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18.24: Nucleophilic Aromatic Substitution: Elimination–Addition

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JoVE Core
Organic Chemistry

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Nucleophilic Aromatic Substitution: Elimination–Addition
 
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18.24: Nucleophilic Aromatic Substitution: Elimination–Addition

Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is confirmed through isotopic labeling. The overall mechanism follows an elimination–addition pathway. A strong base generates a carbanionic center on the ring. Next, elimination of the halide produces the benzyne intermediate, which is highly strained and therefore extremely reactive at both ends of the triple bond. Addition of the nucleophile at either end gives the product with 50–50 distribution.

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Keywords: Nucleophilic Aromatic Substitution Elimination-addition Aryl Halides Benzyne Intermediate Nucleophilic Attack Isotopic Labeling Carbanionic Center Halide Elimination Strained Intermediate Reactivity

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