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Topic: Question about Oxymercuration-Demercuration vs, Addition  (Read 1946 times)

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Offline limonade

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Question about Oxymercuration-Demercuration vs, Addition
« on: April 21, 2013, 10:05:55 PM »
For the following reaction how do we know that the first pathway ( the one with the X through it) will not produce the first product by a regular markovnikov addition using sufuric acid as catalyst? Why does it have to be oxymercuration demercuration to get the first product?


Thank you in advance



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Offline TwistedConf

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Re: Question about Oxymercuration-Demercuration vs, Addition
« Reply #1 on: April 21, 2013, 10:15:00 PM »
You should start the process by talking a little bit about how (ie mechanism) your bottom product structure forms. Your answer is actually right there.
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Offline Sophia7X

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Re: Question about Oxymercuration-Demercuration vs, Addition
« Reply #2 on: April 21, 2013, 11:32:06 PM »
Think carbocation rearrangement.
Oxymercuration-demercuration prevents rearrangement because of the formation of the mercurinium ion rather than a carbocation.
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Entropy happens.
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