双语化学辞典Chem Lexicon
类别 · 有机化学 · 羰基化合物 Organic chemistry · Carbonyl compounds

酮Ketone

高中High school
拼音Pinyin tóng 别名Also alkanone

定义Definition

酮是羰基碳原子两侧都连有烃基的有机化合物,通式 RCOR′,官能团为羰基 C=O。最简单的酮是丙酮 CH₃COCH₃。饱和一元酮与同碳数的饱和一元醛互为同分异构体。

Ketones are organic compounds in which the carbonyl carbon is bonded to two hydrocarbon groups, general formula RCOR′, with the carbonyl group C=O as the functional group. The simplest is propanone, CH₃COCH₃. Saturated ketones are isomers of saturated aldehydes with the same number of carbons.

命名与制备Naming and preparation

系统命名用后缀 -one,并标出羰基位次:丙酮 propanone,丁酮 butanone,戊-3-酮 pentan-3-one。酮由仲醇氧化制得:用酸化重铬酸钾加热回流,仲醇被氧化为酮后不再继续氧化。工业上丙酮主要由异丙苯法与苯酚联产。

Systematic names use the suffix -one, with the carbonyl position given: propanone, butanone, pentan-3-one. Ketones are made by oxidising secondary alcohols, heating under reflux with acidified dichromate; the ketone is not oxidised further. Industrially, propanone is made mainly alongside phenol by the cumene process.

主要反应Main reactions

酮不易被氧化,与托伦试剂、费林试剂都不反应,据此可与醛区分。酮能发生羰基的亲核加成:被 NaBH₄ 还原为仲醇,与 HCN 加成生成羟基腈,与 2,4-二硝基苯肼生成橙黄色沉淀。含 CH₃CO– 结构的甲基酮与碱性碘溶液反应生成黄色的三碘甲烷沉淀(碘仿反应)。

Ketones resist oxidation and give no reaction with Tollens' reagent or Fehling's solution, which distinguishes them from aldehydes. They undergo nucleophilic addition at the carbonyl: NaBH₄ reduces them to secondary alcohols, HCN adds to give hydroxynitriles, and 2,4-dinitrophenylhydrazine gives an orange-yellow precipitate. Methyl ketones, containing CH₃CO–, react with alkaline iodine to give a yellow precipitate of triiodomethane (the iodoform test).

用途Uses

丙酮是重要的溶剂,能与水和多数有机溶剂互溶,用于去除指甲油、清洗仪器,也是有机玻璃(聚甲基丙烯酸甲酯)的原料。环己酮用于生产尼龙。人体在糖供应不足时会产生丙酮、乙酰乙酸等酮体。

Propanone is an important solvent, miscible with water and most organic solvents; it removes nail varnish, rinses apparatus and is a raw material for poly(methyl methacrylate). Cyclohexanone is used to make nylon. When glucose is scarce, the body produces ketone bodies such as propanone and acetoacetic acid.

年表Timeline

  • 1833

    比西把干馏醋酸盐得到的液体命名为 acétone

    Bussy names the liquid from distilling acetates acétone

  • 1848

    格梅林提出 Keton(酮)这一类名

    Gmelin introduces the class name Keton (ketone)

  • 1916

    魏茨曼发展发酵法大规模生产丙酮,用于制造无烟火药

    Weizmann develops fermentation to mass-produce acetone for making cordite