1. What is produced when organic compounds are burned?

Some organic compounds are used as fuels. Other organic compounds, including plastics, are burned as waste. Burning these organic compounds releases gases into the atmosphere. All organic compounds consist partly of carbon atoms and many contain hydrogen and other atoms such as oxygen and nitrogen. Coal, crude oil, natural gas (methane) and wood contain organic compounds o all are used as fuels, either directly like coal or natural gas, o o or indirectly as coke from coal or petrol from crude oil etc., and apart from wood, they are finite (limited reserve) fossil (from decayed organic material) fuels.

any hydrocarbons are fuels i.e. a substance burned to release heat energy. When organic compounds are burned in a plentiful supply of air the carbon is oxidised to carbon dioxide and the hydrogen is oxidised to water. In a limited supply of air incomplete combustion occurs forming carbon mono ide and! or carbon. "arbon mono ide is poisonous because it reduces the capacity of blood to carry o ygen.

Combustion e!uations and tests for combustion products are all on the "il #otes web page, lots of e amples and diagrams too.
#ach fossil fuel has a different cost, efficiency and cleanliness on burning. $enerally speaking in $cleanliness$ the order is methane (natural gas) % al&anes in petrol % hea'y oil and from left to right there is also an increase in C() atom ratio in the molecule so more C"* produced too. Some notes on other fuels (but they are designed for more advanced level courses) and a fossil fuel sur'ey on Oil %roducts &otes page +he combustion of plastics (and other organic compounds) which contain chlorine and nitrogen produce poisonous fumes when burnt e.g. choking hydrogen chloride '"l and to ic hydrogen cyanide '"& respectively. #specially where there is a limited supply of air. (he combustion products of carbon (to ic "O and "O)) and hydrogen (')O) are also formed. )ydrogen gas can be used as fuel. o It burns with a pale blue flame in air reacting with o ygen to be o idised to form water. hydrogen , oxygen **+ water or *)*(g) , "*(g) **+ *)*"(l) It is a non,polluting clean fuel since the only combustion product is water and so its use would not lead to all environmental problems associated with burning fossil fuels.

o o

It would be ideal if it could be manufactured by electrolysis of water e.g. using solar cells. 'ydrogen can be used to power fuel cells on the -# tra #lectrochemistry- page.

*. Why are there families of organic compounds? - 'ariety .

Al&anes and al&enes were introduced on the "il #otes page and gi'e details of (i) al&ane combustion (ii) the reaction of bromine with al&enes and (iii) the basics of al&ene polymerisation.

*a /#+0"12C+/"#
"rganic compounds 345 belong to different families, though all organic compounds are based on carbon C, hydrogen ), and other elements such as oxygen " (e.g. ethanol C)6C)*") and nitrogen # e.g. )*#C)*C"") the simplest amino acid (lots more e amples on this page somewhere.). /ost food is chemically organic in nature, apart from some minerals, and many drugs and plastic materials are composed or organic molecules, conse0uently, organic compounds and organic chemistry1s rather important to us. (he compounds in each family have a similar chemical structure and a similar chemical formula. #ach family of organic compounds forms what is called a homologous series. 2ifferent families arise because carbon atoms readily 3oin together in chains (catenation) and strongly bond with other atoms such as hydrogen, o ygen and nitrogen. (he result is a huge variety of 1 organic compounds1 which can be classified into groups of similar compounds i.e. different homologous series. (he 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. (hese days most organic compounds are synthesised from raw materials, in particular the physical separation and chemical manipulation of the products of crude petroleum oil. 34 &ote4 /norganic compounds are all the other compounds not based on carbon, e cept for carbon mono ide "O and carbon dio ide "O), which are considered to be inorganic. # amples are4 water ')O, ammonia &'5, sodium chloride &a"l.5 6 homologous series is a family of compounds which have a general formula4 and have similar chemical properties because they ha'e the same functional group of atoms (e.g. "*" alkene, ",O' alcohol or ,"OO' carbo ylic acid). o 4 atch the general formula pattern with the al&ane and al&ene examples shown below.

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. (he molecular formula represents a summary of all the atoms in the molecule ( see examples below). (he structural or displayed formula shows the full structure of the molecule with all the individual bonds and atoms shown (though there are different 1sub,styles1 of varying detail, see examples below). 7hen 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. # amples of functional groups include4 o o o

the double carbon,carbon bond "*" in al&enes,

the o ygen,hydrogen atom group of the ,O' in alcohols, and the group of four atoms constituting the ,"OO' group in carboxylic acids.

*b A78A#9: - saturated hydrocarbons

(hese are obtained directly from crude oil by fractional distillation (see oil notes). (he saturated hydrocarbons form an homologous series called al&anes with a general formula Cn)*n,* :aturated means the molecule has no C;C double bonds, only carbon-carbon single bonds, and so has combined with the maximum number of atoms i.e. no atoms can add to it. (he alkanes don1t really have a functional group and have 0uite a limited chemistry B8( they are still a clearly defined homologous series. Al&ane examples4 (he gases (names and molecular formula)4 methane "'9, ethane ")':, propane "5';, butane "9'<=, li0uids4 pentane ">'<), he ane ":'<9 etc. (he first four alkane structures are shown on the oil notes page. #ames end in ...ane Carbon always forms < bonds with other atoms and hydrogen < bond with other atoms e.g. Propane: molecular formula C3H8, structural and displayed formula styles include ...

or

or

/somerism occurs when two or more compounds have the same chemical formula but have different structures. e.g. for the molecular formula C<)1= there are two possibilities , one 1linear1 and one with carbon chain 1branching1, both are shown in three ways ... o butane4

o o

or and its isomer methylpropane4

or

or

or

"an you work out the structures of the 5 isomers of " >'<) ? (you will find enough to work out the answers on the 6dvanced @evel page A78A#9:) /somers show 'ariation in physical properties which depend upon the strength of the intermolecular forces. Intermolecular forces are due to weak electrical attractive forces that e ist between all molecules. (a) Aor a homologous series the strength of intermolecular forces increases as the carbon chain length increases (b) Aor isomers (same " number), the forces decrease as the amount of chain branching increases. (his is because the attractive forces are a function of the potential surface,surface contact i.e. the compactness of the molecules. o (a) as the chain length increases the surface,surface contact must increase per molecule, (b) for isomers, with more branching, the chain length decreases and the molecule is more 1compact1 reducing the surface,surface contact per molecule.

Aor e ample in the series ... o (a) from methane ... ethane ... propane ... petrol ... oils ... grease ... wa es etc. the melting point!boiling point rises and so does the viscosity (stickiness.) as the carbon chain length increases. (his trend also indicated by the change from gases to li0uids to solids. See "il >roducts page for more details

(b) 1linear1 butane has a higher boiling point than 1branched1 methylpropane (diagrams above).

Al&anes and al&enes undergo combustion reactions (see "il >roducts notes for plenty of details). C)7"0"A78A#9: (halogenoal&anes)? Al&anes are usually not 'ery reacti'e unless burned. B8( they will react with reacti'e chemicals li&e chlorine when heated or sub3ected to uv light to form chlorinated hydrocarbons. o 2espite the reactivity of chlorine you still need something e tra to initiate the reaction. 6 substitution reaction occurs and a chloro,alkane is formed e.g. a hydrogen is swapped for a chlorine and the hydrogen combines with a chlorine atom ethane , chlorine **+ chloroethane , hydrogen chloride C*)@ , Cl* **+ C*)ACl , )Cl

o o

o o

o o

+ Cl2 ==>

+ HCl

"hloro,alkanes are useful sol'ents in the laboratory or industry but though their vapours can be harmful.

*c A789#9: - unsaturated hydrocarbons

(hese cannot be obtained directly from crude oil and must be made by crac&ing (see oil notes). (he unsaturated hydrocarbons form an homologous series called al&enes with a general formula Cn)*n 2nsaturated means the molecule has a C;C double bond to which atoms or groups can add. Al&ene examples4 #ames end in ...ene o ethene

C2H4 or

or

propene

C3H6 or

or

or

butene or

+he al&enes are more reacti'e than al&anes because of the presence of the carbon*carbon double bond. (he al&enes 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. 9xamples of addition reactions are4 with hydrogen under pressure and in the presence of a nic&el catalyst to form an alkane

+ H2 ==>
ethene B hydrogen **+ ethane

+ H2 ==>
propene B hydrogen **+ propane

Al&enes 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. o see "il #otes for e!uations for ethene and propene

Begetable 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 nic&el catalyst. (he process is called hydrogenation, o o and the change in an 1unsaturated1 part of an oil molecule is -C);C)- , )* **+ -C)*-C)*-

o o

so producing a 1saturated1 section in the molecule. (he structure of $fatty$ saturated(unsaturated(hydrogenated-fats-oils and uses are described in section >c.

Al&enes can add to themsel'es by addition polymerisation to form 1plastic1 or polymeric materials (see below or oil notes) Al&enes are isomeric with cycloal&anes e.g. the molecular formula ":'<) can represent he ene or cyclohe ane

o o

hexene C)6-C)*-C)*-C)*-C);C)* or cyclohexane and note that .... he ene is an unsaturated hydrocarbon with a double bond, the isomeric cyclohe ane does not have a double bond and is a saturated hydrocarbon, so a simple bromine test could distinguish the two similar colourless li0uids, because only the he ene would decoloriCe the bromine water test reagent.

6. What is ethanol and how can we ma&e it? - the $alcohol$ of the homologous series of alcohols.
7hat we call alcohol in e'eryday life is a substance whose chemical name is ethanol. #thanol is 3ust one member of a family of substances called alcohols which have a "-") functional group in their structure. 9thanol structure

or

or

or

9thanol is used as a sol'ent, as a bio-fuel (can be mi ed with petrol or used directly), and used to make 1ethyl esters1 (see below) as well as the 1potent1 chemical present in alcoholic drinks.

(he D alcohol in wines, spirits and beer varies from <,9=D. (he fermentation chemistry to produce alcoholic drinks is outlined below.

(here are health and social issues about the medical and behavioural aspects of alcohol consumption. 6lcohol causes liver damage and addiction problems. Binge drinking and alcohol dependency can cause ma3or social problems both within a family and for the wider community. ethylated spirit is mainly ethanol but poisonous and nasty tasting chemicals like methanol are added so it is not used as a beverage.

9thanol can be produced by fermentation of sugars. (he raw materials are mi ed with water and yeast at 3ust above room temperature. (he yeast contains enCymes which are biological catalysts. (he sugars react to form ethanol and carbon dio ide. (he carbon dio ide is allowed to escape and air is prevented from entering the reaction vessel to stop o idation of ethanol to ethanoic acid (1acetic acid1 or vinegar.). 7hen the reaction is over the ethanol is separated from the reaction mi ture by fractional distillation to make a petrol additive fuel or whisky. o o o e.g. glucose ** enCyme **+ ethanol , carbon dioxide C@)1*"@(a!) **+ *C*)A")(a!) , *C"*(g) (he progress of the fermentation can be followed by measuring the density of the fermented li0uid with a hydrometer. #thanol!alcohol is less dense than water!sugar so the density changes as the sugar is converted into alcohol. #thanol, from a solution made from fermented sugar cane, can be concentrated by fractional distillation. In BraCil it is blended with petrol to give an alternative motor vehicle fuel i.e. an example of a bio-fuel. C*)A")(l) , 6"*(g) **+ *C"*(g) , 6)*"(l)

9thanol can also be produced by the reaction of steam and ethene (from oil crac&ing) in the presence of a strong acid catalyst (%hosphoric acid). (he reversible reaction is carried out at a moderately high temperature (e.g. 5==o") and a high pressure (e.g. := atmospheric pressure). (he higher temperature and catalyst speed up the reaction and increasing pressure moves the e0uilibrium to the right (side least gaseous molecules at 5==o")

+ H2O ==>

Ad'antages and disad'antages of the two methods of ma&ing ethanol 4

ad'antages of fermentation4 cheap and renewable resource like sugar cane (BraCil), sugar beet disad'antages of fermentation4 slow reaction and made by an inefficient batch process, poor 0uality product e.g. low a0ueous concentration, other organic chemicals formed to and yeast cell residues to remove. @arge areas of agricultural land are needed. ad'antages of ethene route4 fast and efficient continuous process, relatively pure product, country may have local oil supply (e.g. &orth Sea for 8E, /iddle #ast countries) disad'antages of ethene route4 using a non,renewable finite resource (crude oil!cracking)

(he alcohols form a homologous series with the functional group "-"). It is the presence of this functional group that gives alcohols their characteristic properties. (he simplest homologous series of alcohols have the general formula Cn)*n,1") e.g. #thanol is shown above, but the simplest alcohol with the lowest carbon number of one is methanol (the <st in the homologous series alcohols is shown below).

o o

or

or

All the alcohols are flammable colourless li!uids with a characteristic 1pleasant1? odour. +hey all beha'e chemically in the same way but the boiling point steadily rises with increase in molecule siCe.

+he next three are propanol (propan-1-ol, 6rd in series), butanol (butan-1-ol, <th in series) and pentanol (pentan-1-ol, Ath in series), note their the names also end in ...ol, which means the molecule is an alcohol.

o o o

propanol butanol pentanol

or

9:+90:? #thyl ethanoate, an ester, is formed by the reaction of ethanoic acid with ethanol e.g. o ethanoic acid , ethanol ethyl ethanoate , water

o o o

, $eneral word e0uation4 carboxylic acid , alcohol **+ ester , water

, )*"

+he procedure for preparing an ester are illustrated in the diagram below.

o o (his techni0ue is called 1heating under reflux1, and ensures the reaction occurs the fastest at highest possible reaction temperature, the boiling point of the mi ture. 'owever, to prevent vapour loss by boiling!evaporation, the vapourised li0uids are condensed back into the reaction flask. (he diagram shows a bunsen burner being used to supply the heat (1my days1), these days its more likely, and safer, to use an electrical heater that the round bottomed flask fits in snugly.

(he colourless ester li0uid is separated and purified from the reaction mi ture by fractional distillation which is fully e plained on the 9lements, Compounds, ixtures #otes (the e ample described is separating an ethanol!alcohol mi ture, but the same principal applies in separating the ester from the water, unreacted alcohol and acid and the sulphuric acid catalyst. Fou can make butyl ethanoate by the reaction4 ethanoic acid , butan-1-ol **+ butyl ethanoate , water

Its an e!uilibrium, and starting with the pure acid plus pure alcohol, you heat the mi ture in and you get about *(6rds con'ersion4 to the ester, and the preparation reaction is catalysed by a few drops of concentrated sulphuric acid.

4 +his means a theoretical maximum reaction yield of about @DE.

Aor more on D yields and 1atom economy1 see calculations section 1<.

If the ester is warmed with water or any dilute acid (faster), it changes back into the original acid and alcohol. (his reverse reaction is called hydrolysis i.e. ethyl ethanoate , water **+ ethanoic acid , ethanol whereas esterification is ethanoic acid , ethanol **+ ethyl ethanoate , water (more on re'ersible reactions and chemical e!uilibrium)

9sters are usually sweet(pleasant smelling and occur widely-naturally in plants used as fragrances (e.g. perfumes) and food fla'ourings (more details in 2:9: of 9:+90: section) .

Alcohols react with sodium to form hydrogen. o o o normal fiCCing is observed and the salt product is soluble in the alcohol itself. e.g. ethanol B sodium **+ sodium etho ide B hydrogen *C*)A") , *#a **+ *C*)A"-#a, , )*

9thanol can be oxidised to form ethanoic acid which is a useful organic chemical. B8( it is this o idation of ethanol that results in alcoholic drinks turning sour (e.g. cider, wine) when e posed to air. #thanoic acid (old name 1acetic acid1) is the basis of vinegar and is also used in making esters (e.g. pear drop essence, or .

o o

+ O2 ==>

+ H2O

(his oxidation can also be done by heating the ethanol with a mixture of sulphuric acid and potassium dichromate(B/) solution. (he mi ture turns from orange to green. 7hen burned, ethanol, like any alcohol, forms carbon dio ide and water C)6C)*")(l) , *"*(g) **+ *C"*(g) , 6)*"(l)

9thanol can be dehydrated to ethene by passing the alcohol vapour over heated aluminium oxide catalyst.

o o

==>

+ H 2O

(his 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.

Alcohols from propanol upwards, i.e. from carbon number 6 or greater, will form isomers. o Fou will find plenty of e amples on the ad'anced organic chemistry page for alcohols. (he steroid, cholesterol, contains the alcohol group -"). "holesterol is an essential steroid to humans but if too much is produced it can cause heart disease. (he image on the right gives the s&eletal formula structure of cholesterol (this structure representation is usually only dealt with at ad'anced le'el). 6ll the lines in the structure represent bonds between carbon atoms e cept the 1wedge dash1 to the ,O' alcohol group in the bottom left of the molecule. 6lso note the 1alkene1 double bond functional group to the right of the ,O' group. GCholesterol image from #/:+H

<. What other families of organic compounds are there? more 'ariations .
<a. +he acids that we find in fruits and in vinegar belong to a homologous series called carboxylic acids and many fragrances and food additives are esters. (ester preparation and uses of esters). <b. >olymers do not form a homologous series but they are all organic compounds having very long molecules.

<a. CA0F"GH7/C AC/1: and 9:+90:

Carboxylic acids form another homologous series and have the functional group -C""). (he structures of the first three members are given below4 #ames end in ...oic acid. o methanoic acid (old name 1formic acid1)

or

or

ethanoic acid (old name 1acetic acid1, in vinegar)

or

or

propanoic acid (old name 1propionic acid1)

or

or

Binegar contains ethanoic acid (old name 1acetic acid1), see abo'e in section 6 oxidation of the alcohol ethanol. It is used as a preservative and in food flavourings. 9thanoic acid is used in the manufacture of the fibre, acetate rayon. Citrus fruits li&e oranges and lemons and many soft drin&s contain the tri-carboxylic

acid citric acid. and contribute to the 1tarter1 or 1sour1 taste of fruit. (he molecule contains three acidic carbo ylic acid groups ,"OO'. o "itric acid is a natural preservative (#55= on food labels) and is found in the largest 0uantities in lemons, limes and grapefruit. It is an anti,o idant. /etal salts from citric acid, i.e. citrates, are used in dietary supplements to deliver trace metal minerals in a biologically available!absorbable chemical form. "itric acid can be used in baking powder to react with sodium bicarbonate giving the raising action from carbon dio ide gas formation. (he same combination can be used to give the fiCCy drink effect in medicines like ant,acid stomach powders.

Aspirin is a carboxylic acid. 6spirin is a drug used for pain relief and is taken regularly by those at risk from heart attacks (see also @b 1rugs). Ascorbic acid ('itamin C) is another carboxylic acid and is present in fresh fruit and vegetables and is vital for good health 6&2 the body cannot synthesise it, so you must eat fruit and 'egetables regularly. o 6 lack of vitamin " can cause the disease scur'y. (he symptoms of scurvy are skin sores, spongy gums and bleeding from mucous membranes. (his is one e ample of malnutrition diseases caused by a vitamin deficiency in a diet.

Carboxylic acids are wea& acids, typically solutions are around p'5 (yellow,orange,pink with universal indicator).

Gsee theory on 9xtra A!ueous Chemistry pageH

+hey react and are neutralised by ... with e amples ... o metals react to form salts and hydrogen e.g. o ethanoic acid B magnesium **+ magnesium ethanoate B hydrogen *C)6C"") , g **+ (C)6C"")* g , )*

al&ali bases react to form a carbo ylic acid salt and water e.g. ethanoic acid B potassium hydro ide **+ potassium ethanoate B water C)6C"") , 8") **+ C)6C""8 , )*"

insoluble bases dissolve and react to form salt and water e.g. Cinc o ide B ethanoic acid **+ Cinc ethanoate B water In" , *C)6C"") **+ (C)6C"")*In , )*"

carbonate and hydrogencarbonate bases to produce a carbo ylic acid salt, water and carbon dio ide e.g. ethanoic acid B sodium hydrogen carbonate **+ sodium ethanoate B water B carbon dio ide C)6C"") , #a)C"6 **+ C)6C""#a , )*" , C"* OI propanoic acid B sodium carbonate **+ sodium propanoate B water B carbon dio ide *C)6C)*C"") , #a*C"6 **+ *C)6C)*C""#a , )*" , C"*

a!ueous ammonia solution forms ammonium salts e.g. methanoic acid B ammonia **+ ammonium methanoate )C"") , #)6 **+ )C""#)< ethanoic acid B ammonia **+ ammonium ethanoate C)6C"") , #)6 **+ C)6C""#)< Strictly speaking, ammonium hydro ide doesn1t really e ist, but in older te ts you will find these reactions written in this way e.g. propanoic acid B ammonium hydro ide **+ ammonium propanoate B water C)6C)*C"") , #)<") **+ C)6C)*C""#)< , )*"

9:+90:? Carboxylic acids react with alcohols to form members of another homologous

series called esters. "oncentrated sulphuric acid acts as a catalyst in this reaction. See the preparation J formation of ethyl ethanoate above in section 5. above. o Structures of other esters made from ethanoic acid4

methyl ethanoate using methanol, and

propyl alcohol). o

propyl ethanoate from using propan,<,ol (n,

and what would the structure of their original alcohols be and what would the structure of butyl ethanoate be?

9sters occur widely in nature and are usually sweet(pleasant smelling li!uids and widely used as fragrances (e.g. perfumes) and food fla'ourings . &atural substances are used in many cosmetics but many mi tures contain synthetic organic compounds. o # amples of plant ester sources4 o @avender oil essence is distilled from the lavender plant

# amples of fla'ouring esters4 %ear drop sweet essence is an ester.

Aactors affecting perfume design e.g. using esters4 :orry, #"+ finished - wor&ing on this section at the moment. 2esigning a perfume , several issues to address by way of design factors.

<b. >"7H 90: - synthetic macromolecules

Some basic notes on polymers and plastics in the "il >roducts #otes e.g. the formation of poly(ethene), polypropene and poly(chloroethene) %J". Some important structure, strength and <2, )2 52 dimension structural concepts) in the -Chemical Fonding- notes. ost polymers (plastics) are made from al&ene compounds containing the -C;C- bond by addition polymerisation.

(he general reaction is small monomer molecule **+ long polymer molecule as the small molecules link together to form a long chain. >oly(chloroethene) is made from chloroethene (old name 1vinyl chloride), "' )*"'"l but the polymer is generally called polyvinylchloride, >BC. +he general e!uation and the formation of 4poly(ethene) and poly(propene) are shown on the "il notes page. (4old!wrong names4 polythene, polyethylene 6&2 polypropylene). (he formation of >BC is shown below.

>olymers (plastics) consist of a tangled mass of 'ery long molecules in which the atoms are 3oined by strong covalent bonds to form long chains, but there are much weaker intermolecular forces holding the material together. In thermosoftening plastics like poly(ethene), poly(propene) or poly(chloroethene) %J", because the inter,molecular attractive forces between the chains are weak, the plastic softens when heated and hardens again when cooled. It also means the polymer molecules can slide over each other. (his means they can be easily stretched or moulded into any desired shape. o 'owever it is possible to manufacture and process plastics in which the polymer chains are made to line up. (his greatly increases the intermolecular forces between the 1aligned1 polymer molecules and strong fibre strands of the plastic can be made. # amples4 (he addition polymer poly(propene) and the condensation polymers nylon and +erylene

7hen a thermosetting plastic is first heated covalent bonds are formed between ad3acent chains of the polymers. (hese strong covalent cross,linkages give the material a high melting point and greatly increased strength and rigidity. (hey also prevent thermosetting plastics from being softened with heat and therefore from being stretched or re,shaped. 'owever it does make a much stronger material and not as flammable. On heating strongly they do &O( melt, but tend to char, gradually giving off gases.

 elamine (used in furniture) and many glues are e amples of thermosetting polymers. >roblems with using plastics are on the "il >roducts #otes page. Some important structure, strength and <2 to 52 dimension concepts are described in the -Chemical Fonding- notes.

<c. "ther :ynthetic >olymers , macromolecules

Condensation polymerisation involves linking lots of small monomer molecules together by eliminating a small molecule. (his is often water from two different monomers, a ' from one monomer, and an O' from the other, the 1spare bonds1 then link up to form the polymer chain. #ylon (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. (more advanced representations on the "rganic #itrogen Compounds advanced structure page.

etc.)

(5 units (his is the same linkage (,"O,&',) that is found in linked amino acids in naturally occurring macromolecules called proteins, where it is called the 1peptide1 linkage. +erylene (a polyester) is formed by condensation polymerisation and the structure of (erylene represented as

etc.)

(5 units (his is the same kind of 1ester linkage1 (,"OO",) found in fats which are combination of long chain fatty carbo ylic acids and glycerol (alcohol with 5 ,O' groups, a 1triol1). +erylene and nylon are good for ma&ing $artificial$ or $man-made$ fibres used in the clothing and rope industries. In the manufacturing process the polymer chains are made to

line up. (his greatly increases the intermolecular forces between the 1aligned1 polymer molecules and strong fibre strands of the plastic can be made. Some important structure, strength and 11 to 61 dimension concepts are in the -Chemical Fonding- notes.

A. #aturally "ccurring :mall

olecules from plants and animals acromolecules li&e starch and

olecules K;% #atural >olymers ; protein

Carbohydrates, >roteins and Lats are the main nutrient constituents of food. ost naturally occurring molecules are based on the elements carbon, oxygen and hydrogen, together with smaller proportions of nitrogen, phosphorus, sulfur (sulphur) and sometimes metal ions li&e iron (in the haemoglobin molecule) and magnesium (in the chlorophyll molecule).

Aa. Carbohydrates

Carbohydrates are a whole series naturally occurring molecules based on the elements carbon, hydrogen and o ygen. +hey are an important source of chemical energy in our diet. (he smaller 'istorically the name 1carbohydrate1 comes from the fact that all their formulae seemed to be based on " (')O)y (see key above) B8( this is not the way to think of their formula. (hey range from relatively small molecules called monosaccharide (means one basic unit), or disaccharide (two basic units combined) to 'ery large natural polymers or macromolecules called polysaccharides (many units combined). 6 summary of them is shown in the &ey diagram abo'e along with some familiar names from biology.

Mlucose is one of the simpler sugar molecules (a monosaccharide). (he structural formula is shown on the left and you should be able to see that there are 9 bonds to each carbon, ) to each o ygen and 3ust < bond to each hydrogen atom. (he right,hand 1shorthand1 s&eletal formula version uses short straight lines to represent bonds. /ost '1s and their bonds are not shown, and at 6S,6) level it is assumed you can interpret these structures 1back to1 a full structure., but they are handy for describing large 1biochemical1 molecules (see polysaccharide below)

:ucrose is a disaccharide made from combining two monosaccharide molecules, glucose and fructose by the elimination of a water. o On hydrolysis sucrose reforms the glucose and fructose. o *C@)1*"@ K;% C1*)**"1* , )*"

+he formation of complex carbohydrates? o +hese are made of smaller carbon, hydrogen and oxygen based molecules combining together e.g. the polysaccharides starch and cellulose are formed from glucose, molecular formula C@)1*"@.

(heir formation can be described in terms of a large number of sugar units 3oined together by condensation polymerisation o e.g. the 1bo 1 diagram below shows 9 units of a natural carbohydrate polymer being formed &ote4 "ondensation polymerisation means the 3oining together of many small 1monomer1 molecules by eliminating an even smaller molecule between them to form the linkage. e.g. )"-GGGGG-") , )"-GGGGG-"-GGGGG-") , )*" etc.

n C@)1*"@ **+ (CA)1="A)n , n)*" (where n is a very large number to form the natural polymer) (he GGGGG or the Grectangles5 below, represent the rest of the carbon chains in each unit (more detail in the 5rd diagram below). plus many )*"

etc.

(his diagram of starch or cellulose is in 1s&eletal formula1 style and both are polymers of glucose , can you see the connection between each 1unit1 and the structure of glucose itself? (he resulting natural polymer is called a polysaccharide. Acid hydrolysis of complex carbohydrates (e.g.. starch) gi'es simple sugars . o (his can be brought about by e.g. warming starch with hydrochloric acid solution to form glucose. (CA)1="A)n , n)*" ;;% n C@)1*"@ (where n is a very large number)

(he hydrolysis products from polysaccharides can be analysed with paper chromatography.

Ab. >roteins and Amino Acids

and 1#A

Amino acids are carbo ylic acids (like ethanoic acid) but one of the hydrogen atoms of the )nd carbon atom is substituted with an amino group (a nitrogen B two hydrogens gives

,&')). 6nother hydrogen on the same )nd carbon can be substituted with other groups of atoms (I) to give a variety of amino acids. or (he simplest is aminoethanoic acid or 1Mlycine1

and another amino acid called *-aminopropanoic acid or 1Alanine1 All amino acids ha'e the general structure )*#-C)(0)-C"") (see diagram by >b heading). o o 0 can vary, think of it as the 10est of the molecule. I * ' for $lycine, I * "'5 for 6lanine.

6mino acids can polymerise together, by condensation polymerisation, forming proteins or polypeptides. o o (he peptide linkage is formed by elimination of water between two amino acids. '&',"'(I)-C"") , )#),"'(I),"OO' **+ ')&,"'(I)-C"-)#-"'(I),"OO' B )*" etc. so ... n ')&,"'(I),"OO' **+ ,&',"O,"'(I),&',"O,"'(I),&',"O,"'(I),&',"O,"'(I), etc. n units long So proteins are condensation polymers of amino acids.

>roteins ha'e the same (amide) lin&ages as nylon but with different units. >roteins are an important component of tissue structure and enCymes (powerful biological chemical catalysts) are also protein molecules. %roteins tend to adopt a particular three dimensional shape (52) which aids its function. When proteins are heated with a!ueous hydrochloric acid or sodium hydroxide solution they are hydrolysed to amino acids. o see chromatography below, about how amino acids are identified in proteins.

1#A (deo yribonucleic acid) are the molecules that carry the genetic code or molecular 1blueprint1 for all forms of life. Aor e ample it encodes through its base components the e act se0uence of amino acids needed to synthesise a particular protein.

A spot of coo&ing chemistry.

o Lood is coo&ed for se'eral reasons? +he high coo&ing temperature &ills harmful microbes-bacteria, as long as coo&ed for the re!uired time at a high enough temperature.

/t may impro'es the texture. /t may impro'e the fla'our and taste (but remember some foods might taste better raw e.g. lettuce.) /t ma&es it easier for the body to digest the food.

o o /ost of meat from animals consists of protein together with smaller amounts of water and fat. #ggs and fish are also good sources of protein. >rotein molecules ha'e a definite shape (diagram <. above). 1uring the coo&ing of meat irre'ersible chemical changes ta&e place. +he complex and specific structure of protein molecules is partly bro&en down in the cooking process. (he high coo&ing temperature promotes particular chemical reactions to happen. (he structure changes and some of the chemical bonds are bro&en and new molecules can be formed that ha'e a different taste-fla'our and texture giving the food its own characteristic 1cooked1 character. (he breaking down of protein comple protein molecules is called denaturing. 6 similar process happens in the cooking of carbohydrate foods like potatoes which are broken down into far more readily digestible molecules.

o o o

o o

o o ,

Ac. Lats, "ils and

argarine

"ils and Lats are an important way of storing chemical energy in living systems and are also a source of essential long-chain fatty acids.

/ost of them are esters of the tri,alcohol (1triol1) glycerol (systematic name propane, <,),5,triol, but that can wait until 6S,6) level). (he carbo ylic acids which combine with the glycerol are described as 1 long-chain fatty acids1. (he resulting ester is called a 1triester1 or 1triglyceride1 and they are ma3or components in animal fat, vegetable oils, processed fats like margarine etc.. (he 1long,chain fatty acids1 can be saturated, with no "*" double bonds, and so forming saturated oils or fats (<st diagram below of the triglyceride formed from palmitic acid).

(he 1long,chain fatty acids1 can be unsaturated, with one or more C;C double bonds, and so forming unsaturated oils or fats ()nd diagram below of the triglyceride formed from oleic acid).

:ome sub-notes on "il and Lat :tructure? (health issues dealt with further down) o +hey ha'e the same lin&ages as +erylene but with different units . o (hey are not as big as polymer molecules, but a lot bigger than a single petrol or sugar molecule. (here can be 1 to 6 different saturated or unsaturated fatty acid components , so lots of variation possible in structure of the oil or fat. (he diagrams 3ust assume three molecules of the same 1fatty1 acid. onounsaturated fats ha'e one C;C double bond in them, polyunsaturated fats usually ha'e at least three C;C bonds in their molecular structure.

Aor the same molecular siCe in terms of carbon number, unsaturated fats ha'e slightly lower intermolecular forces because the "*" double bond produces a kink in the carbon chain and they can1t pack as closely together as the saturated molecules. (his gives unsaturated fats a lower melting point and so they tend to occur as e.g. vegetable oils rather than saturated low melting solids from meat and dairy products.

'owever, this means these unsaturated oils are not as con'eniently $spreadable$ as 1butter1. (o overcome this problem, 1margarine1 was invented. (he vegetable oils are reacted with hydrogen gas using a nic&el catalyst. (heses are called hydrogenated fats and ha'e higher melting point so that they are a low melting solid at room temperature rather than the sticky vegetable oil you might use is cooking and salad dressings. +his reaction adds hydrogen atoms to the double bonds making a more saturated and more 1spreadable1 higher melting soft solid fat that we call 1margarine1. Saturated means no double bond and unsaturated means double bond in this conte t. (he reaction for any double bond is4 %C);C)K , )* **+ -C)*-C)*-, which is converting an unsaturated part of the molecule to a saturated structure. F2+ it does mean that it is more like animal fat now but various blendes have been developed to suit your dietary needs or desires. argarine and other $spreadable$ fats based on 'egetable oils are 0uite a mi ture of molecules known as an emulsion. 6 typical mi ture might be <9,)<D saturated fats (triglycerides with almost no double bonds in the hydrocarbon chains) <>,5=D monounsaturates in which there is about one double bond per molecule. <9,))D polyunsaturates which have more than one double bond per molecule. In terms of melting points, the order is saturates + monounsaturates + polyunsaturates.

Sodium chloride and water (1salt1 solution1), small amounts of protein and carbohydrate and whey or buttermilk are added to the fat!oil mi ture. (o stop the salt solution separating out from the 1oily1 fats an emulsifier is added, which &eeps the a!ueous salt solution dispersed in the fats or they would separate into two layers and affect the look and taste.

Incidentally the emulsifiers may be mono, or di,glycerides of fatty acids, that is molecules like the vegetable oils but only < or ) fatty acids attached to the glycerol rather than 5, which leaves ) or < ,O' hydro y groups on the glyceride molecule. (hese molecules have the bifunctional structure because through the action of intermolecular forces they bind with both fats (via hydrocarbon chain, 1water hating1 hydrophobic end of molecule) and bind with water too (via hydroxy group "), the 1water loving1 hydrophilic end of molecule) so holding the emulsion or dispersion together. Since fats and oils are important to our diet, there is the ever present danger of over, consumption (speaking as someone who loves chips and spicy crisps.). So there are health and social, as well as 1molecular1 issues to address. o o 7e need oils and fats as sources of important essential fatty acids . 7e need both saturated and unsaturated fats or oils. (he main sources of saturated fats are from meat and dairy products e.g. 1dripping1 and butter. (he main sources of unsaturated fats are plant oils e.g. olive oil.

It is recommended that we do not overdo the fat intake but we do need both saturated and unsaturated fats. 'owever, too much saturated fat raises cholesterol levels and is not too good for the heart.

:"A>
$+raditional$ soap is a product of the hydrolysis of fats. o 1Soapy1 soaps (not modern detergents) are the sodium salts of long chain fatty acids formed by heating fatty oils with sodium or potassium hydro ide to hydrolyse them. o (his reaction breaks the fat molecule down into one glycerol molecule (triol alcohol) and three sodium salts of the long chain carbo ylic fatty acids.

Ad. Chromatography - a method of analysis

)ydrolysis means breaking down a molecule with water to form two or more products. o 'ydrolysis is accelerated if the substance is heated with acid or al&ali solutions. When proteins are heated with a!ueous acid they are hydrolysed to amino acids . Acid hydrolysis of complex carbohydrates (e.g.. starch) gi'es simple sugars .

(1)

(*)

(6)

>aper or +hin layer chromatography is used to separate coloured compounds (illustrated above). < to > represent five pure compounds, : is a mi ture. Ied, brown and blue make up the mi ture because its spots horiContally line up with the three known colours. o (he substances (solutes) to be analysed must dissolve in the sol'ent, which is called the mobile phase because it moves. (he solvent may be water or an organic li0uid like an alcohol (e.g. ethanol) or a hydrocarbon, so,called non,a0ueous solvents. (he paper or thin layer of material on which the separation takes place is called the stationary or immobile phase because it doesn1t move. (he distance a substance moves, compared to the distance the solvent front moves (top of grey area on diagram )) is called the reference or 0f 'alue and has a value of =.= (not moved , no good), to <.= (too soluble , no good either), but 0f ratio 'alues between =.< and =.K can be useful for analysis and identification. 0f ; distance mo'ed by dissol'ed substance (solute) ( distance mo'ed by sol'ent

'owever, amino acids and sugars are colourless, but can still be separated in this way, so read on. +hin layer or paper chromatography can still used to separate and identify the products of hydrolysis of carbohydrates and proteins because you make them coloured by using another chemical reagent. o (he hydrolysis can be done by boiling the carbohydrate or protein with hydrochloric acid. (he hydrolysed mi ture is then 1spotted1 onto the pencil base line of the chromatography paper. Enown sugars or amino acids are also spotted onto the base line too. (he prepared paper is then placed vertically in a suitable solvent, which rises up the paper.

Since the products are colourless, the dried chromatogram is treated with another chemical to produce a coloured compound. &inhydrin produces purple spots with amino acids and resorcinol makes coloured spots with sugars.

Fou can then tell which amino acids made up the protein or the sugars from which the carbohydrate was formed. (he number of different spots tells you how many different amino acids or sugars made up the natural macromolecule. Spots which horiContally match the standard known molecule spots confirm identity. :tarch gives one spot because only glucose is formed on hydrolysis. (CA)1="A)n , n)*" **+ n C@)1*"@ (where n is a very large number)

o o

/ore on thin layer(paper chromatography. &ote that if organic compounds are gases or volatile (easily vapourised) li0uids, they can be analysed using gas-li!uid chromatography (in section :. of the $"S# # tra Industrial "hemistry page).

@. Bitamins, 1rugs-analgesic medicines and Lood Additi'es

@a Bitamins are particular essential molecules with particular roles in li'ing systems which are #"+ proteins, carbohydrates, fats or mineral salts. One of the most important ones in any diet is Bitamin C or Ascorbic Acid. Its structure is related to 1simple1 sugars but humans are one of the few mammals that are unable to synthesise vitamin ". o It is essential for healthy tissue and one of its functions is the removal of dangerously reactive chemical species called free radicals (see further on). Bitamin C is present in fruit and 'egetables but the amount is reduced by prolonged storage and coo&ing.. )>= years ago, as many as )!5 of a ship1s crew died from vitamin " deficiency causing scurvy. In <L9L it was decided to give sailors citrus fruits to recover from scurvy but wasn1t until )== years later that vitamin " was recognised. In contrast to the other water,soluble vitamins, vitamin " has no clear cut role as a catalyst or part of an enCyme. It does, however, have a range of other important functions4 "ollagen formation. Jitamin " in collagen formation which is found wherever tissues re0uire strengthening, especially in tissues with a protective, connective, or structural function. "ollagen is critical to the maintenance of bone and blood vessels and is essential in wound healing. 6ntio idant activity. 6scorbic acid can act as an antio idant by donating electrons and hydrogen ions, and reacting with reactive o ygen species or free radicals. Iron absorption. Jitamin " is important for the effective absorption of iron and reduces iron(III) Ae5B to iron(II) Ae)B. It helps in the synthesis of vital cell compounds. 2uring times of physical and emotional stress, as well as during infection, there is increased production of o ygen radicals. (herefore there is increased reliance on vitamin "1s activity as an antio idant. Jitamin " is vital for the function of the immune system, but the effectiveness of large doses of vitamin " in preventing and alleviating the symptoms of the common cold is still a matter of debate.

(wo of the earliest signs of deficiency (prevention of collagen synthesis) relate to its roles in maintaining the integrity of blood vessels. (he gums around the teeth bleed more easily, and the capillaries under the skin break spontaneously producing tiny haemorrhages. If you are short of vitamin " for say )= days, scurvy can develop

and is characterised by further haemorrhaging, muscles depletion, rough,brown,dry, scaly skin, deep bruising. 7ounds fail to heal properly and bone fails to rebuild properly too and you are further likely to suffer from anaemia and infections. o :" 9A+ yer fruit and 'eg $guys$ (as well as a few crisps.) A#1 &eep yer health and still pass those dreaded exams....

@b 1rugs e.g. in analgesic medicines can be defined as an e ternally administered

substances which modifies or affects chemical reactions in the body, usually for the bodies greater well,being. %oisons can be defined in the same way, but hopefully not intentionally and have undesired effects. A $drug$ is a specific molecule with a particular pharmacological or physiological action on an organism(animals chemistry and a medicine is the complete formulation of the means of administering the drug to a patient i.e. the method of deli'ery. o Analgesics are drugs used to reduce pain and are a type of anti,inflammatory agent. o +he molecular structure of three well &nown analgesics are shown in the diagram below. 6ll are used for 1headache1 treatment, and hopefully using this website and others will help minimise their use.

+he central hexagonal ring of @ carbon atoms is called a $benCene$ or $aromatic$ ring. +he <th outer electron of carbon (group <) is delocalised, so the expected <th bond per C atom forms part of a $communal$ system (more on this at ad'anced le'el, but the co'alence rule of < for carbon is not bro&en., you ha'e seen this situation before, chec& out graphite. Hou can show a benCene ring as a simple hexagon with a circle in it)

from

+ NaOH ==>

+ H2O

(he modern pharmaceutical industry has its origins in herbal and other traditional medicine. e.g. 6n e tract of willow herb e tract can be made from the leaves, bark and seeds of the willow tree. 6mongst other ailments it was given to help curing feverish headaches and relief of pain in childbirth. 7hen ingested the body hydrolyses and o idises the naturally occurring 1precursor1 molecule to form salicylic acid4 which is the 1active1 molecule in the body. in the <;K=1s the $erman chemist 'offmann e perimented with various chemical modifications of salicylic acid and found the best and chemically stable form was 1aspirin1 (shown below). 'e tried the 'ariations on his own father. who survived to provide valuable 1clinical trials1 , hardly acceptable these days. 4 $"il of winter green$ from certain plants is the methyl ester of salicylic acid and has similar 1medicinal effects1. 6spirin (and the others shown) are not very soluble in water. :oluble aspirin is made by neutralising the carbo ylic acid with the alkali sodium hydro ide to make the much more soluble sodium salt of the acid. (he reaction, using skeletal formula, is shown in the diagram below the three analgesic drug structures. #ew drugs and testing them4 It costs a lot of money to develop a new medicine so the price charged by the pharmaceutical company must cover the cost of research, production and marketing. %atents are taken out to protect the company1s commercial interests in the new medicine. (here can be a range of formulations of a particular medicine when you buy it over the counter e.g. tablet of <==D aspirin, soluble aspirin (via &a B salt of the acid from neutralisation) and aspirin might form part of a mi ture including substances that have other beneficial effects. (he main point here is that aspirin, like many drugs, can have multi, functional effects, hopefully all beneficial. F2+ this, sadly, is not always the case, because with any new drug there is always the danger of un&nown side-effects. (herefore there is a tremendous responsibility on pharmaceutical companies to ensure the development of safe and effective drugs. 7ots of time and money spent on disco'ering and de'eloping new drugs and there are lots of factors to consider4 o Arom the discovery of a potentially useful molecule, sometimes called the 1lead molecule1, which can be from natural source or produced in some other pro3ect etc.

o o

Is there room in the commercial market place for it? 1o research to see if its safe, otherwise further development is a waste of time and money or if not safe, can its molecular structure be modified? Can the modification be safe? and more effecti'e? In what form, can it be!needs to be, administered in? for clinical trials. Carefully clinical trials in 'arious phases, noting particularly if any side-effects which may be harmful. 1o you test new drugs on animals? - an emoti'e issue, can nonanimal testing always allow the safe de'elopment of new products? 1o you test new drugs on patients in a life threatening situation, gi'e them a last chance at some ris&? >atient health and safety issues 'ersus 'ery big drug company commercial interests are a matter of public concern. 6ny new drug must finally pass all the tests before legally licensed for patient consumption ... sadly, the $drug companies$ and the $powers to be$ do not always get it right (e.g. phthalidomide), but do not the benefits outweigh the occasional tragedy which we should do our best to a'oid?

o o

@c Lood additi'es are chemicals added to food to gi'e particular effects e.g.

colourings, fla'ourings preser'ation and sweetening . (he addition of some of them is controversial i.e. health concerns like nitrates are carcinogenic, food colourings causing behavioural problems, but proving these 1cause and effect1 claims are not easy. o Colourings to make food more attractive, to fit in with the consumers perception of what it should look like. Fou can use paper(thin layer chromatography to investigate the composition of food colourings.

Lla'ourings to make food more 1tasty1, less 1bland1, and to fit in with the consumers perception of what it should taste like. >reser'ati'es are to increase the 1shelf,life1 of packaged food, decrease risk of food poisoning by inhibiting bacteria!microbe growth

Antioxidants prevent o idation of oils!fats by o ygen in the air. O ygen from air reacts with food and the o idation causes deterioration in 0uality and taste. :weeteners counter bitterness or pander to our taste. 9mulsifiers and stabilisers help keep a mi ture of ingredients together i.e. prevent oily!fatty components separate out fro water!a0ueous based components. # amples are margarine and mayonnaise. See 9xtra A!ueous Chemistry #otes on colloids in section <b for a more detailed description of emulsions in general, and on this page itself emulsifiers in margarine (section Ac).

o o

Lood pac&aging has become more and more important as consumers demand a greater 'ariety of products which are increasingly sold through super-mar&ets. o o o If the packaging is air,tight no harmful bacteria can get in. # cess water can be removed which inhibits the growth of mould or bacteria. 6ir!o ygen can be removed or replaced with an unreactive gas like nitrogen!carbon dio ide, to stop o idation of the food 6&2 removes the need to use antio idant chemicals.

9-numbers are reference numbers used by the 9uropean 2nion to help identification of food additi'es. o 6ll food additives allowed and used in the #uropean 8nion are identified by an #, number. (he -#- stands for -#urope- or -#uropean 8nion-. &ormally each food additive is assigned a uni0ue number, though occasionally, related additives are given an e tension (e.g. a,b,i or ii etc.) to another #,number. (he "ommission of the #uropean 8nion assigns 9-numbers after the additi'e is cleared by the :cientific Committee on Lood (:CL), the body responsible for the safety e'aluation of food additi'es in the #uropean 8nion. 6 summary is given below.

o o

91==-1NN, food colours

9*==-*NN, preser'ati'es 96==-6NN, anti-oxidants, phosphates, and complexing agents 9<==-<NN, thic&eners, gelling agents, phosphates, emulsifiers 9A==-ANN, salts and related compounds 9@==-@NN, fla'ourings 9D==-ONN, not used for food additi'es (used for animal feed additi'es.) 9N==-NNN, surface coating agents, gases, sweeteners 91===-16NN, miscellaneous additi'es 91<==-1<NN, starch deri'ati'es

#,numbers are only used for substances added directly to food products, so contaminants, enCymes and processing aids, which may be classified as additives in the 8S6, are not included in the #,number system. (here is an #8 directive on food labelling which re0uires food additives to be listed in the product ingredients whenever they are added for technological purposes. o (his includes colouring, sweetening and flavour enhancement as well as for preservation, thickening, emulsifying and the like. Ingredients must be listed in descending order of weight, which means that are generally found close to the end of the list of ingredients. 'owever, substances used in the protection of plants and plant products, flavourings and substances added as nutrients (e.g., minerals, trace elements or vitamins) do not need to be included in the ingredient list. Because of this, some substances that are regulated as food additives in other countries may be e empt from the food additive definition in the #8.

D. CLC$s, "Cone and Lree 0adicals

CLC$s - what is so good about them? (before we get into the problems they cause.) o 6 CLC is a covalently bonded relatively small molecule of carbon, chlorine and fluorine atoms. o :orry, #"+ finished - wor&ing on this section at the moment.

/f enough energy is supplied by heat or by visible!uv electromagnetic radiation, or the is weak enough, a co'alent bond can brea& in two ways. (his illustrated with the molecule chloromethane C)6Cl. +he bond brea&s une'enly where the electron bond pair can stick with one fragment and a positive and negative ion form. o e.g. C)6Cl **+ C)6, , Cl- (at 6S,6) level this is called heterolytic bond fission)

shows what happens to the molecule, or

+he bond brea&s e'enly, where the bonding pair of electrons are e0ually divided between two highly reactive fragments called free radicals. o Aree radicals are characterised by having an unpaired electron not involved in a chemical bond. (he . means the 1lone1 electron on the free radical, which is not part of a bond anymore, and wants to pair up with another electron to form a stable bond , that1s why free radicals are so reactive. e.g. C)6Cl **+ C)6. , .Cl fission) (at 6S,6) level this is called homolytic bond

shows what happens to the molecule

In the stratosphere small amounts of unstable oCone "6 (trioxygen) are formed by free radical reactions. (he chemistry of free radicals is important in the current environmental issue of oCone layer depletion.

Chlorofluorocarbons (CLC1s for shorthand) are organic molecules containing carbon, fluorine and chlorine e.g. dichlorodifluoromethane has the formula ""l)A) (shown in right diagram). (hey are very useful low boiling organic li0uids or gases, until recently, e tensively used in refrigerators and aerosol sprays e.g. repellents. (hey are relati'ely unreacti'e, non-toxic and ha'e low flammability , so in many ways they are 1ideal1 for the 3ob they do.

'owever it is their chemical stability in the environment that eventually causes the oCone problem but first we need to look at how oCone is formed and destroyed in a 1natural cycle1. (his presumably has been in balance for millions of years and e plains the uv oCone protection in the upper atmosphere. "Cone is formed in the stratosphere by free radical reactions . 1ordinary1 stable oxygen "* (dioxygen) is split (dissociates) into two by high energy ultra'iolet radiation (u' photon energy $wa'e pac&ets) into two o ygen atoms (which are themselves radicals) and then a 1free1 o ygen atom combines with an o ygen molecule to form oCone. "* , u' **+ *". then ". , "* **+ "6

(he oCone is a highly reactive and unstable molecule and decomposes into dio ygen when hit by other uv light photons. (he o ygen atom radical can do several things including ... "6 , u' **+ "* , ".

(his last reaction is the main u' screening effect of the upper atmosphere and the oCone absorbs a lot of the harmful incoming uv radiation from the Sun. /f the oCone le'els are reduced more harmful u' radiation reaches the 9arth$s surface and can lead to medical problems such as increased ris& of sunburn and s&in cancer and it also accelerates s&in aging processes. +here is strong e'idence to show there are $holes$ in the oCone layer with potentially harmful effects, so bac& to the CLC problem for some explanations and solutions.

(he chemically 'ery stable CLCs diffuse up into the stratosphere and decompose when hit by ultraviolet light (uv) to produce free radicals, including free chlorine atoms, which themselves are highly reactive free radicals. e.g. CCl*CL* **+ CClL*. , Cl. (note the ","l bond is weaker than the ",A bond)

(he formation of chlorine atom radicals is the root of the problem because they readily react with oCone and change it back to much more stable ordinary o ygen. "6 , Cl. **+ "* , Cl". bye bye oCone. and no uv removed in the process.

and then4 Cl" , " **+ Cl , "* , which means the 1destructive1 "l is still around. (he two reactions above involving chlorine atoms are known as a catalytic cycle because the chlorine atoms from "A"1s etc. act as a catalyst in the destruction of oCone.

(herefore many countries are banning the use of CLCs, but not all despite the fact that scientists predict it will take many years for the depleted oCone layer to return to its 1original1 O5 concentration and alternatives to "A"1s are already being marketed.

For a coooool site :

http://nutsandbolts.washcoll.edu/style.html