双语化学辞典Chem Lexicon
化合物 · 有机化学 · 卤代烃 Organic chemistry · Halogenoalkanes

溴乙烷Bromoethane

高中High school
拼音Pinyin xiù yǐ wán 别名Also 乙基溴;ethyl bromide; EtBr

定义Definition

溴乙烷 CH₃CH₂Br 是无色、易挥发的液体,沸点约 38 °C,难溶于水。它是典型的伯卤代烃,在不同条件下与 OH⁻、CN⁻、NH₃ 发生亲核取代,或在醇溶液中发生消除反应,是学习卤代烃反应的代表物。

Bromoethane, CH₃CH₂Br, is a colourless, volatile liquid boiling at about 38 °C and barely soluble in water. A typical primary halogenoalkane, it undergoes nucleophilic substitution with OH⁻, CN⁻ and NH₃, or elimination in alcoholic solution, and serves as the standard example of halogenoalkane chemistry.

反应一览Summary of reactions

NaOH 水溶液加热回流:CH₃CH₂Br + OH⁻ → CH₃CH₂OH + Br⁻(取代);NaOH 或 KOH 的乙醇溶液加热:CH₃CH₂Br + OH⁻ → CH₂=CH₂ + H₂O + Br⁻(消除);KCN 乙醇溶液加热回流:生成丙腈;过量氨的乙醇溶液在密封管中加热:生成乙胺。

Aqueous NaOH under reflux: CH₃CH₂Br + OH⁻ → CH₃CH₂OH + Br⁻ (substitution). NaOH or KOH in ethanol, heated: CH₃CH₂Br + OH⁻ → CH₂=CH₂ + H₂O + Br⁻ (elimination). KCN in ethanol under reflux gives propanenitrile; excess ammonia in ethanol heated in a sealed tube gives ethylamine.

取代与消除的竞争Substitution versus elimination

水作溶剂有利于取代,乙醇作溶剂、温度较高有利于消除。伯卤代烃主要按 SN2 机理取代;叔卤代烃更易发生 SN1 和消除。

Water as solvent favours substitution, while ethanol and higher temperature favour elimination. Primary halogenoalkanes substitute mainly by SN2; tertiary ones favour SN1 and elimination.

化学性质Chemical properties

水解:CH₃CH₂Br + NaOH → CH₃CH₂OH + NaBr

Hydrolysis: CH₃CH₂Br + NaOH → CH₃CH₂OH + NaBr

与氰化钾反应:CH₃CH₂Br + KCN → CH₃CH₂CN + KBr

With potassium cyanide: CH₃CH₂Br + KCN → CH₃CH₂CN + KBr