What is the purpose of glacial acetic acid in the oxidation of benzhydrol?

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Discussion Overview

The discussion revolves around the role of glacial acetic acid in the oxidation of benzhydrol to benzophenone, specifically in the context of a laboratory experiment involving sodium dichromate. Participants are exploring the chemical interactions and purposes of the reagents used in the reaction, including the role of NaHCO3 in the extraction process.

Discussion Character

  • Exploratory
  • Technical explanation
  • Debate/contested
  • Homework-related

Main Points Raised

  • One participant seeks to understand the function of glacial acetic acid in the oxidation process, questioning how it interacts with benzhydrol and whether it interferes with the oxidation by donating protons.
  • Another participant notes that converting an alcohol to a ketone is an oxidation process, but does not elaborate on the role of acetic acid.
  • A different participant mentions a previous experiment where glacial acetic acid reacted with NaOCl, suggesting that the acid's role was to form hypochlorous acid, which then participated in the reaction with alcohol, raising questions about the dichromate's role in the current experiment.
  • There is a question about whether dichromate acts as a catalyst in the oxidation process.

Areas of Agreement / Disagreement

Participants express uncertainty regarding the specific roles of glacial acetic acid and dichromate in the reaction. There is no consensus on how these chemicals interact or their individual contributions to the oxidation process.

Contextual Notes

Participants have not fully resolved the assumptions regarding the interactions of glacial acetic acid with benzhydrol and the role of dichromate, leaving open questions about the mechanisms involved in the oxidation reaction.

Who May Find This Useful

This discussion may be useful for students and researchers interested in organic chemistry, particularly those studying oxidation reactions and the roles of different reagents in chemical transformations.

Delta what
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In a lab we oxidized benzhydrol to produce benzophenone. We use glacial acetic acid and sodium dichromate dehydrate to oxidize the benzhydrol. Then we set up the first extraction with water and CH2Cl2 and the second with NaHCO3 and CH2Cl2.

I am trying to figure out what all of the chemicals used are doing.
Especially what the glacial acetic acid is doing?
I am also not quite getting the purpose of the NaHCO3.

I believe that the dichromate is a catalyst that produces a complex with the benzhydrol.
I can't figure out what the acid is doing. My major barrier is that I thought that the lab was trying to remove the hydrogen from the benzhydrol (oxidize it) and wouldn't the acid get in the way of this since it is all to willing to give up its proton (I am guessing more so then the benzhydrol).
[PLAIN]http://://o.quizlet.com/mXl.vLVhNjF3Y6JD7WMDyg_m.png
[PLAIN]http://://o.quizlet.com/mXl.vLVhNjF3Y6JD7WMDyg_m.png
 
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Hint: converting an alcohol to a ketone is just an oxidation.
 
Totally get that this conversion is oxidation. I was wondering why I would put something in the reaction put that would be more likely to undergo a loss of a proton over the alcohol. In another experiment we utilized glacial acetic acid and NaOCl. The purpose of the acid there is to react with the OCl making the hypochlorous acid that then undergoes an addition reaction with the alcohol. Then the alcohol hydrogen is taken by water and then the carbon's hydrogen is taken by another water. Then the chlorine leaves and a ketone is formed. I am still not getting the dichromate and glacial acetic acid's relation.
 
If it is an oxidation - does the dichromate play a role of a catalyst?
 

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