Examples and Reaction Conditions
A typical reactions would be when methyl iodide or ethyl chloride are reacted with powdered sodium metal in anhydrous ether. An alkane containing double the number of carbon atoms is formed, i.e. methyl iodide gives ethane, and ethyl chloride gives n-butane.
The solvent, ether in this case, must be anhydrous (free of moisture) because the alkyl anions are so basic (the pKa of the alkyl proton is 48–50) that they readily deprotonate water to hydroxide ion, forming alkanes, and reducing the yield of the desired product.
Due to several limitations (see below) this reaction is very seldom used, especially since alkanes can be obtained from variety of natural sources, such as crude oil or by transformations of fatty acids. However, Wurtz coupling is useful in closing small, especially three-membered, rings: bicyclobutane was prepared this way using 1-bromo-3-chlorocyclobutane and sodium, giving 95% yield of the product:
Read more about this topic: Wurtz Reaction
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