Organolithium reagent

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organolithium mechanism

Methyllithium is shown below reacting with an aldehyde. Firstly, the MeLi reacts with the ethanal to form the alkoxide. The metal atom will coordinate with the negatively charged oxygen atom. Water is then added to protonate the oxygen.

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E. C. Ashby, J. Laemmle and H. M. Neumann, Acc. Chem. Res., 1973, 7, 272–280.

B. Goldfuss, Synthesis (Stuttg)., 2005, 0, 2271–2280.