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Organomagnesium halides, commonly known as Grignard reagents, convert acid halides to tertiary alcohols. The reaction requires two equivalents of the Grignard reagent and proceeds via a ketone intermediate.

Grignard reagents are a source of carbanions and function as nucleophiles. The mechanism begins with the nucleophilic attack by the carbanion at the carbonyl carbon of the acid halide to form a tetrahedral intermediate. Next, the carbonyl group is re-formed, and the halide ion departs, forming a ketone. The addition of another equivalent of the carbanion generates a tertiary alkoxide ion. Protonation of the alkoxide gives a tertiary alcohol as the final product.

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Grignard ReactionAcid HalidesAlcoholsGrignard ReagentsCarbanionsNucleophilesCarbonyl CarbonTetrahedral IntermediateKetone IntermediateTertiary AlcoholAlkoxide IonProtonation

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14.14 : Acid Halides to Alcohols: Grignard Reaction

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14.1 : Carboxylic Acid Derivatives: Overview

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14.2 : Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

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14.3 : Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

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14.4 : Structures of Carboxylic Acid Derivatives

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14.5 : Physical Properties of Carboxylic Acid Derivatives

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14.6 : Acidity and Basicity of Carboxylic Acid Derivatives

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14.7 : Spectroscopy of Carboxylic Acid Derivatives

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14.8 : Relative Reactivity of Carboxylic Acid Derivatives

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14.9 : Nucleophilic Acyl Substitution of Carboxylic Acid Derivatives

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14.10 : Acid Halides to Carboxylic Acids: Hydrolysis

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14.11 : Acid Halides to Esters: Alcoholysis

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14.12 : Acid Halides to Amides: Aminolysis

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14.13 : Acid Halides to Alcohols: LiAlH4 Reduction

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14.15 : Acid Halides to Ketones: Gilman Reagent

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