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Topic: How to synthesize ethanamine (ethlyamine) from propene?  (Read 3712 times)

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Offline origination

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How to synthesize ethanamine (ethlyamine) from propene?
« on: April 11, 2015, 10:05:00 AM »
Can anyone show me the synthesis pathways for the formation of ethanamine (ethlyamine) from propene as starting material?  The attempted solution is as in the photo attached but I know that it is not the correct pathway. ==  I have increased the carbon atom by one...

Offline critzz

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #1 on: April 11, 2015, 10:16:27 AM »
Your pathway would result in two additional carbon atoms. The LiAlH4 nitril reduction doesn't remove a carbon atom, but will only reduce the tripple bond.
How about ozonolysis of the propene double bond as first step? 

Offline origination

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #2 on: April 11, 2015, 10:40:57 AM »
Your pathway would result in two additional carbon atoms. The LiAlH4 nitril reduction doesn't remove a carbon atom, but will only reduce the tripple bond.
How about ozonolysis of the propene double bond as first step?

Thanks for your suggestion but unfortunately it is not the most appropriate pathway. Can you think of the other possible ways to solve the problem? Thank you ~

Offline critzz

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #3 on: April 11, 2015, 12:26:05 PM »
This is what I had in mind.



You could swap the ozonolysis step for OsO4, NaIO4.

Honestly I do not know another way to reduce the carbon count and form ethylamine from propene.  :P

Offline Enthalpy

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #4 on: April 14, 2015, 04:51:33 PM »
What are the drawbacks of metathesis? Dangerous metal?

Now that propylene as a byproduct doesn't suffice for polypropylene any more, it's obtained from ethylene and butene anyway.

Offline Dan

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #5 on: April 15, 2015, 05:56:06 AM »
Honestly I do not know another way to reduce the carbon count and form ethylamine from propene.  :P

Lemieux–Johnson oxidation is an alternative to ozonolysis.
My research: Google Scholar and Researchgate

Offline critzz

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #6 on: April 15, 2015, 07:27:19 PM »

Lemieux–Johnson oxidation is an alternative to ozonolysis.


You could swap the ozonolysis step for OsO4, NaIO4.


Yeah, I didn't remember the name of the reaction though. ^^

Offline Dan

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Re: How to synthesize ethanamine (ethlyamine) from propene?
« Reply #7 on: April 16, 2015, 05:57:06 AM »

Lemieux–Johnson oxidation is an alternative to ozonolysis.


You could swap the ozonolysis step for OsO4, NaIO4.


Yeah, I didn't remember the name of the reaction though. ^^

Sorry, I didn't read your post properly...
My research: Google Scholar and Researchgate

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