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Write the mechanism for the alkylation reaction of acetylide anion with bromoethane to give 1-butyne.

Write the mechanism for the alkylation reaction of acetylide anion with bromoethane to give 1-butyne.

Chemistry
Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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**Problem XIX:** **Title:** Reaction Mechanism for Alkylation **Objective:** Write the mechanism for the alkylation reaction of acetylide anion with bromoethane to give 1-butyne. **Explanation:** The alkylation of acetylide anions involves a nucleophilic substitution reaction where the acetylide anion attacks the bromoethane to form 1-butyne. Here's how the mechanism can be illustrated: 1. **Formation of the Acetylide Anion:** - The acetylide anion \((\text{C}_2\text{H}_3^{-})\) is typically generated by deprotonating acetylene \((\text{HC}\equiv\text{CH})\) using a strong base (e.g., sodium amide, \(\text{NaNH}_2\)). 2. **Nucleophilic Attack:** - The acetylide anion acts as a nucleophile and attacks the electrophilic carbon atom of bromoethane \((\text{C}_2\text{H}_5\text{Br})\). - This results in the substitution of the bromide ion and the formation of a carbon-carbon bond, yielding 1-butyne \((\text{HC}\equiv\text{CCH}_2\text{CH}_3)\). 3. **Leaving Group:** - The bromide ion \((\text{Br}^{-})\) serves as the leaving group, departing with the pair of electrons it shares with the carbon. **Conclusion:** The alkylation reaction transforms an acetylide anion into an extended alkyne chain, effectively increasing the hydrocarbon length by introducing a new alkyl group via nucleophilic substitution. This is a highly useful reaction in organic synthesis for constructing carbon-carbon bonds.
Transcribed Image Text:**Problem XIX:** **Title:** Reaction Mechanism for Alkylation **Objective:** Write the mechanism for the alkylation reaction of acetylide anion with bromoethane to give 1-butyne. **Explanation:** The alkylation of acetylide anions involves a nucleophilic substitution reaction where the acetylide anion attacks the bromoethane to form 1-butyne. Here's how the mechanism can be illustrated: 1. **Formation of the Acetylide Anion:** - The acetylide anion \((\text{C}_2\text{H}_3^{-})\) is typically generated by deprotonating acetylene \((\text{HC}\equiv\text{CH})\) using a strong base (e.g., sodium amide, \(\text{NaNH}_2\)). 2. **Nucleophilic Attack:** - The acetylide anion acts as a nucleophile and attacks the electrophilic carbon atom of bromoethane \((\text{C}_2\text{H}_5\text{Br})\). - This results in the substitution of the bromide ion and the formation of a carbon-carbon bond, yielding 1-butyne \((\text{HC}\equiv\text{CCH}_2\text{CH}_3)\). 3. **Leaving Group:** - The bromide ion \((\text{Br}^{-})\) serves as the leaving group, departing with the pair of electrons it shares with the carbon. **Conclusion:** The alkylation reaction transforms an acetylide anion into an extended alkyne chain, effectively increasing the hydrocarbon length by introducing a new alkyl group via nucleophilic substitution. This is a highly useful reaction in organic synthesis for constructing carbon-carbon bonds.
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