ORGLIST: allene hydration

From: Witek Mozga (mozgaw$##$rocketmail.com)
Date: Wed Sep 06 2000 - 12:15:28 EDT

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Hello everybody,

I have just read in a book that allene undergoes hydration to give
acetone:
                H+
CH2=C=CH2 + H2O -> CH3-CO-CH3
(To see correctly use courier font)

But this means that when protonated, allene forms the less stable
cation:

          H+ +
CH2=C=CH2 -> CH2=C-CH3 -> CH3-CO-CH3

instead of the more stable allilic one:

               +
CH2=C=CH2 -X-> CH2-CH=CH2

Does anybody know why is this so? Or maybe
there is an error in the book?

With kindest regards,

Witek Mozga

mozgaw$##$rocketmail.com
mozga$##$trimen.pl
http://www.trimen.pl
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