1

SUMMARY
Organic Chemistry
p. 75-130
Organic Chemistry

ORGANIC MOLECULES

FORMULAE

 We use different type of formulae to write organic compounds. For example:

H H
Name: Structural formula  
ethane H–C–C–H
 
H H
Condensed structural formulae CH3–CH3 or CH3CH3

Molecular formula C2H6

General formula CnH2n+2

Learn
definitions!
TERMINOLOGY

 Organic molecule: molecule containing carbon atoms.

 Hydrocarbon: organic compound that consist of hydrogen and carbon only.
 Structural formula: chemical formula shows which atoms are attached to which within the
molecule. Atoms are represented by their chemical symbol and lines are used to represent ALL
the bond that hold the atoms together.
 Condensed formula: chemical formula that shows the way in which atoms are bonded together
in the molecule, but does not show all bond lines.
 Molecular formula: chemical formula that indicates the type of atoms and the correct number of
each in a molecule.
 Homologous series: a group of organic molecules that can be represented with the same
general formula (or: in which one member differs from the next with a CH2 group).
 Saturated molecule: molecule which contains no multiple bonds between carbon atoms in the
hydrocarbon chain.
 Unsaturated molecule: molecule which contains one or more multiple bonds between carbon
atoms in the hydrocarbon chain.
 Functional group: A bond, or an atom, or a group of atoms that determine(s) the physical and
chemical properties of a group of organic compounds.
 Structural isomers: organic molecules with the same molecular formula, but different structural
formulae.
 Chain isomers: molecules with the same molecular formula, but different type of chains.
(Different lengths of the parent chain, e.g. butane and 2–methylpropane.)
 Positional isomers: molecules with the same molecular formula, but different positions of the
side chain or functional groups on the parent chain. (The same length of parent chain, e.g.
butan-1-ol and butan-2-ol.)
 Functional isomers: molecules with the same molecular formula, but different functional
groups. (From different homologous series, e.g. methyl ethanoate and ethanoic acid.)
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NAMING OF MOLECULES

 FOR THE PARENT CHAIN: Prefixes and suffixes:

Prefixes Suffixes
1C meth(an)... alkanes ...ane
2C eth(an)... alkenes ...ene
3C prop(an)... alkynes ...yne
4C but(an)... alcohols ...ol
5C pent(an)... carboxylic acids ...oic acid
6C hex(an)... esters ...oate
7C hept(an)... aldehydes ...al
8C oct(an)... ketones ...one
haloalkanes do not have its own suffix;
(alkyl halides) are regarded as side chains
on a parent chain

 Alkanes, alkenes and alkynes: without “an” (e.g. butane, butene, butyne).
 For the rest: add “an” between prefix and suffix. (e.g. butanol, butanoic acid, …butanoate,
butanal, butanone).

 Naming the molecules using the IUPAC-rules:

 Find the functional group of the molecule.

 Find the longest chain of C atoms in the molecule, containing the functional group. This is the
parent chain (base).
 Number the C atoms in this chain:
 1 priority: smallest number on functional group;
st

 2 priority: smallest number on first side chain;

nd

 3 priority: smallest number on side chain first alphabetically.

rd

 Now write the parent chain: prefix + suffix. Number for base INSIDE the parent chain.
 Write the side chains (substituents) IN FRONT OF the parent chain:
 alphabetically;
 the number of the side chain IN FRONT OF its name;
 for more than one of a same side chain: “di” for 2, “tri” for 3.
 Side chains: –CH3  methyl
–CH2 –CH3  ethyl
–C  chloro
–Br  bromo

 The name is one word. Only use hyphens and commas, no spaces. (Acids and esters are
exceptions: e.g. ethanoic acid; methyl ethanoate.)
 For side chains the number of the C atom is written in front of the name: e.g. 2–methyl…. .
 In the parent chain the number of the C atom is written inside the name: e.g. butan–2–one. This
occurs only with alkenes, alkynes, alcohols and ketones.

st
For aldehydes and carboxylic acids the functional group is always on the 1 C atom; the number
1 is never shown in the name.
Example: CH3 OH
 Punctuation marks are specifically used: | |
 Hyphens: 1. Between a side chain and its number; CH3 – CH – C – CH3
2. Between different side chains; | |
3. In the parent chain. Br CH3
 Commas: Between two C atom numbers. Parent chain: butan–2–ol
 Note: There is no mark or space in front of the parent chain. Side chains: bromo on 3, methyl on 2 and 3
3–bromo–2,3–dimethylbutan–2–ol
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FIRST FIVE HOMOLOGOUS SERIES

HOMOLOGOUS FUNCTIONAL
EXAMPLE NAME
SERIES GROUP

alkanes   CH3 CH3

2,3-dimethylpentane
– C – C– | |
General formula: CnH2n+2
  CH3 – CH – CH – CH2 – CH3

CH2 – CH3

alkenes   |
Nr. in 4-ethyl-3-methylhept-
–C=C– CH3 – CH2 – C = C – CH2 – CH2 –CH3
base General formula: CnH2n 3-ene
|
CH3
CH3

alkynes 
4,4-dimethylpent-2
Nr. in –CC– CH3 – C ≡ C – C – CH3
General formula: CnH2n-2 -yne
base 
CH3

| Br
haloalkanes 4-bromo-1-
– C – C/Br/I 
General formula: CnH2n+1X chloropentane
(X = F, Cl, Br, I)
| CH3 – CH – CH2 – CH2 – CH2 – C

Nr. in
| CH2 – CH – CH2 – CH3
base alcohols 2-methylbutan-1-ol
– C – O–H  
General formula: CnH2n+2O
| O–H CH3

CARBONYL COMPOUNDS O
||
 The next groups contain a carbonyl group:
 – C –

CH3 O
aldehydes O  ||
General formula: CnH2nO || CH3 – CH2 – CH – CH – C – H 2,3-dimethylpentanal
–C–H |
CH3

O CH3
ketones | || |
–C–C–C– ||  Nr. in
General formula: CnH2nO 3-methylpentan-2-one
| | CH3 – C – CH – CH2 – CH3 base

O O
carboxylic acids
|| ||
General formula: CnH2nO2 pentanoic acid English:
–C–O–H CH3 – CH2 – CH2 – CH2 – C – O – H
These two
are the
O ONLY
|| | O names
esters written as
–C–O–C– ||
General formula: CnH2nO2 methyl butanoate two words!
| CH3 – CH2 – CH2 – C – O – CH3

REMARKS:

 Note the difference in condensed structural formulae:

Propanol: CH3–CH2–CH2–OH Propanal: CH3–CH2–CHO
Propanoic acid: CH3–CH2–COOH Propanone: CH3–CO–CH3
Methyl ethanoate: CH3–COO–CH3
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Only a carbonyl Carbonyl + another O atom

Note the difference O O

On the tip || aldehyde || carboxylic acid
between the 4 types
–C–H –C–O–H
of carbonyl
O O
compounds:
In the middle || ketone || ester
–C– –C–O–

 Note the different names for functional groups:

O O O
–O–H || || ||
–C– –C–H – C – O –H

hydroxyl carbonyl formyl carboxyl

(Carbonyl + hydroxyl)

 The aldehydes and ketones are functional isomers with the general formula CnH2nO.
The esters and carboxylic acids are functional isomers – with the general formula CnH2nO2.
e.g.
O O O O
|| || || ||
CH3– CH2 – C – H and CH3 – C – CH3 CH3– CH2 – C – O–H and CH3 – C – O – CH3

propanal: C3H6O propan-2-one: C3H6O propanoic acid: C3H6O2 methyl ethanoate: C3H6O2

 Alcohols and haloalkanes can be primary, secondary or tertiary, e.g.:

CH3
|
CH3 – CH2 – CH2 – O–H CH3 – CH – CH3 CH3 – C – CH3
primary alcohol secondary | tertiary |
The OH group is attached to a C atom alcohol O–H alcohol O–H
which is bonded to ONE other C atom The OH group is attached to a C atom The OH group is attached to a C atom
(∴ on the tip of the chain). which is bonded to TWO other C atoms. which is bonded to THREE other C atoms.

FIVE REACTIONS

1. COMBUSTION (OXIDATION)

 The alkanes are fossil fuels, and crude oil is a natural mixture of alkanes. E.g. petrol, diesel and
jet fuel are all natural alkanes.
 Alkanes (fossil fuels) react with oxygen during combustion. The combustion ALWAYS yields
CO2 (carbon dioxide) and H2O, which are inorganic products.
 These reactions are highly exothermic.
 These reactions are written in molecular formulae.
 E.g. combustion of propane: C3H8 + 5O2  3CO2 + 4H2O

2. ESTERFICATION (CONDENSATION)

 Carboxylic acids react with alcohols and yields esters and H2O.
 The reaction takes place in the presence of a H2SO4 catalyst.

e.g. H O H H O H
| || | | || |
H – C – C – O–H + H–O – C – H  H–C–C–O–C– H + O–H
H2SO4
| | | | |
H H H H H
carboxylic acid + alcohol  ester + water
ethanoic acid methanol methyl methanoate
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3. ADDITION

 Addition takes place when an atom/group is added to the organic molecule.

 It takes place in unsaturated molecules with double and triple bonds (alkenes and alkynes).

TYPE of ADDITION ADDITION OF ..... EXAMPLE

H H H H
| | | |
Halogenation Addition of halogen C2/Br2 H–C=C–H + Br–Br → H – C – C – H
| |
Br Br
Add halogen to alkene. This is a spontaneous reaction.
H H H H
| | | |
Hydrogenation Addition of H2 H–C=C–H + H–H → H–C–C–H
Pt | |
H H
Use a Pt of Pd catalyst. Dissolve alkene in a non-polar solvent.
H H H H H
| | | | |
Hydration Addition of water H–C=C–H + O–H → H–C–C–H
H2SO4 | |
H O–H
Add excess H2O to alkene with strong acid (H2SO4 or H3PO4) as catalyst.
H H H H
| | | |
Hydrohalogenation Addition of HCl/HBr/HI H–C=C–H + H–Br → H–C–C–H
| |
H Br
Add HCl/HBr/HI to alkene.

 Hydrogenation is used in the manufacturing of margarine form plant oils (like sunflower and
canola). In the process the double bonds in the oils are converted into more saturated
compounds. (The oils are “solidified”.)

 Use the Markovnikov rule for the main product if 2 products are possible: in the main product
the halogen or the OH group adds to the C atom with the most side chains, ∴ tertiary (and not
secondary) or secondary (and not primary).

H H H Hidration van H H H H H H
| | | prop-1-ene | | | | | |
H–C–C=C–H H–C–C–C–H H–C–C–C–H
| | | | | | |
H H O-H H H H O-H
Main product is By product is
secondary alcohol primary alcohol

H H H
| Hidrohalogenation of | |
H–C–H 2-methylbut-2-ene H–C–H H–C–H
( + HBr)
H H H H H H H H H
| | | | | | | | |
H–C–C=C–C–H H–C–C–C–C–H H–C–C–C–C–H
| | | | | | | | | |
H H H Br H H H H Br H
Main product is By product is
tersiary haloalkane secondary haloalkane
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4. ELIMINATION

 Elimination takes place when a molecule is removed from an organic molecule.

 It takes place in saturated molecules: alkanes, alcohols, halo alkanes.
 The product is always an alkene.

TYPE of ELIMINATION OF ... EXPAMLE

ELIMINATION

H H H H H
| | | | |
Dehydration Elimination of water H–C–C–H → H–C=C–H + O–H
from an alcohol | | Δ,H2SO4
H O–H

Heat with concentrated H2SO4 (or H3PO4) as a catalyst.

H H H H
| | | |
Dehydrohalogenation Elimination of HCl/HBr/HI H–C–C–H → H–C=C–H + H–Br
from a haloalkane | | Δ,NaOH(c)
H Br
OR
H H H H H
mutual conversion

| | | | |
H – C – C – H + NaO-H → H – C = C – H + O-H
| | (c)
H Br + NaBr
Dissolve haloalkane in pure ethanol. Heat under reflux (vapour condenses
and return to the reactor during heating) with a concentrated strong
base, such as NaOH or KOH.
2 possible crackings of butane:
A long alkane is broken into
Cracking  a shorter alkane and CH3CH2CH2CH3  CH4 + CH2=CH–CH3
of alkanes  a shorter alkene CH3CH2CH2CH3  CH3CH3 + CH2=CH2
Thermal cracking: High pressure and high temperature, without a catalyst.
Catalytic cracking: Low temperature with a catalyst.

 Use the Zaitsev rule for the main product if two products are possible: the main product
contains the more highly substituted double bond, (e.g. double bond rather forms “in the middle”
and not “on the tip”).

H H
H | |
| H–C–H H–C–H
Dehydration of
H–C–H
3-methylbutan-2-ol H H H H H H
H H H | | | | | |
| | | H–C–C=C–C–H H–C–C–C=C–H
H–C–C–C–C–H | | | |
| | | | H H H H
H H O-H H
Main product By product
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5. SUBSTITUTION

 Substitution takes place when an atom/group is replaced by another atom/group.

 It takes place in saturated molecules: alkanes, alcohols and halo alkanes.

TYPE of
SUBSTITUTION ... IS REPLACED BY... EXAMPLE

H H H H
| | | |
Alkane + halogen H is replaced by C/Br H – C – C – H + Br–Br → H – C – C – H + H–Br
| | light | |
H H H Br

Reaction is slow, will only take place in sunlight (or heated).

H H H H
| | | |
Haloalkane + KOH C/Br is replaced by OH H – C – C – H + NaO–H → H – C – C – H + NaBr
Hydrolysis | | (aq) Δ | |
H Br H O–H
Dissolve haloalkane in ethanol. Add a diluted strong base, such as NaOH or
KOH, and heat .
H H H H
| | | |
With H2O hydrolysis
also takes place, but H – C – C – H + O–H → H – C – C – H + H– Br
| | | Δ | |
slower.
H Br H H O–H

Dissolve haloalkane in ethanol. Add water.

H H H H
| | | |
Alcohol + OH is replaced by C/Br H – C – C – H + H–Br → H – C – C – H + H–O
HC/HBr/HI | | NaBr,H2SO4 | | |
H O–H H Br H
 Primary and secondary alcohols: Add solid NaBr (or KBr) with concentrated
H2SO4 as catalyst. (The alcohol then reacts with HBr which forms from NaBr
and H2SO4.)
 Tertiary alcohols: Add alcohol to HBr at room temperature.

 It is easy to distinguish between ADDITION, ELIMINATION and SUBSTITUTION reactions.

Addition Elimination Substitution

double bond single bond single bond double bond single bond single bond
in reactant in product in reactant in product in reactant in product

 Note the difference between dehydrohalogenation and

hydrolysis. In both a haloalkane is treated with a strong
base. (such as NaOH or KOH). CH3–CH2 + NaOH(c)  CH2=CH2 + HBr + H-O
| dehydrohalogenation |
 Dehydrohalogenation: Treat haloalkane with
Br H
 CONCENTRATED NaOH.
 Elimination with alkene as product.
CH3–CH2 + NaOH (aq)  CH3–CH2 + NaBr
 Hydrolysis: Treat haloalkane with | hidrolysis |
 DITLUTED NaOH: Br O–H
 Substitution with alcohol as product.
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DISTINGUISH BETWEEN SATURATED AND UNSATURATED MOLECULES

Method to test if a compound is saturated (alkane), or unsaturated (alkene): Add the unknown
compound to bromine. The rate at which the bromine loses its colour determines if the added
compound is saturated or unsaturated.

 Unsaturated molecules (alkenes) react spontaneously and quickly with bromine.

 After adding the bromine, the brown colour of the bromine disappears immediately. It shows
that the unsaturated molecule react spontaneously with bromine and yields colourless
products.
 The reaction is halogenation (addition).
E.g. CH2=CH2 + Br2(brown)  CH2Br–CH2Br (colourless)

 Saturated molecules (alkanes) do not react with bromine.

 The brown colour of bromine remains unchanged. Only in light and after a while some
discolouring takes place. It shows that the saturated molecule reacts non-spontaneously with
bromine and yields colourless products.
 The reaction is substitution.
E.g. CH3–CH3 + Br2(brown)  CH3–CH2Br(colourless) + HBr (colourless)

POSSIBLE REACTIONS PER HOMOLOGEOUS SERIES

 ALKANES
 Combustion: Reaction with oxygen;
 Substitution: Reaction with halogens;
 Elimination: Cracking.

 ALKENES
 Addition:
 Halogenation: Addition of halogens;
 Hydrogenation: Addition of hydrogen;
 Hydration: Addition of water;
 Hydrohalogenation: Addition of a hydrogen halide.

 ALCOHOLS
 Elimination: Dehydration – elimination of water;
 Substitution: Reaction with a hydrogen halide;
 Esterfication: Reaction with carboxylic acids.

 HALOALKANES
 Elimination: Dehydrohalogenation – elimination of hydrogen halide;
 Substitution: Reaction with strong base (like NaOH).

 CARBOXYLIC ACIDS
 Esterfication: Reaction with alcohols.
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PHYSICAL PROPERTIES OF ORGANIC MOLECULES

The following physical properties of series of organic compounds are compared:

 Boiling point:
 The temperature at which the vapour pressure of a substance equals atmospheric
pressure.
 The stronger the intermolecular forces, the higher the boiling point.
 Melting point:
 The temperature at which the solid and liquid phases of a substance are at equilibrium.
 The stronger the intermolecular forces, the higher the melting point.
 Vapour pressure:
 The pressure exerted by a vapour at equilibrium with its high vapour low vapour
liquid in a closed system. pressure pressure
 The stronger the intermolecular forces, the lower the vapour
pressure.
 Liquids with a high vapour pressure evaporates easily.
 Liquids with a low vapour pressure do not evaporate easily.

 When the physical properties of homologous series are

compared, the compounds are compared on the ground of:
1. type of functional group; evaporate evaporate
2. molecular mass (or length of chain); easily difficult
3. degree of branching.

1. TYPE OF FUNCTIONAL GROUP

 In this case different homologous series are compared.

 For this discussions it is very important to identify the type of intermolecular forces between the
molecules:

Type of molecule Polarity Example Intermolecular forces

Symmetrical molecules non-polar alkanes, alkenes and very London

molecules alkynes weak

Asymmetrical molecules polar molecules haloalkanes, relatively dipole-dipole

(dipoles) aldehydes, strong
ketones and esters

Asymmetrical molecules polar molecules alcohols strong

with H atoms bonded to (strong dipoles) Hydrogen bond
highly electronegative carboxylic acids very
O atom (molecules with strong
hydroxyl: –O-H) *

* The hydrogen bond between carboxylic acids is stronger than that of the alcohol with the same
length. The carboxylic molecule has an additional polar side (the carbonyl group); therefore the
carboxylic acid can form two hydrogen bonds between two adjacent acid molecules.

 The stronger the intermolecular forces of a homologous group; Learn this argument!
 the more energy is needed to overcome the intermolecular forces;  First identify the molecule as
either polar or non-polar.
 ∴ the higher the boiling and melting points;  Name the IMF in each.
 ∴ the lower the vapour pressure (do not evaporate easily).  Compare the strength of the IMF.
Use the words “weak”, “relative
strong”, “strong”, and “very
strong”.
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E.g. compare the boiling points of butane and butan–1–ol:

 Butane is non–polar. The intermolecular forces in butane are very weak London forces.
 Butan–1–ol is strong polar (due to the prescence of a hydroxyl group). The intermolecular forces
in butan–1–ol are very strong hydrogen bond.
 More energy is needed to overcome the intermolecular forces in butan–1–ol.
 Therefore the boiling point is butan–1–ol is higher.

2. MOLECULAR MASS

 When molecular masses are compared, all of the compounds belong to the same homologous
series, therefore all of the compounds have the same type of intermolecular forces.

 The more C atoms, and therefore the longer the chain in an organic molecule; the
 greater the area in which intermolecular forces can be established; Learn this
 the stronger the intermolecular forces; argument!
 ∴ more energy is needed to overcome the intermolecular forces;
 ∴ the higher the boiling and melting points;
 ∴ the lower the vapour pressure (do not evaporates easily).

3. DEGREE OF BRANCHING CH3–CH2–CH2–O–H CH3 –CH– CH3

|
 In this case positional isomers are compared, e.g. propan–1–ol O–H
UNBRANCHED
 If the molecule is more branched; propan–2–ol
 the molecule is more compact; BRANCHED
 the smaller the area in which intermolecular forces can be established;
 the weaker the intermolecular forces;
Learn this
 ∴ less energy is needed to overcome the intermolecular forces: argument!
 ∴ the lower the boiling and melting points;
 ∴ the higher the vapour pressure (evaporates easier).

POLYMERISATION

The following 5 questions can be asked:

1. Define terms.
2. Distinguish between addition and condensation polymerisation.
3. Identify the monomers in given addition polymers.
4. Write the equation for the addition polymerisation of polythene. (ONLY!)
5. Name the uses of polythene.

TERMS
 Macro molecule: a molecule that consists of a large number of atoms. (More than 100.)
 Monomer: small organic molecules that can be covalently bonded to each other in a repeating
pattern.
 Polymer: a large molecule composes of smaller monomer units covalently bonded to each other
in a repeating pattern.
 Polymerisation: a chemical reaction in which monomer molecules join to form a polymer.
 Addition polymerisation: a polymer formed when unsaturated monomers join to form large
molecules by breaking the double bonds in the monomers.
 Addition polymer: a polymer formed when unsaturated monomers combine through an addition
reaction.
 Condensation polymerisation: a reaction in which two monomers with different functional
groups undergo a condensation reaction, with the loss of small molecules, usually H 2O.
 Condensation polymer: a polymer formed by two monomers with different functional groups that
are linked together in a condensation reaction in which a small molecule, usually H2O, is lost.
 11

The only equation that

ADDITION POLYMERISATION OF ETHENE you should be able to
write

H H H H H H H H H H H H H H
| | | | | | | | | | | | | |
C=C + C=C + C=C C–C–C–C–C–C C–C
| | | | | | | | | | | | | |
H H H H H H H H H H H H H H
ethene ethene ethene polytene
monomers polymer repeat unit

 Uses of polythene:
 Low density polyethylene (LDPE) is light, soft, flexible, water resistant and a non-reactive
chemical: plastic bags, telephone cables, water pipes, toys, etc.
 High density polyethylene (HDPE) have higher melting point than LDPE and is tougher and
more durable: bottles for milk, juice, shampoo, motor oil, etc.
 Ethene (monomer) is a gas at room temperature; polythene (the polymer) a solid.
 Polythene is also known as polyethylene. (The IUPAC name is polyethene.)

CONDENSATION POLYMERISATION

e.g. n H–O – R1 – O–H + H–O – R2 – O–H  R1– O –R2 + nH2O

n