Can an organic ion have a charge of -3?

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SUMMARY

An organic ion can indeed have a charge of -3, contrary to the common assumption that it typically carries a charge of -1. In the discussion, participants analyzed compounds such as disodium oxalate and trisodium citrate to illustrate how multiple acidic protons can contribute to a higher negative charge. The conclusion drawn is that a compound must possess three functional groups capable of reacting with sodium to achieve a -3 charge, while also considering the presence of a single -COOH group for a -1 charge scenario.

PREREQUISITES
  • Understanding of organic chemistry functional groups
  • Knowledge of acid-base reactions involving sodium hydroxide (NaOH)
  • Familiarity with the concept of anions and their charges
  • Basic principles of ion formation in organic compounds
NEXT STEPS
  • Research the structure and properties of disodium oxalate
  • Explore the reactivity of trisodium citrate with sodium hydroxide
  • Study the formation of organic ions with multiple functional groups
  • Learn about the role of acidic protons in determining ion charge
USEFUL FOR

Chemistry students, organic chemists, and educators looking to deepen their understanding of organic ion formation and acid-base reactions.

Janiceleong26
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Homework Statement


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Homework Equations

The Attempt at a Solution


I can't seem to see how an organic ion with charge -3 is formed. I thought an organic ion will always have a charge of -1? Like sodium ethoxide CH3CH2CO-Na+ ?
I know that Na can only react with alcohols and carboxylic acids, so B and D are probably out, though B has carboxylic acid grp and D has alcohol grp in it..
 
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Janiceleong26 said:
I thought an organic ion will always have a charge of -1?

Why? What is a charge of the anion in disodium oxalate? Trisodium citrate?

Janiceleong26 said:
I know that Na can only react with alcohols and carboxylic acids

You are looking for a compound that has a single proton acidic enough to be neutralized by NaOH, and three protons that can react with Na. You are right about B & D being out.
 
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Borek said:
Why? What is a charge of the anion in disodium oxalate? Trisodium citrate?
You are looking for a compound that has a single proton acidic enough to be neutralized by NaOH, and three protons that can react with Na. You are right about B & D being out.
-2 and -3 :biggrin: sorry I didn't know about this, now that I've know now...we have to find a compound that has three functional groups that can react with Na right? Which is A or C. But since they say J reacts with NaOH (aq) to produce an organic ion with -1 charge, which means there should only be 1 -COOH grp, so ans. is C
Thanks!
 

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