0244Pb8 -2010.cwk (WP)

0244Pb8 -2010.cwk (WP) - following one). Would Brainpan ’...

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Problem 8, Chemistry 0244 - 2010. Here are two problems more or less stolen from Marc Loudon s fine book: (a) Explain why 2,3-dimethyl-1,3-butadiene forms a Diels-Alder Adduct with maleic anhydride, but 2,3-di- tert -butyl-1,3-butadiene does not. (b) This one I ll quote exactly. Sorry about the copyright violation, Marc. “Knowing that conjugated dienes react in the Diels-Alder reaction, a student, M. T. Brainpan, has come to you, a noted authority on the Diels-Alder reaction, with an original research idea: to use conjugated alkynes as the diene component in the Diels-Alder reaction (such as the
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Unformatted text preview: following one). Would Brainpan ’ s idea work? Explain.” + O O O maleic anhydride Well, now evaluate your answer, which was no doubt exactly what was sought by this question, in the light of the following result of Johnson and Bradley (a former teacher in this course). You will have to suspend disbelief and do some creative arrow pushing. Think of what compound ( B ) must have been to have formed the final product, A . 600 °C A B This problem is very similar to one on an old 301X final....
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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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