February 23, 2020, 04:19:02 AM
Forum Rules: Read This Before Posting


Topic: What is more electrophilic?  (Read 6140 times)

0 Members and 1 Guest are viewing this topic.

Offline Exploring

  • Regular Member
  • ***
  • Posts: 23
  • Mole Snacks: +0/-0
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

  • Chemist
  • Full Member
  • *
  • Posts: 470
  • Mole Snacks: +50/-8
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

  • Regular Member
  • ***
  • Posts: 23
  • Mole Snacks: +0/-0
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +404/-70
  • Gender: Male
    • My research history
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?
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Offline Exploring

  • Regular Member
  • ***
  • Posts: 23
  • Mole Snacks: +0/-0
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

  • Chemist
  • Full Member
  • *
  • Posts: 470
  • Mole Snacks: +50/-8
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

  • Chemist
  • Sr. Member
  • *
  • Posts: 5038
  • Mole Snacks: +404/-70
  • Gender: Male
    • My research history
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?
Development Chemists do it on Scale, Research Chemists just do it!
My Research History

Sponsored Links