Академический Документы
Профессиональный Документы
Культура Документы
Reactions of Alkanes
Alkanes are insoluble in water but are soluble in non-polar solvents. There are weak dispersion forces between molecules as evidenced by their low melting and boiling points. The stability of the carbon-carbon bonds and the non polar nature of the molecules means that alkanes are very resistant to reaction. Most reactions involving alkanes are either combustion or substitution.
Combustion
Alkanes are used as fuels. Combustion reactions involving alkanes release large amounts of heat energy. Methane is the major component in natural gas and octane is an important component of petrol. The combustion equations for these two alkanes are:
CH4(g) + 2O2(g) CO2(g) + 2H2O(g) + energy 2C8H18(g) + 25O2(g) 16CO2(g) + 18H2O(g) + energy
Substitution Reactions
In substitution reactions, one or more of the hydrogen atoms in an alkane is replaced by a different atom or functional group. This involves breaking the carbon-hydrogen bonds and making new bonds with the substituted group or atom. An example of this is the reaction between a chlorine molecule and a hydrocarbon. The chlorine molecule breaks into separate atoms and because these are unstable with only 7 outer electrons the chlorine free radicals attack the carbon-hydrogen bonds. RH + Cl2 RCl + HCl
Reactions of Alkenes
Ethene:
Is unsaturated Is a non-polar molecule Is insoluble in water Is a flammable gas Participates in addition reactions Polymerises to produce polyethene.
Since ethene is a small, non-polar molecule, the only attractive forces between its molecules are dispersion forces and ethene therefore has a very low boiling temperature.
Addition Polymerisation
A type of addition reaction of ethene is involved in making polyethene. The number, n, in this reaction is very large. A molecule made by linking a large amount of small molecules is called a polymer. The singular small molecule is called a monomer. A reaction where many monomer react together to produce a polymer is called addition polymerisation.
Reactions of Chloroalkanes
When a more electronegative atom such as chlorine has been substituted for a hydrogen, the hydrocarbon becomes polar. Electrons are more attracted to the chlorine atom, which makes the carbon atom at the other end of the bond susceptible to be attacked by anions. For example, chloromethane is converted to methanol when it reacted with hydroxide ions. The chlorine atom is substituted by an OH functional group. The carbon-chlorine bond is also susceptible to attack by the negatively charged end of a polar molecule, like in the case of ethanol.
Reactions of Alkanols
Alkanols can undergo substitution reaction. The amino functional group can be introduced to the chain by a substitution reaction between ammonia and an alkanol. Ethylamine is formed by passing ammonia and ethanol vapour over aluminium oxide heated to about 400 degrees. CH3CH2OH(g) + NH3(g) CH3CH2NH2(g) + H2O(l)
Carboxylic acids such as ethanoic acid react with bases, reactive metals and carbonates.
Esters
Esters are a group of organic compounds responsible for some of the natural and synthetic flavours and smells in ice cream, lollies, flowers and fruits.
Ester Pentyl Propanoate Ethyl Butanoate Octyl Ethanoate 2-Methylpropyl Methanoate Ethyl Methanoate Pentyl Ethanoate Smell of Flavour Apricot Pineapple Orange Raspberry Rum Banana
Esters cont
Esters composed of small molecules are volatile and have distinctive odours. They have low boiling points that allow them to evaporate easily and reach your nose. Esters of larger molecular size are oils and waxes. Esters are made by a condensation reaction between a carboxylic acid and an alkanol. Reactions that involve the combination of two reactants and the elimination of a small molecule, such as water, are called condensation reactions.
For example, gently heating a mixture of ethanol and pure ethanoic acid with a trace amount of sulfuric acid added produces an ester (ethyl ethanoate) and water. The sulfuric acid acts as a catalyst.
Esters cont
The general equation for the esterification reaction involving a carboxylic acid and an alkanol is shown below.
Esters cont
Esters have two part names. The first part is derived from the name of the alkanol from which is is made, where yl replaces anol. The second part comes from the carboxylic acid, where ic is replaced by the suffix ate.
Reaction Pathways
The reaction pathway selected needs to take into account the yield and purity of the product and also minimise any unwanted side-products and waste materials. Time and cost factors also need to be considered. There is also a lot of current interest in working out green synthetic routes- ones that minimise waste, use more environmentally friendly solvent, require less energy and help to preserve the worlds resources.
Propanoic acid is a carboxylic acid containing three carbon atoms. It is prepared by the oxidation of the primary alkanol propan1-ol. This in turn can be formed by the reaction of 1-chloropropane with sodium hydroxide. 1-chloropropane can be prepared by reacting propane with chlorine. A number of chlorine-substituted products will be formed. These are separated by fractional distillation.
The substitution reaction of propane is chosen rather than an addition reaction of propene because the addition of HCl to propene with result in the formation of unwanted 2chloropropane. Having synthesised ethanol and propanoic acid, ethyl propanoate can be prepared using a condensation reaction.
The reaction pathways for the preparation of ethanol, propanoic acid and ethyl propanoate can be summarised.
The ester can be separated from the reaction mixture and purified by fractional distillation. Its identity can then be verified using instrumental analysis such as IR, NMR or Mass Spectroscopy.
Worked Example
In a particular synthesis, the yield of AB is 80% and the yield of BC is 70%. Calculate the overall percentage yield for the preparation of C from A. When A reacts to form B, only 80% or 80/100 of the theoretical mass of B is formed. Then, when B forms C, only 70% of 70/100 of C is formed. Hence the overall yield of C = (80/100) x (70/100) x 100% = 56%
Fractional Distillation
Is a technique used to separate liquids that have different boiling points. It is commonly used in the lab to separate volatile liquids from a reaction mixture. Industrial applications of fractional distillation include:
Separation of the fraction from crude oil Production of oxygen and nitrogen by fractional distillation of air Extraction of ethanol in the fermentation of sugar