Tert-Butyllithium

Tert-Butyllithium (t-BuLi) is a chemical compound that is commonly used in organic chemistry as a strong base and as a reagent in the formation of carbon-carbon bonds. It is a organolithium reagent, which are known for their high reactivity and are frequently used in synthesis reactions.

Structure and Properties

File:Tert-Butyllithium.jpg

Structure of Tert-Butyllithium

Tert-Butyllithium is a clear, colorless liquid at room temperature. It is highly reactive and can ignite on contact with air. The compound has a tetrahedral geometry, 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 butyl groups are attached to the lithium atom through a covalent bond.

Synthesis

Tert-Butyllithium is typically synthesized by the reaction of tert-butyl bromide with lithium metal in a suitable solvent such as diethyl ether. The reaction is highly exothermic and must be carried out under an inert atmosphere to prevent ignition.

Uses

Tert-Butyllithium is a powerful base and is used in a variety of organic synthesis reactions. It is particularly useful in the formation of carbon-carbon bonds, a key step in the synthesis of many organic compounds. It can also be used to deprotonate weakly acidic compounds, such as alcohols and amines, and to initiate polymerization reactions.

Safety

Due to its high reactivity, tert-butyllithium must be handled with care. It can ignite on contact with air and can cause severe burns if it comes into contact with skin or eyes. It should be stored under an inert atmosphere and used only by trained personnel.

See Also

• Organolithium reagent
• Organic synthesis
• Carbon-carbon bond formation

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