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?


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
    Dec 31 '15 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...
    Dec 31 '15 at 21:18
  • $\begingroup$ > there will no formation of alkanes || O'Rly ? Wurtz synthesis with lithium is a thing. $\endgroup$
    – permeakra
    Jan 1 '16 at 19:33

Your Answer

By clicking “Post Your Answer”, you agree to our terms of service, privacy policy and cookie policy

Not the answer you're looking for? Browse other questions tagged or ask your own question.