22. Carboxylic Acid Derivatives: NAS

What are the products of the following reactions?

d.

Propose mechanisms for the following reactions.

(a)

(b)

Why do the nitro groups change the relative leaving tendencies of the carboxy and 2,4-dinitrophenoxy groups in the tetrahedral intermediate in Problem 11?

Write a mechanism for each of the following reactions:

a. the uncatalyzed hydrolysis of methyl propionate.

The Principle of Microscopic Reversibility states that a forward reaction and a reverse reaction taking place under the same conditions (as in an equilibrium) must follow the same reaction pathway in microscopic detail. The reverse of the Fischer esterification is the acid-catalyzed hydrolysis of an ester. Propose a mechanism for the acid-catalyzed hydrolysis of ethyl benzoate, PhCOOCH₂CH₃.

(b) Finish the solution for Solved Problem 20-1 by providing a mechanism for the acid-catalyzed hydrolysis of ethyl formate.