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Topic: What is more electrophilic?  (Read 8115 times)

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Offline Exploring

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What is more electrophilic?
« on: September 29, 2011, 04:02:56 PM »
a bit of help.. who is more electrophilic, the carbon (of the carbonyle group obviously) of the benzaldehyde or de carbon of the O=C=O , that is CO2 molecule?
I a finding lots of problems about comparing which is more/less electrophilic/nucleophilic.
 thank you very much for your *delete me*!


Edit: All caps removed. This is your first warning, if you type in all caps again you will be temporarily banned. Dan
« Last Edit: September 29, 2011, 06:09:20 PM by Dan »

Offline opsomath

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Re: What is more electrophilic?
« Reply #1 on: September 29, 2011, 04:24:00 PM »
All caps titles are highly electrophilic and have been known to react explosively with good Lewis bases.

*ahem* I'll show myself out...

Anyway, it depends on the reaction. CO2 is a stronger Lewis acid than benzaldehyde, so in that sense it is more electrophilic.
« Last Edit: September 29, 2011, 06:09:41 PM by Dan »

Offline Exploring

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Re: What is more electrophilic?
« Reply #2 on: September 30, 2011, 03:57:56 AM »
sorry for the caps  :-[,
and  thnsk for the answer.  As fas as I understand carbon dioxide is a weak electrophile... and when comparing aldehydes and ketones, aldehydes are more reactive.
In the presence of the same electrophile, if i have a solution of benzaldehye and I bubble CO2 , i presume IĀ“llhave a mixture of the two reaction products.. CO2+E  and E+BzCHO, or it totally depends on the E (electrophile?)?

Offline discodermolide

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Re: What is more electrophilic?
« Reply #3 on: September 30, 2011, 05:09:26 AM »
sorry for the caps  :-[,
and  thnsk for the answer.  As fas as I understand carbon dioxide is a weak electrophile... and when comparing aldehydes and ketones, aldehydes are more reactive.
In the presence of the same electrophile, if i have a solution of benzaldehye and I bubble CO2 , i presume IĀ“llhave a mixture of the two reaction products.. CO2+E  and E+BzCHO, or it totally depends on the E (electrophile?)?


Examine the charges generated when an electrophile is attacked by both types of carbonyl, which cation is more stabilized?
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Offline Exploring

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Re: What is more electrophilic?
« Reply #4 on: September 30, 2011, 06:37:27 AM »
I think it totally depends on the nucleophile.
if your Nu have protons available to have a proton transfer fron the Nu to the O-
you either can hace a carboxilic acid or a Nu=C-Ar

Offline opsomath

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Re: What is more electrophilic?
« Reply #5 on: September 30, 2011, 09:15:17 AM »
Practically speaking, it is easier to do a reaction with benzaldehyde as the electrophile. So for instance if you were bubbling CO2 through a solution of benzaldehyde in ether, and added in a Grignard reagent, you would get mostly the secondary alcohol and not the carboxylic acid. That's largely just because of the low solubility of CO2, though; if you instead added a mixture of dry ice and benzaldehyde, I think you would largely get the carboxylic acid. I'd have to try it to be sure, though; the dry ice would be solid so it would be complicated by that.

Offline discodermolide

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Re: What is more electrophilic?
« Reply #6 on: September 30, 2011, 12:31:56 PM »
I think it totally depends on the nucleophile.
if your Nu have protons available to have a proton transfer fron the Nu to the O-
you either can hace a carboxilic acid or a Nu=C-Ar

When the pi electrons of the C=O attack the electrophile you end up with a C+-O- as a reaction intermediate. Which of the two structures can assist in stabilizing the C+ in a more efficient fashion?
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