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Topic: Synthesis of an organic compound that does not exist.  (Read 4761 times)

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Offline meowmiXX

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Synthesis of an organic compound that does not exist.
« on: March 21, 2011, 11:35:34 PM »
I have been working on an extremely difficult organic synthesis, involving the synthesis of the following organic compound that doesnt exist from molecules containing ONLY two or three carbons:


So far I figured that I could make pyridine from a diels alder reaction with cis-2-butene and a cyanide, then I could add a chlorine to the para position with Cl2 and AlCl3, then I could make the other ring and attatch them with a reaction between the chlorine and a double bond. Thats about as far as Ive gotten. If anyone has any better ideas please let me know. Keep in mind each step can only include the addition of molecules with two or three carbons.

Offline nox

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Re: Synthesis of an organic compound that does not exist.
« Reply #1 on: March 21, 2011, 11:47:43 PM »
cis-2-butene has 4 carbons

Offline meowmiXX

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Re: Synthesis of an organic compound that does not exist.
« Reply #2 on: March 22, 2011, 01:02:08 AM »
Sorry, cis-2-propene

Offline AWK

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Re: Synthesis of an organic compound that does not exist.
« Reply #3 on: March 22, 2011, 02:17:42 AM »
There is no cis-propene - just propene.
3 C + CN is 5 atoms not 6  (pyridine)
« Last Edit: March 22, 2011, 08:15:38 AM by AWK »
AWK

Offline Honclbrif

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Re: Synthesis of an organic compound that does not exist.
« Reply #4 on: March 22, 2011, 08:13:03 AM »
You might be able to get away with a Chichibabin Pyridine synthesis <http://en.wikipedia.org/wiki/Chichibabin_pyridine_synthesis> starting with acetaldehyde, but doing this from such small fragments is going to be pretty annoying. If you don't mind me asking, why the restrictions?
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Offline Honclbrif

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Re: Synthesis of an organic compound that does not exist.
« Reply #5 on: March 22, 2011, 08:22:47 AM »
J. Med. Chem. 1998, 41, 5084-5093. Check out compounds 19 and 24.
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Offline orgopete

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Re: Synthesis of an organic compound that does not exist.
« Reply #6 on: March 23, 2011, 12:14:22 PM »
…Keep in mind each step can only include the addition of molecules with two or three carbons.

This is the most important comment. What chemistry was being discussed in class if we are going to guess the appropriate chemistry?

I could imagine a double Mannich with acetone, formaldehdye, and benzylamine to give the piperidinone. If cyanide were added to the imine from the ketone and allylamine, base hydrolysis to the amide, and cyclization with formaldehyde would give the product. Obviously, if Diels-Alder reactions are being discussed in class, this would be going in the wrong direction. My route is all about carbonyl chemistry.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline Camus023

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Re: Synthesis of an organic compound that does not exist.
« Reply #7 on: March 24, 2011, 10:35:40 AM »
you can search the similary structure comound in scifinder
then maybr you can find some useful synthesis method for you target molecular

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