Oraganometallic Compounds

structure of a Grignard reagent

alkyl-MgBr (important for the formation of carbon-carbon bonds)

structure of an oxirane/epoxide

(used with a Grignard reagent to break the ring OR used with a Gilman cuprate/reagent to break the ring and add the R-group)

structure of a Gilman cuprate

(act as methylating agents when subjected to conjugate addition reactions with alkynes)

structure of a ketone

(R-C=O-R)

structure of an aldehyde

(R-CHO)

structure of an acyl

(a moiety group derived from removing an R-group from a carboxylic acid)

structure of mCPBA

(peroxy acid that is used widely as an oxidant in organic synthesis)

structure of an ylide

(a neutral dipolar molecule w/ a negatively charged atom directly attached to a positively charged heteroatom; the negatively charged atom is a nucleophilic center and the onium group is usually a good leaving group)

alkyl halide + [metal]°, ether

preparation of a Grignard reagent

R-Li + CuI, ether

preparation of a Gilman Cuprate

R-Mg-X + HCl

protonation that results in R-H (alkane) + ClMgX

R-Li + HCl

protonation that results in R-H (alkane) + LiCl

alkyl halide + Gilman cuprate

results in the formation of a new C-C bond via SN2 as the halide leaves (LG) because Gilman cuprates are too basic

alkyl halide + Grignard reagent

results in the formation of a new C=C bond via E2 because Grignard reagents are too basic (only one R group will react)

structure of a Simmons-Smith reagent

Ch2I2, Zn(Cu), ether

alkene + CH2I2, Zn(Cu), ether

(Simmons-Smith rxn) results in breaking of the double bond and

CH2I2 + Zn(Cu), ether

results in a carbenoid

structure of a carbenoid

(a reactive intermediate that includes a metal; reacts similarly to a carbene)

structure of a carbene

(highly reactive, uncharged molecule that can act an electrophile or nucleophile; reacts similarly to a carbenoid)

structure of a phenyl group

structure of a benzene

structure of diethyl ether

(used as a solvent when the rxn calls for an absence of water)

structure of acetylide

(metal is bonded with an alkyne via ionic bonds; the other carbon is bonded to an R group)