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Topic: HOCl+allyl alcohol=??  (Read 4723 times)

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Offline harini_5

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HOCl+allyl alcohol=??
« on: July 17, 2008, 01:03:12 PM »
When HOCl is added to propene, the product is 1-chloro 2-propanol.My book says this is because the electrophile generated is Chloronium ion and the addition follows Markovnikov’s rule. Accepted .But when the same HOCl adds to allyl alcohol, the product I expected is 3-chloro propan 1, 2 diol. But actually, it is just the reverse; chlorine goes to the beta position. Why is it so? What is the mechanism of this reaction?

Offline macman104

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Re: HOCl+allyl alcohol=??
« Reply #1 on: July 17, 2008, 01:55:33 PM »
Look at the resonance of the allyl alcohol system.

Offline harini_5

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Re: HOCl+allyl alcohol=??
« Reply #2 on: July 18, 2008, 07:41:27 AM »
Can you please give the mechanism???
Thanks in advance!

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