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1-bromobutane

Written by the Fiveable Content Team ā€¢ Last updated September 2025
Written by the Fiveable Content Team ā€¢ Last updated September 2025

Definition

1-bromobutane, also known as n-butyl bromide, is an alkyl halide compound with the chemical formula CH3CH2CH2CH2Br. It is a colorless, volatile liquid that is commonly used as a precursor in organic synthesis reactions, particularly in the context of alkylation of acetylide anions.

5 Must Know Facts For Your Next Test

  1. 1-bromobutane is a primary alkyl halide, meaning the bromine atom is attached to the primary carbon of the butyl group.
  2. The presence of the bromine atom makes 1-bromobutane a good electrophilic alkylating agent, allowing it to participate in nucleophilic substitution reactions.
  3. In the context of 9.8 Alkylation of Acetylide Anions, 1-bromobutane can be used to alkylate acetylide anions, forming new carbon-carbon bonds.
  4. The alkylation of acetylide anions with 1-bromobutane is a useful synthetic method for the preparation of substituted alkynes.
  5. The reactivity of 1-bromobutane in these alkylation reactions is influenced by factors such as the strength of the nucleophilic acetylide anion and the leaving group ability of the bromine atom.

Review Questions

  • Explain the role of 1-bromobutane in the alkylation of acetylide anions.
    • 1-bromobutane is an important reagent in the alkylation of acetylide anions, which are negatively charged carbon-based species with the general formula R-Cā‰”Cā». The presence of the bromine atom in 1-bromobutane makes it a good electrophilic alkylating agent, allowing it to participate in nucleophilic substitution reactions with the acetylide anion. This alkylation process introduces the butyl group from 1-bromobutane onto the acetylide anion, forming a new carbon-carbon bond and producing a substituted alkyne product.
  • Describe the factors that influence the reactivity of 1-bromobutane in the alkylation of acetylide anions.
    • The reactivity of 1-bromobutane in the alkylation of acetylide anions is influenced by several factors. The strength of the nucleophilic acetylide anion is important, as stronger nucleophiles will more readily displace the bromine atom from 1-bromobutane. Additionally, the leaving group ability of the bromine atom plays a role, as better leaving groups facilitate the substitution reaction. Other factors, such as the steric hindrance around the reaction site and the solvent used, can also impact the efficiency and selectivity of the alkylation process involving 1-bromobutane.
  • Analyze the synthetic utility of the alkylation of acetylide anions using 1-bromobutane.
    • The alkylation of acetylide anions using 1-bromobutane is a valuable synthetic method for the preparation of substituted alkynes. These alkylation reactions allow for the introduction of the butyl group from 1-bromobutane onto the acetylide anion, creating new carbon-carbon bonds and yielding functionalized alkyne products. This synthetic transformation is widely used in organic chemistry, as substituted alkynes are important building blocks for the synthesis of more complex organic molecules. The versatility and efficiency of this alkylation reaction, coupled with the availability and reactivity of 1-bromobutane, make it a powerful tool in the arsenal of organic chemists for the construction of diverse molecular architectures.