卤素加成
烯烃 → 二卤代烷:查看反应物、产物、反应条件与来源依据,探索相关转化和合成路径。
- 试剂
- 溶于有机溶剂中的 Br2
- 条件
- 室温
- 反应类别
- 亲电加成
- 方程式
- RCH=CHR' + Br2 -> RCHBr-CHBrR'
概览
溴加成将烯烃转化为邻二溴代烷。
转化
- 方程式
- RCH=CHR' + Br2 -> RCHBr-CHBrR'
- 试剂
- 溶于有机溶剂中的 Br2
- 反应环境
- 室温
- 反应类别
- 亲电加成
- 机理
- 亲电加成
- Evidence level
- 教材核心内容
参考步骤
Microscale reference: bromine addition test
Cyclohexene + bromine → brominated addition product
物料与用量
- Potassium bromate(V), 0.1 mol dm⁻³ — 10 drops
- Potassium bromide, 0.2 mol dm⁻³ — 20 drops
- Hydrochloric acid, 1 mol dm⁻³ — five drops
- Hexane — enough to half-fill the preparation well
- Cyclohexene — three drops
- Prepared bromine-in-hexane solution — three drops
仪器装置
- 24-well plastic plate
- Standard plastic pipettes used as micro separating funnels
- Plastic Petri dish
- Eye protection
实验步骤
- Combine ten drops of bromate solution, 20 drops of bromide solution and five drops of hydrochloric acid in one well; leave for five minutes for bromine formation.
- Add hexane until the well is about half-full, draw the liquid into a plastic pipette, invert it and mix gently until bromine transfers into the upper hexane layer.
- Separate the lower aqueous layer and place the bromine-containing hexane layer in a clean well.
- Place three drops of bromine-in-hexane solution in a test well, add three drops of cyclohexene, and record the rapid loss of bromine colour.
后处理与分离
- Do not isolate or handle the small-scale addition product in this diagnostic method.
- Decontaminate remaining bromine solution using the disposal procedure specified by the source and local laboratory rules.
关键控制条件
- Use a well-ventilated laboratory, eye protection and suitable gloves; bromine and hexane are hazardous and hexane is highly flammable.
- Keep liquids contained in the plastic pipette during extraction and invert gently so solvent is not expelled.
- Bromine decolourisation detects unsaturation; product analysis is listed separately.
底物范围
- 适用范围
- Alkenes add bromine across the double bond to form vicinal dibromoalkanes.
- 来源说明
- The displayed reagent and equation are specifically for bromination. Chlorine can undergo the analogous addition, but it requires its own reagent record; stereochemical outcomes depend on substrate and conditions.
相关反应
- Hydrochlorination: Alkenes → Chloroalkanes
氯化氢在烯烃双键两端加成,可生成氯代烷。
- Hydrobromination: Alkenes → Bromoalkanes
溴化氢在烯烃双键两端加成,可生成溴代烷。
- Hydroiodination: Alkenes → Iodoalkanes
碘化氢在烯烃双键两端加成,可生成碘代烷。
- Elimination: Chloroalkanes → Alkenes
碱促进的消去反应脱去 HCl,生成烯烃。
- Elimination: Bromoalkanes → Alkenes
碱促进的消去反应脱去 HBr,生成烯烃。
- Elimination: Iodoalkanes → Alkenes
碱促进的消去反应脱去 HI,生成烯烃。
- Cracking: Alkanes → Alkenes
热裂解或催化裂解将长链烷烃转化为较短的分子,其中包括烯烃。
- Hydrogenation: Alkenes → Alkanes
氢化将烯烃还原为烷烃。
- Dihydroxylation: Alkenes → Diols
冷的稀高锰酸盐溶液可将烯烃氧化为邻二醇,避免较强条件下的氧化断裂。
- Addition polymerisation: Alkenes → Addition polymers
烯烃可通过链式加成形成加聚物。
- Hydration: Alkenes → Alcohols
催化水合将烯烃转化为醇。
- Dehydration: Alcohols → Alkenes
脱水将醇转化为烯烃。
- Epoxidation: Alkenes → Epoxides
过氧酸以协同步骤将氧转移到烯烃双键两端,形成两个 C-O 键并断开 C=C 的 π 键。两个键从同一面形成,使烯烃取代基的相对立体关系在环氧产物中保留。
参考文献
- Pearson Edexcel Level 3 Advanced GCE in Chemistry specificationPearson Education Limited · Pearson qualifications · 2024
Supports the textbook-core organic reaction routes used for displayed route and mechanism content.
- Testing for unsaturation with bromine on a microscaleRoyal Society of Chemistry · RSC Education · 2018
Microscale bromine-in-hexane preparation and three-drop alkene addition test.