markownikoff's rule

by Saoist
Tags: markownikoff, rule
Saoist is offline
Oct16-05, 12:45 PM
P: 29
looked in books/googled for info about this...i know what it IS, but don't understand why it happens. anyone?
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Oct16-05, 01:09 PM
Sci Advisor
P: 284
Originally it was based on empirical evidence (it was just the product that you got from certain reactions) and was used as a predictive tool. It can be rationilized by thinking about the intermediates of a reaction mechanism. If a carbocation is formed then it will be more stable at the more substituted carbon and therefore a nucleophile would be more likely to attack at that position.
net_nubie is offline
Oct17-05, 04:54 PM
P: 15
Well, I ain't sure of this but consider a 1-Methyl-2-butene. When HCl adds across the double bond, Cl radical will attract the electrons of the C=C towards itself creating a partial +ve charge on the C atoms. This partial positive charge is handled better by a 3rd degree C atom than the 2nd degree C atom. Thus the -ve part of the addendum will go the the C with more substituents, which is the Markonikov's rule.

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