Bromoalkanes
Bromoalkanes are haloalkane variants used in substitution, elimination and Grignard-forming routes.
- Functional group
- C-Br
- Also known as
- alkyl bromides, alkyl bromide, bromoalkane, organic bromide, haloalkane
Overview
Alkyl bromides with a C-Br bond.
Bromoalkanes are haloalkane variants used in substitution, elimination and Grignard-forming routes.
Bromoalkanes are tracked as a reference-scheme haloalkane branch with preparation routes from alcohols or alkenes and downstream substitution, elimination and organomagnesium formation routes.
Identifiers
- Functional group
- C-Br
- Also known as
- alkyl bromides, alkyl bromide, bromoalkane, organic bromide, haloalkane
Properties
- Functional handle
- C-Br
- Route boundary
- preparation and downstream branch
Diagnostic tests
silver nitrate hydrolysis test
- Reagent
- aqueous silver nitrate in ethanol
- Conditions
- warm in a water bath
- Positive observation
- cream precipitate of AgBr forms
- Negative observation
- no halide precipitate
- Interpretation
- The precipitate colour identifies bromide; comparable substrates hydrolyse faster than chloroalkanes and slower than iodoalkanes.
- 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
- Bromomethane
Bromomethane is an organic compound with the molecular formula CH3Br.
- Bromoethane
A two-carbon primary halogenoalkane used to connect reaction pathways.
- 1-Bromopropane
A primary bromoalkane for comparing nucleophilic substitution with elimination.
- 2-Bromopropane
A secondary bromoalkane linking substitution, elimination and positional isomerism.
- 1,2-Dibromoethane
A vicinal dibromoalkane with bromine on adjacent carbon atoms.
- 1,2-Dibromopropane
The vicinal dibromide associated with bromine addition to propene.
- 1-Bromobutane
A straight-chain primary bromoalkane with four carbon atoms.
- 2-Bromobutane
A secondary bromoalkane with a stereogenic bromine-bearing carbon.
- 2-Bromo-2-methylpropane
A tertiary bromoalkane whose bromine-bearing carbon has no hydrogen.
Connected reactions
- Bromination: Alcohols → Bromoalkanes
Bromide and acid conditions convert alcohols into bromoalkanes.
- Hydrobromination: Alkenes → Bromoalkanes
Addition of hydrogen bromide across an alkene can form a bromoalkane.
- Cyanation: Bromoalkanes → Nitriles
Cyanide substitution forms a nitrile and extends the carbon chain by one carbon.
- Amination: Bromoalkanes → Amines
Ammonia substitutes bromide to form a primary amine; excess ammonia limits further alkylation.
- Hydrolysis: Bromoalkanes → Alcohols
The C-Br bond can be displaced by hydroxide to form an alcohol.
- Elimination: Bromoalkanes → Alkenes
Base-promoted elimination removes HBr to form an alkene.
- Free radical bromination: Alkanes → Bromoalkanes
Photochemical bromination can convert alkanes into bromoalkanes.
- Grignard formation: Bromoalkanes → Grignard reagents
Bromoalkanes 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: Bromomethane (CID 6323)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: Bromoethane (CID 6332)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 1-Bromopropane (CID 7840)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-Bromopropane (CID 6358)National Center for Biotechnology Information · PubChem
Identity, molecular formula, molecular weight and aliases retrieved via PUG REST on 2026-09-08.
- PubChem Compound Summary: 1,2-Dibromoethane (CID 7839)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.
- PubChem Compound Summary: 1,2-Dibromopropane (CID 6553)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.
- PubChem Compound Summary: 1-Bromobutane (CID 8002)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.
- PubChem Compound Summary: 2-Bromobutane (CID 6554)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.
- PubChem Compound Summary: 2-Bromo-2-methylpropane (CID 10485)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.