Module 7: Organic Chemistry

Nomenclature
Nomenclature of organic chemicals

Alkanes
Saturated organic compounds containing only carbon and hydrogen atoms. A compound is
saturated when no more atoms can bind to the compound.

Alkenes
Unsaturated organic compounds containing only carbon and hydrogen atoms and at least one
double bond.

Alkynes
Unsaturated organic compounds with only carbon and hydrogen atoms with at least one triple
bond.

Alcohols
A hydroxyl (-OH) functional group attached to a saturated carbon atom.

Primary- the carbon bonded to the -OH group is only bonded to one alkyl group.
Secondary- the carbon bonded to the -OH group is also bonded to two alkyl groups.
Tertiary- the carbon atom bonded to the -OH group is also bonded to three alkyl groups.

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Aldehydes and Ketones
An aldehyde is where a carbon atom is double bonded to an oxygen and single bonded to a
hydrogen and then bonded to some further chemical group.
Ketones are a double bonded oxygen and has two separate single bonds to further chemical
groups.

Carboxylic acids
A chemical compound containing a -COOH group.

Amines
Amino functional groups consist of one nitrogen atom covalently bonded to two hydrogen
atoms.

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Amides
The amide functional group is represented in a condensed structural formula as -CONH2 and is
always located at the end of a hydrocarbon chain.

Halogenated organic compounds

When hydrocarbons react with halogens, they will take on the halogen atom.
Fluorine = Fluoro-
Chlorine = Chloro-
Bromine = Bromo-
Iodine = Iodo-

Structural isomers

Chain isomers
Isomers that differ based on the carbon backbone.

Position isomers
Isomers that differ based on the location of the various functional groups.

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Functional group isomers
Change the functional groups whilst keeping the molecular formula the same. For example,
cyclohexane and hex 1-ene. The two compounds have the same molecular formula but are
totally different.

Hydrocarbons
Structure and bonding of organic chemical compounds

Boiling points-
• Alkane:
The boiling points increase as the size of the alkane molecule increase, they contain only weak
dispersion as they are non-polar.
• Alkenes and alkynes:
Are also nonpolar so the forces of attraction between then are only weak dispersion forces.
These kinds of molecules also have low boiling points. Alkenes and alkynes boiling points
increase with size.
• Haloalkanes:
Contains dipole dipole attractions as they are polar. Their boiling point is higher.

Melting points-
Melting points are affected by the same factors as boiling points. Chains with even numbers of
carbon atoms pack more efficiently

Solubility in water-
The nonpolar nature of alkanes, alkenes and alkynes makes then insoluble in water. \

Solubility in organic solvents-

Alkanes mix with other nonpolar liquids such as those that contain alkenes or symmetrical haloalkanes.
This is because the forces of attraction between molecules of these liquids are also weak dispersion
forces and are similar in strength.

Procedures required to safety handling and dispose of organic substances

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Organic substances are often flammable and toxic in high quantities. Ensuring distance between
organic substances and the experimenters face and decrease the fire risk by not using open flames is
important.
Disposal of chemicals is an extremely important part of everyday chemistry. Ensuring safe procedures
are developed and followed through on is vital to the continuing of chemical research in society.
Liquid organic liquids chemicals cannot be poured down the sink. Organic liquids need to be packaged
in specialised containers which every lab will stock. These containers will typically be distinguished by
whether or not the compound in question contains some form of halogen. These containers when full
are sealed firmly and then generally transported by an independent company to disposal centres.

The environmental, economic and sociocultural implications of obtaining

and using hydrocarbons

Environmental
Extracting fuels in mines is destructive
Burning fossil fuels produces greenhouse gases

Economic
Mining boom in Australia has benefited the economy
Over reliance on fossil fuels has grown the renewable energy market

Sociocultural
The sale of land to mining corporations and the mining activity extinguishes access to native
Aboriginal titles.
We have become dependent on fossil fuels. The value of these fuels has resulted in wars.

Products of Reactions Involving Hydrocarbons

Reactions of unsaturated hydrocarbons

Unsaturated hydrocarbons and hydrogen

When hydrogen gas is added to unsaturated hydrocarbons it will react to incorporate the additional
hydrogen atoms into the molecule. Thus, becoming saturated.

Unsaturated hydrocarbons and halogens

When we add some sort of halogen to unsaturated hydrocarbons, they will react to incorporate the
additional halogen into the molecule just like the previous example.

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Unsaturated hydrocarbons and hydrogen halides
Hydrogen halides will also react with unsaturated hydrocarbons. The reaction will look like this:

Unsaturated hydrocarbons and water

Water will only react with unsaturated carbons under acidic conditions and produces an alcohol.

Reactions of saturated hydrocarbons

Condensation reactions require a catalyst such as UV light.

Alcohols
The structural formulae, properties and functional group

Primary

Secondary

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Tertiary

Properties within and between the homologous series of alcohols

Alcohols are polar due to the presence of the hydroxide group; intermolecular hydrogen bonds are
present. Colourless liquids. The boiling point of alcohol is therefore very high as the intermolecular
forces are large. Boiling points of secondary and tertiary alcohols will be lower than for the equivalent
primary alcohol. Alcohols are very soluble in water.

Measure and compare the enthalpy of combustion for a range of alcohols

Aim
The measure and compare the heat of combustion of various alcohols.

Materials

Spirit burner Electronic balance

Propan-1-ol Steel can

Measuring cylinder Thermometer

Retort stand and clamp Bench mat

Procedure
1. Using a retort stand and clamp, set up a steel can 3-4 cm above the wick of a spirit
burner.
2. Pour 200mL of water into the can and record its temp.
3. Weigh the spirit burner filled with alcohol. Record mass.
4. Light the burner and heat the water. Stir continuously.
5. When the water temperature rose 20 degrees, extinguish the burner and record the
highest temperature reached.

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 6. Measure and record the mass of the burner and unburnt alcohol. Use this info to
deduce the mass of alcohol consumed.

Results

Alcohol Propan-1-ol

Initial alcohol + burner 281.74g

Initial temp of water 19 ℃

Final temp of water 59℃

Final mass alcohol + burner 278.97g

Mass of alcohol burnt 2.77g

Temp change of water 40℃

• Energy absorbed in the can

ΔH= McΔT (H2O) + McΔT (Al)
= (200g x 4.18 x 40) + (16.08 x 0.90 x 40)
= 34018.88 J
= 34 kJ

• Molar heat of combustion

n= m/MM
= 2.77/60.064
= 0.046

ΔHcomb= ΔHtotal/n fuel

= 34.01888/0.046
= 739.5 kJ/mol

The reactions of alcohols

Combustion
Complete combustion occurs when all of the products are either water or CO2.
Incomplete combustion occurs when some of the products include other substances such as
soot or carbon monoxide. Incomplete combustion will occur when there isn’t enough oxygen in
the reaction.
To combust anything, you need to overcome some initial activation energy, typically by
exposing the alcohol to a flame.

Alcohol + CO2 → CO2 + water

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Dehydration
The easiest way to remove one hydrogen atom and the hydroxyl functional group. A catalyst is
needed. (Sulphuric acid).

Alcohol + catalyst → Alkene + water

Substitution with HX
There are a number of complicated steps that go into this reaction process.

Alcohol + hydrogen halide + catalyst → halogenated hydrocarbon + water

Oxidation
Primary alcohols may partially oxidised to form aldehydes. Primary alcohols may fully oxidise to
form carboxylic acid. Secondary alcohols will oxidise to form ketones. Tertiary alcohols won’t
oxidise.

The production of alcohols

Fermentation is the process by which yeast ‘eats’ and decomposes some sort of biomass (glucose).
This fermentation process must be completed under certain conditions including:
• pH neutral water
• Contain enzymes (yeast) to catalyse the reaction
• Low O2 concentration
• Nutrients for yeast to use
• Alcohol concentration of <14%
• A warm temp (30 degrees)

Yeast can produce ethanol concentrations up to approx. 14-15% before the yeast itself is killed. To
produce higher alcohol concentrations the product must be distilled.

Compare and contrast fuels from organic sources to biofuels

Ethanol from biomass

Sugar cane → cellulose → glucose → ethanol → fractional distillation → ethylene

• Advantages of ethanol
Reduces the consumption of fossil fuels
It can be dehydrated into ethene to produce plastic
Ethanol undergoes complete combustion
Fairly inexpensive to produce
Widespread, ethanol could reduce greenhouse gas emissions
It is renewable

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 • Disadvantages of ethanol
It requires fuel to operate so it’s ‘carbon neutrality’ is questionable
Arable land is required to grow sugar cane
There is increased engine wear as ethanol absorbs moisture and accelerates corrosion
It only produces around 66% of the energy of a fossil fuel
Widespread use would require the modification of fuel lines and engines

Reactions of Organic Acids and Bases

Structure, properties and functional groups

Aldehydes and ketones

Contains dipole-dipole attractions.
Higher boiling points than alkanes (not as high as amines, amides & carboxylic acids)
Small ketones and aldehydes are soluble in water.

Amines and amides

Amines have lower boiling points than alcohols because intermolar forces between molecules.
Amides have higher boiling points because they have more atoms that can donate or accept hydrogen.

Carboxylic acids
Soluble in water
High boiling point due to hydrogen point.
When reacting with an alcohol an ester form.

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Production of a simple ester

Aim
To prepare several esters that are widely used as artificial fragrances and flavours.

Materials
Small volumes of pentan-1-ol and ethanol
Small amounts of glacial ethanoic acid and decanoic acid
Salicylic acid
Concentrated sulfuric acid
Semi micro test tubes
Test tube rack
250mL beaker with 100mL of boiling water
2x 250mL beakers

Procedure
1. Label two semi micro test tubes ‘A’ and ‘B’. place 10 drops of pentan-1-ol in each test tube.
2. Add 10 drops of glacial ethanoic acid to test tube A and a similar volume of salicylic acid to test
tube B. then add two drops of concentrated sulfuric acid to each tube.
3. Heat the mixture for 10 minutes in a beaker of boiling water and then pour each one into a
250mL beaker containing 200mL of cold water.
4. Try to identify the odour of the esters produced by cautiously wafting the vapour from the ester
towards you.
5. Wash out beakers thoroughly and repeat steps 1-4 using clean test tubes and other
combinations of alcohols and carboxylic acids.
6. Record results

The difference between an organic acid and base

Organic acids agree with the Bronsted Lowry definition of acids, they donate protons.
Organic bases agree with the Bronsted Lowry definition of bases, they accept protons.

Organic acids and bases have quite varying pH., depending on their ability to ionise in solution and
their intramolecular bond strength.

The structure and action of soaps and detergents

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Making soap
Soaps are made when animal and vegetable fats are boiled with a strong base (usually NaOH).
When heated with NaOH, the triglyceride breaks up to form sodium salts of carboxylic acids and
glycerol. This process is called saponification

The action of soap

A surfactant is a soap ion containing a hydrophilic head and a hydrophobic tail. When a small amount
of soap dissolves in water, the anions accumulate at the surface with the hydrophilic heads in the water
and hydrophobic tails out of the water. At higher concentrations, the soap molecules cluster together in
the liquid – these are called micelles.

When in contact with grease or oil

The non-polar tails of the soap molecules absorb onto the grease. The charged heads of the
surfactants form a layer around the grease.
Water penetrates between the grease and the surface below it, causing a grease droplet to form.
The grease droplet is held in solution and attracted to the water molecules.

Reaction pathways for chemical synthesis

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Tips:
• If it’s a double bond add water
• If saturated add Cl2
• To make an alcohol add NaOH
• To make a carboxylic acid add K2Cr2O7

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Polymers
Structure, properties and uses of addition polymers

Addition Polymers
They are formed by joining together thousands of smaller molecules (called monomers) through
polymerisation.

Polyethylene
Two types:
High density polyethylene (HDPE)
• High boiling point, rigid, strong, high density.
• Uses- piping, insulation for wires

Low density polyethylene (LDPE)

• Low boiling point, very flexible, not strong, pliable.
• Uses- glad wrap, plastic bottles

Polyvinyl Chloride
Very chemically stable, fire resistant, durable, mouldable, rigid, low flexibility, water resistance, low
melting point.
Uses- pipes, fittings, building materials.

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Polystyrene
Rigid due to the benzene group, lightweight, brittle, hard.
Uses- insulation, toys and utensils.

Polytetrafluoroethylene
More commonly known as Teflon, flexible, stick proof, very high boiling point.
Uses- coating of utensils, pans, medical equipment.

The structure, properties and uses of condensation polymers

Condensation polymerisation
Form when different monomers bond together in regular patterns.

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Nylon
Strong and elastic, water resistant, resilient, heat resistant.
Uses- clothing.

Polyesters
Hydrophobic polymer, very durable, chemical resistant, elastic and strong.
Uses- clothing items, commonly used to make bottles.

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