Friday 3rd January 2021

Dehydration of alcohols
LO: To be able to
• outline the mechanism for the formation of an alkene by eliminating water from alcohols

Starter: Classify each one as primary, secondary or tertiary.

1) CH3CH2CH2CH2OH
2) CH3CH2OH
3) CH3CH(OH)CH3
4) CH3CH2CH(OH)CH3
5) CH3CH2CH2CH2CH(OH)CH3
Classify each one as primary, secondary or tertiary.

1) CH3CH2CH2CH2OH

2) CH3CH2OH

3) CH3CH(OH)CH3

4) CH3CH2CH(OH)CH3

5) CH3CH2CH2CH2CH(OH)CH3
Task: Answer the following questions

Ethanol produced industrially by fermentation is

separated by fractional distillation and can then be
used as a biofuel.

Q1) Explain the meaning of the term biofuel

Q2) Explain why biofuels are considered a carbon

neutral fuel? Include 3 equations that support this
statement.

Q3) Give one advantage of using biofuels rather

than fossil fuels ?

Q4) Give three disadvantages of using biofuels?

Task: Answer the following questions

Ethanol produced industrially by fermentation is

separated by fractional distillation and can then be
used as a biofuel.

Q1) Explain the meaning of the term biofuel

- A fuel produced from plant or animal

waste
Task: Answer the following questions
Ethanol produced industrially by fermentation is separated
by fractional distillation and can then be used as a biofuel.

Q2) Explain why biofuels are considered a carbon neutral

fuel? Include 3 equations that support this statement.

The plants grown to produce bioethanol take in carbon

dioxide from the atmosphere as they grow. When you burn
the fuel produced from the plants, you only release the same
amount of carbon dioxide that the plant took in. This is
described as carbon neutral.

-6CO2 + 6H2O C6H12O6 + 6O2

-C6H12O6 2C2H5OH + 2CO2
-2C2H5OH + 6O2 4CO2 + 6H2O
Task: Answer the following questions

Ethanol produced industrially by fermentation is

separated by fractional distillation and can then be
used as a biofuel.

Q3) Give one advantage of using biofuels rather

than fossil fuels ?

-Biofuels are sustainable/renewable

-Burning a biofuel releases the same
amount of carbon dioxide that the plant
took in as it grew, so biofuels are nearly
carbon neutral
Task: Answer the following questions

Ethanol produced industrially by fermentation is

separated by fractional distillation and can then be
used as a biofuel.

Q4) Give three disadvantages of using biofuels?

-Land which is being used to grow crops for fuel

cannot be used to grow crops for food
-Trees may be cut down to create more land to
grow crops for biofuels, this can destroy habitats
-Fertilisers which are added to soil to increase
biofuel crop production can pollute waterways
-Most car engines cannot run on biofuel unless
they are modified.
 So is bioethanol carbon
neutral?
Not entirely…

This does not take into account any energy

needed to irrigate plants, fractionally distil
the ethanol from the reaction mixture or
process the fuel. If the energy for these
processes comes from fossil fuels then the
ethanol produced is not carbon neutral.
What do we mean by the term carbon
neutral?
• There is no net carbon dioxide
emission to the atmosphere

OR
• There is no change in the total amount
 of carbon dioxide present in the
atmosphere
Elimination reactions

You can make alkenes by eliminating water from

alcohols in a dehydration reaction.

Alcohol Alkene + Water

CnH2n+1OH CnH2n + H20

This allows you to produce alkenes from renewable

resources!
Dehydration of ethanol
Dehydration is the removal of water.
It is also known as an Elimination
Reaction.

Alcohol Alkene + Water

CnH2n+1OH CnH2n + H20

Alcohols are dehydrated with excess hot

concentrated sulphuric acid OR by
passing their vapours over heated
Aluminium oxide.
E.g. Dehydration of ethanol

A lone pair of electrons from the

oxygen bonds to an H+ from the
acid. The alcohol is protonated giving
the oxygen a positive charge.

The positively charge oxygen pulls

electrons away from the carbon. A
water molecule leaves, creating an
unstable carbocation intermediate.

The carbocation loses a H+ and the

alkene is formed.

The product is usually a mixture with

water, acid and reactant in it, so the
alkene has to be separated out.
 Task:
Draw the mechanism for the
dehydration of propan-1-ol
Draw the mechanism for the
dehydration of propan-1-ol
 Dehydration of longer chain or
branched alcohols

Dehydration of a secondary alcohol can result in

more than one product, because the double bond
can go on either side of the carbon that had the
OH group on it.
 heat/conc. H2SO4
alcohol alkene
-H2O

Task: Write the displayed equations for the

dehydration reactions of:
a) butan-1-ol
b) butan-2-ol. Name the three products.
 heat/conc. H2SO4
alcohol alkene
-H2O

Task: Write the displayed equations for the

dehydration reactions of:
a) butan-1-ol
 heat/conc. H2SO4
alcohol alkene
-H2O

Task: Write the displayed equations for the

dehydration reactions of:
b) butan-2-ol. Name the three products.
Exam question
Answers:
Purifying the product of a reaction
The products of organic reactions are often impure.

In dehydration reaction of alcohols to form alkenes, the

mixture at the end contains the product, the reactant,
acid, water and other impurities. To get a pure alkene,
you need a way to separate it from the other substances.

Distillation is a technique which uses the fact that

different chemicals have different boiling points, to
separate them.
Distillation
A technique of heating a liquid to create a vapour which is
then collected separately from the original liquid when
cooled. It is based on the different boiling points of the
components.

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