Chapter 7

Organic Chemistry
 7.2 – Hydrocarbon Families
Key Knowledge and Skills
Families of organic compounds:
❖ The grouping of hydrocarbon compounds into families (alkanes,
alkenes and alkynes) based upon similarities in their physical and
chemical properties including general formulas and general uses
based on their properties
 New Vocab!
Term Definition

Organic Chemistry The study of carbon-containing compounds and their properties

Hydrocarbon Compound containing only carbon and hydrogen

Homologous Series Series of organic compounds with the same general formula, in which the
formula of one molecule differs from the next by a —CH2 group
Saturated Hydrocarbon Hydrocarbons containing only single covalent bonds

Unsaturated Hydrocarbon Hydrocarbons containing one or more double or triple covalent bonds

Alkane Hydrocarbons that contain only single carbon-carbon bonds and have the
general formula CnH2n+2
Alkene Hydrocarbons that contain one carbon–carbon double bond and have the
general formula CnH2n
Alkyne Hydrocarbons that contain one carbon–carbon triple bond and have the
general formula CnH2n-2
 What is Organic Chemistry?
Carbon forms more compounds than all other elements combined because:
❖ Carbon has four valence electrons so carbon can potentially form
covalent bonds with four different atoms
❖ Carbon atoms can form strong covalent bonds with other carbon atoms
❖ The covalent bonds formed can be single, double or triple bonds
❖ Carbon can bond to itself to form molecules of varied length and shape

❖ Carbon-based molecules are all around you - caffeine, petrol, pesticides,

plastics and artificial flavours are all carbon-based compounds
❖ Many of these compounds are produced from crude oil
❖ The branch of chemistry that studies the chemistry of carbon
compounds is known as organic chemistry
❖ Compounds formed between carbon and hydrogen are called
hydrocarbons
 7.2 - 1: Quick Check Q’s
1. State why carbon forms more compounds than all other elements
combined?

2. State the name of the branch of chemistry that is the study of

organic compounds.

3. State the general name for compounds that are formed between
carbon and hydrogen.
 General Properties of Hydrocarbons
❖ In hydrocarbon molecules, the electronegativities of carbon and hydrogen
atoms are similar; this means that the C—H bond is nonpolar and, because of
the symmetry of the molecule, hydrocarbon molecules are nonpolar.
❖ The intramolecular bonds within hydrocarbons, are strong covalent bonds.
❖ The intermolecular bonds between hydrocarbon molecules are very weak
dispersion forces.
❖ Smaller hydrocarbons have very low melting and boiling points because of the
very weak dispersion forces between the molecules. As the length of the
chain of carbon atoms increases, so does the melting and boiling point
because more dispersion forces are present.
❖ Smaller alkanes are gases, and larger alkanes are solids at room temperature.
❖ Hydrocarbons are insoluble in water as they are nonpolar and water is polar;
hydrocarbons are more likely to dissolve in nonpolar solvents.
 7.2 - 2: Quick Check Q’s
1. Explain why hydrocarbons are nonpolar. Refer to bond polarity
and symmetry in your answer.

2. Identify the intramolecular forces present in hydrocarbons.

3. Identify the intermolecular forces present between hydrocarbon

molecules.

4. Explain why larger hydrocarbons have higher melting/boiling

points compared to smaller hydrocarbons.

5. Explain why hydrocarbons are insoluble in water.

 Uses of Hydrocarbons
❖ Alkanes - are widely used as transport fuels; they burn readily
and release a large amount of energy

❖ Alkenes - are widely used in the petrochemical industry as

precursors for many other useful substances; they are also the
raw materials for the manufacture of a wide range of plastics

❖ Alkynes - the most useful alkyne is ethyne, a gas used with

oxygen for high temperature cutting and welding
 Hydrocarbons and Homologous Series
❖ Hydrocarbons are composed only of carbon
and hydrogen
❖ Hydrocarbons can be classified into several
groups or series

❖ A series of molecules in which each member

differs by a ‘CH2’ from the previous member is
known as a homologous series

Compounds that are members of the same

homologous series have:
❖ a similar structure
❖ a pattern to their physical properties
❖ similar chemical properties
❖ the same general formula
 Working Out Formulas
❖ Use the general formulas below to work out the
molecular formula for hydrocarbon compounds

❖ n = the number of carbons

Alkane Hydrocarbons that contain only single carbon-carbon bonds and have the
general formula CnH2n+2
Alkene Hydrocarbons that contain one carbon–carbon double bond and have the
general formula CnH2n
Alkyne Hydrocarbons that contain one carbon–carbon triple bond and have the
general formula CnH2n-2
E.g:
● Alkane with 3 carbons = C3H8
● Alkene with 3 carbons = C3H6
● Alkyne with 3 carbons = C3H4
 7.2 - 3: Quick Check Q’s
Calculate the molecular formula for the following:
a) An alkane with 6 carbons

b) An alkene with 8 carbons

c) An alkyne with 10 carbons

 7.3 – Drawing/Naming
Hydrocarbons
Key Knowledge and Skills
Families of organic compounds:
❖ Representations of organic compounds (structural formulas,
semi-structural formulas) and naming according to the International
Union of Pure and Applied Chemistry (IUPAC) systematic
nomenclature (alkanes, alkenes & alkynes)
 New Vocab!
Term Definition

IUPAC International Union of Pure and Applied Chemistry - developed the naming
system for organic compounds
Isomers Have the same molecular formula but a different arrangement of atoms
 Naming Organic Compounds
❖ Over the years, as organic chemistry grew and more
and more compounds were either discovered or
synthesised, naming them increasingly became a
problem.

❖ To solve the naming problem, the International Union

of Pure and Applied Chemistry (IUPAC) developed a
set of rules by which any organic substance could be
systematically named depending on the structure of
its molecules.

❖ This system is in widespread use today, although

many common substances still retain their ‘old’
names in everyday use.
Representing Organic Compounds
 Alkanes
❖ Methane is the first in a series of compounds known as the
alkanes
❖ Alkanes are hydrocarbons that contain only single bonds

❖ All the carbon–carbon bonds in alkanes are single covalent

bonds – these molecules are said to be saturated
❖ Each member of the alkane series differs from the previous
member by a ‘CH2’ unit

❖ The name of an alkane ends in ‘ane’ and alkanes have the

general formula: CnH2n+2
Naming Alkanes
 Naming Alkanes - Steps
The following rules apply when naming alkanes:
1. Identify the longest carbon chain
2. Number the carbon atoms starting from the end closest to the branch if a branch is
present
3. Name the side branches and the main chain
4. Combine all components to write the full name (alkanes should end in ‘ane’)
* Place the number and position of each of the alkyl groups at the beginning of the name
* If two identical side chains are present, use ‘di-’ as a prefix; for three use ‘tri-’; for
four use ‘tetra-’
*If there are side chains of different lengths on the molecule, list them in alphabetical
order at the start of the name, with their numbers to indicate their respective positions
 Naming Alkanes – Straight Chain Example

1. Identify the longest carbon chain

= 5 carbons
2. There are no side branches
3. 5 carbons prefix = pent
4. Therefore this is ‘pentane’
 7.3 - 1: Quick Check Q’s
a) Draw the following alkane structural formula in your book:

b) Name this alkane.

c) Write the semi-structural formula of this alkane.

 Naming Alkanes – Single Branch Example

1. Identify the longest carbon chain

= 5 carbons
2. Number the carbon atoms starting from the
end closest to the branch if a branch is
present 5 4 3 2 1

3. Name the side branch and the main chain

= 2-methyl
= pentane
4. Combine all components to write the full name
= 2-methylpentane
 7.3 - 2: Quick Check Q’s
a) Draw the following alkane structural formula in your book:

b) Name this alkane.

c) Write the semi-structural formula of this alkane.

 Naming Alkanes – Multiple Branch Example

1. Identify the longest carbon chain

= 6 carbons
2. Number the carbon atoms starting from the
end closest to the branch if a branch is
present
3. Name the side branches and the main chain 1 2 3 4 5 6

= 2-methyl
= 3-methyl
= hexane
4. Combine all components to write the full name
= 2,3-dimethylhexane
 7.3 - 3: Quick Check Q’s
a) Draw the following alkane as a structural formula in your book:

b) Name this alkane.

c) Write the semi-structural formula of this alkane.

 Alkenes
❖ Alkenes are a homologous series of hydrocarbons with at
least one carbon–carbon double bond
❖ The general formula for the alkenes with one double
bond is CnH2n

❖ The presence of a carbon–carbon double bond means the

alkenes are described as unsaturated molecules

❖ The name of an alkene ends in ‘ene’

❖ The simplest alkene is ethene (C2H4)
 Naming Alkenes - Steps
The following rules apply when naming alkenes:
1. Identify the longest carbon chain
2. Number the carbon atoms starting from the end closest to the double bond
3. Name the side branches and the main chain
4. Combine all components to write the full name (alkenes should end in ‘ene’)
* The position of the double bond needs to be indicated: example if on the 2nd carbon: but-2-ene
* Place the number and position of each of the alkyl groups at the beginning of the name
* If two identical side chains are present, use ‘di-’ as a prefix; for three use ‘tri-’; for four use
‘tetra-’
*If there are side chains of different lengths on the molecule, list them in alphabetical order at the
start of the name, with their numbers to indicate their respective positions
 Naming Alkenes – Straight Chain Example

1. Identify the longest carbon chain

= 5 carbons
2. Identify which carbon the double bond is on
= carbon 2
3. There are no side branches
4. 5 carbons prefix = pent, double bond = carbon 2
5. Therefore this is ‘pent-2-ene’
 7.3 - 4: Quick Check Q’s
a) Draw the following alkene structural formula in your book:

b) Name this alkene.

c) Write the semi-structural formula of this alkene.

 Naming Alkenes – Single Branch Example
1. Identify the longest carbon chain
= 4 carbons
2. Number the carbon atoms starting from the end
closest to the double bond
3. Name the side branch and the main chain
= 3-methyl
= but-1-ene
4. Combine all components to write the full name
= 3-methylbut-1-ene
 7.3 - 5: Quick Check Q’s
a) Draw the following alkene structural formula in your book:

b) Name this alkene.

c) Write the semi-structural formula of this alkene.

 Naming Alkenes – Multiple Branch Example
1. Identify the longest carbon chain
= 4 carbons
2. Number the carbon atoms starting from the end
closest to the double bond
3. Name the side branch and the main chain
= 2-methyl
= 3-methyl
= but-1-ene
4. Combine all components to write the full name
= 2,3-dimethylbut-1-ene
 7.3 - 6: Quick Check Q’s
a) Draw the following alkene structural formula in your book:

b) Name this alkene.

c) Write the semi-structural formula of this alkene.

 Alkynes
❖ Alkynes are a homologous series of hydrocarbons with
one carbon–carbon triple bond
❖ The general formula for the alkynes with one triple
bond is CnH2n–2

❖ The presence of a carbon–carbon triple bond means

the alkynes can also be described as unsaturated
molecules

❖ The names of alkynes end with ‘yne’

❖ The simplest alkyne is ethyne (C2H2)

 Naming Alkynes - Steps
❖ The following rules apply when naming alkynes:
1. Identify the longest carbon chain
2. Number the carbon atoms starting from the end closest to the triple bond
3. Name the side branches and the main chain
4. Combine all components to write the full name (alkynes should end in ‘yne’)
* The position of the triple bond needs to be indicated: example if on the 3rd carbon: pent-3-yne
* Place the number and position of each of the alkyl groups at the beginning of the name
* If two identical side chains are present, use ‘di-’ as a prefix; for three use ‘tri-’; for four use
‘tetra-’
*If there are side chains of different lengths on the molecule, list them in alphabetical order at the
start of the name, with their numbers to indicate their respective positions
 7.3 - 7: Quick Check Q’s
a) Draw the following alkyne structural formula in your book:

b) Name this alkyne.

c) Write the semi-structural formula of this alkyne.

 7.3 - 8: Quick Check Q’s
a) Draw the following alkyne structural formula in your book:

b) Name this alkyne.

c) Write the semi-structural formula of this alkyne.

 7.3 - 9: Quick Check Q’s
a) Draw the following alkyne structural formula in your book:

b) Name this alkyne.

c) Write the semi-structural formula of this alkyne.

 Structural Isomers
❖ Molecules that have the same molecular formula but have different arrangements of
atoms are said to be structural isomers of each other

❖ Isomerism is very common in organic chemistry and is one of the main reasons that
carbon can form such a huge range of compounds
❖ The more carbon atoms in the molecule, the more possible isomers there are – this
grows exponentially (see table below)

❖ Structural isomers have different physical properties, as well as names, because the
molecules have different shapes
 7.3 - 10: Quick Check Q’s
a) Define the term ‘isomer’.

b) State what happens to the number of isomers possible as the

length of the carbon chain increases.

c) Explain whether isomers can have the same name.

 Structural Isomers of Alkanes
❖ There is only one molecule that can be formed
with the molecular formula of methane (CH4),
ethane (C2H6) and propane (C3H8)
❖ However, alkanes that have four or more
carbon atoms have more than one possible
structure
❖ Isomers result from branches in the carbon
chain

Example:
❖ butane and 2-methylpropane both share the
molecular formula C4H10, however the atoms
are arranged differently and they have
different names
 7.3 - 11: Quick Check Q’s
a) Draw the structural formulas of the three isomers of pentane.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 Structural Isomers of Alkenes
❖ For alkene molecules that contain more than three carbon atoms,
structural isomers will exist
❖ Isomers may result from branches in the carbon chain, or if the
carbon–carbon double bond is in different positions

Example:
❖ but-1-ene, but-2-ene and methylpropene all share the molecular
formula C4H8, however the atoms are arranged differently and they
have different names
 7.3 - 12: Quick Check Q’s
a) Draw the structural formulas of three isomers of heptene.
Ensure at least one isomer has a branch.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 Structural Isomers of Alkynes
❖ For alkyne molecules that contain more than three carbon
atoms, structural isomers will exist
❖ Isomers may result from branches in the carbon chain, or if the
carbon–carbon triple bond is in different positions
Example:
❖ pent-1-yne, pent-2-yne and 3-methylbut-1-yne all share the
molecular formula C5H8, however the atoms are arranged
differently and they have different names
 7.3 - 13: Quick Check Q’s
a) Draw the structural formulas of three isomers of hexyne.
Ensure at least one isomer has a branch.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 7.4 – Haloalkanes, Alcohols
and Carboxylic Acids
Key Knowledge and Skills
Families of organic compounds:
❖ Representations of organic compounds (structural formulas,
semi-structural formulas) and naming according to the International
Union of Pure and Applied Chemistry (IUPAC) systematic nomenclature
(haloalkanes, alcohols and carboxylic acids)
❖ The grouping of hydrocarbon compounds into families (haloalkanes,
alcohols and carboxylic acids) based upon similarities in their physical
and chemical properties including general formulas and general uses
based on their properties
 New Vocab!
Term Definition

Functional Group An atom or group of atoms attached to or part of a hydrocarbon chain that
influence the physical and chemical properties of the molecule
Haloalkane Alkanes that contain at least one halogen (F, Cl, Br or I) atom.

Alcohol Alkanes that contain an OH group and have the general formula CnH2n+1OH

Carboxylic Acid Alkanes that contain a COOH group and have the general formula CnH2n+1COOH

Ester An organic compound formed from a condensation reaction between an alcohol

and a carboxylic acid; they contain a COO group
 Functional Groups
❖ Many organic molecules contain other atoms as well as carbon and
hydrogen
❖ The presence of different atoms in organic compounds increases
their chemical reactivities
❖ While carbon atoms are covalently bonded only to other carbon and
hydrogen atoms in alkanes, alkenes and alkynes, it is possible for
carbon to form covalent bonds with other atoms or groups of atoms
called functional groups
❖ A functional group is an atom or a group of atoms that gives a
specific set of chemical properties to a molecule containing those
atoms

For example:
❖ The functional group of alkanes is the carbon-carbon single bond
❖ The functional group of alkenes is the carbon-carbon double bond
❖ The functional group of alkynes is the carbon-carbon triple bond
 7.4 - 1: Quick Check Q’s
a) Define the term ‘functional group’.

b) State the functional group that is present in:

i) alkanes
ii) alkenes
iii) alkynes
 Haloalkanes
❖ Haloalkanes are the products formed when alkanes and halogens react.

❖ Haloalkanes are not classified as hydrocarbons, because they contain a

halogen atom (Cl, F, Br or I).

❖ The functional group in haloalkanes is the halogen.

❖ Haloalkanes are used as flame retardants in fire extinguishers,

refrigerants, aerosol spray propellants, solvents and pharmaceuticals.
❖ Because of their toxicity and impact on the environment, the use of
some haloalkanes has been reduced over time.
 7.4 - 2: Quick Check Q’s
a) State how haloalkanes are made.

b) Explain whether haloalkanes are hydrocarbons.

c) Identify the functional group present in haloalkanes.

 Naming Haloalkanes - Steps
The following rules apply when naming alkanes:
1. Identify the longest carbon chain
2. Number the carbon atoms starting from the end closest to the halogen
3. Name the halogen (fluoro, chloro, bromo or iodo)
4. Combine all components to write the full name (haloalkanes should end in ‘ane’)
* The position of the halogen needs to be indicated: example if chlorine is on the 2nd
carbon: 2-chloro
* If two identical halogens are present, use ‘di-’ as a prefix; for three use ‘tri-’; for
four use ‘tetra-’: example: 2,3-dichloro
 Naming Haloalkanes – Single Halogen Example

1. Identify the longest carbon chain

= 4 carbons
2. Identify which carbon the halogen is on
= carbon 1
3. 4 carbons prefix = but, halogen =
1-chloro
4. Therefore this is ‘1-chlorobutane’

*if it was an F atom = 1-fluro

*if it was a Br atom = 1-bromo
*if it was an I atom = 1-iodo
 7.4 - 3: Quick Check Q’s
a) Draw the following haloalkane structural formula in your book:

b) Name this haloalkane.

c) Write the semi-structural formula of this haloalkane.

 Naming Haloalkanes – Multiple Halogen Example

1. Identify the longest carbon chain

= 3 carbons
2. Identify which carbon the halogens are on
= carbon 1 and 2
3. 3 carbons prefix = prop, halogen =
1,2-dibromo
4. Therefore this is ‘1,2-dibromopropane’

*if it was an F atom = 1,2-difluro

*if it was a Cl atom = 1,2-dichloro
*if it was an I atom = 1,2-diiodo
 7.4 - 4: Quick Check Q’s
a) Draw the following haloalkane structural formula in your book:

b) Name this haloalkane.

c) Write the semi-structural formula of this haloalkane.

 7.4 - 5: Quick Check Q’s
a) Draw the following haloalkane structural formula in your book:

b) Name this haloalkane.

c) Write the semi-structural formula of this haloalkane.

 7.4 - 6: Quick Check Q’s
a) Draw the following haloalkane structural formula in your book:

b) Name this haloalkane.

c) Write the semi-structural formula of this haloalkane.

 Structural Isomers of Haloalkanes
❖ For haloalkane molecules that contain more than two carbon
atoms, structural isomers will exist
❖ Isomers may result from branches in the carbon chain, or if the
halogen atoms are in different positions

Example:
❖ 1,1-dichloroethane and 1,2-dichloroethane both share the
molecular formula C2H4Cl2, however the atoms are arranged
differently and they have different names
 7.4 - 7: Quick Check Q’s
a) Draw the structural formulas of three isomers that have the
formula C3H6F2.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 Alcohols
❖ The functional group in alcohols is made up of
an oxygen atom bonded to a hydrogen atom

❖ This ‘OH’ group is known as a hydroxyl group

and replaces one hydrogen in the structure of an
alkane

❖ The general formula for an alcohol is CnH2n+1OH

❖ This is an example of a homologous series, as
each alcohol differs by a ‘CH2’ unit
 7.4 - 8: Quick Check Q’s
a) Name and give the formula of the functional group present in
alcohols.

b) State the general formula for alcohols.

 Naming Alcohols - Steps
The following rules apply when naming alcohols:
1. Identify the longest carbon chain and the functional group that is present (OH = alcohol)
2. Number the carbon atoms starting from the end closest to the functional group
3. Name the side branches and the main chain
4. Combine all components to write the full name (alcohols should end in ‘ol’)

* The position of the OH group needs to be indicated: example if on the 3rd carbon: pentan-3-ol
* Place the number and position of each of the alkyl groups at the beginning of the name
* If two identical side chains are present, use ‘di-’ as a prefix; for three use ‘tri-’
*If there are side chains of different lengths on the molecule, list them in alphabetical order at
the start of the name, with their numbers to indicate their respective positions
 Naming Alcohols – Straight Chain Example

1. Identify the longest carbon chain

= 3 carbons
2. Identify which carbon the OH
functional group is on
= carbon 1
3. 3 carbons prefix = propan, OH = 1-ol
4. Therefore this is ‘propan-1-ol’
 7.4 - 9: Quick Check Q’s
a) Draw the following alcohol structural formula in your book:

b) Name this alcohol.

c) Write the semi-structural formula of this alcohol.

 Naming Alcohols – Straight Chain with Branch Example

1. Identify the longest carbon chain

= 4 carbons
2. Identify which carbon the OH
functional group is on
= carbon 2
3. Identify which carbon the branch is on
= carbon 3
4. 4 carbons prefix = butan, OH = 2-ol,
branch = 3-methyl
5. Therefore this is ‘3-methylbutan-2-ol’
 7.4 - 10: Quick Check Q’s
a) Draw the following alcohol structural formula in your book:

b) Name this alcohol.

c) Write the semi-structural formula of this alcohol.

 7.4 - 11: Quick Check Q’s
a) Draw the following alcohol structural formula in your book:

b) Name this alcohol.

c) Write the semi-structural formula of this alcohol.

 Structural Isomers of Alcohols
❖ Alcohols with more than two carbon
atoms have more than one position
where the hydroxyl functional group
may be and can therefore have
structural isomers

❖ Isomers may result from branches in the

carbon chain, or if the OH group is in
different positions

Example:
❖ All of the alcohols to the right share the
molecular formula C4H9OH, however the
atoms are arranged differently and they
have different names
 7.4 - 12: Quick Check Q’s
a) Draw the structural formulas of three isomers that have the formula
C5H11OH. Ensure at least one of the isomers has a branch.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 Carboxylic Acids
❖ Carboxylic acids are compounds that are
weak acids which are often present in food,
giving it a sour taste

❖ Carboxylic acids are identified by the

presence of a carboxyl functional group
(COOH) which replaces one hydrogen in the
structure of an alkane
❖ This functional group can only be present on
the first carbon - it cannot be moved to
other carbons in the structure

❖ The general formula for an alcohol is

CnH2n+1COOH
❖ This is an example of a homologous series, as
each carboxylic acid differs by a ‘CH2’ unit
 7.4 - 13: Quick Check Q’s
a) Name and give the formula of the functional group present in
carboxylic acids.

b) State the general formula for carboxylic acids.

 Naming Carboxylic Acids - Steps
The following rules apply when naming carboxylic acids:
1. Identify the longest carbon chain
2. Identify the functional group that is present (COOH = carboxylic acid)
3. Number the carbon atoms starting from the end closest to the functional group
4. Name the side branches and the main chain
5. Combine all components to write the full name (carboxylic acids should end in ‘oic acid’)

* Place the number and position of each of the alkyl groups at the beginning of the name
* If two identical side chains are present, use ‘di-’ as a prefix; for three use ‘tri-’
*If there are alkyl side chains of different lengths on the molecule, list them in alphabetical order
at the start of the name, with their numbers to indicate their respective positions
 Naming Carboxylic Acids – Straight Chain Example

1. Identify the longest carbon chain

= 4 carbons
2. 4 carbons prefix = butan, COOH = oic
acid
3. Therefore this is ‘butanoic acid’
 7.4 - 14: Quick Check Q’s
a) Draw the following carboxylic acid structural formula in your book:

b) Name this carboxylic acid.

c) Write the semi-structural formula of this carboxylic acid.

 Naming Carboxylic Acids – Branch Example

1. Identify the longest carbon chain

= 3 carbons
2. Identify which carbon the branch is on
= carbon 2
3. 3 carbons prefix = propan, COOH = oic
acid, branch = 2-methyl
4. Therefore this is ‘2-methylpropanoic acid’

*We also call this ‘methylpropanoic acid’

- As there is no other carbon the methyl can
be put on, we do not need to number the
methyl for this compound
 7.4 - 15: Quick Check Q’s
a) Draw the following carboxylic acid structural formula in your book:

b) Name this carboxylic acid.

c) Write the semi-structural formula of this carboxylic acid.

 7.4 - 16: Quick Check Q’s
a) Draw the following carboxylic acid structural formula in your book:

b) Name this carboxylic acid.

c) Write the semi-structural formula of this carboxylic acid.

 Structural Isomers of Carboxylic Acids
❖ The carboxyl group can only occur on the end of a molecule

❖ Carboxylic acids can form isomers with different branches, but the
carbon atom in the carboxyl group is always carbon number 1

Example:
❖ The below carboxylic acids share the molecular formula C4H9COOH,
however the atoms are arranged differently and they have different
names
 7.4 - 17: Quick Check Q’s
a) Draw the structural formulas of three isomers that have the formula
C7H15COOH.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 Esters
❖ Esters are responsible for many of
natural odours and flavours - many
esters have a fruity smell

❖ Esters are formed when carboxylic

acids react with alcohols in a
condensation reaction (releases
water)

❖ Esters are identified by the presence

of the functional group (COO) -
called an ester link

❖ The esters we are dealing with do not

have branches, so we do not need to
worry about them when
naming/drawing
 7.4 - 18: Quick Check Q’s
a) Name and give the formula of the functional group present in
esters.

b) Describe how esters are made.

 Naming Esters - Steps
The following rules apply when naming esters:
1. Identify the functional group that is present (COO = ester)
2. Number the carbon atoms that are attached to the C side of the functional
group – this part comes from the carboxylic acid and will end in ‘oate’
3. Number the carbon atoms that are attached to the O side of the functional
group – this part comes from the alcohol and will end in ‘yl’
4. Combine the ‘yl’ portion with the ‘oate’ portion

Example:
An ester made from ethanoic acid and pentanol would be called pentyl ethanoate
 7.4 - 19: Quick Check Q’s
Name the esters produced from the following alcohols and
carboxylic acids:

a) Butanol and Propanoic Acid

b) Ethanol and Heptanoic Acid

c) Octanol and Pentanoic Acid

 Naming Esters Example

1. Circle the ester bond

2. Count the carbons on the side of the
single bonded oxygen
= 2 = eth(yl)
3. Count the carbons on the side of the
double bonded oxygen
= 3 = prop(anoate)
4. Therefore this is ‘ethyl propanoate’
 7.4 - 20: Quick Check Q’s
a) Draw the following ester structural formula in your book:

b) Name this ester.

c) Write the semi-structural formula of this ester.

 7.4 - 21: Quick Check Q’s
a) Draw the following ester structural formula in your book:

b) Name this ester.

c) Write the semi-structural formula of this ester.

 Structural Isomers of Esters
❖ Esters can form isomers by moving the ester
functional group.

Example:
❖ The esters to the right share the molecular formula
C4H8O2, however the atoms are arranged differently
and they have different names →
 7.4 - 22: Quick Check Q’s
a) Draw the structural formulas of three ester isomers that have
the formula C7H14O2.

b) Name each isomer.

c) Write the semi-structural formulas of each isomer.

 7.4 - 23: Quick Check Q’s
Butanoic acid and Octan-1-ol are placed in a test tube to react.

a) Write the worded chemical equation for this reaction.

b) Draw the reaction using structural formulas.

 Properties of Organic
Compounds
Key Knowledge and Skills
Families of organic compounds:
❖ The grouping of hydrocarbon compounds into families based upon
similarities in their physical and chemical properties including
general formulas and general uses based on their properties
Properties of Hydrocarbons
Properties of alkanes, alkenes and alkynes include:
❖ Non-polar
❖ Insoluble in water
❖ The only attractive force between the molecules is
dispersion forces
❖ As the number of carbons and the size of the molecules
increase, the strength of the dispersion forces
increases, so the melting and boiling points increase
❖ If a molecule is branched instead of a straight chain,
this lowers the boiling point; branches prevent the
molecules from coming closer together and so the
dispersion forces have less effect
❖ Alkenes and alkynes have higher boiling points than
alkanes, due to their double/triple bonds - alkyne
molecules grip/stick together the most, followed by
alkenes and then alkanes
1: Quick Check Q’s
For the molecules: hexane, ethane and propane answer the
following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Describe whether these molecules soluble in water.
2: Quick Check Q’s
For the molecules: pentane, 2-methylbutane and
2,2-dimethylpropane answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Describe whether these molecules soluble in water.
3: Quick Check Q’s
For the molecules: but-1-yne, butane and but-1-ene answer the
following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Describe whether these molecules soluble in water.
Haloalkanes
Properties of haloalkanes include:
❖ Haloalkanes have higher melting and boiling points than
the corresponding alkanes because their molecules are
polar; the halogen atoms are strongly electronegative so
there are dipole-dipole forces present between
haloalkane molecules, which require more energy to
break than dispersion forces
❖ The melting and boiling points increase with increasing
molecular size (more dispersion forces)
❖ Haloalkanes are only slightly soluble in water but are
more soluble in organic solvents
❖ They are more reactive than alkanes
4: Quick Check Q’s
For the molecules: 1-chloropropane, 1-chloropentane and
1-chloroheptane answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Describe whether these molecules soluble in water.
5: Quick Check Q’s
For the molecules: 2-bromooctane, octane and oct–2-ene
answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Describe whether these molecules soluble in water.
 Alcohols
Properties of alcohols include:
❖ Higher boiling points than hydrocarbons - boiling point increases
as the size of the alcohol molecule increases
❖ Are liquids at room temperature – unlike hydrocarbons which
tend to be gases
❖ Have an ‘OH’ group, which allows hydrogen bonding to occur
between molecules and strengthens the intermolecular bonding
❖ Can be soluble in water as the ‘OH’ group allows hydrogen bonds
to form between water molecules and alcohol molecules
❖ Solubility decreases as the length of the carbon chain increases -
a longer carbon chain means that more of the molecule is
nonpolar and the molecule becomes less polar overall
6: Quick Check Q’s
For the molecules: pentan-2-ol, butan-2-ol and heptan-1-ol
answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Order the molecules from least to most soluble.
e) Justify your order.
7: Quick Check Q’s
For the molecules: pentan-2-ol, pentane and pent-2-yne
answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Describe whether these molecules soluble in water.
 Carboxylic Acids
Properties of carboxylic acids include:
❖ Are commonly found in nature: for example giving a
sour taste to lemon juice and vinegar, or making an
ant bite sting
❖ Are polar - oxygen is much more electronegative
than carbon and hydrogen
❖ Have higher boiling points compared to alcohols –
this is a direct result of the presence of hydrogen
bonds between carboxylic acid molecules
❖ Have high solubility – can form x2 hydrogen bonds
with water molecules
❖ Solubility decreases as they increase in size - a
longer carbon chain means that more of the
molecule is nonpolar
8: Quick Check Q’s
For the molecules: ethanoic acid, hexanoic acid and nonanoic
acid answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Order the molecules from least to most soluble.
e) Justify your order.
9: Quick Check Q’s
For the molecules: propan-1-ol, propane and propanoic acid
answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Order the molecules from least to most soluble.
e) Justify your order.
 Esters
Properties of esters include:
❖ Esters have relatively low boiling points because the
intermolecular attraction is dipole–dipole (and
dispersion forces) instead of the hydrogen bonding that
occurs in carboxylic acids/alcohols
❖ The bigger the ester, the higher the boiling point as
there are more dispersion forces present
❖ Although esters cannot form hydrogen bonds with
themselves, they can with water - this leads to the
same solubility trend that is observed for alcohols and
carboxylic acids
❖ Smaller esters are moderately soluble but, as the
number of carbons increases, they become less and
less soluble
10: Quick Check Q’s
For the molecules: methyl ethanoate, butly ethanoate and
propyl ethanoate answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Order the molecules from least to most soluble.
e) Justify your order.
11: Quick Check Q’s
For the molecules: hexan-1-ol, propyl propanoate and hexanoic
acid answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Order the molecules from least to most soluble.
e) Justify your order.
12: Quick Check Q’s
For the molecules: hept-1-ene, heptanoic acid, hept-1-yne,
heptan-2-ol, heptane, 1-fluroroheptane and ethyl pentanoate
answer the following questions:
a) Draw the structural formula of each molecule.
b) Order the molecules from lowest to highest boiling point.
c) Justify your order.
d) Order the molecules from least to most soluble.
e) Justify your order.