0244Pb5-10.cwk (WP)

0244Pb5-10.cwk (WP) - been there in order to give the...

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Problem 5, Chemistry 0244 - 2010 Long ago and not very far away, a Princeton undergraduate did the following reaction: C C R R heat R R 1 (a) Write a mechanism for this reaction. This part should be very easy now. Yet, this result is surprising because without that three-membered ring, the reaction takes an entirely different course: C C R R heat R R 2 (b) Write a mechanism for the reaction forming 2 . This part is harder, but WORK BACKWARD and it should not be too tough. Ask yourselves: what molecule must have
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Unformatted text preview: been there in order to give the product 2 ? (c) Now a really tough one: How does the three-membered ring in 1 change the course of the reaction? For all the answers, see: Tetrahedron Lett. 1969 , 3953 and 3957 (Volume 10, issue 45). It s in the Chemistry Library. You could look it up. Henry Gingrich says to watch out - in these old papers the NMR discussion is in terms of tau, not delta. delta = 10 tau....
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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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