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Topic: 3-ethyl-2-pentene with HCl in presence of peroxides  (Read 3839 times)

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Offline Steenrod

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3-ethyl-2-pentene with HCl in presence of peroxides
« on: September 18, 2012, 06:04:59 AM »
I found this question in my book:

How does 3-ethyl-2-pentene react with HCl in presence of peroxides?

I feel the answer should be according to anti-Markovnikov's addition but the answer in my book states it occurs by Markovnikov's addition.

My question is :
Why does this happen? Any explanation is appreciated.
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Offline discodermolide

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Re: 3-ethyl-2-pentene with HCl in presence of peroxides
« Reply #1 on: September 18, 2012, 06:07:55 AM »
It may be that the peroxides epoxidise the double bond. This epoxide is then opened by the HCl.
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Offline AWK

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Re: 3-ethyl-2-pentene with HCl in presence of peroxides
« Reply #2 on: September 18, 2012, 07:46:47 AM »
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Offline Schrödinger

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Re: 3-ethyl-2-pentene with HCl in presence of peroxides
« Reply #3 on: September 18, 2012, 07:54:12 AM »
Aah, the peroxide effect. This effect (a free radical mechanism) is observed only with HBr and not the other halogens. That's why, despite the peroxides, the product is still the Markovnikov product.
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Offline Steenrod

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Re: 3-ethyl-2-pentene with HCl in presence of peroxides
« Reply #4 on: September 18, 2012, 01:01:22 PM »
Thank you very much!
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