Reacción de Grignard

Reacción de Grignard
Tipo de reacción Reacción de acoplamiento
Identificadores
reacción de grignard
ID ontología RSC RXNO: 0000014
Lleva el nombre de Victor Grignard
Se añade una solución de un compuesto carbonilo a un reactivo de Grignard.

La reacción de Grignard (pronunciada /ɡriɲar/) es una reacción química organometálica en la que haluros de alquilo, vinilo o aril - magnesio (reactivo de Grignard) se agregan a un grupo carbonilo en un aldehído o cetona.[1]​[2]​ Esta reacción es importante para la formación de enlaces carbono-carbono.[3]​[4]​ La reacción de un haluro orgánico con magnesio no es una reacción de Grignard, pero proporciona un reactivo de Grignard.[5]​

Un ejemplo de una reacción de Grignard.

Las reacciones y los reactivos de Grignard fueron descubiertos y reciben el nombre del químico francés François Auguste Victor Grignard (Universidad de Nancy, Francia), quien lo publicó en 1900 y recibió el Premio Nobel de Química de 1912 por este trabajo.[6]​

Mecanismo de reacción

El carbono unido al magnesio funciona como un nucleófilo, atacando el átomo de carbono electrofílico que está presente dentro del enlace polar de un grupo carbonilo. La adición del reactivo de Grignard al carbonilo generalmente se realiza a través de un estado de transición de anillo de seis miembros.[7]​

El mecanismo de la reacción de Grignard.
El mecanismo de la reacción de Grignard.

Véase también

Referencias

  1. ↑ Smith, Michael, 1946 October 17- (2007). March's advanced organic chemistry : reactions, mechanisms, and structure. (6th ed. edición). Wiley-Interscience. ISBN 0471720917. OCLC 69020965. Consultado el 1 de julio de 2019. 
  2. ↑ Chapter 19: Carboxylic Acids. Organic Chemistry 4e Carey. mhhe.com
  3. ↑ Shirley, D. A. (1954). «The Synthesis of Ketones from Acid Halides and Organometallic Compounds of Magnesium, Zinc, and Cadmium». Org. React. 8: 28-58. 
  4. ↑ Huryn, D. M. (1991). «Carbanions of Alkali and Alkaline Earth Cations: (ii) Selectivity of Carbonyl Addition Reactions». En Trost, B. M., ed. Comprehensive Organic Synthesis, Volume 1: Additions to C—X π-Bonds, Part 1. Elsevier Science. pp. 49-75. ISBN 978-0-08-052349-1. doi:10.1016/B978-0-08-052349-1.00002-0. 
  5. ↑ IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). ISBN 0-9678550-9-8. doi 10.1351/goldbook.
  6. ↑ Grignard, V. (1900). «Sur quelques nouvelles combinaisons organométaliques du magnésium et leur application à des synthèses d'alcools et d'hydrocabures». Compt. Rend. 130: 1322-25. 
  7. ↑ Maruyama, K.; Katagiri, T. (1989). «Mechanism of the Grignard reaction». J. Phys. Org. Chem. 2 (3): 205-213. doi:10.1002/poc.610020303. 

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