Alkanes are hydrocarbons. Hydrocarbons contain the atoms carbon and hydrogenonly. Hydrocarbons are used as fuels, as a lot of energy is released during complete combustion.
Equations
These are the general word equations. You will need to be able to use these to write equations with specific substances.
XY→X++Y−XY→X⋅+Y⋅
Properties of hydrocarbons
The shorter the length of the hydrocarbon:
the less viscous they are
the more volatile and flammable they are
the lower the boiling point
Alkanes have induced dipole-dipole interactions. The longer the hydrocarbon chain, the greater number of electrons are able to interact giving rise to more induced dipole-dipole interactions. The more induced dipole-dipole interactions there are the more energy is required to break them, leading to properties such as a higher boiling point.
Branched alkanes have a lower boiling point as they cannot pack closely together, reducing the number of induced dipole-dipole interactions.
Alkanes
Alkanes are the simplest hydrocarbons. Aliphatic alkanes have the general formulaCnH2n+2. Whereas cyclic alkanes have the general formula CnH2n. They are saturated compounds as each carbon atom has four single bonds. Each carbon atom adopts a tetrahedral shape (Td) due to the presence of four pairs of bonding electrons. As bonding electrons repel equally a bond angle of 109.5° is adopted giving rise to a tetrahedral shape around the carbon.
Examples
NAME
MOLECULAR FORMULA
Methane
CH4
Ethane
C2H6
Propane
C3H8
Butane
C4H10
Cyclopentane
C5H10
Reactions of alkanes
Alkanes can undergo bond fission. There are two types of bond fission:
Heterolytic fission
Homolytic fission
Heterolytic fission
Heterolytic fission is when one atom receives both electrons. Two different ions are formed, a cation and an anion.
Homolytic fission
Homolytic fission is when both atoms in the bond receive one electron each. The species formed are radicals and they are uncharged and they have unpaired electrons.
Free-radical substitution
Free radical substitution is when a free-radical replaces another atom or group of atoms in a molecule. Alkanes can react with halogens in photochemical reactions. Free-radical substitution have a three step mechanism.
Example
CH4+Cl2UVCH3Cl+HCl
Mechanism for the reaction between methane and chlorine:
Step 1 - Initiation: production of free radicals. This is done via homolytic fission where the energy for the breaking of the bond is provided by energy from sunlight (photodissociation).
Cl2UV2Cl⋅
Step 2 - Propagation: chain reaction of free radical formation and consumption.
The free radical produced is very reactive and goes onto react with a molecule of methane. The methyl radical can then go on to attack chlorine molecule forming another chlorine radical. And this process continues.
Cl⋅+CH4→⋅CH3+HCl⋅CH3+Cl2→CH3Cl+Cl⋅
Step 3 - Termination: free radicals react together to form a stable molecule. There are many possible reactions for termination. For example,
Cl⋅+⋅CH3→CH3Cl⋅CH3+⋅CH3→C2H6
A problem which arises is that a mixture of products is obtained. A chlorine radical may go on to react with chloromethane to form dichloromethane, which in turn may go on to form trichloro- and tetrachloromethane. This is not ideal as it requires time and energy to separate the mixture and obtain the desired product. Furthermore, for longer chain carbons, the free-radical attack may happen anywhere along the chain leading to isomers.
Example
Reaction between butane and bromine can lead to the formation of 1-bromobutane and 2-bromobutane.
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Combustion, oxidation and thermal decomposition
Unit 2
Hydrocarbons: alkanes and alkenes
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Alkanes and free radical substitution
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FAQs - Frequently Asked Questions
What is free-radical substitution?
Free radical substitution is when a free-radical replaces another atom or group of atoms in a molecule.
What are radicals?
Radicals are a species with unpaired electrons.
What is photodissociation?
Photodissociation is a process where the energy for the breaking of a bond is provided by energy from sunlight.