feb_17 - 2/17/2010 Predict the major product of the...

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Unformatted text preview: 2/17/2010 Predict the major product of the following reaction. Predict the major product of the following reaction. O Br H N O O CH3 Br H N O O O CH3 Br H N O CH3 O O CH3 O CH3 O CH3 O Br H N O O Br H N O O Br H N O O A B C D A B C D Predict the major product of the following reaction. OCH3 Br2 FeBr3 OCH3 Br OCH3 OCH3 + Br + very fast Br 4% trace 96% NO2 Br2 FeBr3 NO2 Br NO2 NO2 + Br + A B C D very slow Br trace 93% trace electronic Predict the major product of the following reaction? What is the major product of the following reaction? A Cl B C O H Br2 FeCl3 Br 90% Br H Cl Br H Cl A OH Cl Cl ? B C Br H H Br 1 2/17/2010 Which of the following compounds is more reactive in electrophilic aromatic substitution? In electrophilic aromatic substitution chlorobenzene reacts at slower a slower rate than benzene? O H Cl O H A B Why is chlorobenzene much less reactive than phenol in electrophilic aromatic substitution? Why is chlorobenzene much less reactive than phenol in electrophilic aromatic substitution? Poor orbital overlap of the 3p-orbital on Cl inhibits electron donation to the ring. Electronegativities O H Cl Electronegativities O H Cl Cl A. Steric effects B. Electronic effects A. Resonance B. Inductive O H Good orbital overlap of the 2p-orbital on O allows electron donation to the ring. Review: O CH3 O Br Br2/ FeBr3 CH3 O + CH3 Br reacts faster faster than benzene Cl Br Br2/ FeBr3 Br Cl Cl Br + Br 90% O N O react slower slower than benzene O N O Br Br2/ FeBr3 10% Br 2 2/17/2010 Starting with benzene give reactants and reagents that would produce the product shown. NO2 Starting with benzene give reactants and reagents that would produce the product shown. Br HNO3 H2 SO4 NO2 Br2 FeBr3 O Br2 FeBr3 AlCl3 O Cl O Br Zn(Hg) HCl O 1. /A lCl3 Cl /Fe 2. Br2 /FeBr3 D Br 3. Zn(Hg) HCl /Fe 1. Br2 /FeBr3 1. HNO3/H2SO4 2. Br2/FeBr3 1. Br2/FeBr3 1. 2. HNO3/H2SO4 Cl O /A lCl3 1. Br2 /FeBr3 /Fe 2. /A lCl3 Cl 2. /A lCl3 Cl /Fe 2. Br2 /FeBr3 A B A B C 3. Zn(Hg) HCl Propose a mechanism for the following reaction. Is the aromatic compound the A. acid or B. base? Starting with benzene and any reactants containing four carbon atoms or less, give a good synthesis of the following compound. H2/Pd-C O O + O AlCl3 Hint: Use the Diels-Alder Reaction AlCl3 H Cl + H H O H O O Starting with benzene and any reactants containing four carbon atoms or less, give a good synthesis of the following compound. Starting with benzene and any reactants containing four carbon atoms or less, give a good synthesis of the following compound. H2/Pd-C O O + H2/Pd-C O PCC O O + O PCC Li Br Br2 FeBr3 Li O H3O Br Li Li O H3O O H Li HO H O Zn(Hg), HCl O Br2 O O Cl AlCl3 H Li HO H Br FeBr3 3 2/17/2010 What is the major product of the following reaction? H H HNO3 H2SO4 What is the major product of the following reaction? H H HNO3 H H H H H H H H N NH2 NH2 N N N N N A NO2 B NO2 H2SO4 H NO2 H NO2 H NO2 NO2 H H N H HNO3 H2SO4 H H N H H H N H H H N H H NO2 H NO2 NO2 What is the major product of the following reaction? H H HNO3 H2SO4 H NO2 H NO2 H NO2 NO2 H H H H H H H H How could the following transformation be accomplished? H N H HNO3 H2SO4 O Cl C CH3 OH NO2 NH2 N N N N N H H N H HNO3 H2SO4 H H N H H H N H H H N H H H N H H N O C CH3 HNO3 H2SO4 H N O C CH3 NO2 H H NO2 H NO2 NO2 NO2 How could the following transformation be accomplished? O H N C CH3 Br2/FeBr3 Can aromatic rings be oxidized? O 1. KMnO4, OH 2. H3O O OH OH Cl O H N C CH3 H N O C CH3 Br H N O C CH3 H N O C CH3 O 1. O3, CH3CO2H 2. H2O2 HO HO O Br Cl Br A B Cl Br C D Br 4 2/17/2010 Can aromatic rings be reduced? Can aromatic rings be reduced with other reagents? H H2/Ni Na NH3, EtOH H EtO H H H slow fast faster H EtO H H H H Na H H What is the product of the following reaction? What about substituted aromatic rings? OCH3 Na NH3, EtOH H H OCH3 H H H OCH3 OCH3 Na NH3, EtOH H H OCH3 H H H OCH3 A H B H A OCH3 or H B H OCH3 What about substituted aromatic rings? Are these compounds useful? OCH3 Na NH3, EtOH H H OCH3 H H EtO H OCH3 H H OCH3 Na NH3, EtOH H H OCH3 H H H H2O O Na HO HO HO OCH3 EtO H OCH3 H H OCH3 H H O CH3 Li, NH3 EtOH O CH3 H H2O O envoid 5 2/17/2010 What is the major product of the following reaction? H H HNO3 H2SO4 What is the major product of the following reaction? H H HNO3 H H H H H H H H N NH2 NH2 N N N N N A NO2 B NO2 H2SO4 H NO2 H NO2 H NO2 NO2 H H N H HNO3 H2SO4 H H N H H H N H H H N H H NO2 H NO2 NO2 What is the major product of the following reaction? H H HNO3 H2SO4 H NO2 H NO2 H NO2 NO2 H H H H H H H H N N N N N H H N H HNO3 H2SO4 H H N H H H N H H H N H H H N H NO2 H H NO2 H NO2 NO2 34 6 ...
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This note was uploaded on 04/06/2010 for the course CHE 326 taught by Professor Fowler during the Spring '08 term at SUNY Stony Brook.

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