- We have seen in the chapter on alkenes that ethene C2H2 can be changed to ethanol C2H5OH by passing a mixture of ethene and steam over H3PO4 catalyst at 300 ºC and 70 atm. Ethanol is used as a solvent in perfumes and varnishes, and a useful fuel in many cars manufactured in the US. The ethanol that is present in alcoholic drinks such as wine and beer is made by fermentation of glucose.
- Ethanol CH3CH2OH is the second member of a homologous series of alcohols which has a general formula of CnH2n+1OH. All alcohols contain the functional group -OH which is responsible for the chemical properties of alcohols. The first member of alcohols is methanol CH3OH which contains only one carbon atom (n = 1). The third (n = 3) and fourth (n = 4) members of the alcohols are propanol and butanol respectively. When n is greater than 2, isomerism exists. Complete the following table and try to draw out all the full structural formulas of these alcohols including the isomers of propanol and butanol.
Name | Number of carbon atoms, n | Molecular formula | Relative molecular mass | Structural formula |
Methanol |
|
| 32 |
|
Ethanol | 2 |
|
| CH3CH2OH |
Propanol |
| C3H8O |
|
|
Butanol |
|
|
| CH3CH2CH2CH2OH |
- Generally, down the series when the molecular mass of the alcohol increases, the boiling point increases. For example, methanol (n = 1) boils at 68 ºC, ethanol (n = 2) boils at 78 ºC and butanol (n = 4) boils at 118 ºC. Isomers however have different boiling points even though they have the same molecular formula. For example, propan-1-ol boils at 97.2 ºC but propan-2-ol boils at 82.3 ºC.
- Alcohols, like alkanes and alkenes, are flammable. Ethanol, for example, undergoes complete combustion in sufficient supply of oxygen to produce carbon dioxide and water. Write down the balanced equation for the combustion of 1 mole of ethanol. Use the following information to calculate the enthalpy of combustion of 1 mole of ethanol. You should get -1020 kJ/mol. Because ethanol is runny and volatile and its combustion is so exothermic, ethanol can be used as a fuel for motor vehicles. What is one advantage of using ethanol over fossil fuels to run motor vehicles?
Bond | Bond energy (kJ/mol) |
H-C | 413 |
C-C | 348 |
C-O | 743 |
O-H | 463 |
O=O | 498 |
C=O | 743 |
- Laboratory experiments sometimes use ethanol. For example, in Biology experiments, ethanol is used as a solvent to dissolve the green pigment, chlorophyll, in leaves. Care must be taken to keep ethanol from open Bunsen flames because ethanol is flammable. If you happen to spill ethanol on the laboratory bench and it catches fire, do not pour water because, water, being denser than ethanol would spread the ethanol over a larger area. Instead, you should use the fire blanket to put out the fire.
- Besides undergoing combustion, alcohols can also be oxidized by atmospheric oxygen to form weak acids called carboxylic acids. This oxidation can also be achieved by other oxidizing agents such as acidified potassium dichromate or acidified potassium permanganate. For example, ethanol C2H5OH can be oxidized by acidified potassium dichromate to ethanoic acid CH3COOH. In this redox reaction, the orange dichromate is changed to green Cr3+(aq). This reaction is used in breathalyzers to test for alcoholic breathe in drivers. Why is this a redox reaction? If potassium permanganate is used, what do you think would be observed?
- Ethanoic acid is the second member of another homologous series called carboxylic acids which has the general formula, CnH2n+1COOH. The first member, methanoic acid HCOOH (n = 0), commonly called formic acid, boils at 101 ºC. Note that in this case, n for the first member is not 1. Ethanoic acid CH3COOH (n = 1), commonly called acetic acid, boils at 118 ºC while propanoic acid CH3CH2COOH (n = 2) boils at 141 ºC. Therefore, like other homologous series, the boiling point of carboxylic acids increases as relative molecular mass increases. Try to draw out the full structural formulas of the first few members of the carboxylic acids.
- The first few members of carboxylic acids are soluble in water. Down the series, however, the solubility of carboxylic acids decreases. From n = 9 onwards, the carboxylic acids become insoluble in water. The insoluble carboxylic acids which have long chain of carbon atoms are often referred to as fatty acids.
- Fatty acids are said to be saturated if they contain only C-C single bonds, and are said to be unsaturated if they contain C=C double bonds. Do you still remember, from the topic on alkenes, how you can change unsaturated fatty acid to saturated fatty acid? What catalyst do you use?
- The functional group of carboxylic acid is -COOH which is responsible for its acidic properties. Therefore, carboxylic acids can react with alkalis to form a salt and water, with metals to evolve hydrogen gas, and with carbonates to evolve carbon dioxide. Make sure you know how to describe the tests for hydrogen gas and carbon dioxide gas. Try to write out the chemical equations for the reaction between carboxylic acid with sodium hydroxide, with magnesium, and with calcium carbonate. Note that ethanoate CH3COO- has a charge of +1.
- Carboxylic acids are, however, weak acids meaning that they dissociate partially to give H+(aq). In an aqueous solution of ethanoic acid, for example, only about 0.4% of the ethanoic acid molecules dissociate to become ethanoate ions CH3COO-(aq) and protons H+(aq). Vinegar, which contains about 1.0 mol dm-3 of ethanoic acid, has a pH of 2.4.
(12 and 13 are only for Pure Chemistry)
- If we heat ethanoic acid and ethanol in the presence of sulfuric acid catalyst under reflux as shown below, we will get a sweet-smelling compound, called ethyl ethanoate CH3COOC2H5, that floats on top of the reaction mixture. Ethyl ethanoate is a class of compounds called esters which contain the -COO- ester linkage. The reaction that forms esters is called esterification. At the same time, water is formed as a by-product. Since a small molecule is formed as a by-product, esterification is also described as a condensation reaction. Note that the reaction is reversible. To prevent the reaction from going backward reforming the reactants, concentrated sulfuric acid, which is a dehydrating agent, is used to absorb the water.
- We can produce different esters by heating different alcohols and carboxylic acids using the same conditions. Try writing chemical equations for the formations of different esters. Esters tend to smell very pleasant and so they are used as perfumes and flavorings. They are also used as solvents such as in inks and adhesives as they can dissolve many organic compounds.
Now, try to draw out the flow chart of reactions involving ethane, ethene, ethanol and ethanoic acid.