This reaction occurs in three steps. The alkyl halide is treated with lithium metal, and solvated in dry ether, which converts the alkyl halide into an alkyl lithium compound, R-Li. The starting R-X can be primary, secondary or tertiary alkyl halide:
R-X + 2Li → R-Li + Li-X
The second step requires the alkyl lithium compound to be treated with cuprous iodide (CuI). This creates a lithium dialkyl cuprate compound. These compounds were first synthesized by Henry Gilman of Iowa State University, and are usually called Gilman reagents in honor of his contributions:
2RLi + CuI → R2CuLi + LiI
The lithium dialkyl cuprate is then treated with the second alkyl halide, which couples to the compound:
R2CuLi + R'-X → R-R' + RCu + LiX
If second alkyl halide is not the same as the first, then cross-products are formed.
It is important to note that for this reaction to work successfully, the second alkyl halide must be a methyl halide, benzyl halide, primary alkyl halide or a secondary cyclo alkyl halide. The relative simplicity of this reaction makes it a useful technique for synthesizing organic compounds.
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This reaction occurs in three steps. The alkyl halide is treated with lithium metal, and solvated in dry ether, which converts the alkyl halide into an alkyl lithium compound, R-Li. The starting R-X can be primary, secondary or tertiary alkyl halide:
R-X + 2Li → R-Li + Li-X
The second step requires the alkyl lithium compound to be treated with cuprous iodide (CuI). This creates a lithium dialkyl cuprate compound. These compounds were first synthesized by Henry Gilman of Iowa State University, and are usually called Gilman reagents in honor of his contributions:
2RLi + CuI → R2CuLi + LiI
The lithium dialkyl cuprate is then treated with the second alkyl halide, which couples to the compound:
R2CuLi + R'-X → R-R' + RCu + LiX
If second alkyl halide is not the same as the first, then cross-products are formed.
It is important to note that for this reaction to work successfully, the second alkyl halide must be a methyl halide, benzyl halide, primary alkyl halide or a secondary cyclo alkyl halide. The relative simplicity of this reaction makes it a useful technique for synthesizing organic compounds.
Alkyl halide react with lithium dialkyl cuprate to give alkane
R' - X + R2CuLi--> R'--R+LiX + R-Cu
eg,
CH3CI+(CH3)2CuLi -> CH3-CH3
Both Symmetric and asymmetric alkanes are synthesised through this reaction.
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