Tert-butyllithium

Tert-butyllithium (also known as t-BuLi) is a chemical compound used extensively in organic chemistry. It is a strong base and a powerful nucleophile, which makes it a valuable reagent in the synthesis of organic compounds.

Structure and Properties

Tert-butyllithium is a organolithium reagent, which means it contains a carbon-lithium bond. The compound is a colorless liquid at room temperature and is highly reactive. It is usually handled in solution, typically in hydrocarbon solvents such as pentane or hexane.

The structure of tert-butyllithium is tetrahedral, with the lithium atom located at the center of the tetrahedron. The four carbon atoms are located at the corners of the tetrahedron, and the hydrogen atoms are attached to the carbon atoms.

Synthesis

Tert-butyllithium is synthesized by the reaction of tert-butyl bromide with lithium metal in a hydrocarbon solvent. The reaction is highly exothermic and must be carried out under carefully controlled conditions to prevent a violent reaction.

Uses

Tert-butyllithium is used as a strong base and a powerful nucleophile in organic synthesis. It can deprotonate a wide range of acids, including water, alcohols, and carboxylic acids. It can also add to carbonyl compounds to form new carbon-carbon bonds.

Safety

Tert-butyllithium is highly reactive and can ignite spontaneously in air. It must be handled with care, using appropriate safety precautions. It can cause severe burns and eye damage, and may be fatal if swallowed or inhaled.

See also

• Organolithium reagent
• Nucleophile
• Base (chemistry)