Chloroalkanes
Alkyl chlorides with a C-Cl bond; useful entry points into alcohols, nitriles, amines and alkenes.
- Functional group
- C-Cl
- Also known as
- alkyl chlorides, alkyl chloride, chloroalkane, halogenoalkane, haloalkane, organic chloride
Overview
Alkyl chlorides with a C-Cl bond used as reaction handles.
Alkyl chlorides with a C-Cl bond; useful entry points into alcohols, nitriles, amines and alkenes.
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
- Functional group
- C-Cl
- Also known as
- alkyl chlorides, alkyl chloride, chloroalkane, halogenoalkane, haloalkane, organic chloride
Properties
- Functional handle
- C-Cl
- Bond polarity
- C(delta+)-Cl(delta-)
- Leaving group
- Cl-
- Reaction profile
- substitution / elimination
- Materials role
- substitution handle; bridge to materials applications
Diagnostic tests
silver nitrate hydrolysis test
- Reagent
- aqueous silver nitrate in ethanol
- Conditions
- warm in a water bath
- Positive observation
- white precipitate of AgCl forms slowly
- Negative observation
- no halide precipitate
- Interpretation
- The precipitate colour identifies chloride and the formation time reflects slower C-Cl hydrolysis.
- Scope
- Comparison test for chloro-, bromo- and iodoalkanes.
- Limitations
- Compare similar structures under the same solvent and temperature. Existing halide salts can also precipitate with silver ions.
- Evidence
- textbook core
Related compounds
- Chloromethane
Chloromethane is a simple molecule-level example of the chloroalkane family.
- Chloroethane
Chloroethane is a representative primary alkyl chloride in the chloroalkane reaction network.
- 1-Chloropropane
1-Chloropropane is an organic compound with the molecular formula C3H7Cl.
- 2-Chloropropane
2-Chloropropane is an organic compound with the molecular formula C3H7Cl.
- 2-Chloro-2-methylpropane
A tertiary chloroalkane structurally related to tert-butanol.
Connected reactions
- Chlorination: Alcohols → Chloroalkanes
Alcohols can be converted into chloroalkanes to create a better leaving group for downstream substitution.
- Chlorination with thionyl chloride: Alcohols → Chloroalkanes
Thionyl chloride converts alcohols into chloroalkanes with sulfur dioxide and hydrogen chloride as by-products.
- Hydrochlorination: Alkenes → Chloroalkanes
Addition of hydrogen chloride across an alkene can form a chloroalkane.
- Hydrolysis: Chloroalkanes → Alcohols
The C-Cl bond can be displaced by hydroxide to form an alcohol.
- Cyanation: Chloroalkanes → Nitriles
Cyanide substitution forms a nitrile and extends the carbon chain by one carbon.
- Amination: Chloroalkanes → Amines
Ammonia substitutes chloride to form a primary amine; excess ammonia limits further alkylation.
- Elimination: Chloroalkanes → Alkenes
Base-promoted elimination removes HCl to form an alkene.
- Free radical chlorination: Alkanes → Chloroalkanes
Photochemical chlorination can convert alkanes into chloroalkanes.
- Grignard formation: Chloroalkanes → Grignard reagents
Chloroalkanes can react with magnesium in dry ether to form Grignard reagents.
References
- 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.