NSSCAS Chemistry Theme 4 Topic 4.1 - Tsumeb
NSSCAS Chemistry Theme 4 Topic 4.1 - Tsumeb
NSSCAS Chemistry Theme 4 Topic 4.1 - Tsumeb
Theme 4
Organic Chemistry
Theme 4 consists of SEVEN topics
4.1 Foundations of organic chemistry
4.2 Hydrocarbons
4.3 Halogen derivatives
4.4 Hydroxyl compounds
4.5 Isomerism: structural and
stereoisomerism
4.6 Carbonyl compounds
4.7 Carboxylic acids and derivatives
4.1 Foundations of organic chemistry
4.2.1 Alkanes
4.2.2 Alkenes
4.2.3 Hydrocarbons as fuels
4.1.1 Organic chemistry terminology
• interpret and use the following terminology associated with
organic reactions:
functional group
homolytic fission and heterolytic fission
free radical, initiation, propagation, termination
nucleophile, electrophile
addition, substitution, elimination, hydrolysis, condensation
oxidation and reduction
• recall and use systematic nomenclature to name alkanes, alkenes,
halogenoalkanes, alcohols, aldehydes, ketones, carboxylic acids,
esters and amines, with chain length up to six carbon atoms,
including:
– numbering the carbon atoms in a direction to give the lowest prefix
possible e.g. 1-chlorobutane (not 4-chlorobutane)
– the use of the prefixes mono-, di-, tri-, tetra-, penta-, hexa-.
(in equations for organic redox reactions, the symbols [O] and [H] are
acceptable for oxidising and reducing agents)
What is organic chemistry?
– General formula
– Structural formula
– Displayed formula
– Skeletal formula
– Condensed formula
General formula
• The general formula is an algebraic formula that
can be applied to chemicals in the same family of
compounds.
• The following are the general formulae for
alkanes, alkenes and alcohols as examples:
– Alkanes -
– Alkenes -
– Alcohols - OH
Structural formula
• The structural formula shows the order of the
arrangement of atoms joined together in an
organic compound without showing all the bonds.
• Only double (=) and triple () bonds are shown
• These formulae are usually written in one line.
• Examples:
– Ethane:
– Ethene: =
– Ethanoic acid: COOH
- 2-methylbutane: CH()
Displayed
formula
• The skeletal formula shows only the functional groups. The carbon and
hydrogen atoms are simplified and hidden.
• In a skeletal formula:
– there is a carbon atom at each junction and at the end of the bond, there is no
carbon atom at a place occupied by another functional group.
– there is enough hydrogen atoms bonded to each carbon so that each carbon has
four bonds only.
Homologous series
• A homologous series is a group (family) of compounds which
have the same functional group and general formula.
• A functional group is the reactive group attached to the
compound’s chain that defines the physical and chemical
properties of the compounds in a specific homologous series.
homologous series prefix / suffix example
name
Basic rules for naming organic compounds conti…
2. Look for the functional group (containing oxygen) and decide on the suffix
(ending). The functional group on the molecule normally tells you the ending of
the name (suffix). Other functional groups and substituents (not containing
oxygen) are indicated by prefixes (e.g. alkyl groups and halogens). of which the
position of each is shown by its locant (carbon number on the main chain).
3. Number the carbon chain so that the functional group sits on the lowest
possible number carbon.
4. Make a note of the carbon number the functional group is attached to. Place
this number before the suffix. For example, butan-1-ol.
5. Any side chains and less important functional groups are written as prefixes in
alphabetical order.
6. If there is more than 1 identical functional group or side chain, put di- (2), tri-
(3) or tetra- (4).
7. Consecutive numbers are separated by a comma and a number and a letter/
word is separated by a hyphen (e.g. 2,2-dichloropentane) which is generally taken
as locant-prefix-parent-locant-suffix.
Basic rules for naming organic compounds
8. If the compound contains double or triple bonds between carbon
atoms, it must be indicated using infixes.
infixes meaning
ketones
carboxylic acids H
esters R
amines
Bond fission
• Bond fission is the breaking of a covalent bond.
• The electron pair in the bond can be distributed
in two ways depending on the type of bond
fission.
• There are two types of fission.
– homolytic fission (homolysis)
– heterolytic fission (heterolysis)
homolylitic fission
–O
electrophile
• An electrophile is an electron-deficient species
which can accept electrons and is attracted to
regions of negative charge or electron-rich sites.
• Electrophiles are often positively-charged or
carry a partial positive charge.
• Some examples of electrophiles are:
–,
Activity
1. Write an equation to show the heterolytic
fission of the C-Cl bond in chloromethane.
Include a curly arrow in your answer. (2)
Which of the following species H2 , H+ , OH-
is likely to act as:
i. Nucleophile
ii. Electrophile
iii. Free radical when exposed to UV light
Some common organic reactions
2.
4.1.2 Shapes of organic molecules
• Skeletal formula
NB: Naming alkanes and deduce their
molecular formulae from given formulae
Naming unbranched alkanes
TIPS: Naming branched alkanes
• Identify the longest unbroken carbon chain and name it.
This chain is called the parent chain.
• Identify all of the substituents (groups appending from the
parent chain) and name them.
• Number the carbons of the parent chain from the end that
gives the substituents the lowest numbers. Indicate the
positions of the substituents.
• If the same substituent occurs more than once, the location
of each point on which the substituent occurs is given. In
addition, the number of times the substituent group occurs
is indicated by a prefix (di, tri, tetra, etc.).
• Assemble the name, by listing the substituents in
alphabetical order.
Naming branched alkanes
•
Practice - Naming branched alkanes
Practice - Naming branched alkanes
Physical properties of alkanes
• Alkanes are non-polar, thus they are soluble in
non-polar solvents like .
• They are, in general, insoluble and less dense
than water.
• The boiling point of straight-chain alkanes
increases with the size of molecule. This is
because the number of electrons in each
molecule increases, resulting in the increased
strength of van der Waals'. Thus more energy is
required to break these forces.
Physical properties of alkanes …
• For a branched alkane, it is more volatile and its boiling
point is lower than its counterpart with the same number
of carbon atoms. This is because they are more spherical
and have a lower surface area. Thus less temporary
dipoles can be set up and the van der Waals' forces are
weaker, less energy is required to overcome it.
• The density of liquid alkanes increases slightly. The mass
of each succeeding molecule increases but due to the
increased strength of van der Waals' forces, the
molecules are more closer together. This results in higher
ratio of mass/volume.
Cycloalkanes
• Cycloalkanes are alkanes that are joined up as a
ring.
• The smallest possible cycloalkane is
cyclopropane.
• Cycloalkanes have two hydrogen less than the
corresponding straight-chain alkanes.
• Cycloalkanes have the general formula
• The general formula is the same for
cycloalkanes and alkenes, however,
cycloalkanes (like straight chain alkanes) only
consists of single bonds
Examples of cycloalkanes
Reactions of alkanes
• Alkanes are saturated and generally unreactive
because they are non-polar, hence they are
unattractive towards nucleophiles and
electrophiles.
• Alkanes will only react with non-polar reagents
in the presence of heat or ultraviolet light.
• You are required to describe the chemistry of
alkanes as exemplified by:
– Combustion
– Substitution by chlorine and bromine (free radical
reactions)
Complete combustion of alkanes
• Alkanes undergo complete combustion under
excess oxygen gas to give carbon dioxide and water.
• For example: (g) + 2 (g) → (g) + 2O(g) ΔH° = 890 kJ
mol⁻¹
• In general, + (x + ) x + () O
• Larger alkanes are more difficult to ignite. This is
because alkanes only burn in the gaseous state and
larger alkanes have stronger van der Waals' forces
that hold them together. Therefore more energy is
required to vaporise it.
Incomplete combustion of alkanes
• When the supply of oxygen is limited, alkanes
undergo incomplete combustion. The possible
products are carbon monoxide, carbon and
water.
• For example:
2C (g) + 3 (g) → 2CO (g) + 4O (g)
or (g) + (g) → C(s) + 2 O(g)
Halogenation
• Alkanes undergo halogenation via free-radical
substitution to give a range of products.
• In free-radical substitution, hydrogen atoms in the
molecule are gradually substituted by halogen atoms.
– Reagent: Chlorine gas, or bromine gas,
– Condition: The presence of ultraviolet (UV) light or sunlight
– Product : Halogenoalkanes (alkanes with halogens)
• Free-radical substitution proceeds via a chain
reaction. During a chain reaction, for every reactive
species you start off with, a new one is generated at
the end, and this keeps the process going.
Halogenation – free radical substitution
• Free-radical substitution proceeds via a chain
reaction. During a chain reaction, for every reactive
species you start off with, a new one is generated at
the end, and this keeps the process going.
• When methane reacts with chlorine in sunlight, the
greenish-yellow colour fades and steamy acidic
fumes of hydrogen chloride can be observed.
• Reaction: + Cl + HCl
• However, this is a chain reaction and does not end here.
More hydrogen atoms will be substituted as long as
there are sufficient chlorine atoms.
free radical substitution of hydrogen by
chlorine
Substitution reaction
• Substitution by chlorine
• Substitution by bromine
Halogenation – free radical substitution - Step 1: initiation