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Friday_session_6___solutions - Chem 3580 Spring 2009 Friday...

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Chem 3580 - Spring 2009 Friday Session 6 1. Propose a plausible mechanism for the reaction shown below. Draw all important resonance structures for intermediates. O O O O H OEt O O O O O mixture of isomers + EtOH 2. Propose a practical laboratory synthesis of the compounds shown below from the indicated starting compounds. Use any necessary inorganic reagents and, where appropriate, use any other organic reagents containing no more than 4 carbon atoms, unless otherwise restricted.. More than one step is needed in each case. OH O ! Br + OH O H O OH OH OH PBr 3 Br OH H 2 Pd/C OH PCC H O i1. LDA (1 equiv) 2. Br H O ! Na 2 Cr 2 O 7 , H + OH O ! To avoid compliations with the C=Cin the acidic medium the CHO can be oxidized by Ag 2 O, H 2 O or Ag 2 O, H 2 O ——————————————————————————————————————— O O O O O OH OH CN O OH O OH + CN O OMe O OMe CN O OMe Heat O O OH OH O O O Heat 1. NaCN H 3 O + P 2 O 5 2. H 3 O + O O O Cl O O Cl + (CH 3 ) 2 CuLI HO O O HO EtO O + CN !
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