Alcohols, Carboxylic acids

and Esters

Alcohols
What Are Alcohols?
Alcohols are organic chemical compounds which
form a homologous series.
They are compounds in which one or more
hydrogen atoms in an alkane (saturated
hydrocarbon) are replaced by hydroxyl (OH) groups.
The hydroxyl group (OH) is the part of the molecule
that is responsible for the characteristic reactions
and chemical properties of the alcohol. This is
otherwise known as the 'functional group'

Ethanol
Ethanol is an alcohol, which as we
know, is a member of the
homologous series.
Ethanol can be represented in a
number of different forms:
C2H5OH
CH3CH2OH

Facts about Ethanol!

Ethanol can:
Dissolve in water to form a neutral solution.
React with sodium to from hydrogen.
Burn in air.
Be used as fuels and solvents, and is the
main alcohol in alcoholic drinks!
Ethanol can be oxidised to ethanoic acid (by
chemical oxidising agents or microbial
action).

So what does Ethanol look

like?
The molecular structure of ethanol
looks like this:

The OH part of
Ethanol is sometimes
referred to as the
functional group!

Methanol
Methanol is another alcohol, which as
we know, is also a member of the
homologous series.

Methanol can be represented as a

formula:
CH3OH

Methanol
The molecular structure of methanol
look like this:

The OH part of methanol is

sometimes referred to as the
functional group!

Facts about Methanol

Methanol can:
Dissolve in water to form a neutral
solution.
React with sodium to from hydrogen.
Burn in air.
Be used as fuels and solvents, and is
the main alcohol in alcoholic drinks!

The Manufacture of
Ethanol

Can you recall the properties and

uses of ethanol?
Properties: volatile liquid (evaporates
quickly at room temperature,
colourless, burns readily in air with a
blue flame, good solvent
Uses: biofuels, solvents, feedstock
for synthesis, cleaner etc

How do we make ethanol?

Think about home
brewing/winemaking? What process
do we use?
Fermentation is a key process for
obtaining ethanol. It is relatively
cheap and requires wheat or beet
sugar.
The process involves the anaerobic
respiration of yeast at temperatures
between 20 and 40C and at pH 7.

Conditions for fermentation

Why is temperature important?
Outside an optimum temperature the yeast does not work (high
temperatures kill the yeast).
Why do you think pH is important?
Outside an optimum pH the yeast does not work (extremes of
pH kill the yeast).
Why do you think it is important to shut out oxygen?
To make ethanol the yeast must respire anaerobically (without
oxygen).
What effect will increasing ethanol concentration have on
the yeast?
Eventually the ethanol concentration will be too high for the
fermentation to continue. This means only a dilute solution can
be made.

How do we obtain a concentrated

solution?
Ethanol has a different boiling point
to water. We can therefore separate
water and ethanol using distillation.

Other methods of obtaining ethanol

For homework research the
different methods of obtaining
ethanol including fermentation. You
might also come across a method
using algae!

Produce a minimum of 1 page in your

class book or e-mail a word
processed sheet.

Plenary Balancing chemical

equations
Glucose (a simple sugar) is created in
the plant by photosynthesis.
Can you balance the following
equation for photosynthesis?
__CO2 + ___ H2O C6H12O6 + __ O2
6 CO2 + 6 H2O C6H12O6 + 6 O2

Plenary part 2
During ethanol fermentation, glucose
is decomposed into ethanol and
carbon dioxide.
Can you balance this equation?
C6H12O6 __ CH3CH2OH+ __CO2
C6H12O6 2 CH3CH2OH+ 2 CO2

Plenary part 3
During combustion ethanol reacts
with oxygen to produce carbon
dioxide, water, and heat:
Can you balance this equation?
CH3CH2OH + __ O2 __ CO2 + __ H2O
CH3CH2OH + 3 O2 2 CO2 + 3 H2O

Carboxylic acid
A carboxylic acid is an organic acid
that contains one or more carboxyl
groups. They usually have higher
boiling points than water and are
usually quite weak acids. These
longer chain acids tend to be rather
soluble in less-polar solvents such as
ethers and alcohols.

Ethanoic Acid
Ethanoic acid can be found in your
kitchen, any ideas? Yes, its vinegar!
Ethanoic acid is one of the simplest
carboxylic acids.
The COOH part of ethanoic acid is
sometimes referred to as the
functional group!

Facts about Carboxylic acids

Carboxylic acids:
Dissolve in water to produce acidic solutions.
React with carbonates to produce carbon dioxide.
React with alcohols in the presence of an acid
catalyst to produce esters.
Do not ionise completely when dissolved in water
and so are weak acids.
Aqueous solutions of weak acids have a higher
pH value than aqueous solutions of stronger
acids with the same concentration.

Esters
Esters are chemical compounds
made by condensing acids with
alcohols. Esters with low molecular
weight are commonly used as
fragrances and found in essential oils
and pheromones.

Making an Ester
Ethyl ethanoate is synthesized in industry mainly via
the classic Fischer esterification reaction of ethanol
and acetic acid. This mixture converts to the ester in
about 65% yield at room temperature:
CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2O
The reaction can be accelerated by acid catalysis
and the equilibrium can be shifted to the right by
removal of water. It is also prepared in industry using
the Tishchenko reaction, by combining two
equivalents of acetaldehyde in the presence of an
alkoxide catalyst:
2 CH3CHO CH3COOCH2CH3

What do esters look like?

-Ethyl ethanoate Ethyl ethanoate is the organic compound
with the formula CH3COOCH2CH3. This
colourless liquid has a characteristic sweet
smell and is used in glues, nail polish
removers, decaffeinating tea and coffee,
and cigarettes.

The COO part of ethyl ethanoate is

sometimes referred to as the