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When methyl benzoate bears a substituent at the para
Chapter 21, Problem 21.56(choose chapter or problem)
When methyl benzoate bears a substituent at the para position, the rate of hydrolysis of the ester group depends on the nature of the substituent at the para position. Apparently, a methoxy substituent renders the ester less reactive, while a nitro substituent renders the ester more reactive. Explain this observation.
Questions & Answers
QUESTION:
When methyl benzoate bears a substituent at the para position, the rate of hydrolysis of the ester group depends on the nature of the substituent at the para position. Apparently, a methoxy substituent renders the ester less reactive, while a nitro substituent renders the ester more reactive. Explain this observation.
ANSWER:Step 1 of 2
This experiment tells us that when methyl benzoate bears a substituent at the para position, the rate of hydrolysis of the ester group depends on the nature of the substituent at the para position.
A methoxy substituent renders the ester less reactive, while a nitro substituent makes the ester more reactive towards hydrolysis. We're asked to explain this observation.
The rate of hydrolysis depends on the electrophilicity of the esters carbonyl carbon. If it is a
powerful electrophile, the ester will readily hydrolyze as the carbonyl carbon will be an attractive
target for the water nucleophile. If it is a weak electrophile, the ester will be difficult to hydrolyze.