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Topic: picoline chemistry  (Read 4780 times)

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Offline Senobim

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picoline chemistry
« on: May 28, 2014, 03:45:23 AM »
Hello, guys I would like to ask for your help. I am not sure how 2-methylpiridine will react with ethyl carbonate.

Thanks in advance,

I attached .jpg file
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Offline discodermolide

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Re: picoline chemistry
« Reply #1 on: May 28, 2014, 04:50:47 AM »
You cannot compare the two reactands, one is an aldehyde the other a carbonate.
So with diethyl carbonate what do you think will happen? You won't get the structure you have drawn.

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Offline Senobim

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Re: picoline chemistry
« Reply #2 on: May 28, 2014, 05:11:03 AM »
another guess would be
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Offline discodermolide

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Re: picoline chemistry
« Reply #3 on: May 28, 2014, 06:17:12 AM »
That looks to be a better guess!
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Offline Senobim

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Re: picoline chemistry
« Reply #4 on: May 28, 2014, 06:21:50 AM »
Thanks! ;]
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Offline Senobim

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Re: picoline chemistry
« Reply #5 on: May 28, 2014, 10:02:17 AM »
And I have another question, from aldol condensation, i am totally unsure about second eq. reaction.

Reaction takes place in KOH,MeOH
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Offline discodermolide

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Re: picoline chemistry
« Reply #6 on: May 28, 2014, 10:05:19 AM »
Have you forgotten to draw the ketone attached to the furan ring?
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Offline Senobim

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Re: picoline chemistry
« Reply #7 on: May 28, 2014, 10:22:27 AM »
i forgot to draw metoxy group attached to the benzene ring ;]]]
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Offline discodermolide

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Re: picoline chemistry
« Reply #8 on: May 28, 2014, 10:32:21 AM »
The second product is just another aldol of the anion of the furanyl-methyl ketone with the ketone in the first aldol product.
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Offline Senobim

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Re: picoline chemistry
« Reply #9 on: May 28, 2014, 10:47:47 AM »
Could you comment, what's wrong with my second structure, please.
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Offline discodermolide

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Re: picoline chemistry
« Reply #10 on: May 28, 2014, 12:48:28 PM »
You added an extra carbon atom.
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Offline Senobim

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Re: picoline chemistry
« Reply #11 on: May 28, 2014, 01:42:26 PM »
so it must be like this
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Offline discodermolide

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Re: picoline chemistry
« Reply #12 on: May 28, 2014, 02:00:46 PM »
No like this
O=C(C1=COC=C1)/C=C(C2=CC=CO2)/C=C/C3=CC=CC=C3OC
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Offline Senobim

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Re: picoline chemistry
« Reply #13 on: May 28, 2014, 03:57:34 PM »
Thank you!
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Offline Senobim

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Re: picoline chemistry
« Reply #14 on: May 31, 2014, 03:52:10 PM »
I am still having trouble to understand this concept. Could Furfural become enolate ion?
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