Role of HNO3 in nitration of benzene

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SUMMARY

The discussion centers on the role of nitric acid (HNO3) in the nitration of benzene, specifically its function as a proton donor. Participants clarify that HNO3 dissociates to produce the nitronium ion (NO2+) and that hydroxide (OH-) is not a product of this dissociation. The confusion arises from the misconception that HNO3 can act as an alkaline substance, while it is established as an acid due to its ability to donate protons. The presence of sulfuric acid is also highlighted as essential for generating a good leaving group during the reaction.

PREREQUISITES
  • Understanding of acid-base chemistry, specifically Brønsted-Lowry acid-base theory.
  • Knowledge of the nitration mechanism in organic chemistry.
  • Familiarity with the role of nitronium ions in electrophilic aromatic substitution.
  • Basic concepts of dissociation reactions in acids and bases.
NEXT STEPS
  • Study the mechanism of electrophilic aromatic substitution in detail.
  • Learn about the role of sulfuric acid in nitration reactions.
  • Explore the properties and behavior of nitronium ions (NO2+) in organic synthesis.
  • Investigate the differences between strong acids and their dissociation products.
USEFUL FOR

Chemistry students, organic chemists, and anyone interested in understanding the mechanisms of nitration reactions and acid-base interactions in organic synthesis.

desmond iking
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Homework Statement


in this case, the HNO3 can be dissociated into NO2+ and OH- ion. what makes it a proton donor. p/s : the ans is HNO3 is a proton donor for this question.


Homework Equations





The Attempt at a Solution



since the HNO3 can be dissociated into NO2+ and OH- ion, why it 's called as proton donor (acid), i would called it as alkaline... can someone explain on this plaese?
 

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desmond iking said:

Homework Statement


in this case, the HNO3 can be dissociated into NO2+ and OH- ion. what makes it a proton donor. p/s : the ans is HNO3 is a proton donor for this question.

Homework Equations


The Attempt at a Solution



since the HNO3 can be dissociated into NO2+ and OH- ion, why it 's called as proton donor (acid), i would called it as alkaline... can someone explain on this plaese?

I do not see how ##HNO_3## could act as a proton donor when clearly a stronger acid is present.
 
You got the nitric acid dissociation into NO2+ wrong - OH- is not between products.

Hint: actually it is not HNO3 that dissociates into NO2+.
 
Psst... hydroxide does not function well as a leaving group. So, why do you need the sulfuric acid for? Could it help create a good leaving group?
 

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