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EK Lecture Question 64
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Vasil_5264
#1 Posted : Monday, June 08, 2020 11:50:55 PM
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Hello,
For question 64, I thought that the reactivity of carboxylic acid derivatives was increased by the addition of electron withdrawing groups to destabilize the partial positive charge on the carbonyl carbon. with that in mind, I am wondering why this question says that putting electron withdrawing groups would actually stabilize the Ester, and make it less reactive?
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INSTR_Katerina_102
#2 Posted : Wednesday, June 10, 2020 1:10:41 AM
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Hi,

This question is contentious for me as well.

The mindset of the question is of the reactivity of the aromatic ring, not the carboxylic acid (as you need to be in an aqueous environment to hydrolyze the ester, and we assume that the compound is being transported as a dry solid).

The aromatic ring is reactive by the mode of electrophilic aromatic substitution, forming a carbocation in the process - when you make the ring more electron deficient, this mode of reactivity is less viable due to destabilization of this intermediate.

However, I would agree that the carboxylic ester is rendered more reactive by this. This question as a result is a bit on the ambiguous side.
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