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Topic: Catalytic Hydrogenation of Alkenes - is trans product possible?  (Read 2632 times)

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Offline dorratz

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Catalytic Hydrogenation of Alkenes - is trans product possible?
« on: October 22, 2016, 10:52:59 AM »
Hello

I have a question about this catalytic Hydrogenation of Alkenes


Does anyone can give me another example where there will be a trans product because of steric hinderence? I couldn't find one in the book / internet.

Thanks
Dor

Offline dorratz

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Catalytic hydrogenation of Alkene - a question about the products
« Reply #1 on: October 22, 2016, 01:00:36 PM »
Hey

I got a question about this:


Why don't I get two products?

My answer is :

so in my opinion the products are diastereomers.

Thanks
Dor

Offline AWK

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Re: Catalytic hydrogenation of Alkene - a question about the products
« Reply #2 on: October 22, 2016, 02:03:08 PM »
There are no chiral centre in 2-methylpentane.
AWK

Offline dorratz

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Re: Catalytic hydrogenation of Alkene - a question about the products
« Reply #3 on: October 22, 2016, 05:06:26 PM »
Yepp, damn right. I was too tired to see it.

Thanks
Dor

Offline orgopete

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Re: Catalytic Hydrogenation of Alkenes - is trans product possible?
« Reply #4 on: October 22, 2016, 08:57:13 PM »
I cannot think of any way of inserting a palladium, platinum, or nickel catalyst into the more hindered side. If one wished to get the trans product from alpha-pinene knowing that the top face is sterically hindered, then I'd try a radical addition of HBr or just add bromine. For HBr, I'd expect the hydrogen to add from the least hindered side. The reductive hydrobromination would give the trans-pinane.
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Offline dorratz

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Re: Catalytic Hydrogenation of Alkenes - is trans product possible?
« Reply #5 on: October 23, 2016, 05:18:15 AM »
Thanks a lot.

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