C C=O(s) O N-H CN C C5H10O 4000 3000 2000 1500 wave number cm-1 1000 15500 4000 3000 2000 1500 wave number cm-1 1000 16500 An unknown compound has the formula C5H8O2 and the following ir spectrum. What structural information do you know about the unknown? C-H -C-H =C-H O-H (s) CO2H CC C=C C=O(s) N-H CN C5H8O2 4000 3000 2000 1500 wave number cm-1 1000 500 17 4000 3000 2000 1500 wave number cm-1 1000 500 18 3 9/30/2009 Draw Draw the two chair conformations of the following cyclohexane. Choose the more stable structure. CH CH3 H Cl Cl Cl H CH CH3 H Cl Cl H CH3 CH CH CH3 H Cl Cl H Cl Cl H CH CH3 Cl Cl H CH CH3 HH Cl Cl CH CH3 A B H C D H 19 4 ...
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