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15.12: Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

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Organic Chemistry

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Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

15.12: Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-⁠haloenolate ions, which often participate in other side reactions.


However, α-haloacids undergo SN2 reactions with strong basic nucleophiles. Under this condition, the base abstracts the acidic proton of the acid forming its conjugate base. The anion further participates in a substitution reaction, and the final acidification results in α-substituted acids.


In α-halocarbonyl compounds, nucleophilic substitution via an SN1 pathway is forbidden, as it generates less stable α-carbocation intermediate.


α-Halocarbonyl Compounds Nucleophilic Substitution SN2 Pathway & 945;-haloketones Less Basic Nucleophiles Strong Basic Nucleophiles & 945;-⁠haloenolate Ions Side Reactions & 945;-haloacids Acidic Proton Conjugate Base Substitution Reaction & 945;-substituted Acids SN1 Pathway & 945;-carbocation Intermediate

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