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Topic: Synthesis of Alkene from Alkyne and Alkyl Halide  (Read 2629 times)

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Offline Cait

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Synthesis of Alkene from Alkyne and Alkyl Halide
« on: October 21, 2013, 09:51:48 PM »
Are there any suggestions on how this alkene could be synthesized from an alkyne and an alkyl halide. My organic chemistry class has been learning about substitution and elimination reactions so I am assuming the mechanism for the reaction must be one of those two options. However, the only method I have learned for synthesizing an alkene from an alkyne is hydrogenation, so I am not sure where to begin with this question.

CCC(C)C=CCC


Offline orgopete

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Re: Synthesis of Alkene from Alkyne and Alkyl Halide
« Reply #1 on: October 22, 2013, 12:40:39 AM »
If you are asking us what reaction discussed in class will lead to this product, we missed the class. If alkene coupling reactions were covered, that is a possible route. If alkyne coupling and cis and trans reductions to Alkenes was covered, that could lead to the product. If Wittig reactions were covered, that might give the product. What seems like a good idea from what you learned in class?
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Offline spirochete

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Re: Synthesis of Alkene from Alkyne and Alkyl Halide
« Reply #2 on: October 22, 2013, 12:57:23 PM »
It's probably two steps. Do you know how to alkylate a terminal alkyne?

Offline Babcock_Hall

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Re: Synthesis of Alkene from Alkyne and Alkyl Halide
« Reply #3 on: October 22, 2013, 01:24:19 PM »
Sometimes it is best to start with the product and work backward one step at a time.  Can you think of something with the same number of carbons that could be made into your product?

Offline Cait

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Re: Synthesis of Alkene from Alkyne and Alkyl Halide
« Reply #4 on: October 24, 2013, 01:41:00 PM »
Thank you for your help. I talked with my professor about this question and he informed me that he had mistakenly given the question to the class and that we have not yet covered the information needed to answer it.
 

Offline zsinger

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Re: Synthesis of Alkene from Alkyne and Alkyl Halide
« Reply #5 on: October 26, 2013, 06:15:58 PM »
WITTIG.
"The answer is of zero significance if one cannot distinctly arrive at said place with an explanation"

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