In Corey House synthesis the first step is formation of Alkyl Lithium. why can't we react alkyl lithium with alkyl halide to produce alkanes. Rather we choose to prepare Gilman's reagent? Does it have something to do with the reactivity of alkyl lithium?


1 Answer 1


As $\ce{R-Li}$ is very reactive ( even more than $\ce{RMgX}$ ). To decrease the reactivity of $\ce{R-Li}$ , it is reacted with $\ce{CuX}$ to form Gilman Reagent which is less reactive than $\ce{R-Li}$ to produce alkanes.

If $\ce{R-Li}$ reacts directly with $\ce{R'-X}$, there will no formation of alkanes, but interchange reaction occurs.

$$\ce{RLi + R'X --> RX + R'Li}$$

  • $\begingroup$ thanks for the answer... can you also tell me how to determine the reactivity of organometallic compounds as u said R-Li is more reactive than RMgX .. and Happy New year !!!! $\endgroup$
    – adi_chem
    Commented Dec 31, 2015 at 21:11
  • $\begingroup$ As Li is more electropositive than Mg. There is easy breaking of R-Li bond more instant than in case of RMgX to give a strong base R(-)ve. if u satisfy. please, approve and upvote the answer. $\endgroup$
    – solanki...
    Commented Dec 31, 2015 at 21:18
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    $\begingroup$ > there will no formation of alkanes || O'Rly ? Wurtz synthesis with lithium is a thing. $\endgroup$
    – permeakra
    Commented Jan 1, 2016 at 19:33

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