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Organic chemistry is defined as the chemistry of
compounds that consist primarily of carbon and hydrogen.
Atoms of nitrogen, oxygen and the halogens are also sometimes part of organic molecules.
The chemistry of carbon
Carbon atoms have the ability to form strong covalent bonds with other carbon atoms and also with atoms of other non-metals. Carbon atoms bond with other carbon atoms to form chains or ring structures. These chains can be
thousands of atoms long.
Catenation – the ability of carbon atoms to bond with themselves to form chain or ring structures.
Diamond Graphite . Graphite and diamond are two examples.Important features of carbon Allotropes of carbon exist. Allotropes are different crystalline structures of the same element.
This means it can form 4 bonds and has 4 valence electrons (4 electrons in the outermost energy level). . Carbon has a valency of 4. Carbon will form a maximum of FOUR bonds with other elements.
A carbon atom in the ground state 2p 2s 1s Electron configuration: 1s² 2s²2p² .
valence electrons are unpaired i.e. . the 2s electron moves to higher 2p orbital.A carbon atom in the “excited” state 2p 2s 1s Electron configuration: C 1s² 2s¹2p³ Couper Structure In the excited state.
H H H H C H H C H H Alkanes H C H Saturated hydrocarbons – hydrocarbons which have all four bonds to the carbon atoms in its structure singularly occupied.The hydrocarbons Hydrocarbons – organic molecules that are made up of carbon and hydrogen atoms only. .
Alkenes H H H C C H Alkynes H C C H .The Hydrocarbons Unsaturated hydrocarbons – organic molecules which have multiple bonds (double or triple) to the carbon atoms within its structure.
.Homologous series Homologous series – a family of organic molecules which are identified by the same functional group and obey the same general formula.
Functional group s of hydrocarbons: Alkanes C C Alkenes C C Alkynes C C . atom or group of atoms in the organic molecule which identifies to which homologous series that molecule belongs and is responsible for the chemical properties of that molecule.Functional group Functional group – a bond.
No of C atoms 1 2 3 4 5 6 7 8 Prefix Meth eth prop but pent hex hept oct - . Alkynes (triple bond) end in –yne. The functional group determines the suffix: Alkanes (single bonds) end in -ane. This determines the prefix of the name. Alkenes (double bond) end in -ene.Naming the hydrocarbons Number the longest continuous chain of carbon atoms from the end nearest the functional group.
Types of formulae Structural formula – the structure of an organic molecule showing all the bonds to all the atoms in the molecule. H H 2 H 3 H 4 H H 2 H 3 H 4 H 1 C H C H C H C H H H 1 C H C C C H H Butane But-2-ene .
Types of formulae Semi (condensed) structural formula – the structure of an organic molecule that only shows the most important bonds in the molecule. CH CH CH CH 3 CH CH CH CH 3 3 2 2 3 Butane CH 3 But-2-ene C C CH 3 But-2-yne .
2 .Types of formulae Molecular formula – only indicates the number and types of atoms present in the organic compound. Alkenes Alkynes CnH2n+2 CnH2n CnH2n . C3H8 General formula: Alkanes C5H10 C3H4 Draw the structural formulae for these molecules and name them.
They are hydrocarbons with single bonds between the carbon atoms. . Methane to butane are gases followed by liquids. As the size of the molecule increases. The larger molecules (more than 12 carbon atoms) are solids at room temperature. They are saturated. This makes the alkanes quite unreactive.Alkanes Alkanes are non-polar molecules containing only carbon and hydrogen atoms. the strength of the van der Waal’s forces increases hence boiling points increase.
methane ethane propane CH4 C2 H6 C3H8 .Name these alkanes and write down the molecular formula for each molecule.
Complete Exercise 1 .
Alkenes The alkenes contain at least one double bond between two carbon atoms. This makes them unsaturated hydrocarbons. H C H H C H The simplest alkene is ethene (ethylene). . Ethene is an important commercial organic chemical and is used to make the plastic polythene (polyethylene).
1 .ene .1 2 3 4 H2C = CH – CH2 – CH3 But .
The simplest alkyne is ethyne (acetylene). . (3 000 0 C). This makes them unsaturated hydrocarbons. It is used in the oxyacetylene torch to cut metals.Alkynes The alkynes contain at least one triple bond between two carbon atoms. The combustion of ethyne and oxygen releases a massive amount of heat.
HC C – CH2 – CH3 But-1-yne 1 2 3 4 .
Branched organic molecules Alkyl substituent – a carbon based “side chain” which is attached to the longest continuous carbon chain in an organic molecule. Alkyl group structure CH3 CH3-CH2CH3-CH2-CH2- Alkyl name methyl ethyl propyl .
Identify the functional group of the molecule – this determines the ending of the name.Rules for naming organic compounds (IUPAC rules) 1. Br H C H Cl C H H C CH C CH CH 2 3 3 CH 3 Alkene .
Find the longest continuous carbon chain that contains the functional group.2. Br H C H Cl C H H C CH C CH CH 3 CH 2 3 3 6 carbon atoms = hexene. . and allocate its prefix according to the number of carbon atoms in the chain (see table for prefixes).
.3. Br 1 H C H Cl H C H 3 2 3 4 C C C CH 3 5 H CH 2 3 6 CH hex -2-ene. Number them so that the functional group is on the carbon of lowest possible number. Double and triple bonds take preference over side chains. Number the carbon atoms in the chain.
Alkyl groups must be named in alphabetical order.Name the alkyl group according to the number of carbon atoms it has and give it a number according to the carbon atom it is attached to.4-di-methyl-hex-2-ene .4. Br 1 H C H Cl H C H 3 2 3 4 C C C CH 3 5 H CH 2 3 6 CH 4.
bromo -. Br 1 H C H Cl H C H 3 2 3 4 C C C CH 3 5 H CH 2 3 6 CH 1-bromo-2-chloro-4. it is treated as an alkyl group.5. and iodo – are used. They must be named in alphabetical order. The prefixes: fluoro-. chloro-.If a halogen atom is attached to the carbon chain.4-di-methyl-hex-2-ene .
tri and tetra to indicate this. use the Greek prefixes di.6.1.2-tri-chloro-pent-2-ene .If there is more than one alkyl group of the same kind. Br 1 C Cl Cl 2 C H 3 4 C C Br H Cl 5 CH 3 1.3-di-bromo-1.
Branched organic molecules 1 2 3 4 CH3 – CH – CH2 – CH3 CH3 2–methyl-butane .
3–di-methyl-butane .Branched organic molecules 1 2 3 4 CH3 – CH – CH – CH3 CH3 CH3 2.
Branched organic molecules 1 2 3 CH3 4 5 CH3 CH2 C CH2 CH3 CH2 CH3 3-ethyl-3-methyl-pentane .
Branched organic molecules 1 2 3 4 H2C = CH – CH – CH3 CH3 3–methyl-but-1 -ene .
3–di-methyl-but-1-ene .Branched organic molecules 1 2 CH3 3 4 H2C = CH – C – CH3 CH3 3.
Branched organic molecules HC C – CH – CH3 CH3 3-methyl-but-1-yne 1 2 3 4 .
4-tri-chloro-pentane .5-di-methyl-hex-2-ene (c) 4-bromo-4-chloro-3-ethyl-pent-1-yne (d) 2-bromo-3.3.3-di-bromo-butane (b) 4.Exercise 2 Draw the semi structural formula for each of the following: (a) 2.
Dienes These alkene molecules contain two double bonds situated throughout the longest continuous carbon chain. Examples (a) 1 2 3 4 5 H2C = C – CH = CH – CH3 CH3 2–methyl–penta–1.3-diene .
2-diene .4-diene (c) 1 2 3 4 H2C = C = C – CH3 CH3 3–methyl–buta–1.1 2 3 4 5 (b) H2C = C – CH2 CH = CH CH3 6 CH3 2–methyl–hexa–1.
4-diyne .Diynes These alkyne molecules contain two triple bonds situated throughout the longest continuous carbon chain. Example 1 2 3 4 5 HC C – CH – C CH3 CH 3–methyl–penta–1.
. Both are structural formulae with molecular formulae CH 3 C6H14 2 CH3 C CH 3 2 CH 3 CH3 CH CH 3 CH CH 2 CH 3 CH 2. Isomer s– organic molecules which has the same molecular formula but different structural formulae.2-di-methyl-butane 2-methyl-pentane These two molecules are said to be ISOMERS.Isomerism Examine the two structural formulae shown below.
Draw the isomers of C5H12 .
1-tri-chloro-ethane (c) 2-bromo-2-chloro-1. Br.methyl-butane . I Exercise 3: Draw the structural formula for: (a) chloromethane (b) 1.1.Alkyl halides (Haloalkanes) Functional group: C X where X = F. Cl.1-trifluoro-ethane (d) 3-bromo-2-chloro-2.1.
Complete Exercise 4 .
aftershaves and any other household products. perfumes. Functional group: C OH Hydroxyl group .Alcohols Ethanol is used widely as a solvent in paints. glues. The strong hydrogen bonds in alcohols result in alcohols having higher melting and boiling points than hydrocarbons of similar size.
Alcohols Alcohol molecules have a non-polar hydrocarbon end and a polar –OH section. Non polar end Polar end Alcohols are solvents for polar and non-polar solutes. .
(OH) ethanol propan-1-ol 2-methyl-propan-1-ol .Alcohols Alcohols are named using the ending –ol. Number the longest chain beginning at the end nearest the hydroxyl group.
Alcohols Propan-2-ol Butan-2-ol Pentan-3-ol .
.2.Alcohols 2-methyl-propan-2-ol 2-methyl-butan-2-ol Propan – 1.3.triol Glycerine/Glycerol CH2 – CH – CH2 OH OH OH .
.Alcohols Alcohols are oxidized to carboxylic acids when treated with strong oxidizing agents.
This acid can be found in stinging nettles and ants. They are relatively weak acids.Carboxylic acids The first member of the acid series is methanoic acid (CHOOH). . O C H OH O Functional group: Carboxyl group C OH The names end in –oic acid.
O CH3 C OH .Carboxylic acids Ethanoic acid is the sour component of vinegar.
Carboxylic acids Butanoic acid gives the unpleasant smell to rancid butter. O CH3 CH2 CH2 C OH .
3-di-methyl-butanoic acid 4 3 Nomenclature Number the longest carbon chain beginning at the carboxyl group.Carboxylic acids CH3 2 1 CH3 – C – CH2 – C . (COOH) .OH O CH3 3.
Esters are used as food flavourings and in perfumes and used as solvents and adhesives.Esters Esters are the compounds which are largely responsible for the flavours and scents of fruits and flowers. O Functional group: C O C .
Esters An ester is the product of an acid catalysed condensation reaction between an alcohol and a carboxylic acid.C .O .OATE methyl ethanoate Methanol Ethanoic acid .CH Acid Nomenclature The prefix in the name of the ester is derived from the ALCOHOL and the suffix 3 from the name of the ACID. O CH3 . Alcohol The name ends in .
Ester formation (esterification) Acts as a catalyst and dehydrating agent O CH3 – CH2 – CH2 – C butanoic acid H SO (Concentrated) .O Oxygen link (‘bridge’) CH2 H SO CH2 CH3 + + + H2O (Concentrated) butanoic acid carboxylic acid + + propan-1-ol alcohol propyl butanoate ester water water .OH + H O CH2 CH2 CH3 propan-1-ol O CH3 – CH2 – CH2 – C .
Use the oxygen atom as a divider when naming the molecule.ethanoic + ethanol acid ethyl ethanoate + water NB. .
O CH2 CH2 CH3 CH3 REACTANTS butan-1-ol + propanoic acid butyl propanoate O CH3 – O .C CH2 CH2 CH3 CH3 methanol + pentanoic acid methyl pentanoate .Name the following O CH3 – CH2 – C .
Draw the products H H OH + O C OH H C H C H H methanol H SO (Concentrated) ethanoic acid H O H H C O C C H + H2O H H methyl ethanoate .
Draw the semi-structural formula for each of the following esters: (a) pentyl ethanoate (b) ethyl propanoate (c) propyl butanoate .
Complete Exercise 5 .
O H C H Nomenclature Aldehydes are named by attaching the suffix ‘-al’. .Aldehydes O Functional group: C H carbonyl group The simplest aldehyde is methanal (Formaldehyde). The longest chain is numbered beginning at the end nearest to the carbonyl group. the C=O on an outer carbon is polar. In aldehydes.
CH3 CH .CH3 H -C=O Propanal 5.Aldehydes 1. CH3 H -C=O Ethanal 3.CH3 H-C=O 3–methyl butanal H -C=O CH3 2. CH2 .CH3 4.4-di-methyl hexanal .CH .CH .C = O Methanal 2. H H.CH2 . CH3 CH2 .CH2 .
. The simplest ketone is propanone (acetone).Ketones Functional group: O C carbonyl group In a ketone. the C=O (carbonyl group) on an inner carbon is polar. the carbon atom in the carbonyl group is bonded to a carbon on both sides. O CH3 C CH3 In ketones.
The longest chain is numbered beginning at the end nearest to the carbonyl group. .Ketones Nomenclature Ketones ( R – CO – R ) are named by attaching the suffix ‘ – one’. The C in the carbonyl group has the lowest number.
CH3 CH CH3 2–methyl hexan-3-one O C .C . O CH2 CH3 4.Ketones 1.CH2 hexan-3-one 2.C .CH2 CH2 CH3 2.CH3 propanone 3. O CH3 .CH2 CH3 CH3 CH CH3 CH3 CH2 . CH3 O CH .C .5-di-methyl-hexan-3-one .
Higher melting and boiling points indicate stronger intermolecular forces within the substance. The strength of the intermolecular forces increases with increasing size of the molecule. liquid or gas phase.Intermolecular forces Intermolecular forces exist between molecules in the solid. . The strength of these forces decreases from solids to liquids to gases.
They are non-directional and act over distances which are large in comparison to the size of the molecule. .Van der Waals forces These are weak forces between particles carrying small positive and negative charges.
Van der Waals forces 1. Van der Waals force Aldehydes and ketones form polar molecules . Dipole-dipole: Attraction between the end of one polar molecule and the end of another.
Van der Waals force These are very weak forces but they increase in strength as the length of the chain increases because they act over a larger surface area. Hydrocarbons and some alkyl halides form non-polar molecules. Temporary dipoles: Van der Waals force Non-polar molecules can form induced (temporary) dipoles when the nucleus of one molecule attracts the electron cloud of another. .2.
d. Hydrogen bonds are stronger than v. O. Hydrogen bond force end of The H end of one molecule attracts the another molecule. Waals forces and act over shorter distances. or F.Hydrogen bonds These intermolecular forces occur between molecules that contain hydrogen bonded to a small highly electronegative atom such as N. .
Hydrogen bonds Alcohols and carboxylic acids can form hydrogen bonds between the molecules. .
forces the greater the energy required.M. To move the molecules apart requires energy.Physical properties Molecules in solids and liquids are held together by intermolecular forces. . the stronger the I.
p and b.p than those with shorter chains.p than those with v. forces increase.d Waals forces.Trends in physical properties Boiling and melting points increase as the strength of the I.M. Molecules which form hydrogen bonds will have higher m. . Molecules with longer chains will have higher m.p and b.
M.Trends in physical properties Vapour pressure is the pressure which the vapour above a liquid exerts on the surface of the liquid. forces will vapourize easily. A high vapour pressure indicates weak I. Alkyl halides vapourize readily so they are used as propellants in aerosol sprays.M. . Substances with weak I. forces.
forces become stronger and liquids become more viscous.M. As the length of the carbon chain increases. .Trends in physical properties Viscosity. A liquid with low viscosity flows easily. Liquids in which the molecules can form hydrogen bonds will have a higher viscosity. This is an indication of how “runny” a liquid is. the I.
.M.Solvent properties For the molecules of one substance to mix with molecules of another. forces between the molecules must be of the same kind and strength. We say a solid dissolves in a liquid or that two liquids are miscible. the I. Alkyl halides form non-polar molecules and this makes them important solvents for fats and oils which also have non-polar molecules.
Simple alcohols mix readily with water because of their ability to form hydrogen bonds.Solvent properties The hydrocarbons form non-polar molecules and therefore they do not dissolve in water which is held together by hydrogen bonds. .
The reaction is exothermic and a great deal of energy is released. Propane burns as follows: C3H8 + 5O2 → 3CO2 + 4H2O + energy . Alkanes Propane is the gas used in bunsen burners in the laboratory. alkenes and alkynes burn in oxygen and form carbon dioxide and water.Combustion reactions Alkanes.
Combustion reactions If propane burns in limited oxygen then carbon (black) is produced: C3H8 + 2O2 → 3C + 4H2O .
C2H4 + 3O2 → 2CO2 + 2H2O + energy .Combustion reactions Alkenes Ethene burns with a blue flame.
along with oxygen. which is used to cut metals.Combustion reactions Alkynes Ethyne is used. 2C2H2 + 5O2 → 4CO2 + 2H2O + energy . in an oxy-acetylene torch.
Ethanol C2H5 OH + 3O2 → 2CO2 + 3H2O + energy .Combustion reactions Alcohols burn in oxygen to form carbon dioxide and water.
Addition reactions take place when a double or triple
bond is broken and new molecular fragments are added to both ends of the bond with nothing being taken away.
If we break the double bond in ethene, each carbon
will have one electron to bond to a new atom.
H H C H C H H H C H C H
We can then add the following:
H H C H C H
A halogen Cl2
H H C H C H
H H C H C H
We can then add the following: A hydrogen halide HCl
Addition reactions Hydrogenation CH2 = CH2 + H2 → CH3 – CH3 ethene ethane Halogenation (chlorination) CH2 = CH2 + Cl2 → CH2Cl– CH2Cl alkene alkyl halide Hydrohalogenation CH2 = CH2 + HCl → CH3– CH2Cl alkene alkyl halide .
OH alkene alcohol .Addition reaction Hydration (addition of water) CH2 = CH2 + H2O → CH3 – CH2.
Test for a double bond To test for a double bond. CH2 = CH2 + Br2 → red-brown CH2Br– CH2Br colourless . react the compound with bromine. due to the addition reaction that takes place. The red-brown colour of the bromine rapidly disappears if a double bond is present.
This is the exact opposite of addition.CH3 → CH2 = CH2 + H2 Eliminating a halogen CH2Cl – CH2Cl → CH2 = CH2 + Cl2 .Elimination reactions Elimination reactions take place when atoms or molecular fragments are removed from adjacent atoms in a molecule leaving a double bond with nothing being added. Eliminating hydrogen CH3 .
Elimination reactions Eliminating hydrogen halide CH3 – CH2Cl → CH2 = CH2 + HCl Eliminating water CH3 – CH2OH → CH2 = CH2 + H2O .
The chlorine uses the sunlight to separate into chlorine atoms. H H H Cl – Cl + energy → 2Cl + H C H H–Cl + Cl C H H One chlorine atom bonds with a hydrogen atom and the other chlorine atom takes its place. Substitution reactions take place when one atom is Substitution reactions replaced by another. Example 1: (Alkane becomes alkyl halide) Halogens such as chlorine will substitute into an alkane molecule in the presence of sunlight. .
Substitution reactions CH4 + Cl2 → CH3Cl + HCl .
H H C H OH H H C H H C H Cl H – Cl + H C H + H2 O HCl + C2H5OH → C2H5Cl + H 2O .Substitution reactions Example 2: (Alcohol becomes alkyl halide) Cl replaces OH in a molecule of ethanol.
Substitution reactions Example 3: (Hydrolysis) Bases (or water) with haloalkanes produce alcohols. H H C H Br H H C H H C H OH + KBr KOH + H C H KOH + C2H5Br → C2H5OH + KBr .
Complete Exercise 6 .
The long chains are called polymers. . The process is known as addition polymerisation. The small molecules are known as monomers.Plastics and Polymers Plastics are made by joining small molecules which have C = C bonds into very long chains which have C – C bonds.
Monomers – small similar molecules which can join to make a chain.Definitions Macromolecules – very large molecules having molecular weights that may be several millions of atomic mass units. .
Polymers – long chains of monomers which are covalently bonded together. .
Polymerization – the process by which monomers join to make a chain. .
Addition polymerization which is a molecular fragment with an unpaired electron. R The free radical adds to the double bond of the monomer and creates another free radical. . H H H H R + C H C H R C H C H The pi bond of the carbon – carbon double bond is broken. 1. There are three steps in the production of the chain: 1. Initiation: The reaction is initiated by a free radical.
H R H H H H R H H H C H C H + C H C H C H C H C H C H Successive additions of this kind happen very fast and a chain may grow to 1000 units or more within a second. 2. . Propagation: The new free radical adds to the double bond of another monomer molecule and creates another free radical with a longer chain.
The formation of the chain will end if: (a) two radicals join together H R C H H C H H C H H H C H H C H H C H H C H H C H H H C H H C H H C H H C H H C H H C H R + C H R C H R . 3. Termination: This is the step which terminates the chain.
H R C H H C H H H C H H C H H C H H C H H C H H H C H H C H H H C H H C H R R + C H H R C H H +C H C H C H . The formation of the chain will end if: (b) one radical removes a hydrogen atom from another radical forming an alkane and an alkene.
Complete Exercise 7 .
2. Condensation polymerization These polymers are made from two different monomers which have reactive groups at both ends of their molecules. . a dialcohol O HO C O C OH A molecule with two OH groups. HO CH2 CH2 OH Long chain of carbon atoms. a dicarboxylic acid A molecule with two COOH groups.
The monomers join to each other in an alternating structure and eliminate a small molecule. O HO OH O + O HO C C OH O C OH HO O C + H2O ester . such as H2O.
O O O O C C n a polyester .
CH2 .CH2 .O .C .C .C - a polyester .O .O .Making a polyester Example: O HO CH2 CH2 OH O CH2 C OH + HO C ethan-1.2-diol propan-1.3-dicarboxylic acid O O O O .CH2 .CH2 .O .CH2 .CH2 .C .
(CH2)2 .C .OH O O O O .O .(CH2)2 .OH + HO .CH2 – O .C .O .C .CH2 .C .C - H2O molecules are eliminated = = = = .C .CH2 – O .(CH2)2 . Draw two repeating units of the polyester when the following monomers are used: O O = = HO .
Complete Exercise 8 .
Properties of plastics They are polymers of carbon. The longer the molecules the stronger the intermolecular forces. . They are strong because the molecules are long.Plastics Plastics are man made macromolecules. They are light because the atoms from which they are made are small.
They are unreactive. this means that they are difficult to dispose of because they will not rot away – they are not biodegradeable. They are electrical and thermal insulators. Some plastics catch fire easily and they may give out poisonous gases. . They are divided into two groups called thermoplastics and thermosets.
These plastics contain long thin molecules with
tangled chains. The forces between the chains are weak Van der Waals forces.
This means that the chains can move easily over each
other on heating, flexing and stretching.
Thermoplastics melt on heating and when cool they
set into a new shape.
They contain a network of large molecules with
strong cross-links which form when the plastic is made.
This means that on stretching the molecules cannot
slide over each other.
They will char or break down at high temperatures,
rather than melt.
. They are rigid and will break rather than bend. They are moulded into shape when they are being made. because the shape cannot be changed later.