If you react HBr/ROOR with cis-2-butene, what is the product? Would there be some sort of shift?
Dumb Organic Question
- Thread starter rpatel8
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Well, with cis-2-butene, wouldn't either side be the same since there is one H on both carbons. The reason I posted this was I am looking at a road map from my organic class and it says the product is 1-bromo-2-methylpropane but that doesn't make sense to me
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wouldn't it just be 2-bromobutane? i really dont think a methyl shift occurs with radicals.. i never read about it in my text book. hope that helps 😕
Thats what I thought as well. I don't know how correct this roadmap is but I found it in my stack of coursework from the past few years. It also says the reaction of the same alkene with B2H6/H2O2 forms 2-methylpropanol. This is confusing to me. I'm hoping that this is just wrong as my DAT is on wednesday
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to your original question, you would get the same product if the Br was added to the second or third carbon, it would be the same compound, 2 bromobutane; not sure what you meant, but there isn't any shift in radical mechanisms
this however is a different reaction. BH3 THF/H202, OH gives an anti-markovnikov syn addition of an OH over a double bond. So it should be 2-butanol, not 2-methylpropanol, maybe you just accidentally missnamed the compound while taking notes
this however is a different reaction. BH3 THF/H202, OH gives an anti-markovnikov syn addition of an OH over a double bond. So it should be 2-butanol, not 2-methylpropanol, maybe you just accidentally missnamed the compound while taking notes
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i guess the ultimate question is.. how did the text get their answer? it seems like something completely different than what we were taught
It would be 2-bromobutane. The bromine would add across the double bond first in a radical fashion, leaving a radical on the C3 carbon. There no possible way to have any type of shift to give a more stable radical.
