氯代烷
含 C-Cl 键的氯代烷，可作为制备醇、腈、胺和烯烃的起点。
- 官能团
- C-Cl
- Also known as
- alkyl chlorides, alkyl chloride, chloroalkane, halogenoalkane, haloalkane, organic chloride
概览
Alkyl chlorides with a C-Cl bond used as reaction handles.
Chloroalkanes are treated as a gateway family: the C-Cl bond can be substituted or eliminated, then connected to materials application routes through amines, nitriles, ammonium compounds and polyamide-related chemistry.
Identifiers
- 官能团
- C-Cl
- Also known as
- alkyl chlorides, alkyl chloride, chloroalkane, halogenoalkane, haloalkane, organic chloride
性质
- 反应位点
- C-Cl
- 键的极性
- C(delta+)-Cl(delta-)
- 离去基团
- Cl-
- 反应特征
- 取代／消去
- 在材料中的作用
- 取代反应位点；可进一步连接材料应用
Diagnostic tests
硝酸银水解试验
- 试剂
- 硝酸银水溶液与乙醇的混合液
- 条件
- 在水浴中温热
- Positive observation
- 缓慢生成白色 AgCl 沉淀
- Negative observation
- 不生成卤化银沉淀
- Interpretation
- 沉淀颜色表明存在氯离子，形成所需时间反映 C-Cl 键水解较慢。
- 适用范围
- 用于对比氯代烷、溴代烷和碘代烷的试验。
- 来源说明
- 应在相同溶剂和温度下，比较结构相近的化合物。样品中原有的卤化物盐也能与银离子形成沉淀；卤代芳烃和卤代烯烃不遵循普通卤代烷的水解规律。
- 证据
- 教材核心内容
Related compounds
- 氯甲烷
Chloromethane is a simple molecule-level example of the chloroalkane family.
- 氯乙烷
Chloroethane is a representative primary alkyl chloride in the chloroalkane reaction network.
- 1-氯丙烷
1-氯丙烷是一种有机化合物，分子式为 C3H7Cl。
- 2-氯丙烷
2-氯丙烷是一种有机化合物，分子式为 C3H7Cl。
- 2-氯-2-甲基丙烷
结构上与叔丁醇对应的叔氯代烷。
Connected reactions
- Chlorination: Alcohols → Chloroalkanes
醇可转化为氯代烷，为后续取代反应引入更易离去的基团。
- Chlorination with thionyl chloride: Alcohols → Chloroalkanes
氯化亚砜将醇转化为氯代烷，同时生成二氧化硫和氯化氢。
- Hydrochlorination: Alkenes → Chloroalkanes
氯化氢在烯烃双键两端加成，可生成氯代烷。
- Hydrolysis: Chloroalkanes → Alcohols
氢氧根可取代 C-Cl 中的氯，形成醇。
- Cyanation: Chloroalkanes → Nitriles
氰根取代生成腈，使碳链增加一个碳原子。
- Amination: Chloroalkanes → Amines
氨取代氯，形成伯胺；过量氨可限制进一步烷基化。
- Elimination: Chloroalkanes → Alkenes
碱促进的消去反应脱去 HCl，生成烯烃。
- Free radical chlorination: Alkanes → Chloroalkanes
光化学氯化可将烷烃转化为氯代烷。
- Grignard formation: Chloroalkanes → Grignard reagents
氯代烷可在无水乙醚中与镁反应，形成格氏试剂。
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.
- PubChem Compound Summary for ChloromethaneNational Center for Biotechnology Information · PubChem · 2026
Used for basic identifiers and compound metadata.
- PubChem Compound Summary for ChloroethaneNational Center for Biotechnology Information · PubChem · 2026
Used for basic identifiers and compound metadata.
- PubChem Compound Summary: 1-Chloropropane (CID 10899)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 2-Chloropropane (CID 6361)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 2-Chloro-2-methylpropane (CID 10486)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and selected English aliases retrieved via PUG REST on 2026-09-16. Chinese search names are curated nomenclature translations. Unspecified stereochemistry remains unspecified.