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Na

NaOH

2Li
R-X + ? → Li-X + R-Li

R-O-R
X = Cl, Br, I

Ether

R-MgX
Grignard addition to acid chloride

R-MgX
Grignard addition to esters

Ether

H2O (Any acidic proton, H2O, C2H5OH, CH3OH)

NaBH4

1) LiAlH4
2) H+/H2O

H2
Raney Ni
