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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sharbeldam on October 24, 2020, 03:47:35 AM

Title: ester hydrolysis speed
Post by: sharbeldam on October 24, 2020, 03:47:35 AM

To determine which of the following esters will go a faster basic hydrolysis for instance in this question in the picture:
i would say it's C but can you tell me if my logic is right?

Because the leaving group has a minus charge on the oxygen and a NO2 which is a strongly withdrawing so it stabilizes the charge, hence we will get a more stable product (leaving group).

*OR*

Since C has a NO2 withdrawing group, the carbonyl carbon has more positive delta so the base would wanna attack it faster.

Both explanations lead to the same answer but which is truer?

Thanks in advance.

Title: Re: ester hydrolysis speed
Post by: wildfyr on October 26, 2020, 11:32:34 AM

I think anion stability is the primary driver.

Title: Re: ester hydrolysis speed
Post by: Disjointcape on October 28, 2020, 10:16:15 PM

In terms of faster basic hydrolysis, I think kinetically, the most important factor would be having the most electrophilic carbonyl--the most electron poor carbonyl of the ester.