What makes ethanoic acid a weaker electrophile than ethanoyl chloride?

Answer 1

Consider the leaving group on the ipso carbon: chloride versus hydroxide ion.

Acetyl chloride, #H_3C-C(=O)Cl#, has a #Cl^-# leaving group. Acetic acid, #H_3C-C(=O)OH#, has an #HO^-# leaving group. Of course, hydroxide is a much stronger base (and stronger nucleophile) than chloride, and the differential ease of substitution reflects this
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Answer 2

The presence of an electronegative oxygen in ethanoic acid delocalizes electron density, reducing its electrophilic character compared to ethanoyl chloride, which lacks this electron-donating oxygen.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.

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