{[ promptMessage ]}

Bookmark it

{[ promptMessage ]}

0244Pb5-10.cwk (WP)

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

Info iconThis preview shows page 1. Sign up to view the full content.

View Full Document Right Arrow Icon
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
Background image of page 1
This is the end of the preview. Sign up to access the rest of the document.

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....
View Full Document

{[ snackBarMessage ]}