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Ethylene (ethene)
Although ethylene is a widely used raw material very little of it is found in either natural gas or crude oil. Instead it has to be produced from other hydrocarbons by a process called cracking. Cracking: process in which large hydrocarbons are broken down into smaller ones with the help of heat and/or a catalyst.
Cracking
During the cracking process bonds within the hydrocarbon molecule are broken. Ethene is produced in one of two ways:
From crude oil by catalytic cracking of
http://www.chemguide.co.uk/organicprops/alkanes/cracking.html
2 carbon atom chain, non-polar (insoluble in water, low melting and boiling points, both undergo combustion with oxygen
How do they differ?
Reactions of ethene
Like all alkenes, ethene undergoes addition reactions. Why? Answer: When the double bond is broken additional atoms or groups of atoms can be added one to each C atom previously linked by the double bond.
Addition of hydrogen
Addition of hydrogen to ethene results in the
formation of ethane.
Ethylene + CH2= CH2 (g) + hydrogen H2 (g) ethane CH3-CH3 (g)
Alkene + hydrogen
alkane
Addition of halogens
Addition of a halogen (eg: Cl, Br) to ethene
Alkene + halogen
di-halo-alkane
CH3-CH2Cl(l)
haloalkane
Addition of water
Addition of water (in the presence of an acidic
Alkene + water
alkanol
Reactions of alkanes
1. Combustion reaction: Alkanes burn in air to
Alkane + oxygen
Reactions of alkanes
1. Substitution reaction: Alkanes react with Cl2,
Br2, I2 (halogens) when exposed to ultraviolet light C6H14 (l) + Br2 (l)
hexane + bromine
C6H13Br(l) + HBr(aq)
bromohexane haloalkane
Alkane + halogen
Polymerisation
Reaction in which many small molecules (monomers) combine to form one large molecule (polymer). There are two main types of polymerisation reactions:
Addition polymerisation Condensation polymerisation
Addition polymerisation
In the process of addition polymerisation monomers simply add together without the loss of any atoms. Basically the double bond opens out to form single bonds with neighbouring molecules. Addition reactions involve unsaturated hydrocarbons.
Addition polymerisation
Condensation polymerisation
Condensation polymerisation involves a reaction between two monomers which have different functional groups. Small molecules such as water are eliminated during this reaction.
Condensation polymerisation
Amine functional group NH 2
Synthetic polmers
Ethene is the simplest monomer capable of undergoing addition polymerisation. Some important synthetic polymers formed from ethene include: Poly(ethene) (polyethelyne) Poly (vinyl chloride) PVC Poly (styrene) Poly (acylonitrile) PAN Poly (propene) (polypropylene)
Biopolymers
Polymers produced by living organisms are called biopolymers. Examples include:
Cellulose Starch Proteins Nucleic acids
Alcohols
Alcohols are a family of carbon compounds
that contain the hydroxy group (-OH). Alkanols are a specific group of alcohols where one or more hydrogen atoms in an alkane are replaced by an OH functional group. Alkanols are represented by the general formula ROH where R = alkyl group
Ethanol
Alcohols : Nomenclature
Add the suffix ol in place of the e on the
name of the hydrocarbon to which the OH group is attached. A number indicates the position of the carbon atom containing the -OH group. If there are more than one OH group add the suffixes -diol, -triol and so on.
1,2 ethanediol
Ethanol
Primary alcohol
The carbon atom attached to the _OH group has two carbon atoms bonded to it.
Secondary alcohol
The carbon atom attached to the _OH group has two carbon atoms bonded to it.
Tertiary alcohol
The carbon atom attached to the _OH group has two carbon atoms bonded to it.
Ethanol as a solvent
Ethanol is a good solvent because it is a very polar molecule. When ethanol and water are mixed they readily dissolve in each other. This is due to the polar nature of the O-H bond.
C + O H+
The polar end of the ethanol molecule interacts with other polar molecules to form dipole-dipole forces or hydrogen bonds eg: with water
Ethanol as a solvent
Ethanol and hexane (a non-polar molecule) readily dissolve in each other.
The non - polar end of the ethanol molecule (the alkyl chain) forms dispersion forces with other non-polar molecules. This enables ethanol to act as a solvent for some non-polar molecules.
Production of Ethanol
1. Hydration of ethanol: industrial ethanol is
produced by the acid catalysed addition of water to ethene, represented by the equation: CH2 = CH2 (g) + H20 (g) CH3 - CH2OH(g)
Production of ethanol
2. Fermentation: process in which glucose is broken down to ethanol and carbon dioxide by the action of enzymes in yeast (these act as catalyst). C6H12O6 (aq) 2CH3 - CH2OH (aq) +2CO2 (g)
Ethanol as a fuels
The combustion of ethanol is an exothermic reaction. C2H5OH(g) + 3O2 2CO2(g) + 3H2O(g)
The amount of heat released can be expressed as the molar heat of combustion: Heat liberated on complete combustion of one mole of a substance
Calorimetry
Calorimetry is a method used to determine heat of combustion. Essentially we measure the change in temperature of measured mass of water heated by the combustion of a measured amount of fuel. This is then used to calculate heat energy release per mole of substance burned.
4. Calculate how much heat could have been produced by one mole of the substance
Oxidation-reduction
Reactions which involve the transfer of electrons are called oxidation-reduction reactions. OXIDATION = LOSS OF ELECTRONS REDUCTION = GAIN OF ELECTRONS Zn (s) + 2HCl (aq) Oxidation: Zn (s) ZnCl2 (aq) + H2 (g) Zn 2+ (aq) + 2eH2 (g)
Displacement reactions
Displacement reactions are oxidation-reduction reactions in which a metal converts the ion of another metal to the neutral atom. In these reactions the metal dissolves and the ions of the other metal are reduced to elemental metal and deposit out of solution.
Example:
Cu
ions have a greater tendency to gain electrons than Zn 2+ ions. As a result there is a transfer of electrons from the Zn metal to the Cu (II) ions. As the reaction proceeds Zn metal dissolves and goes into solution as Zn ions and Cu metal is formed
2+
Oxidation states
In many oxidation-reduction reactions it is not
obvious which species has been reduced and which has been oxidised. To overcome this problem we use a system of assigning oxidation states to atoms to keep track of the number of electrons transferred or shared in oxidation-reduction reactions. Oxidation state is an arbitrary number assigned according to a set of rules.
2.
3. 4.
5.
Uncombined elements have an oxidation state of 0 Ions have an oxidation state equal to their charge (eg: Na+ = +1) Oxygen in compounds has a charge of -2 in oxides and -1 in peroxides Hydrogen in compounds has a charge of +1 when combined with non-metals and -1 when combined with metals The oxidation state of a compound or polyatomic ion is the sum of the oxidation states of all its atoms.
Oxidation state
Note that the number of electrons lost or gained = change in oxidation state
Oxidation involves an increase in oxidation state. Half equation Zn (s) Zn 2+ (aq) + 2eOxidation state 0 2+ Reduction involves a decrease in oxidation state. Half equation: 2H+(aq) + 2eOxidation state: 1+
H2 (g) 0
Electrochemical cells
Redox reactions can be used to generate
electricity in a galvanic cell Example: When zinc metal is placed in CuSO4 solution, following reaction take place: Zn(s) + CuSO4(aq) ZnSO4(aq) + Cu(s) Oxidation: Zn(s) Zn+2 + 2eReduction: Cu+2 + 2e- Cu Overall: Zn(s) + Cu+2 Zn+2 + Cu(s)
Galvanic cell
Each of the two parts of the cell is called a half cell.Each half cell is connected by a salt bridge which completes the circuit and allows ions to travel between each half cell.
the Cu strip where they are accepted by the Cu ions The Cu ions are reduced to Cu atoms which deposit on the strip
measure of the relative tendency of a substance to gain one or more electrons compared to the standard hydrogen half cell. The larger the EO value the greater the oxidising power of a substance e.m.f or voltage of a galvanic cell is the difference in the reduction potentials of the two couples making up the cell.