Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: shon1802 on December 02, 2016, 08:45:10 AM
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Hi,
I need to write the products of the reaction in which 1 mol Br2 is added to 2,3-dimethylpenta-1,3-diene (see attachment).
There are two double bonds there, and I don't know which bond is more reactive - no carbocations are formed so I can't use Markovnikov's rule. Any ideas?
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What sort of reaction is this? Nucleophilic, electrophilic, pericyclic etc?
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Is it possible to distinguish the conjugated bonds as if they were independent? In several reports I've seen, the double bond of the product remained where a single bond is conventionally drawn at the reactant, that is, between both conventional double bonds.
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Look in your book for the section on "addition to conjugated dienes". There will be a discussion of 1,2 vs. 1,4 products. With conjugated dienes, it does seem reasonable to propose a carbocation based on the products that sometimes form. This is contrast to regular alkenes, where a halonium ion is always formed.