Organic Chemistry (sl)
11.1 - Homologous series
An homologous series is a set of compounds whose components
differ by a single repeating functional group. In the case of (straight
chain) alkanes, CH2. Their general formula is CnH2n+2.
Physical properties
The boiling points of alkanes increase as the chains get
longer (increased number of electrons causes increased Van de Waal's forces),
increasing rapidly initially but flattening off. Click diagram to enlarge
11.2 - Hydrocarbons
Compounds containing only hydrogen and carbon. There are
three types alkanes, alkenes and alkynes.
Alkanes have a CH3 group at each end (except
methane has only one CH4) and fill out the required number
with CH2 groups.
Nomenclature (Naming system)
Methane, ethane, propane, butane, pentane, hexane.
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methane
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ethane
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propane
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butane
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Isomerism and branching
Any structure that can be drawn can exist providing the
fundamental rules have been fulfilled.
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Each carbon forms four bonds (may be all single,
one double and two singles, etc)
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Each hydrogen forms one bond
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Each oxygen forms two bonds
This means that one molecular formula can have other possible
structures. This is called isomerism. The
chains formed by the alkanes and other organic molecules do not have
to be straight (actually zigzag) but may be branched ie having "branches"
of carbon atoms attached to the main unbroken chain.
Example:
The alkane C4H10 exists in two isomeric
forms - a straight chain form and a branched form
Alkenes
These structures will be similar to those of the alkanes
except two hydrogens on adjacent carbons are replaced by a double bond
between those carbons. The number '1' in the names refers to the position
of the carbon starting the double bond. No numbering is needed in the
first two members as there can be no ambiguity.
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ethene
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propene
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but-1-ene
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pent-1-ene
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Combustion
This is effectively a technical word for burning. Most
organic compounds burn with the exception of chlorinated (halogenated
) hydrocarbons.
Complete combustion produces CO2 and H2O,
incomplete combustion produces CO, C and H2O (usually occurs
with unsaturated compounds, where there is a limited supply of oxygen).
C produces a 'dirty' flame leaving carbon deposits on everything, CO
is toxic and CO2 is a greenhouse gas. Incomplete combustion
is where the carbon is not completely oxidised.
The combustion of hydrocarbons is an exothermic process
(otherwise there wouldn't be much point in burning them to produce energy
for fuel and heat). This is because the O-H bond is stronger than the
C-H bond, and the C=O bond is stronger than the C-C. This means that,
the C-C and C-H bonds breaking requires energy, but this is more than
made up for by the energy released by the formation of the C=O and O-H
bonds.

11.3 - Other functional
groups
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homologous series name (old name)
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functional group
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naming system
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description
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| Alkanal (aldehyde) |
-CHO |
ends with -anal |
Has a carbonyl C=O at the end of a carbon chain, with the carbon
also attached to a hydrogen |
| Alkanone (ketone) |
-CO- |
ends with -anone |
Has a carbonyl group C=O but it is in the middle of a carbon chain
and the carbon has no hydrogens attached |
| Alkanol (alcohol) |
-OH |
ends with -anol (may also go at the start of the name as hydroxy-
if there is another more important group in the molecule) |
These have an -OH group (or more than one in the case of diols,
triols etc) at any position in the chain. |
| Alkanoic acid (carboxylic acid) |
-COOH |
ends with -anoic acid |
The group must go at the end of a carbon chain as it has a carbon
attached to an oxygen by a double bond and also an -OH group (leaving
the carbon with only one other bond which it uses to attach to the
rest of the carbon chain) |
| Amine |
-NH2 |
ends with -ylamine or starts the name with Amino- (depending on
whether there is a more important functional group int he molecule) |
The NH2 group can go anywhere on the carbon chain. It infers basic
characteristics to the molecule. (ability to accept a proton from
an acid) |
| Amide |
-CONH2 |
ends with -anamide |
The amine group is associated with a carbonyl group inferring
different characteristics to the molecule. It can also be a linking
group -CONH- between two alkyl chains (proteins and nylon) |
| Halogenoalkanes |
-X |
becomes a prefix: chloro- bromo- iodo- folowed by the rest of
the name |
The halogen atom may be added into any position in the chain.
If there is more than one then the prefixes di- tri- tetra- etc
are used. |
| Esters |
-COO- |
name is derived from the acid and alcohol that were used in making
the ester. The alkyl group ending with the -COO was the acid part
and becomes -(name)anoate and the part after the -COO group starts
the name. For example: ethyl ethanoate |
Esters are linkage compoounds formed by condensation (esterification)
reactions between carboxylic acids (or compounds deriving from them)
and alcohols. They also occur naturally and may be polymers (polyester)
see amide linkage above |
| Ethers |
-O- |
derives from the shortest alkyl chain ending in -oxy followed
by the longest alkyl chain eg. methoxyethane CH3-O-C2H5 |
These are linkage compounds where the oxygen bridges two carbon
chains. They are of little importance except as solvents (ethoxyethane) |

Isomerism
Sub divided into structural (positions of the atoms in
the molecule) or stereoisomerism (relative poisitions in space)
Structural isomerism
Stereoisomerism
Chemical properties of the different functional groups
The following table summarises the chemical properties of
the functional groups studied at this level. Some of the reactions must
be known in greater detail than others. If in doubt consult the relevant
section of the syllabus.
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homologous series
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Important reaction types |
reagent and conditions |
product (s) |
| alkanes |
| combustion |
air/oxygen, heat |
carbon dioxide and water |
| free radical substitution
of halogens |
halogen and UV light |
halogenoalkanes (mixture) |
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| alkenes |
| combustion |
air/oxygen heat |
carbon dioxide and water |
| addition |
Br2, Br2(aq), H2 |
dibromoalkane, bromoalcohol, alkane |
| polymerisation |
catalyst |
polyalkene |
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| alcohols |
| combustion |
air/oxygen, heat |
carbon dioxide and water |
| dehydration (elimination) |
phosphoric or sulphuric acid |
alkene |
| oxidation |
sodium dichromate/sulphuric acid |
alkanal, alkanone or carboxylic acid |
| substitution of the -OH
group |
phosphorus pentachloride, sodium |
halogenoalkane, sodium alkoxide |
| esterification |
carboxylic acid |
ester |
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aldehydes
(alkanals) |
| addition |
ammonia |
compound containing hydroxy and amine |
| oxidation |
sodium dichromate/dil. sulphuric
acid |
carboxylic acid |
| reduction |
lithium aluminium hydride |
1º alcohol |
| addition - elimination (condensation) |
amines, hydroxylamine, |
depends on reagent |
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| carboxylic acids |
| acid - base reactions |
base (eg sodium hydroxide) |
salt and water |
| reduction |
lithium aluminium
hydride |
alkanal (or 1º alcohol) |
| esterification |
alcohol/conc. sulphuric acid |
ester |
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haloalkanes
(halogenoalkanes) |
| substitution of the halogen |
sodium hydroxide, ammonia |
alcohol, amine |
| dehydrohalogenation (elimination) |
conc. sulphuric acid |
alkene |
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| amines |
| reaction as a base with an acid |
mineral (strong) acid |
amine salt |
| condensation (addition -
elimination) |
carbonyl compounds |
depends on reagent |
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| amides |
| hydrolysis (breaking apart in solution) |
dilute acid/heat |
amine and carboxylic acid |
| hydrolysis (breaking apart in solution) |
dilute base/heat |
amine and sodium carboxylate |
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| esters |
| hydrolysis (breaking apart in solution) |
dilute acid/heat |
alcohol and carboxylic acid |
| hydrolysis (breaking apart in solution) |
dilute base/heat |
alcohol and sodium carboxylate |
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Resources
Optical activity animation
Polarisation
Useful links
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