0244Pb6-10.cwk (WP)

0244Pb6-10.cwk (WP) - reaction in clear three-dimensional...

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Problem 6, Chemistry 0244 - 2010 (a) In the Diels-Alder reaction of 1,3-butadiene and vinyl acetate ( 1 ) the substituted cyclohexene product contains a stereogenic carbon. Yet the observed optical rotation is zero. How come? Draw all four (yes, four) transition states for this reaction. OAc OAc 1 (b) Draw the endo transition state and the product derived therefrom for the following
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Unformatted text preview: reaction in clear three-dimensional detail. Be exquisitely careful! i = in, o = out, x = exo, n = endo. x o i o i x n n ?? Part (b) is really hard. Go slowly, draw very very carefully. Please get your answer checked before going on....
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Spring '10 term at NYU.

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