0243Pb71an-09

0243Pb71an-09 - required to isomerize around a simple...

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Answers to Problem 71, Chemistry 0243 - 2009 Here is a straightforward 2 -> 3 mechanism: CH 2 OH H 3 O + CH 2 OH 2 CH 2 H CH 2 OH 2 + S N 1 + + + 2 3 The isomeric 4 is more difficult because of stereochemical problems. The allyl cation is made up of overlapping 2 p orbitals, and there is not free rotation. You can t just trivially turn it over so the ring closure can take place. CH 2 OH H 3 O + CH 2 OH 2 CH 2 CH 2 CH 2 + S N 1 + + + There are several possible solutions. First, you might just note that the stereochemical isomerization necessary will not be as costly as the 66 kcal/mol
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Unformatted text preview: required to isomerize around a simple alkene. Alternatively, you might write a deprotonation, rotate, reprotonation scheme. Finally, you might capture that allyl cation with water to give A , rotate, and then do another SN1. There are many possible variations. H 2 O S N 1 CH 2 + CH 2 + CH 2 OH 2 + CH 2 OH CH 2 OH rotate CH 2 + CH 2 rotate CH 2 CH 2 + protonate deprotonate A...
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This note was uploaded on 03/02/2010 for the course CHEM orgo taught by Professor Jones during the Fall '10 term at NYU.

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0243Pb71an-09 - required to isomerize around a simple...

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