0243Pb28-09.cwk (WP)

0243Pb28-09.cwk (WP) - removed(although it is not easy the...

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Problem 28, Chemistry 0243 - 2009 It is not possible to remove a proton from propane to give the propyl anion. There is no base, B: known that is strong enough to do the following reaction. The p K a of propane is too high. CH 2 CH 2 CH 3 H B: CH 2 CH 2 CH 3 BH p a ~ 65 The situation changes when propane is replaced with propene. Now the proton can be
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Unformatted text preview: removed (although it is not easy - the p a is still high: CH 2 CH CH 2 H B: – CH 2 CH CH 2 BH p a ~ 38 Why is it possible to deprotonate propene? Now look at a modified propene in X . Once again, the molecule cannot be deprotonated by any base. Why not? B: – H BH X...
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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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