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Topic: Orgo Mechanism Problem  (Read 2200 times)

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Offline checounce

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Orgo Mechanism Problem
« on: June 11, 2013, 08:47:34 PM »
Attached is a problem that I am not sure how to do. Can someone please point me in the right direction?
The question is:
Which would be the major product of the following reaction?

Offline checounce

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Re: Orgo Mechanism Problem
« Reply #1 on: June 11, 2013, 09:27:05 PM »
I am between 2 and 3. I think it may be 3? We just covered this today and my professor rushed through it and this question is due tonight by 11 pm.

Offline camptzak

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Re: Orgo Mechanism Problem
« Reply #2 on: June 11, 2013, 11:29:17 PM »
hope this isnt to late, the answer is actually 1. The deuterium atoms are added to the same side o the double bond. I think this is called "syn addition"

i they are added to the same side then they must be cis to one another, so the answer has to be 1

also, i think 2 and 3 are the same molecule
"Chance favors the prepared mind"
-Louis Pasteur

Offline Altered State

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Re: Orgo Mechanism Problem
« Reply #3 on: June 12, 2013, 10:01:52 AM »
I also think it's I, check out the mechanism for metal-catalytic hydrogenation:

http://i.imgur.com/yGzM1XE.jpg

Both hydrogen (Deuterium in this case, it's the same), added to the same side of the double bond.

Offline TwistedConf

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Re: Orgo Mechanism Problem
« Reply #4 on: June 12, 2013, 06:31:43 PM »
I am between 2 and 3.

2 and 3 are the exact same compound, and the wrong answer.

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