N-butyllithium

Definition

n-Butyllithium is an organolithium compound with the formula $C_4H_9Li$. It is a highly reactive and versatile reagent used in organic synthesis, particularly in the alkylation of acetylide anions and the Wittig reaction.

5 Must Know Facts For Your Next Test

1. n-Butyllithium is a strong base and a powerful nucleophile, making it a versatile reagent in organic synthesis.
2. In the alkylation of acetylide anions, n-butyllithium is used to generate the acetylide anion, which can then be alkylated with various electrophiles.
3. The Wittig reaction involves the reaction of a phosphorus ylide, generated from n-butyllithium and a phosphine, with a carbonyl compound to form an alkene.
4. n-Butyllithium is highly reactive and must be handled under anhydrous and inert conditions to prevent undesirable side reactions.
5. The reactivity of n-butyllithium can be modulated by the choice of solvent, temperature, and the presence of additives like TMEDA (tetramethylethylenediamine).

Review Questions

• Explain the role of n-butyllithium in the alkylation of acetylide anions.
  • In the alkylation of acetylide anions, n-butyllithium is used to generate the acetylide anion, a carbon-based nucleophile with a negative charge on the carbon atom. The highly reactive n-butyllithium deprotonates a terminal alkyne, forming the acetylide anion, which can then be alkylated with various electrophiles to form new carbon-carbon bonds. This reaction is a powerful tool in organic synthesis for the construction of complex molecules.
• Describe the mechanism of the Wittig reaction and the role of n-butyllithium in this transformation.
  • The Wittig reaction involves the reaction of a phosphorus ylide with a carbonyl compound to form an alkene. The phosphorus ylide is generated by the reaction of n-butyllithium with a phosphine, such as triphenylphosphine. The n-butyllithium acts as a strong base, deprotonating the phosphine to form the nucleophilic phosphorus ylide. This ylide then reacts with the carbonyl compound, typically an aldehyde or ketone, to form the desired alkene product and a phosphine oxide byproduct. The Wittig reaction is a powerful method for the stereoselective synthesis of alkenes, and the use of n-butyllithium is a crucial step in the generation of the reactive phosphorus ylide.
• Evaluate the importance of handling n-butyllithium under anhydrous and inert conditions, and explain the potential consequences of improper handling.
  • n-Butyllithium is a highly reactive and pyrophoric organolithium compound that must be handled with great care under anhydrous and inert conditions, such as in the absence of water and oxygen. Improper handling of n-butyllithium can lead to undesirable side reactions, including the decomposition of the reagent and potential safety hazards. If n-butyllithium is exposed to water or protic solvents, it can undergo hydrolysis, releasing flammable and potentially explosive gases like hydrogen. Furthermore, n-butyllithium is highly nucleophilic and can react with a wide range of functional groups, potentially leading to unwanted side products and compromising the desired synthetic transformation. Proper handling techniques, such as the use of anhydrous solvents, inert atmospheres, and carefully controlled temperatures, are essential to ensure the safe and effective use of n-butyllithium in organic synthesis.

Related terms

Organolithium Compounds: Organolithium compounds are a class of highly reactive and nucleophilic reagents that contain a carbon-lithium bond, which can be used to perform a variety of synthetic transformations.

Acetylide Anions: Acetylide anions are carbon-based nucleophiles with a negative charge on the carbon atom, which can be alkylated using reagents like n-butyllithium.

Wittig Reaction: The Wittig reaction is a method for the synthesis of alkenes involving the reaction of a phosphorus ylide (a nucleophilic phosphorus-containing species) with a carbonyl compound.