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I thought that Grignard reagent might take a proton from water and just form ethane. Does the following reaction take place?

$$\ce{C2H5MgCl + O2 ->[H2O] C2H5OH}$$

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2 Answers 2

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This paper says it does and notes that while the yield of alcohols from aliphatic Grignards is 60-90%, formation of phenols is much less satisfactory. Other methods exist for the formation of phenols from aryl organometallics with much better yields.

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To add on to the answer by Waylander (edited by Nilay Ghosh):

Waylander's reference [1] does not actually propose reacting the Grignard reagent with oxygen in the presence of water. Rather, the reaction with oxygen is carried out in "an ethereal solution", and the water is used to work up the product after the Grignard reagent is oxidized.

The reaction to produce an alcohol is actually not very practical (there are cheaper and more efficient ways to get alcohols), but by reacting under conditions where the oxygen is in excess (saturating the ether with oxygen and adding the Grignard reagent slowly), the reaction can be directed to form a hydroperoxide product.

Reference

  1. Cheves Walling and Sheldon A. Buckler (1955). "The Reaction of Oxygen with Organometallic Compounds. A New Synthesis of Hydroperoxides". J. Am. Chem. Soc. 77, 22, 6032–6038. https://doi.org/10.1021/ja01627a069.
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