Q6A-2005

Q6A-2005 - E and F . (10 points, 10 point bonus) CO 2 Me Ph...

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Chem 41c Quiz 6 Stoltz, Spring 2005 May 27, 2005 Predict the major products (if any) of the following reactions: (5 points each) 1. HNO 3 , H 2 SO 4 NO 2 2. H N HNO 3 , Ac 2 O, 20 °C H N NO 2 3. A remarkable cascade of pericyclic reactions on compound B produces a mixture of racemic compounds C - F simply upon heating. Compound B is prepared by Lindlar reduction of A . In a related system compound G is reduced to H and forms products I and J after prolonged stirring at 23 °C (eventually only J is observed). Your task is the following 1) identify the structures of B and H , 2) Describe a mechanism for the the conversion of H to I and J , (hint: it may be useful to draw an orbital diagram for H although not neccessary) and 3) As a bonus provide the mechanism for the formation of
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Unformatted text preview: E and F . (10 points, 10 point bonus) CO 2 Me Ph H 2 , Lindlar Catalyst CH 2 Cl 2 , 23 C A B Ph CO 2 Me PhCH 3 , 23 100 C H H H Ph H H H H MeO 2 C H H H Ph H CO 2 Me Ph H MeO 2 C H H Ph C D F E C and D are formed at 23 C after prolonged stirring E and F are formed at 100 C stirring during which time the amounts of C and D are diminished Intramolecular 4 + 2 Diels-Alder Cycloadditions CO 2 Me H 2 , Lindlar Catalyst CH 2 Cl 2 , 23 C G H Ph PhCH 3 , 23 C I J Ph Ph Ph Ph H Ph H Ph Ph 8 conrotatory electrocyclization 6 disrotatory...
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This note was uploaded on 01/03/2012 for the course CH 41c taught by Professor List during the Fall '10 term at Caltech.

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Q6A-2005 - E and F . (10 points, 10 point bonus) CO 2 Me Ph...

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