Problem

In the presence of pyridine, acyl chlorides react with alcohols to give esters according t...

In the presence of pyridine, acyl chlorides react with alcohols to give esters according to the following overall equation:

(a) The mechanism of this reaction involves a number of steps and begins with the reaction of pyridine with the acyl chloride to give an acylpyridinium ion.

Write a two-step mechanism for the formation of the acylpyridinium ion, using curved arrows to show the flow of electrons.


(b) Show the electron flow in the next step in which the alcohol reacts with the acylpyridinium ion.


(c) Next, pyridine acts as a Br0nsted base toward the product of part (b). What are the products of this reaction?


(d) A final step completes the mechanism. Write an equation for this step showing the products and the electron flow that leads to them.


(e) Does the sum of the individual steps of the mechanism correspond to the overall equation?

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