Chapter 15 - An Introduction to Organometallic Compounds

Grignard reagents

________ and organolithium compounds react as carbon nucleophiles with a broad variety of electrophilic functional groups, including epoxides (as well as numerous carbonyl- containing species addressed later in the book)

Simmons Smith

The ________ reagent, which is made from diiodomethane and Zn, is a valuable carbenoid (Cu)

Cyclopropanes

________ are formed when dichlorocarbene and the Simmons- Smith reagent react stereospecifically with alkenes.

Addition

________ of the dihalocarbene to an alkene shows syn stereospecificity.

Carbenes

________ are synthesized by photolysis or thermolysis of diazo compounds such as diazomethane.

Gilman reagents

________ are made up of two organic groups linked together by a copper (I) ion, resulting in a negatively charged species that serves as the source of the carbon nucleophile.

alkenyl halide

An alkyl, aryl, or ________ is reacted with two equivalents of lithium metal to produce organolithium reagents.

Dichlorocarbene

________ is made by reacting chloroform with a strong base.

Grignard

Because ________ and organolithium reagents are extremely basic, they will deprotonate functional groups such amines, terminal alkynes, alcohols, thiols, and carboxylic acids.

metal atom

A(n) ________ or ion bonds to a surrounding array of molecules known as ligands in inorganic coordination complexes.

Vinylic halides

________ are typically nonreactive to nucleophilic displacement.

term Carbenes

The ________ refers to neutral compounds that contain a carbon with just six valence electrons; carbenoids are their organometallic- complexed analogues.

organolithium compounds

In ________, the carbon- lithium bond is polar covalent, with a partial negative charge on carbon, making it nucleophilic.

study of chemical compounds

The ________ having carbon- metal linkages is known as organometallic chemistry.

Gilman reagents

________ are particularly useful for forming new carboncarbon bonds via a coupling reaction with an alkyl chloride, bromide, or iodide (alkyl fluorides are inactive under these circumstances), as demonstrated by the following production of 2- methyl- 1- dodecene.

Carbenes

________ like methylene are too reactive to be employed in synthesis.

Grignard reagents

________ are named after their discoverer, Victor Grignard, who discovered organomagnesium compounds.

Gilman reagents

________ with the highest coupling product yields are those made from methyl, primary alkyl, allylic, vinylic, and aryl halides through the respective organolithium compounds.

Carbenes

________ are sp2 hybridized, with one sp2 hybrid orbital containing an empty 2p orbital and a lone pair.

Grignard reagents

________ are made by reacting alkyl, aryl, or alkenyl halides (chlorides, bromides, and iodides, not fluorides) in an ether solvent with a little excess of magnesium metal.