Reacting an Ester: Seeking Approval - Do You Agree?

  • Context: Chemistry 
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Discussion Overview

The discussion centers around a proposed reaction mechanism for forming an ester, with participants evaluating the accuracy and completeness of the mechanism presented. The focus includes the roles of specific reagents and the correctness of the depicted steps in the mechanism.

Discussion Character

  • Technical explanation, Debate/contested

Main Points Raised

  • One participant expresses general approval of the mechanism but questions the last step, specifically noting an issue with four bonds to nitrogen.
  • Another participant echoes the concern about the last step and mentions the omission of a + charge in the preceding formulas.
  • A participant clarifies that in the context of the reaction, pyridine's role is to neutralize HCl produced during the reaction between acyl chloride and alcohol, suggesting that the alcohol is more reactive in the presence of both reagents.

Areas of Agreement / Disagreement

Participants do not fully agree, as there are multiple concerns raised about the last step of the mechanism and the use of pyridine, indicating unresolved issues in the discussion.

Contextual Notes

There are limitations regarding the clarity of the reaction mechanism, particularly concerning the charge states and the roles of the reagents involved, which remain unresolved.

HighFive5
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Homework Statement
Draw the major product of the following reaction sequence.
Relevant Equations
None needed.
Hello all!

I wrote a reaction mechanism for a sequence that forms an ester.

Do you agree with my answer?

Thanks for your help!
 

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Everything looks good except the last step. 4 bonds to nitrogen? And, don’t use pyridine like that.
 
chemisttree said:
Everything looks good except the last step. 4 bonds to nitrogen? And, don’t use pyridine like that.
He only forgot to write in the + charge which is in the two preceding formulae? What does your second sentence mean?
 
In this example where alcohol and pyridine are used together, pyridine’s only function is to neutralize the HCl produced in the reaction between the acyl chloride and the alcohol. Where both are present in the same solution, the alcohol is much more reactive towards the acyl chloride.
 
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