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Chapter 14: Organometallic Compounds |
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Alkane synthesis using R2CuLi
Reaction type: "Nucleophilic Substitution"
Summary
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Organolithium cuprates, R2CuLi, react with alkyl halides
forming a new C-C, giving alkanes.
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Primary alkyl iodides make the best substrates otherwise elimination can
be a problem.
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The R group of the cuprate can also be aryl or vinyl.
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The R' group in the halide can also be aryl or vinyl.
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Although the mechanism looks like a SN2, it is more complex and
is currently not well understood.
Question:
What evidence suggests that these reactions are not just simple SN2
reactions ? 
Related Reactions
