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Topic: Chemiluminescence Ester Formation - Divanillyl Oxalate  (Read 1031 times)

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Offline oesan1

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Chemiluminescence Ester Formation - Divanillyl Oxalate
« on: November 18, 2023, 03:57:39 PM »
The question is

Provide a mechanism for the first nucleophilic attack of vanillin on oxalyl chloride and stop at the formation of the first ester.


But where do you attack first? Is it alcohol on chloride first? How do you begin?

Offline Babcock_Hall

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #1 on: November 18, 2023, 06:17:11 PM »
Why don't you draw and post what you think is correct?

Offline oesan1

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #2 on: November 18, 2023, 08:15:34 PM »
Of course! I tried attacking from the ketone instead of the alcohol. 8)

Offline rolnor

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #3 on: November 19, 2023, 11:34:03 AM »
Here is the structure of vanillin, its an aldehyde, not a ketone. You have a hydroxy group on vanilline, maybe it is important?


https://sv.wikipedia.org/wiki/Vanillin

Offline oesan1

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #4 on: November 19, 2023, 01:00:50 PM »
Yeah, I realized that, forgot to add the hydrogen. Wouldn't the only difference be a balanced oxygen group (the one near the ester)?

Offline Babcock_Hall

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #5 on: November 19, 2023, 05:37:59 PM »
Acid chlorides are quite reactive.

Offline oesan1

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #6 on: November 19, 2023, 06:13:59 PM »
So what would the chlorine atoms do if they are reactive?

Offline rolnor

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #7 on: November 20, 2023, 03:33:28 AM »
If you react an alcohol with an acid chloride, what do you get? You can google "ester formation"

Offline oesan1

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #8 on: November 20, 2023, 09:02:01 AM »
Ohhh, so if I attack the alcohol first, I'd get the chloride sooner!

Offline oesan1

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #9 on: November 20, 2023, 09:03:01 AM »
NOT THE CHLORIDE (the ester)

Offline rolnor

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #10 on: November 20, 2023, 01:02:00 PM »
Alcoholysis of acid chlorides, here;

https://en.wikipedia.org/wiki/Ester

Offline Babcock_Hall

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #11 on: November 20, 2023, 01:24:09 PM »
@OP, I think you are on getting onto the right track now, but it would not hurt to ask yourself, "Is chloride a good leaving group?"

Offline oesan1

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #12 on: November 20, 2023, 01:27:56 PM »
I think it would be, maybe in HCl form?

Offline Babcock_Hall

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Re: Chemiluminescence Ester Formation - Divanillyl Oxalate
« Reply #13 on: November 20, 2023, 04:09:42 PM »
Chloride ion is a very weak base, and weak bases make good leaving groups.  Therefore, a chlorine atom does not need to be protonated in order to leave.  Strong bases, by contrast make poor leaving groups, but they can sometimes be protonated to become good leaving groups.  The second point is tangential to the problem at hand, but it might be useful to you as you work on other chemistry problems.

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