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Topic: Reaction mechanism  (Read 1867 times)

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Offline fatghost13

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Reaction mechanism
« on: April 02, 2013, 12:22:47 AM »
How to describe the reaction mechanism for reaction (1) that cis-1-phenylpropene yields products C and D. and how to explain why this differs from those in parts (a) and (b).
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Offline orgo814

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Re: Reaction mechanism
« Reply #1 on: April 02, 2013, 12:34:06 AM »
It is an anti addition of bromine. Look at the stereochemical relationship between the products
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Offline fatghost13

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Re: Reaction mechanism
« Reply #2 on: April 02, 2013, 01:36:13 AM »
As i do not have any idea to draw the reaction mechanism  that cis-1-phenylpropene yields products C and D. Is there are any reference for me to have a look ?
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Offline Dan

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Re: Reaction mechanism
« Reply #3 on: April 02, 2013, 03:34:15 AM »
I think C and D will form by cis/trans isomerisation of the bromonium via a carbocation - the phenyl ring is key to making this isomerisation energetically feasible. 
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