0244Pb8an-2010.cwk (WP)

0244Pb8an-2010.cwk (WP) - at those bent sp hybridized...

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Answers to Problem 8, Chemistry 0244- 2010. (a) A diene must be in the s-cis form in order for the Diels-Alder reaction to go, not the more stable s-trans form. Those two tert -butyl groups make the s-cis form so much less stable than the s-trans form that there is not enough for the Diels-Alder reaction to take place at a significant rate. (b) The idea is that the product of the Diels-Alder reaction will be too strained to exist (look
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Unformatted text preview: at those bent sp hybridized carbons). Here is the putative product that Brainpan s reaction would give: + O O O O O O (c) Run through the intramolecular Diels-Alder reaction that Johnson and Bradley s molecule would undergo. If product B is formed and then undergoes the reaction shown by the arrows, the ultimate product is A . It seems that Brainpan wasn t so dumb after all. 600 C A B...
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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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