Predicting a reaction between ester and acyl halide

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SUMMARY

The discussion centers on the reaction between an ester derived from aminobenzoic acid and acyl halide CH3COCl. Participants suggest that the reaction may lead to a Friedel-Crafts acylation product, although this typically requires a catalyst. A more definitive outcome proposed is the formation of an amide through an addition-elimination mechanism, where the amino group acts as the nucleophile and chloride anion is eliminated. The specific configuration of the aminobenzoic acid influences the reaction pathway, allowing for ortho, para, or meta substitutions.

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  • Understanding of esterification reactions
  • Knowledge of Friedel-Crafts acylation
  • Familiarity with addition-elimination mechanisms
  • Basic concepts of nucleophiles and electrophiles
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  • Research the mechanisms of Friedel-Crafts acylation in detail
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  • Explore the reactivity of acyl halides with various nucleophiles
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Chemistry students, organic chemists, and researchers interested in reaction mechanisms involving esters and acyl halides.

josephcollins
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HI ppl, I have a question here. I deduced a formula of an acid, aminobenzoic acid and this reacted with ethanol to give the corresponding ester. This ester then reacts with an acyl halide, CH3COCl, any ideas as to the product of this reaction? Thanks, Joe
 
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You may have a friedel craft acylation product of some sort...electrophilic addition to the benzene, ortho/para (although I've not seen this done w/o a catalyst). It all should depend on what your initial configuration of aminobenzoic acid is...as far as I'm concerned, this can be ortho/para and even meta.

A better suggestion is the formation of an amide through addition-elimination, amino group as the nucleophile and elimination of chloride anion.
 

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