Dolbier HW Solutions 250

Dolbier HW Solutions 250 - 244 CONJUGATION IN ALKADIENES...

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This carbocation is a delocalized one and can be captured at either end of the allylic system by water acting as a nucleophile. ( c ) Hydrogen bromide converts the alcohol to an allylic carbocation. Bromide ion captures this carbocation at either end of the delocalized allylic system. ( d ) The same delocalized carbocation is formed from 3-buten-2-ol as from 2-buten-1-ol. Since this carbocation is the same as the one formed in part ( c ), it gives the same mixture of products when it reacts with bromide. ( e ) We are told that the major product is 1-bromo-2-butene, not 3-bromo-1-butene. The major product is the more stable one. It is a primary rather than a secondary halide and contains a more substituted double bond. The reaction is therefore governed by thermody- namic (equilibrium) control.
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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