Reacting an Ester: Seeking Approval - Do You Agree?

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SUMMARY

The discussion centers on a reaction mechanism for ester formation involving acyl chloride and alcohol. Participants critique the mechanism, specifically pointing out an error regarding the nitrogen's bonding and the improper use of pyridine. Pyridine's role is clarified as a neutralizing agent for HCl produced during the reaction, emphasizing that alcohol is more reactive in the presence of both reagents. The conversation highlights the importance of accurately representing charges and understanding reagent functions in organic chemistry reactions.

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  • Knowledge of the role of pyridine in organic reactions
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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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