Predicting a reaction between ester and acyl halide

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In summary, Joe is asking for ideas on the product of a reaction between aminobenzoic acid and ethanol with acyl halide CH3COCl. The suggested product could be a friedel craft acylation product or an amide through addition-elimination. The initial configuration of aminobenzoic acid will determine the outcome, which could be ortho/para or meta.
  • #1
josephcollins
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HI ppl, I have a question here. I deduced a forumla 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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  • #2
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.
 
  • #3


Based on the reactants and products listed, it appears that this is a classic esterification reaction. The aminobenzoic acid and ethanol will undergo a condensation reaction to form the ester (specifically ethyl aminobenzoate). Then, the ester will react with the acyl halide (CH3COCl) in an esterification reaction to form an acylated ester. The product would likely be ethyl 2-acetamidobenzoate. This reaction is commonly known as the Schotten-Baumann reaction. The acyl halide acts as an acylating agent, adding the acyl group to the ester molecule. Overall, the reaction is a substitution reaction, where the acyl group from the acyl halide replaces one of the alkyl groups on the ester molecule.
 

Related to Predicting a reaction between ester and acyl halide

1. What is the purpose of predicting a reaction between ester and acyl halide?

The purpose of predicting a reaction between ester and acyl halide is to understand the chemical properties and behavior of these compounds when they are combined in a reaction. This information can help in the design and optimization of chemical reactions, as well as in the development of new compounds and materials.

2. What factors influence the reaction between ester and acyl halide?

The reaction between ester and acyl halide is influenced by various factors, including the nature of the ester and acyl halide, the reaction conditions (such as temperature and solvent), and the presence of catalysts or other additives. The structure and reactivity of the starting materials also play a significant role in determining the outcome of the reaction.

3. What are the possible products of a reaction between ester and acyl halide?

The possible products of a reaction between ester and acyl halide depend on the specific reaction conditions and the reactivity of the starting materials. In general, the reaction can result in the formation of an ester, an acyl halide, or a mixture of both compounds. Additionally, the reaction may also produce other byproducts or side products due to the complexity of the reaction system.

4. How is the reactivity of ester and acyl halide determined?

The reactivity of ester and acyl halide can be determined by various experimental techniques, such as measuring reaction rates or studying product distributions under different reaction conditions. The chemical structures of the compounds also provide important clues about their reactivity, as well as theoretical calculations and computer simulations.

5. Are there any safety concerns when working with ester and acyl halide?

Yes, there are safety concerns when working with ester and acyl halide as they are both reactive and potentially hazardous compounds. Proper handling and storage precautions should be taken to avoid exposure to these chemicals, and appropriate personal protective equipment should be worn when working with them. It is also important to follow established safety protocols and procedures when conducting reactions involving these compounds.

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