Chapter 8: Organic compounds

Key knowledge
 To understand how we obtain crude oil and how it is used in our everyday lives. To appreciate the materials and products used
in every day life that are made from organic compounds (e.g. synthetic fabrics, foods, natural medicines, pesticides cosmetics,
organic solvents, car parts artificial hearts) and the benefit of those product for society. But to also appreciate the health and/or
environmental hazards they pose.
 To understand that plant-based biomass can be used as an alternative renewable source of organic chemicals (eg solvents,
pharmaceuticals, adhesives, dyes and paints) that are traditionally derived from fossil fuels.
 To understand the grouping of hydrocarbon compounds into families (alkanes, haloalkanes, alkenes, alkynes, alcohols,
carboxylic acids) based on their similarities of physical and chemical properties as well as their general formulae and general
uses based on their properties.
 Be able to represent these organic compounds with structural formulas, semi-structural formulas and naming according to the
International Union of Pure and Applied Chemistry (IUPAC) systematic nomenclature (limited to non-cyclic compound up to
C8 and structural isomers up to C5)

• Crude oil • • Polymer

Key Terms • Boiling point Incomplete combustion
• Dimer • • Renewable
• Addition reaction • Carboxyl group Locant
• Fractional distillation • • Saturated
• Alcohol • Carboxylatre ion Melting point
• Functional group • • Semi structural formula
• Alkane • Carboxylic acid Molecular formula
• General formula • • Stem name
• Alkene • Chemical property Non- renewable
• Haloalkane • • Structural formula
• Alkyl group • Combustion Organic chemistry
• Halogen • • Structural isomer
• Alkyl side chain • Complete combustion Organic compound
• Homologous series • • Substitution reaction
• (branch) • Condensed structural Photosynthesis
• Hydrocarbon • • Terminal carbon
• Bio-derived formula Physical property
• Hydroxyl group • • Unsaturated
• bioethanol Plant sourced biomass
• Weak acid
 8.1 Organic materials
Things you should already know about Carbon explaining why it forms more compound than all the other element put together:
• It has 4 valence electrons allowing it to potentially form covalent bonds with up to 4 different atoms.
• It can form strong covalent bonds with other carbon atoms to form long chains or cyclic compounds.
• It can form covalent bonds as a combination of single, double and triple bonds

Examples of carbon based molecules include: caffeine, petrol, pesticides, plastics and artificial flavours (esters).

Many of these are produced from crude oil. Crude oil is produced by the effects of fossilization (heat and pressure
on dead animals, plants and microorganisms) trapped in the Earth’s crust for millions of years.

Throughout this chapter you will hear the term hydrocarbon, this term describes any compound made from
carbon and hydrogen.

The term organic chemistry is the branch of chemistry that focuses on carbon compounds.

Petroleum
Crude Oil

Fossil fuels (coal, oil and natural gas) come from the remains of plant and animals that were trapped in the earth’s crust millions of years ago. Over millions of years
the high temperatures and pressures caused the oils and fats to turn into hydrocarbons, known as crude oil.

Crude oil has a low density and as a result and would naturally move up to the surface of the earth if it could penetrate through impervious (unable to be passed
through) rock. As a result an oil field is created .

Impervious rock

Petrochemical companies drill into the earth’s crust to tap into crude oil or natural gas deposits. Crude oil is transported from oil fields to oil refineries
where it undergoes fractional distillation in a fractionating tower. In the process the crude oil is separated into its various component (fractions). The
lighter hydrocarbon alkanes are collected at the top of the tower whilst the heavier hydrocarbons are collected closer to the bottom. (See diagram)
Fractional distillation

• The crude oil is heated to over 300 0 C. At these temperature most

hydrocarbons are gases. As they pass into the bottom of the
fractionating tower they rise.

• As the hydrocarbons rise they cool. As seen in the diagram the

smaller hydrocarbons reach the top of the tower (C 1 to C4 )

• When a substance in the vapour reaches a height equal to the

substance boiling point it begins to condense to a liquid.

• The bubble caps direct that condensation to the trays and the
various liquid fractions are collected.

• Heavier fractions undergo a process called cracking. This process

breaks the larger hydrocarbon into smaller molecules using heat
and a catalyst.

Crude oil heated to

>3000 C
While many products can be made from the components of crude oil, the finite availability of this resource means that it will eventually used up if it is
our only source of hydrocarbon raw materials. So what can be done?
• Recycling material that are made from hydrocarbons, such as polymers and making them into new products.
• Replacing petrol and diesel-fuelled cars with electric cars.
• Reusing materials derived from crude oil, rather than disposing them after one use.
• Finding renewable replacement material for those derived from crude oil. These renewable replacement materials may be sourced from plants
Plant sourced biomass
The term plant- sourced biomass refers to a carbon based material that has come from plants. Eg Aspirin
(acetylsalicylic acid) is closely related to the active ingredient in willow bark, obtained from willow trees
which as been used for pain relief for more than 2000 years.

Plants can be an alternative renewable source of organic chemicals that can be transformed into a range of
products. They are able to fix carbon dioxide from the atmosphere into glucose via the process known as
photosynthesis, making a plant source of carbon a renewable resource.

Polyethene from sugar

Ethanol, C2H5OH, is a compound that is used as a starting compound for many other organic
compounds eg polyethene (plastic). Polyethene is used for making common products such as
clingwrap,LEGO and food containers. Polyethene derived from plant sources is known as bio-
polyethene.
Once the plant is harvested, the sugar is extracted and turned into ethanol
(bioethanol).

This process use CO2 from the atmosphere converting it into ethanol and
then releases some in the process of fermentation. Importantly though, not
as much is released as is absorbed.
This is a direct contrast to when ethene is produced from crude oil which
uses very large amounts of CO2 .
Many companies are now using bio-derived polyethene rather than crude
oil derived polyethene, making product more environmentally friendly.
8.2 Hydrocarbons: Alkanes
• Hydrocarbons are composed of only hydrogen and carbon. The simplest hydrocarbon is methane (CH 4). This is a colourless gas and is
the main component of natural gas used in many homes for heating and cooking.

• Hydrocarbons can be classified in several groups . The first group we will look at is the alkanes.

• All alkanes contain only single bonds and due to this are said to be saturated. (This means composed only of
single bonds)
• Each member of the series differs by a –CH2
– unit. This is known as a homologous
series.
• All member of the same homologous series
have a similar structure, a pattern to their
physical properties, similar chemical
properties and the same general formula.
• Alkanes are non-polar, insoluble in water
and have dispersion forces as part of their
intermolecular bonding.
• As the alkane increases in size the strength
of its dispersion forces increases (larger
molecule) and hence B.P and M.P
increases.
• The viscosity (thickness of the liquid)
increases as the alkane gets longer.
• The volatility (intensity of the liquid
burning) decreases as the alkane gets longer .

• As can be seen above the stem name (or parent name) indicates the number
of carbon atoms meth=1, eth = 2, prop= 3, but=4, pent=5, hex=6, hept=7,
oct=8, non= 9 and dec=10.
General formula of an alkane: CnH2n+2 (where n= number of carbon atoms) • Alkanes are named by adding –ane after the stem name

Example an alkane with 10 carbons will 2n+2 H atoms ie C 10H22 (2 x 10 + 2 = 22) : Decane
Reactions of alkanes
• Although alkanes are generally unreactive their main use as fuels mean that they react with oxygen in a combustion reaction. (eg petrol burning in a
car engine or natural gas stove burning)
• If the supply of oxygen is plentiful then the reaction will undergo complete combustion producing carbon dioxide and water.

Note the equation is balanced and all states are provided. You are expected to be able to show the complete combustion of any alkane. Try decane!

Writing formulas of alkanes

• Structural formulas is very similar to valence

structures (showing all bond in the molecule).

• Semi structural formulas (Condensed structural

formulas), show the atoms that are connected to
each carbon but do not show the bonds.

• The shape of the molecule can be drawn in 2-

dimensional format if the shape of the molecule is
not important. Eg butane, C4H10
Structural isomers of alkanes

There is only one molecule that can be formed with methane, ethane and propane.
However alkanes that have four or more carbon atoms have more than one possible structure. Molecules that have the
same molecular formula but have different arrangement of atoms are said to be structural isomers of each other.
eg. butane, C4H10 has two structural isomers.

Pentane, C5H12 and hexane C6H14 have 3 and 5

structural isomers each. Can you draw them?

Alkyl groups
Alkyl group s are a group of C and H atoms that have one less hydrogen than their corresponding alkane of the same name.
So their general formula is –CnH2n+1 so in the example above the CH3 branching off the middle carbon is a methyl group

Structural isomers may have the same number of C and H atoms but their different arrangement gives them different physical and
chemical properties. The 5 isomers of hexane all have different melting and boiling points. Can you suggest why?
The more branching that occurs the less closely that the
molecules can pack together which means that the
dispersion forces between molecules can be overcome at
relatively lower temperatures.
Naming alkanes

The IUPAC system (International Union of Pure and Applied Chemists) is used to name carbon compounds. The IUPAC rules are :

1. Find the longest chain of carbons. This determines the basis of the name.
2. Number the carbon atoms, starting from the end closest to any branch.
3. Name the branch (alkyl group) using the number of carbon atoms. This goes at the beginning of the compound’s name.
4. If there are several branches, list them in alphabetical order, with their numbers to indicate their respective positions.
5. Prefixes such as di- , tri- , and tetra are used if the same group is repeated.

Note the use of the di- to indicate the presence of two methyl side groups and the
numbering to indicate their position along the longest continuous carbon chain. ie 3,3-
indicates that both methyl side branches come off the third carbon atom.
Simo’s revision questions: Check for understanding
1. Give the correct name of the following molecules

a. b.

2. List these molecules in order of increasing height that they are collected from in a
fractionating tower: Butane, ethane, nonane.

3. Draw each of these hydrocarbons

a. 2-methylbutane b. 2,3,4-trimethylhexane

4. a. Name the molecule on the right.

b. Show it’s empirical formula, molecular formula and semistructural formula
c. Draw and name three of the possible isomers of the molecule below.

5. How many hydrogen atoms will the alkane with 16 carbon atoms have?

6. Ethane is a gas at room temperature while pentane is a liquid. Explain carefully why
pentane has a higher boiling point. Include a diagram in your answer.
Hydrocarbons: Alkenes
We mentioned previously that alkane are saturated compounds because they only contain single bonds. Compounds that have double (alkenes) or triple bonds (alkynes) present are said to be unsaturated hydrocarbons.

Alkenes
Alkenes are a homologous series of hydrocarbons with at least one carbon-carbon double bond. The fact that they are double bond means that they are more reactive than alkanes, which do not have a carbon-carbon double bond.

The name of an alkene ends in -ene and the stem name is the same as that used for alkanes.

General formula of an alkene: CnH2n (where n= number of carbon atoms)

Example an alkene with 8 carbons will have 2n H atoms ie C 8H16 (2 x 8 = 16) : Octene

• As can be seen the simplest alkene is ethene

(C2H4) and each subsequent alkene in the series
has an additional –CH2
• The H-C-H bond angle around a carbon atom
with the double bond is 120O
• All alkenes (like alkanes) are non-polar and as
a result do not dissolve in water.
Writing formulas of alkenes Structural isomers of alkenes

Like alkanes, there are a variety of ways for writing For alkene molecules that have four carbons or more structural isomers
the formulas of alkenes. exist. The isomers may result from:
• branches in the carbon chain eg. 2-methylprop-1-ene
• the positioning of the carbon-carbon double bond eg but-2-ene

2-methylprop-1-ene

So the semistructural formula for propene , CH 2 CHCH3 shows

the we have a CH2 bonded to a CH which inturn is bonded to a
CH3
Naming alkenes
• Carbons are numbered from the end of the carbon chain that gives
the lowest number to the first carbon in the double bond.
• The location of the double bond is indicated by this number. ie
but-1-ene and but-2-ene

Although it has been common practice to omit numbers when a structure is unambiguous eg propene not prop-1-ene, the IUPAC rules
state the following:
• A locant ( number indicating the location of a functional group ie double bond or alkyl group) can only be omitted if it is a 1 and
the location is unambiguous.
• If one locant is needed, then all locants should be specified for that molecule.

For example, the locant is omitted in butanoic acid, chloromethane, ethanol, propene. In contrast locants are required in 2-methylpropane
(you can’t say methylpropane) and 2 –methylprop-1-ene (not methypropene or 2 methyl propene)

Naming alkenes

The IUPAC system (International Union of Pure and Applied Chemists) is used to name carbon compounds. The IUPAC rules are :

1. Find the longest unbranched chain of carbons. This chain must include the double bound
2. Number the carbon atoms, starting from the end of the chain that will give the smallest numbers to double bonded carbon atoms.
3. Name the branch (alkyl group) using the number of carbon atoms. This goes at the beginning of the compound’s name.
4. Identify the position of the double bond by the number of the first carbon atom involved in the bond. Use the suffix-ene to indicate the presence of the
double bound eg pent-2-ene
5. If there are several branches, list them in alphabetical order, with their numbers to indicate their respective positions.
6. Prefixes such as di- , tri- , and tetra are used if the same group is repeated.
Name this molecule Can you name these molecules?

3-methylbut-1-ene

2,3-dimethylbut-1-ene

Pent-2-ene

3-methylpent-2-ene
4-methylpent-2-ene
Physical and chemical properties of alkenes

Alkene and alkanes have very similar physical properties because their chain length only differs by two
hydrogen atoms. In contrast though their chemical properties are strongly influenced by the presence of
the carbon- carbon double bond, making them some of the most useful hydrocarbons we derive from
crude oil.

All alkenes are non-polar and hence do not dissolve in water. Like
alkane as the length of the carbon chain increase so too does the
melting and boiling points due to the increasing strength of the
dispersion forces between the molecules.
Reactions of alkenes

• Like alkane, all alkenes undergo complete combustion when there is a plentiful supply of oxygen.
• The products of the reaction are, as in alkanes, carbon dioxide and water.
• You are expected to be able to show the complete combustion of any alkene, including balancing and states of reactant and products.

Addition reactions of alkenes

• The presence of the carbon-carbon double bond allows alkenes to take part in addition reactions. The double bond is broken and a bond is formed
between the carbon and one of the reactants (ie it is added to the alkene). A single C-C bond is formed.
 Hydrocarbons: Alkynes (Please note this is no longer on the Unit 1 and 2 study guide but it is good to know this for Year 12 Chemistry)

Alkynes are a homologous series of hydrocarbons with one carbon-carbon triple bond. The fact that they have a triple bond means that they too
can be described as unsaturated molecules.

General formula of an alkyne: CnH2n-2 (where n= number of carbon atoms)

Example an alkyne with 6 carbons will have 2n-2 H atoms ie C 6H10 (2 x 6 -2 = 10) : hexyne

The name of an alkyne ends in -yne and the stem name is the same as that used for alkanes.
The simplest alkyne is ethyne, C2H2 and each subsequent alkyne in the series has an additional –CH 2 unit.
Writing formulas of alkynes

Structural isomers of alkynes

• Structural isomers exist for alkynes with more than 3 carbon atoms
• Some isomers have branches on the carbon chain eg 2-methylbut-1-yne
• Some isomers have the triple bond in different positions. Eg pent-1-yne and pent-2-yne
• The position of the triple bond can make a significant difference to the boiling point.
Naming alkene and alkynes

1. Find the longest unbranched chain of carbons. For alkenes, the chain must
include the double bond and for alkynes the triple bond.
2. Number the carbon atoms in the chain from the end of the chain that will
give the smallest numbers to double bonded or triple bonded carbon atoms
and to branching groups.
3. Name the branch (alkyl group) using the number of carbon atoms after the
alkane from which they are derived.
4. Identify the position of the double or triple bond by the number of the first
carbon atom involved in the bond. Use the suffix –ene to indicate the
presence of a double bond eh hex-2-ene and –yne to show the presence of a
triple bond eg hex-2-yne.
5. List the number and position of each of the alkyl groups at the beginning of
the compound’s name in alphabetical order.
6. Prefixes such as di- , tri- , and tetra are used if the same group is repeated.
Questions to complete

Q1-5 p 264
Q6-10 p265

Simo’s check for understanding

1. Give the molecular formula of the following:

a. butyne b. butane c. hexane d. ethyne

2. Draw each of the following hydrocarbons.

a. Propyne b. but-2-ene c. 2-methylbutane d. 2,3,4-trimethylhexane

3. Name each of the following:

a. b.
8.3 Haloalkanes
• Haloalkanes are organic compound which have one or more hydrogen atom replaced by a halogen (Br, Cl , I or F).
• This new homologous series contains a functional group, which is an atom or group of atoms that gives a characteristic set of chemical
properties toa molecule containing those atoms.

The halogen elements are in Group 17 of the periodic table. As we know all halogen atoms have 7
valence electrons which means that they can form a single covalent bond with a carbon atom.

The general formula of haloalkanes is CnH2n+1 X, where X is a halogen (F, Cl, Br, I)
Naming structural isomers of haloalkanes c. 1-chloro-2-methylpropane d. 2-chloro-2-methylpropane

a. 1-chlorobutane b. 2-chlorobutane
Isomers may result from branches in the carbon chain or if the halogen atoms are in different locations. ie All the above isomers of
C4H9Cl . Can you name them?

• When naming haloalkane isomers, the carbons are numbered from the end of the carbon chain that is closest to the first halogen in the molecule.
• The location of the halogen in the molecule is indicated by this number. In (a) above we start our counting from the carbon on the left as this is
where the chlorine atom is closest.

Rules for the systematic naming of alkanes

1. Place the name of the specific halo functional group at the start of the parent alkane’s name.
2. Number the carbons of the parent chain, beginning at the end closest to the first halo group.
3. If there is more than one type of the same type of halogen atom, us ethe prefix “di-” or “tri-”.
4. If more than one type of halo functional group or alkyl group is present, lis them in alphabetical order.

2-bromo-2-chloro-3-methylbutane
Try this

2-bromo-3methylpentane
Physical and chemical properties of haloalkanes

The presence of the halogen atom has the effect of making the haloalkane molecule more polar due to the electronegativity of the halogen atom. This is in
complete contrast to the non polar nature of alkanes and alkenes. This influences the physical properties of the haloalkanes, as the intermolecular forces
will be stronger than in alkanes and alkenes.
The halogen atom also affects the chemical properties of these compounds making haloalkanes more reactive than the alkanes and alkenes.

Physical properties and uses of haloalkanes

POLARITY: Most haloalkanes are polar,mainly due to the electronegativity of the halogen atom in
comparison with the H atom making the molecule asymmetrical. Eg chloromethane. The exception to this
is if the molecule is symmetrical as in the case of tetrachloromethane which is non-polar.
SOLUBILITY: As a result of this polarity in asymmetrical molecules haloalkanes are slightly soluble in
water but as the length of the non-polar hydrocarbon chain increases so too does the solubility in water.
MELTING and BOILING POINTS: Like alkanes, as the length of the carbon chain increases so too
does the melting and poiling points due to the increased number of dispersion forces and the presence of
the polar carbon- halogen bond which introduces dipole-dipole attractions further increasing the melting
and boiling points .
SIZE OF HALOGEN: The size of the halogen atom will also influence the strength of the dispersion
forces between haloalkane molecules. As the halogen atom gets larger the boiling point increases
significantly.
 What can you deduce about the boiling point from each of theses two tables?

In table 8.3.3 you can see that the boiling point of each haloalkane increases significantly as the size of the halogen increases from
chlorine to bromine and then iodine.

In table 8.3.4 you can see that the boiling point of each haloalkane with the same halogen increases significantly as the length of
the carbon chain increases and their solubility decreases as the chain length increases due to the increasing influence of the non-
polar part of the molecule.
Chemical properties of haloalkanes

The polarity of the carbon-halogen bond affect the chemical reactivity of haloalkanes. As you may know, the large difference
in the electronegativity between a C-Cl bond ( as compared to the similar electronegativities of C-H bond) means that
haloalkanes will react more readily than alkanes.
As a result of this altered polarity haloalkanes undergo substitution reactions where a hydroxide ion –OH can replace (or
substitute) the Cl atom to make an alcohol which has an –OH group rather than a halogen atom.

Complete Q1-7 p272

 8.4 Alcohols and carboxylic acids
A vast range of organic molecules contain other atoms as well as carbon and hydrogen. This allows the chemical reactivities to be changed as well.
An example is the alcohol methanol, CH 3OH which is very similar to the alkane methane, CH 4 with the only difference that one of the H atoms is
now an –OH group. This makes the molecule polar and enable the compound to be dissolved in water.

Methanol is an example of a group of compounds called alcohols.

Not only is methanol more soluble in water it also has a higher
boiling point . Can you predict why?
methane
methanol

Functional groups
• Whilst in hydrocarbons C atoms are covalently bonded to other carbons or H atom, it is possible for them to form covalent bonds with other
atoms such as –OH (in the example above). These other atoms or groups of atoms are known as functional groups.
• These functional groups give a characteristic set of chemical properties to a molecule containing these atoms.
• Homologous series such as alkanes, alkenes, alkynes, alcohols, carboxylic acids and esters are characterized by the presence of a particular
functional group and in the case of alkenes (carbon-carbon double bond) and alkynes (carbon-carbon triple bond)
• Members of the same homologous series contain the same functional group.
• The presence of the same functional group in these molecules mean that they have similar , although not identical, physical and chemical
properties.
Functional groups include the carbon-
carbon double bond in alkenes,
halogen atoms, hydroxyl groups and
the carboxyl group.

Functional groups
 Alcohols

• Functional groups in alcohols such as methanol and ethanol are made of an –OH group ( an oxygen atom bonded to a H atom). This –OH
group is known as a hydroxyl group.
• As is the case in alkanes, alkenes and alkynes each member of the homologous series of alcohols differs by a –CH 2 unit.
• When naming alcohols as similar pattern is used as in alkanes for the stem name (ie meth- , eth- , pro- etc) but the ending of the name of an
alcohol is always –ol (ie methanol)

Hydroxyl group

Note each semistructural formula

differs by a –CH2 unit
Uses of alcohols
• Many of the small alcohols are used as fuels such as ethanol (E10) mixed with conventional petrol or can be used on its own.
• As in the case of the other hydrocarbons the combustion of alcohols produces carbon dioxide and water.

• Other uses includes in disinfectants, hand sanitisers, solvents, liquor, used as a starting point of other organic compounds, fungicides,
cosmetics and used widely in the plastics industry.

Properties of alcohols
• The boiling points of alcohols increase as the size of the alcohol molecule increases.
• However the boiling points of alcohols are all higher than the corresponding alkanes. Why?
• Alcohols are liquids at room temperatures whereas alkane and alkenes are mainly gases.

• Hydrogen bonding also influences alcohols. H-bonds form

between hydroxyl group and the water molecules.
• This is also the reason that the smaller alcohols are soluble in
water. Why is this not the case for larger alcohols? The larger
alcohols have longer carbon chain which are non polar and
hence the molecule is less polar overall.
 Structural isomers of alcohols

The position of the hydroxyl (-OH) functional group influences the chemical and physical properties of alcohols.

Propan-1-ol Propan-2-ol

Melting point = -126O C Melting point = -89O C

Boiling point = 78O C Boiling point = 82.6O C

Fruity taste (although should not Bitter taste (although should not
be consumed) be consumed)

Less reactive More reactive

Naming alcohols
1. Start with the name of the parent alkane. For propan-2-ol (See above)
2. Remove the ‘e’ from the end and replace with an ‘ol’.
1. Propane
3. The atoms in the longest carbon chain are numbered from 2. Propanol
the end that is closest to the functional group. 3. 2
4. The number of the carbon atom to that the hydroxyl group 4. Propan-2-ol
is bonded is shown before the –ol ending and is separated
by hyphens.
Questions to complete

Q1-6 p 214
Q10-13 p231

Simo’s check for understanding

1. Draw the following molecules.

a. pentan-1-ol b. pentan-3-ol c. 2-methylbutan-1-ol d. 2,2-dimethylpropan-1-ol

2. Which of the following would have he highest boiling point. Why?

butan-1-ol, butane, pentan-1-ol

3. Which of the following is most polar? Why?

octanol (C8H17OH), nonane, or methanol (CH3OH)

4. Name the alcohols below:

a. b. c.
Carboxylic acids
• The carboxylic acids are an important class of organic compounds. These compounds are weak acids often
present in food giving it a sour taste. eg vinegar. Carboxylic acids are also found in some insect venoms whilst
others are formed when wine deteriorates.
Carboxylic acids- Formulas and Structure
• Carboxylic acids can be identified by the functional group called the carboxyl group (-COOH).
• When naming carboxylic acids a similar pattern is used as in alkanes for the stem name (ie meth- , eth- , pro-
etc) but the ending of the name of an carboxylic acid is always –oic acid (ie methanoic acid)
• Successive members of the series differ by a –CH2 unit.
• In this functional group, Carbon is double bonded with the an O atom , single bond to a second oxygen atom
and the second O atom is also bonded to a H atom.
• The –COOH can be regarded as taking the place of a H atom in an alkane, therefore the molecule exhibits a
tetrahedral arrangement in the hydrocarbon part of the molecule but a trigonal planar arrangement in the
carboxyl functional group.

Tetrahedral arrangement in the Trigonal planar arrangement in the

hydrocarbon part of ethanoic carboxylic functional group.
acid (vinegar)

A molecule of ethanoic acid (CH3COOH)

 Naming carboxylic acids

1. Names of carboxylic acids end in ‘oic acid’

2. The carbon in the functional group is counted in the chain
used to name the carboxylic acid ie. CH3COOH has 2 C
atoms and is called ethanoic acid.
3. The carboxyl carbon is always carbon number 1

Structural isomers of carboxylic acids

• Carboxyl group can only occur at the end of the molecule

• Carbon atom in the carboxyl group is always carbon number 1
R groups- are the alkyl groups in front of
the carboxylic acid ie R groups from above
are –H, -CH3 and –C2H5

5-methyl hexanoic acid

Uses of carboxylic acids

• Carboxylic acids are organic acids generally found in nature giving a sour taste to lemon juice and vinegar or
making ant bites sting.

Properties of carboxylic acids

• The carboxyl functional group is made up of a carbonyl group (C=O) and a

hydroxyl group (-OH) – both polar groups with O being more
electronegative than C and H.
• As a result electrons are drawn away from the H atom enabling it to react in
water to form a H+ ion, allowing the functional group to acid as an acid
(proton donator).
• Carboxylic acids are weak acids.
• Carboxylic acids have a higher boiling point than alkanes and even alcohols
due to the presence of H-bonds between carboxylic acid molecules and the
formation of a dimer (two identical molecules bonded together)

Double H- bond in dimer leading to

higher boiling points.
Solubility of carboxylic acids

Carboxylic acids are more soluble in water than alcohols due to the H-bonding that occurs between the carboxyl group of carboxylic acids and water.

The solubility of the carboxylic acids decreases as they increase in size. The reason for this is that larger carboxylic acids have a longer non polar component.

Non- polar section of decanoic acid

Low solubility in water

Questions to complete

Q1-8 p 282
Q14-17 p231

Simo’s check for understanding

1. Draw the following molecules.

a. Propanoic acid b. 2-chloropropanoic acid

2. Which of the following would have the highest boiling point. Why?
butan-1-ol, butane, pentan-1-ol, pentanoic acid

3. Ethanoic acid (vinegar) is a liquid at room temperature while ethane is a gas. Draw both molecules and explain the difference
in boiling points.

Complete Q1-22 p284-286