general mechanism of nucleophilic acyl substitution


  • What is the general mechanism of nucleophilic acyl substitution?

    Nucleophilic acyl substitution (acyl transfer reaction) occurs by a two-step mechanism. First, attack of the carbonyl carbon atom of an acyl derivative by a nucleophile yields a tetrahedral intermediate. The tetrahedral intermediate can then eject a leaving group. The net result is a substitution reaction.
  • What is an example of acyl nucleophilic substitution?

    This is why this reaction type is called a nucleophilic acyl substitution: one acyl X group is substituted for another. For example, in the reaction below, one alcohol X group (3-methyl-1-butanol) is replaced by another alcohol X group (methanol), as one ester is converted to another.
  • What is a nucleophilic acyl substitution reaction of a carboxylic acid?

    Carboxylic acid derivatives tend to undergo a reaction called nucleophilic acyl substitution. In the same fashion as nucleophilic addition, this mechanism starts with a nucleophilic attack on an electrophilic carbonyl carbon, forming a tetrahedral alkoxide intermediate.28 jan. 2023
  • Nucleophilic acyl substitution describes a class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile – such as an alcohol, amine, or enolate – displaces the leaving group of an acyl derivative – such as an acid halide, anhydride, or ester.
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