Orgo 2 - Important Reagents, Reactants, Catalysts

Grignard reagents

R-Mg-X

Organomagnesium compounds.

Prepared by treating organohalide (R-X) w/ Mg in ether solvent.

Very strong base (bond similar to ionic).

React with carbonyl compounds ONLY, ex: aldehydes and acid halides

Ether solvents

Solvents used to stabilize positively charged/polar intermediates. Common examples are diethyl ether and THF (tetrahydrofuran).

Organolithium

R-Li ( + Li-X)

Prepared by treating organohalide (R-X) w/ 2 equivalents of Li (creates Li-X byproduct). Nonpolar solvent used.

Very strong base (bond similar to ionic).

Nonpolar solvent

Dissolves non-polar compounds, solvent itself has no significant dipole moment (usually hydrocarbons).

Ex: hexane, diethyl ether

Gilman reagent

R2-CuLi

Weaker than Grignard reagents, used in used in carbonyl reactions.

1 eq. Gilman replaces carbonyl-X with carbonyl-R

2 eq. Grignard replaces carbonyl-X with R-2Me-OH