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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.

Figure1

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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 : Derivados del ácido carboxílico: descripción general

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14.2 : Nomenclatura de los derivados del ácido carboxílico: halogenuros ácidos, ésteres y anhídridos ácidos

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14.3 : Nomenclatura de los derivados del ácido carboxílico: amidas y nitrilos

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14.4 : Estructuras de los derivados del ácido carboxílico

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14.5 : Propiedades físicas de los derivados del ácido carboxílico

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14.6 : Acidez y basicidad de los derivados del ácido carboxílico

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14.7 : Espectroscopía de derivados del ácido carboxílico

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14.8 : Reactividad relativa de los derivados del ácido carboxílico

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14.9 : Sustitución nucleofílica de acilo de derivados del ácido carboxílico

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14.10 : Halogenuros ácidos a ácidos carboxílicos: hidrólisis

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14.11 : Halogenuros ácidos a ésteres: alcoholisis

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14.12 : Halogenuros ácidos a amidas: aminolis

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14.13 : Halogenuros ácidos a alcoholes: reducción de LiAlH4

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14.15 : Halogenuros ácidos a cetonas: reactivo de Gilman

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