Grade 12 → Haloalkanes and haloarenes ↓
Classification and nomenclature of haloalkanes and haloarenes
Haloalkanes and haloarenes are important classes of organic compounds. They are derived from hydrocarbons where one or more hydrogen atoms are replaced by halogen atoms. This substitution can significantly alter the properties and reactivities of the original hydrocarbon, making haloalkanes and haloarenes valuable in a variety of chemical applications.
Haloalkanes
Definition
Haloalkanes, also known as alkyl halides, are compounds in which one or more hydrogen atoms in aliphatic hydrocarbons are replaced by a halogen atom (fluorine, chlorine, bromine, or iodine). The general formula for haloalkanes is RX
, where R
is an alkyl group and X
is a halogen.
Classification of haloalkanes
Haloalkanes can be classified based on several criteria:
1. Based on the number of halogen atoms
- Monohaloalkane: Contains one halogen atom. Example:
CH3Cl
(chloromethane) - Dihaloalkane: Contains two halogen atoms. Example:
CH2Cl2
(dichloromethane) - Trihaloalkane: It contains three halogen atoms. Example:
CHCl3
(chloroform) - Tetrahaloalkane: Contains four halogen atoms. Example:
CCl4
(carbon tetrachloride)
HH
|
H - C - C - Br
|
HH
2. Depending on the type of carbon atom bonded to the halogen
- Primary (1°) alkyl halide: The halogen is attached to a primary carbon (a carbon atom bonded to only one other carbon). Example:
CH3CH2Cl
(ethyl chloride) - Secondary (2°) alkyl halide: The halogen is attached to a secondary carbon (a carbon atom bonded to two other carbons). Example:
CH3CHClCH3
(2-chloropropane) - Tertiary (3°) alkyl halide: The halogen is attached to a tertiary carbon (a carbon atom bonded to three other carbons). Example:
(CH3)3CCl
(tert-butyl chloride)
3. Based on the type of halogen atom
- Fluoroalkane: Contains fluorine. Example:
CF3H
(trifluoromethane) - Chloroalkanes: Contain chlorine. Example:
CH3Cl
(chloromethane) - Bromoalkane: Contains bromine. Example:
CH2Br2
(dibromomethane) - Iodoalkane: Contains iodine. Example:
CH3I
(iodomethane)
Naming of haloalkanes
IUPAC nomenclature system
The International Union of Pure and Applied Chemistry (IUPAC) system is the most widely accepted method for naming haloalkanes. Naming involves several steps:
Steps of Naming
- Identify the longest continuous carbon chain in the compound that contains a halogen atom. This is the parent chain, and its name will be based on the number of carbon atoms it contains.
- 1 carbon: methane
- 2 carbons: ethane
- 3 carbons: propane
- 4 carbons: butane
- 5 carbons: pentane
- 6 carbons: hexane
- Locate and number the carbon atoms in the parent chain, starting at the end nearest the halogen group.
- Name the halogen substituents in alphabetical order, and specify their position on the parent chain with a number. Use prefixes such as "di-", "tri-", etc. for multiple identical substituents.
- Combine the names of the halogen substituents and the parent chain.
Example: CH3CHClCH2Br
- The longest chain has three carbon atoms: propane
- Numbering starts from the end nearest the halogen: 1-chloro, 3-bromo
- Alphabetical order: 1-Bromo-3-chloropropane
Common naming systems
The common naming system (also called trivial nomenclature) often uses the name of the halide followed by the name of the alkyl group.
Example: CH3Cl
is called methyl chloride.
Haloarenes
Definition
Haloarenes, also known as aryl halides, are compounds in which one or more hydrogen atoms in aromatic hydrocarbons are replaced by halogen atoms. The general formula for haloarenes is Ar-X
, where Ar
is an aryl group and X
is a halogen.
Classification of haloarenes
Haloarenes can be classified based on the orientation of the halogen atoms.
1. Mono-substituted haloarenes
These contain a halogen atom attached to an aromatic ring. Example: C6H5Cl
(chlorobenzene)
/
|O|
/
2. Di-substituted haloarene
These contain two halogen atoms linked by an aromatic ring. These can be further classified depending upon the relative position:
- Ortho-position: adjacent positions (1,2 positions). Example:
1,2-Dichlorobenzene
- Meta-position: one carbon away (1,3 position). Example:
1,3-Dichlorobenzene
- Para-position: The opposite side of the benzene ring (1,4 position). Example:
1,4-Dichlorobenzene
3. Tri or poly-substituted haloarenes
These contain three or more halogen atoms attached to an aromatic ring. The nomenclature will be according to the position and number of each substituent.
Naming of haloarenes
IUPAC nomenclature system
The IUPAC nomenclature for haloarenes is usually straightforward:
- The parent name is the aromatic compound (usually benzene).
- Name and number the substituted substances along with their respective positions.
Example: C6H4BrCl
- The original name is benzene.
- Bromine and chlorine are substituents, named alphabetically.
- Example name: 1-Bromo-2-chlorobenzene
Common naming system for haloarenes
As with haloalkanes, haloarenes may be named using common terminology, which often supersedes systematic names:
- Example:
C6H5Cl
is named chlorobenzene in both systems.
Comparison of haloalkanes and haloarenes
Although haloalkanes and haloarenes are similar in some respects such as having halogen substituents, they differ due to the nature of the carbon chain (aliphatic vs aromatic) to which they are attached. For example, haloarenes are generally less reactive than haloalkanes due to the displacement of electrons in the aromatic ring which stabilizes the bond between carbon and halogen.
Concluding notes
Understanding the classification and nomenclature of haloalkanes and haloarenes is essential for identifying these compounds in organic chemistry and communicating about them effectively. They serve as basic building blocks in many synthetic processes, pharmaceuticals, and industrial applications.