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Topic: predicting major products  (Read 3035 times)

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Offline mandy9008

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predicting major products
« on: December 01, 2009, 05:08:55 PM »
i don't know how to get to the product when the following compounds react under acidic conditions, H2SO4. I thought that the OH group would be the leaving group, forming a double bond in its place. i know that H2SO4 is only a catalyst, which means that the elements will not be incorporated into the product.
thanks!

Offline Oxygen

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Re: predicting major products
« Reply #1 on: December 01, 2009, 09:29:09 PM »
An acid will make better leaving groups (charge stabilization)...it's likely that the -OH can pick up a hydrogen and generate a + charge which would then make it favorable leaving group...

Offline orgopete

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Re: predicting major products
« Reply #2 on: December 01, 2009, 10:48:40 PM »
I suppose you can generate some secondary alcohol from the primary alcohol with sulfuric acid. Presumably, protonation of the alcohol, which when heated can eliminate water and to rearrange from a primary carbocation to a more stable secondary carbocation. If this is captured by the water, it would give the secondary alcohol. However, I think it is a little unfair to expect that one can efficiently do so as loss of water would be a faster reaction from the secondary alcohol than the primary alcohol. Also, for the loss of water to occur, conditions for removal also are not good for trapping of a carbocation with water. 
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