(a) You learned in Sec. 19.7 that carbonyl-addition reactions can occur under basic conditions. The hydrolysis of methyl benzoate is also promoted by ^–OH. Write a mechanism for the hydrolysis of methyl benzoate in NaOH solution.

(b) A student has suggested the following transformation, arguing that it can be driven to completion with a large excess of methanol and sodium methoxide.

In fact, this reaction does not occur because, under the basic conditions, the carboxylic acid undergoes a different reaction. What is that reaction?

Transcribed Image Text:

Ph-C-OH + CH3OH (large excess) CH30 Ph-C-OCH3 + H₂O