Вы находитесь на странице: 1из 20

ORGANIC CHEMISTRY NOTES. The compounds in each family have a similar chemical structure and a similar chemical formula.

Each family of organic compounds forms what is called a homologous series. Different families arise because carbon atoms readily join together in chains and strongly bond with other atoms such as hydrogen, oxygen and nitrogen. The result is a huge variety of 'organic compounds' which can be classified into groups of similar compounds i.e. different homologous series. The term organic compound comes from the fact that most of the original organic compounds studied by scientists-chemists came from plants or animals, i.e. of natural origin. These days most organic compounds are synthesized from raw materials, in particular the physical separation and chemical manipulation of the products of crude petroleum oil.

A homologous series is a family of compounds which have a general formula* and have similar chemical properties because they have the same functional group of atoms (e.g. C=C alkenes, C-OH alcohol or -COOH carboxylic acid). Members of a homologous series have similar physical properties such as appearance, melting/boiling points, solubility etc. but show trends in them e.g. steady increase in melting/boiling point with increase in carbon number or molecular mass. The molecular formula represents a summary of all the atoms in the molecule e.g. butane is C4H10. The structural or displayed formula shows the full structure of the molecule with all the individual bonds and atoms shown (though there are different 'sub-styles' of varying detail)

e.g. all represent ethane When a specific group of atoms in a molecule give it a particular set of characteristic reactions, that group of atoms is called the functional group of the molecule. Examples of functional groups include: o the double carbon-carbon bond C=C in alkenes, o the oxygen-hydrogen atom group of the -OH in alcohols, o and the group of four atoms constituting the -COOH group in carboxylic acids.
o

ALKANES - saturated hydrocarbons The alkanes are a series of hydrocarbon molecules (made of carbon and hydrogen atoms). They are referred to as 'saturated' hydrocarbons because they do NOT contain a double bond and other atoms cannot add to them. The physical properties and chemical reactions of alkanes with oxygen (combustion, burning) and chlorine (to form a chloroalkane) are fully described with word and symbol equations.

Alkanes are a group of hydrocarbon molecules in which all the carbon and hydrogen atoms are only joined by single covalent bonds (e.g. C-H or C-C). Alkanes are known as saturated molecules because other atoms cannot add to them ( Physical properties: The first four in the series are shown below and are all colourless smelly highly flammable gases. The much larger alkanes are colourless liquids and the biggest members of the series are white waxy solids.
Page 1 of 20

They are not very reactive unless burned! The principal source of alkane hydrocarbons is crude oil. (1) is the molecular formula: a summary of the totals of each atom of each element in one molecule (2) is a 'shorthand' version of the full structural formula (3) is called the structural formula: it shows how all the atoms are linked by covalent bonds the dashes! (4) is a '3D' representation of the structural formula (3) showing the spatial arrangement of the atoms.

methane (main molecule in natural gas) (1) (3) (4)

(1)

(2)

(3)

ethane

(4)

(1)

(2)

propane

(3)

Page 2 of 20

(1)

(2)

butane

(3)

or

A brief guide to the structure and nomenclature of alkanes CnH2n+2 n = formula of alkane name of alkane

1 CH4

2 C2H6

3 C3H8

4 C4H10

5 C5H12

6 C6H14

7 C7H16

8 C8H18

9 C9H20

10 C10H22

methane ethane propane butane pentane hexane heptane octane nonane decane

The primary suffix name is based on the longest carbon chain and ending in ...ane. o 1 carbon, methane; 2 carbons, ethane; 3 carbons in chain, propane; 4 carbons in chain, butane. After these four preserved 'old trivial' names, the name is 'numerically' systematic e.g. C5 carbon chain pentane; C6 chain hexane, C7 chain heptane, C8 chain octane, C9 chain nonane, C10 chain decane etc. The table above lists the molecular formula and names of the first ten linear alkanes (the term linear applies to butane onwards) If all the carbon atoms of the molecule are in one continuous chain, it is referred to as unbranched or linear. E.g. pentane is linear or unbranched. If another chain of carbon atoms starts out of the main carbon chain, it is referred to as branching, giving rise to 'branched' alkane, one with a side-chain.
o

E.g. 3-ethylpentane is branched, because it has an 'ethyl branch' from the 3rd carbon atom in the main chain. o The longest continuous chain of 5 carbon atoms forms the basis of the name. o The 3- denotes the position of the carbon chain branch i.e. the lowest number possible for the start of the side-chain. The positions of the substituent alkyl groups (side chains or 'branches') are denoted by using the lowest possible number(s) o e.g. 2, 3 etc. for the associated carbon atoms in the main chain, where the 1st carbon atom in the chain is considered as C atom 1. If there is more than one 'type' of substituent e.g. using the prefixes: methyl... and ethyl.... etc., they are written out in alphabetical order (BUT di, tri are ignored in using this rule).
o

Page 3 of 20

Ways of representing the structure of molecules and classes of formulae This is illustrated by looking at the structure of the propane, 2-methyl propane and butane molecules. Follow the sequence of bullet points down, and then back up, so you are quite clear on the relationship between all the structural and formula styles.

The empirical formula means the simplest possible formula showing the whole number stoichiometric ratio of the different atoms (elements) in the compound. It derives from an elemental analysis of a compound. o E.g. for propane it is C3H8, and for butane or 2-methylpropane it is C2H5. The molecular formula summarises all the atoms in the molecule BUT does not show their arrangement at all. o C3H8 is the molecular formula for propane and C4H10 that of butane and 2methylpropane. o Note that for propane, the empirical formula is identical to the molecular formula BUT for 2-methylpropane and butane, they are not identical. In the case of the latter, the molecular formula is 'twice' the empirical formula. o Note also, that the molecular formula, does NOT distinguish the two structural isomers butane and 2-methylpropane ('methylpropane'). The 2- is not strictly required, since the branching must occur on the middle carbon as you will see below, where we introduce a more advanced structure notation that allows the unambiguous representation of molecular structures. An 'abbreviated' or 'shortened' structural formula is unambiguous if you know how to interpret it! It shows how groups of atoms are linked or sequenced in a molecule. It is the minimum possible representation to distinguish different structures of the same molecular formula i.e. structural isomers like methylpropane and butane.
o o o o

propane 2-methylpropane

or

butane or Note that methylpropane and butane can now be distinguished, BUT, you must be able to envisage these correctly into a full structure that shows how all the atoms are 'connected', and this is explained next. A full structural/graphic/displayed formula gives a '2D' projection-representation of the molecule and must clearly show how all the atoms are connected i.e. in this case all the C-C and C-H covalent bonds, but does it not give the full 3D structural, or spatial arrangement, of the atoms, though for most purposes, this level of detail is quite sufficient.

propane

Page 4 of 20

2-methylbutane

Butane You can use a mixture of styles of the abbreviated/structural/graphic/displayed formulae.

e.g. 2-methylbutane ISOMERISM

Isomerism occurs when two or more compounds have the SAME MOLECULAR FORMULA but exist in at least two different structures (i.e. different molecules in some way). The different molecules are known as ISOMERS. They may be quite similar, or significantly different, in terms of their physical and chemical properties. The existence of isomers is one of the reasons why such a huge array of different organic compounds exists. o Other reasons for the diversity of organic compounds include (i) carbon chain catenation i.e. the ability of carbon chains to link together and (ii) the formation of stable bonds with elements such as oxygen, nitrogen, hydrogen etc. In order to analyse a molecular formula for its possible isomers, you need to know what forms of isomerism can occur and then 'take the molecular formula apart' and reconstruct the atoms in as many different ways that seem possible. BUT ensure the 'reconstructs' are genuinely different in some way and obey the isomerism criteria. So, beware!, what seems different on 2D paper might not be in 3D reality, especially as there is free rotation about single bonds, so using models for simpler molecules is extremely useful at the start of studying isomerism. Chain isomers of the alkane molecular formula C5H12

(1)

, pentane, volatile colourless liquid, bpt 34oC, linear.

Page 5 of 20

(2) ,2- methylbutane (2-methylbutane), volatile colourless liquid/gas, o bpt 28 C, minimum branching.

(3),

, 2,2-dimethylpropane, colourless gas, bpt 9.5oC, maximum branching. Reactions of alkanes.

Equations for the complete combustion of a hydrocarbon When a hydrocarbon molecule (reactant) burns in an excess of air-oxygen there are only two products of the reaction. The carbon atoms are oxidised on combining with oxygen to form carbon dioxide molecules, and the hydrogen atoms are oxidised to water molecules ('hydrogen oxide'). General word equation: Hydrocarbon + oxygen ==> carbon dioxide + water Word equations e.g. methane + oxygen ==> carbon dioxide + water and the corresponding symbol equation is CH4(g) + 2O2(g) ==> CO2(g) + 2H2O(l) Note that one CO2 for every C, and one H2O for every two H's in the hydrocarbon molecule.

In terms of displayed formula the equation would be written as...

... in which every individual atom is shown and how it is bonded ('connected') with other atoms in the molecule. All the dashes represent the covalent bonds between the atoms in the molecules. Another example is the combustion of propane... Propane + oxygen ==> carbon dioxide + water C3H8(g) + 5O2(g) ==> 3CO2(g) + 4H2O(l) and in terms of displayed formula and balancing numbers ...

Page 6 of 20

and the above diagrams show how the atoms have rearranged themselves in the reaction after the reactant bonds are broken (C-H, O=O and C-C in ethane etc. below)) and the new bonds formed in the products (C=O and O-H). Note the number of atoms of each element must be the same on each side of the equation (1C, 4H's and 4 O's, Law of Conservation of mass) and the products are different substances with different properties compared to the reactants. for ethane the symbol equation is ... 2C2H6(g) + 7O2(g) ==> 4CO2(g) + 6H2O(l) and for pentane the symbol equations is ... C5H12(l) + 8O2(g) ==> 5CO2(g) + 6H2O(l) The Incomplete Combustion of hydrocarbons

If there is not enough oxygen present to completely burn the fuel to carbon dioxide and water other products may form causing pollution and fuel inefficiency. o This is referred to as incomplete combustion. The most common partially burned products are likely to be carbon C (soot) and deadly carbon monoxide CO. o Carbon-soot, a fine black powder-dust is potentially harmful and readily formed in fires i.e. its classically produced by smoky yellow flames. The soot, like any fine solid 'dust' is harmful when absorbed on the sensitive tissue of the linings of the nose, throat and lungs. Soot deposits cause coughing and sore throat and are ejected from your body through sneezing, coughing, and nose blowing. Coarse particles (10 microns) are inhaled into your windpipe and settle there, causing irritation and more coughing. Soot is also a 'carrier' of polycyclic aromatic hydrocarbons (PAH's) on it which are carcinogenic. o Even very low concentrations of carbon monoxide can be fatal. Why? Oxygen is carried around the body by a complicated protein molecule in red blood cells called haemoglobin. The bonding between oxygen and haemoglobin is quite weak to allow easy oxygen transfer for cell respiration. Unfortunately, the bonding between carbon monoxide and haemoglobin is stronger, so oxygen is replaced by carbon monoxide and blocks normal cell respiration. The consequences are reduced blood oxygen concentration leading to unconsciousness and eventually death! There is also less heat released in incomplete combustion compared to complete combustion since not all the carbon atoms of the fuel are fully combined with the maximum amount of oxygen. o e.g. for the incomplete combustion of methane the word and symbol equations are as follows ... methane + oxygen ==> carbon + water CH4(g) + O2(g) ==> C(s) + 2H2O(l) for soot (mainly carbon) formation and
Page 7 of 20

methane + oxygen ==> carbon monoxide + water 2CH4(g) + 3O2(g) ==> 2CO(g) + 4H2O(l) for the formation of carbon monoxide

Methane and chlorine

Substitution reactions happen in which hydrogen atoms in the methane are replaced one at a time by chlorine atoms. You end up with a mixture of chloromethane, dichloromethane, trichloromethane and tetrachloromethane.

This reaction takes place in the presence of UV light but not in darkness. The reaction between methane and bromine is similar to this but slower.

The SEPARATION of the crude oil mixture into fractions and the USES of these fractions A fraction is a mixture of a restricted boiling point range of molecules; they have a similar number of carbon atoms and physical properties. The uses of the fractions depend on their physical and chemical properties.

Crude oil is a complex mixture of mainly hydrocarbon compound molecules. A mixture consists of two or more elements or compounds which are not chemically combined. The chemical properties of each substance in the mixture are unchanged. This means crude oil can be separated by physical methods, in this case by fractional distillation, because they have different boiling and condensation points. The crude oil is heated to vapourise it (evaporated or boiled). The most volatile fraction, i.e. the molecules with the lowest boiling points, boil or evaporate off first and go to the top of the column. The rest separate out according to their boiling/condensation point so that the highest boiling fraction, i.e. the less volatile molecules with higher boiling points, tend to condense more easily lower down the column. The bigger the molecule, the greater the intermolecular attractive forces between the molecules, so the higher the boiling or condensation point. Note: Covalent chemical bonds like C-C or C-H are not broken in the process, only the intermolecular force of attraction is weakened to allow the initial evaporation or boiling.

Page 8 of 20

THE FRACTIONAL DISTILLATION OF CRUDE OIL

names of fractions Fuel Gas, LPG, Refinery Gas Gasoline, Petrol

C atoms boiling USES of the fraction - mainly in the range depends on its physical molecule in oC properties -160 to 20oC methane gas fuel, C3-4 easily liquefied, portable energy source bottled gas for cooking (butane), higher pressure cylinders (propane) easily vaporised, highly flammable, easily ignited, car fuel no good as a fuel, but valuable source of organic molecules to make other things, cracked to make more petrol and alkenes less flammable than petrol, domestic heater fuel, jet fuel car and larger vehicle fuel

1 to 4

5 to 11

20 to 60oC 60 to 180oC 120 to 240oC 220 to 250oC

Naphtha Paraffin, Kerosene

7 to 13

10 to 16

Diesel oil, Gas 15 to 25 oil Fuel oil, lubricating oils and Waxes

20 to 70

not so easily evaporated, not as flammable, safe to store for 250 to central heating oil, quite viscous 350oC (sticky) and can also be used for lubricating oils, clear waxes and polishes forms a thick, black, tough and resistant adhesive on cooling, over used as waterproofing material o 350 C and to sticks rock chips on roofs or road surfaces

Bitumen

over 70

Cracking - a problem of supply and demand, other products Cracking is a thermal decomposition process by which large alkane hydrocarbon molecules are broken down by passing them over a heated catalyst at high pressure. The products are smaller alkanes used for fuels (e.g. petrol or diesel) and alkenes which are used to make polymers-plastics and other important compounds. There are two good economic reasons for cracking oil fractions - (i) there arent enough of fuels like petrol or diesel in the original crude oil and (ii) alkenes are NOT found in oil, so must be manufactured from oil. Either way, it means the vast majority of crude oil can be turned into useful products.

CRACKING is done by heating some of the less used fractions to a high temperature vapour and passing over a suitable hot catalyst at high pressure. o The cracking reaction is an example of thermal decomposition - a reaction that breaks down molecules into smaller ones using heat.
Page 9 of 20

The main products from cracking alkanes from oil are smaller alkanes (e.g. for petrol or diesel) and alkenes (e.g. for polymers-plastics). The equations below illustrate the process, small molecules are used to show the overall molecular change clearly BUT in practice the 'starter' molecules are likely to be more those shown in equations (3) and (4). o The cracking involves breaking single carbon-carbon bonds to form the alkanes (saturated hydrocarbons) and alkenes (unsaturated hydrocarbons) products.
o

(1) butane ethane ethene.....or

(2) butane (3) C8H18 (4) C12H26 methane propene

C6H14 + C2H4 (making a petrol fuel molecule + ethene for polymers/plastics) C9H20 + C3H6 (making a diesel fuel molecule + propene for polymers/plastics) The ALKENE hydrocarbons series (unsaturated)

Alkenes are hydrocarbons containing a carbon...carbon double bond (C=C) as well as single bonds. These are called unsaturated molecules because two atoms can join onto the bond when it opens up. The first two in the series are shown below and are colourless smelly gases. They are extremely reactive and important compounds in the chemical industry and are converted into very useful compounds e.g. plastics. They are made from cracking crude oil in the petrochemical industry processes (1) is the molecular formula: a summary of the totals of each atoms of each element in one molecule; (2) is a 'shorthand' version of the structural or displayed formula (3); (3) is called the structural or displayed formula: it shows how all the atoms are linked with the covalent bonds ethene (1) , (2) , (3) propene (1) , (2a) , (2b) , (3)

Page 10 of 20

(1)

, (2)

butene

Three important reactions of alkenes (1) Addition of bromine: A test to distinguish between ALKANE and ALKENE hydrocarbons

Hydrocarbons are colourless. Bromine dissolved in water or trichloroethane solvent forms an orange (yellow/brown) solution. When bromine solution is added to both an alkane or an alkene the result is quite different. The alkane solution remains orange - no reaction. However, the alkene decolourises the bromine as it forms a colourless dibromo-alkane compound.

.... or

ethene + bromine ==> 1,2-dibromoethane

Alkenes are unsaturated molecules, atoms can add to them via the C=C double bond, so a reaction occurs. Alkanes are saturated - no double bond - and atoms cannot add - so no reaction.

Page 11 of 20

.... or

2nd example of bromine addition to a double bond. propene + bromine ==> 1,2dibromopropane

(2) Alkenes can add hydrogen to form a saturated alkane molecule

H2 propene + hydrogen ==> propane

Alkenes will react with hydrogen gas over a nickel catalyst 150oC The reaction process is used to make margarine from vegetable oils.

More on ALKENES - unsaturated hydrocarbons


These cannot be obtained directly from crude oil and must be made by cracking. The unsaturated hydrocarbons form a homologous series called alkenes with a general formula CnH2n Unsaturated means the molecule has a C=C double bond to which atoms or groups can add. Alkene examples: Names end in ...ene o ethene C2H4 or propene

or

C3H6 or butene

or

or

or The alkenes are more reactive than alkanes because of the presence of the carbon=carbon double bond. The alkenes readily undergo addition reactions in which one of the carbon=carbon double bonds breaks allowing each carbon atom to form a covalent bond with another atom such as hydrogen or bromine.
Page 12 of 20

Examples of addition reactions are: with hydrogen under pressure and in the presence of a nickel catalyst to form an alkane

+ H2 ==> ethene + hydrogen ==> ethane

+ H2 ==> propene + hydrogen ==> propane Alkenes react by 'addition' with bromine and decolourises the orange bromine water because the organic product is colourless, and this is a simple test to distinguish an alkene from an alkane. Vegetable oils contain unsaturated fats and can be hardened to form margarine by adding hydrogen on to some of the carbon=carbon double bonds using a nickel catalyst. The process is called hydrogenation, o and the change in an 'unsaturated' part of an oil molecule is o -CH=CH- + H2 ==> -CH2-CH2o So producing a 'saturated' section in the molecule. Alkenes readily burn, just like alkanes, to give carbon dioxide and water. o e.g. ethene + oxygen ==> carbon dioxide + water o C2H4 + 3O2 ==> 2CO2 + 2H2O o However, they are NOT used as fuels for two reasons. 1. They are far too valuable for use to make plastics, anti-freeze and numerous other useful compounds. 2. They burn with a more smokey flame than alkanes due to less efficient and more polluting combustion. Alkenes can add to themselves by addition polymerisation to form 'plastic' or polymeric materials. The formation of big polymer molecules called polyalkenes from small molecules called alkenes
o

Poly(ethene) from ethene is a cheap but very useful plastic used for plastic bags and bottles (old or commercial names: polyethylene, polythene and polyethene). It is an example of a thermoplastic, because it can be heated to soften it, reshape it e.g. in an injection mould system, and on cooling retains its new shape - bottle, bowl, toy etc.
Page 13 of 20

The formation of PVC is shown below. Poly(chloroethene), PVC, made from chloroethene (old name vinyl chloride) is much tougher than poly(ethene) and very hard wearing with good heat stability. So it is used for covering electrical wiring and plugs. It is also replacing metals for use as gas and water drain pipes and has found a use as artificial leather and readily dyed to bright colours! Old names : polyvinyl chloride, shortened to PVC)

poly(propene)

Poly(propene) from propene is stronger and more hard wearing than polythene and is used for making crates, fibres and ropes (old or commercial names: polypropylene, polypropene and polypropene). What is ethanol and how can we make it? The 'alcohol' of the homologous series of alcohols!

What we call alcohol in everyday life is a substance whose chemical name is ethanol. Ethanol is just one member of a family of substances called alcohols which have -OH functional group in their structure.

Ethanol structure

or

or
Page 14 of 20

or

The first formula is the simplest formula to show the structure of ethanol and the last image is the full graphic structural displayed formula of ethanol, i.e. it shows all the atoms and the bonds linking them together in the molecule. o o Ethanol ('alcohol') is a colourless toxic liquid that boils at 79 C. Ethanol is used as a solvent, as a bio-fuel (can be mixed with petrol or used directly), and used to make esters' as well as the 'potent' chemical present in alcoholic drinks! o The % alcohol in wines, spirits and beer varies from 1-40%. The fermentation chemistry to produce alcoholic drinks is outlined below. o There are health and social issues about the medical and behavioural aspects of alcohol consumption. Alcohol causes liver damage and addiction problems. Binge drinking and alcohol dependency can cause major social problems both within a family and for the wider community. o Methylated spirit is mainly ethanol but poisonous and nasty tasting chemicals like methanol are added so it is not used as a beverage! Ethanol can be produced by fermentation of sugars. The raw materials are mixed with water and yeast at just above room temperature. The yeast contains enzymes which are biological catalysts. The sugars react to form ethanol and carbon dioxide. The carbon dioxide is allowed to escape and air is prevented from entering the reaction vessel to stop oxidation of ethanol to ethanoic acid ('acetic acid' or vinegar!). When the reaction is over the ethanol is separated from the reaction mixture by fractional distillation to make a petrol additive fuel or whisky! o e.g. glucose == enzyme ==> ethanol + carbon dioxide o C6H12O6(aq) ==> 2C2H5OH(aq) + 2CO2(g) o The progress of the fermentation can be followed by measuring the density of the fermented liquid with a hydrometer. Ethanol/alcohol is less dense than water/sugar so the density changes as the sugar is converted into alcohol. o Ethanol, from a solution made from fermented sugar cane, can be concentrated by fractional distillation. In Brazil it is blended with petrol to give an alternative motor vehicle fuel i.e. an example of a bio-fuel. C2H5OH(l) + 3O2(g) ==> 2CO2(g) + 3H2O(l) + heat energy from the exothermic reaction o The natural fermentation process would have discovered by accident after its products were sampled and so beer has been brewed for thousands of years. Most people in medieval times would have drunk weak beer every day because it was less harmful than polluted water supplies apart from pure natural spring water. Ethanol can also be produced by the reaction of steam and ethene (from oil cracking) in the presence of an acid catalyst (Phosphoric acid). The reversible reaction is carried out at a moderately high temperature (e.g. 300oC) and a high pressure (e.g. 60 atmospheric pressure). The higher temperature and catalyst speed up the reaction and increasing pressure moves the equilibrium to the right (side least gaseous molecules at 300 oC) o ethene + water ==> ethanol o CH2=CH2 + H2O ==> CH3CH2OH (or C2H5OH)
o

o + H2O ===> Advantages and disadvantages of the two methods of making ethanol: o Advantages of fermentation: It uses a cheap and renewable resource like sugar cane (Brazil) and sugar beet. Cheap labour from the local population or migrant workers.

Page 15 of 20

Disadvantages of fermentation: slow reaction and made by an inefficient batch process, poor quality product e.g. low aqueous concentration of ethanol. The resulting solution has 4-10%, rest water and waste products e.g. other organic chemicals formed to and yeast cell residues to remove. The alcohol must also be distilled from the fermentation mixture, also a costly process. Large areas of agricultural land are needed and tend towards monoculture agriculture - in many countries more food should be grown. o Advantages of ethene route: A fast and efficient continuous process in the petrochemical industry which produces a relatively pure product in bulk. Some countries may have local oil supply (e.g. North Sea for UK, Middle East countries). o Disadvantages of ethene route: using a non-renewable finite resource of crude oil. The alcohols form a homologous series with the functional group -OH. It is the presence of this functional group that gives alcohols their characteristic properties. The simplest homologous series of alcohols have the general formula CnH2n+1OH e.g. Ethanol is shown above, but the simplest alcohol with the lowest carbon number of one is methanol (the 1st in the homologous series alcohols is shown below).
o

or or All the alcohols are flammable colourless liquids with a characteristic 'pleasant'? odour. o They all behave chemically in the same way but the boiling point steadily rises with increase in molecule size. The next three are propanol (3rd in series), butanol (4th in series) and pentanol (5th in series), note their names also end in ...ol, which means the molecule is an alcohol.
o o

o o o

propanol butanol pentanol

or

Reactions of alcohols.

Ethanol can be oxidised to form ethanoic acid which is a useful organic chemical. BUT it is this oxidation of ethanol that results in alcoholic drinks turning sour (e.g. cider, wine) when exposed to air. The fruit material already contains the enzymes that catalyse the oxidation of ethanol ('alcohol') in the presence of air. o ethanol + oxygen ==> ethanoic acid + water o CH3CH2OH + O2 ==> CH3COOH + H2O
o o

+ O2 ==> + H2O This oxidation can also be done by heating the ethanol with a mixture of sulphuric acid and potassium dichromate (VI) solution. The mixture turns from orange to green.
Page 16 of 20

When burned, ethanol, like any alcohol, on complete combustion forms carbon dioxide and water Ethanol + oxygen ==> carbon dioxide + water CH3CH2OH(l) + 3O2(g) ==> 2CO2(g) + 3H2O(l)

Ethanol can be dehydrated to ethene by passing the alcohol vapour over heated aluminium oxide catalyst. o ethanol ===> ethene + water o CH3CH2OH ===> CH2=CH2 + H2O

==>

+ H2O

This reaction is potentially an important source of organic chemicals e.g. plastics from a renewable resource since the ethanol can be made by fermentation of carbohydrates etc. Carboxylic acids and esters Carboxylic acids are a group of organic compounds which have weakly acidic properties. They react with bases/alkalis to for salts and release carbon dioxide from carbonates. They react with alcohols (another organic series of compounds) to form organic compounds called esters which are used as solvents and components in perfumes and food flavorings.

Carboxylic acids form another homologous series and have the functional group -COOH. The structures of the first three members are given below: Names end in ...oic acid. o methanoic acid (old name 'formic acid') or or ethanoic acid (old name 'acetic acid', in vinegar)
or or propanoic acid (old name 'propionic acid')

or or ESTERS: Carboxylic acids react with alcohols to form members of another homologous series called esters. Concentrated sulphuric acid acts as a catalyst in this reaction.

+ + H2O sometimes more simply written as CH3COOH + CH3CH2OH CH3COOCH2CH3 + H2O


Page 17 of 20

Condensation polymerisation Involves linking lots of small monomer molecules together by eliminating a small molecule. This is often water from two different monomers, a H from one monomer, and an OH from the other, the 'spare bonds' then link up to form the polymer chain.

Nylon (a polyamide) is formed by condensation polymerisation, the structure of nylon represented below where the rectangles represent the rest of the carbon chains in each unit.

(3 units etc.) This is the same linkage (-CO-NH-) that is found in linked amino acids in naturally occurring macromolecules called proteins, where it is called the 'peptide' linkage.
o Nylon-6,6 Terylene (a polyester) is formed by condensation polymerisation and the structure of Terylene represented as

(3 units etc.) This is the same kind of 'ester linkage' (-COOC-) found in fats which are combination of long chain fatty carboxylic acids and glycerol (alcohol with 3 -OH groups, a 'triol'). Terylene (polyester) and nylon are good for making 'artificial' or 'man-made' fibres used in the clothing and rope industries. o In the manufacturing process the polymer chains are made to line up. o This greatly increases the intermolecular forces between the 'aligned' polymer molecules and strong fibre strands of the plastic can be made. Three problems associated with using and disposing of Polymers or Plastics

1. Polymers or plastics cannot be easily broken down by micro-organisms i.e. most, at the moment, most are NOT biodegradable (non-biodegradable) which leads to waste disposal problems and 'non-rotting' litter around the environment. o Land-fill sites are getting full and recycling isn't as easy as it may seem. o Incineration i.e. using waste plastic as fuel must be very efficient to avoid any other pollution problem. 2. Can we burn waste plastic? o When plastic materials burn they can produce highly toxic gases such as carbon monoxide, hydrogen cyanide and hydrogen chloride (particularly from PVC and other plastics containing chlorine and nitrogen). o The toxic fumes cause deaths in house fires and controversial problems with alleged inefficient waste incinerators as they will definitely cause environmental problems if burned on waste tips! 3. How can we recycle plastics? What ways are used to recycle plastics? o It is difficult to recycle plastics because of separation into the various types of polymer and their different physical properties. BUT this should not prevent us from trying and it would be beneficial to prolong the life of the finite crude oil reserves AND reduce pollution and space in land-fill sites. o There are problems in trying to sort out the different plastics into useful categories, they are not easy separate, and you can't just use any old mixture of polymers.
Page 18 of 20

o o

At the moment, a lot may have to be sorted by hand - lack of automation makes the sorting more costly. However, people are coming up with ideas. A company in Scarborough, England, is collecting waste plastic. This is shredded and compressed into porous pads and used for good 'underground' drainage layers for footpaths, golf greens and sand bunkers etc. and has a good working life because the material isn't biodegradable! Clear soft drink bottles are made from PET (polyethene/polyethylene terephthalate) which can be recycled as fibre-fill for pillows and carpets. This saves 90% of the energy costs compared to the original manufacturing process. Energy costs are a big economic recycling factor; its not just about making naturally occurring resources like oil last longer. However, it takes about 20,000 drinks bottles to make a tonne of recycled PET. New plastics are being developed which are more biodegradable or can be recycled, so will the paper bag and cardboard package make a comeback? (in Ireland you have to bring your own bag or buy one, and not necessarily a plastic one!), this isn't a recycling process BUT it does reduce environmental pollution. In 1988 Australia issued bank notes made from recycled poly(propene). These plastic notes apparently have the advantage of being more difficult to forge and they last longer. Waste poly(propene)/polypropylene can be ground up and recycled to make pipes, compost bins and flower pots Other ideas include making more durable plastic bags that can be used many times for shopping. Ideally some recycled thermoplastics and scrap material from a plastic product manufacturing process, can be heated and remoulded in the same process or another product. It is possible in some cases to break the plastic material down with heat (a sort of 'cracking') into smaller organic hydrocarbon molecules that can act as chemical feedstock like oil, from which you can make other valuable products including plastics. Less green, but useful purpose is to use scrap plastic as a fuel, but complete incineration is not always easy to be efficient. All of these will slow down the rate at which valuable oil-petroleum deposits are depleted - the latter are finite, so we should make the best use of them.

air chemically coal compounds crust distillation evaporating flammable fossil fractional fuels gas greater higher hydrocarbons less mixture molecules organisms physical pressure sedimentary similar temperatures two unchanged viscous (1) Crude oil is extracted from the Earths remains of marine fuels the action of heat and . It was formed from the

which lived millions of years ago. The , oil and natural have formed by

over millions of years, in the absence of


Page 19 of 20

, on material from animals and plants (organic material) which has been covered by layers of (2) Crude oil is a consists of rock. of a very large number of compounds. A mixture or more elements or not

combined together. The chemical properties of each substance in the mixture are . This makes it possible to separate the substances in a mixture by methods including distillation. (3) Most of the compounds in crude oil consist of hydrogen and carbon atoms only and are called made up of . They can be

separated into fractions, each of which contains molecules with a number of carbon atoms, by number of different the oil and allowing it to condense at a . This process is .

(4) The hydrocarbon molecules in crude oil vary in size. The larger the molecules the the number of carbon atoms in a hydrocarbon ... (a) the its boiling point, (b) the it flows and the more the less molecules as volatile it is, (c) the less easily

it is, and (d) the less easily it ignites, meaning it is, and this limits the usefulness of hydrocarbons with large .

Page 20 of 20

Вам также может понравиться