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A Level Chemistry CIE Your notes

16.1 Alcohols
Contents
Producing Alcohols
Reactions of Alcohols
Classifying & Testing for Alcohols
Acidity of Alcohols

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Producing Alcohols
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Production of Alcohols
Alcohols are compounds that contain at least one hydroxy (-OH) group
The general formula of alcohols is C n H2n+1OH
Alcohols can be prepared by a wide range of chemical reactions

Electrophilic addition of alkenes

When hot steam is reacted with an alkene, using concentrated phosphoric(VI) acid (H3 PO 4 )as a
catalyst, electrophilic addition takes place to form an alcohol

The electrophilic addition of ethene using water

Electrophilic addition of steam to alkenes forms alcohols

Oxidation of alkenes
Cold, dilute KMnO 4 is a mild oxidising agent and oxidises alkenes
The C-C double bond is not fully broken and a diol is formed
A diol is a compound with two hydroxy, -OH, groups
Oxidation of ethene using cold, dilute KMnO 4

The oxidation of alkenes using cold, dilute KMnO4 forms a diol

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Nucleophilic substitution of halogenoalkanes

The halide atom in halogenoalkanes can be substituted when heated with aqueous NaOH in a Your notes
nucleophilic substitution reaction
Nucleophilic substitution of bromoethane using NaOH

The nucleophilic substitution of halogenoalkanes using NaOH forms an alcohol

Reduction of aldehyde & ketones

Aldehydes and ketones can be reduced by reducing agents such as NaBH4 or LiAlH4
Aldehydes are reduced to primary alcohols
The carbon attached to the hydroxy group is bonded to one other alkyl group
Ketones are reduced to secondary alcohols
The carbon attached to the hydroxy group is bonded to two other alkyl groups
The reduction of ethanal and propanone

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Your notes

The reduction of aldehydes and ketones forms primary and secondary alcohols respectively

Reduction of carboxylic acids

Similarly, carboxylic acids are reduced by NaBH4 or LiAlH4 to primary alcohols

The reduction of ethanoic acid

The reduction of carboxylic acids forms primary alcohols

Hydrolysis of ester
Esters are made by a condensation reaction between an alcohol and a carboxylic acid
When an ester is heated with dilute acid or alkali, hydrolysis will take place and the carboxylic
acid and alcohol will be reformed

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Acidic and alkaline hydrolysis of ethyl ethanoate

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The hydrolysis of esters forms alcohols

Alcohol production reactions table

Reaction Type Reagents Conditions Product

Heat
Electrophilic Alkene
Alcohol
addition Steam H3PO 4 catalyst

Alkenes Shaking of
Oxidation Diol
Cold, dilute KMnO 4 reagents
Nucleophilic Halogenoalkanes
Heat Alcohol
substitution Aqueous NaOH
Aldehydes / Primary / secondary
Reduction LiAlH4 or NaBH4
ketones alcohol

Reduction Carboxylic acid LiAlH4 Primary alcohol

Dilute acid or alkali

Hydrolysis Esters Alcohol
Heat

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Exam Tip
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The symbol [O] is used to represent oxygen provided by an oxidising agent

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Reactions of Alcohols
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Reactions of Alcohols
Alcohols are reactive molecules which undergo a wide range of reactions

Combustion of alcohols
Alcohols react with oxygen in the air when ignited and undergo complete combustion to form
carbon dioxide and water
Alcohol + oxygen → carbon dioxide + water
The complete combustion of ethanol

Complete combustion of alcohols produces carbon dioxide and water

Substitution of alcohols
In the substitution of alcohols, a hydroxy group (-OH) is replaced by a halogen to form an
halogenoalkane
The substitution of the alcohol group for a halogen can be achieved by reacting the alcohol with:
HX (rather than using HBr, KBr is reacted with H2 SO 4 or H3PO 4 to make HBr that will then react
with the alcohol)
PCl3 and heat
PCl5 at room temperature
SOCl2
Substitution of alcohols

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Your notes

The substitution of alcohols produces halogenoalkanes

Reaction with Na
When an alcohol reacts with a reactive metal such as sodium (Na), the oxygen-hydrogen bond in
the hydroxy group breaks
Though the reaction is less vigorous than sodium reacting with water, hydrogen gas is given off
and a basic compound (alkoxide) is formed
If the excess ethanol is evaporated off after the reaction a white crystalline solid of sodium
alkoxide is left
Alcohol + sodium → sodium alkoxide + hydrogen

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The longer the hydrocarbon chain in the alcohol, the less vigorous the reaction becomes

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The reaction of ethanol with sodium metal

Alcohols react with Na to form a basic sodium alkoxide salt and hydrogen gas

Oxidation of alcohols
Primary alcohols can be oxidised to form aldehydes which can undergo further oxidation to form
carboxylic acids
Secondary alcohols can be oxidised to form ketones only
Tertiary alcohols do not undergo oxidation
The oxidising agents of alcohols include acidified K2 Cr 2 O 7 or acidified KMnO 4
Acidified potassium dichromate(VI), K2 Cr2 O 7, is an orange oxidising agent
Acidified means that that the potassium dichromate(VI) is in a solution of dilute acid (such as
dilute sulfuric acid)
For potassium dichromate(VI) to act as an oxidising agent, it itself needs to be reduced
This reduction requires hydrogen (H+) ions which are provided by the acidic medium
When alcohols are oxidised the orange dichromate ions (Cr2 O 72-) are reduced to green
Cr3+ ions
Acidified potassium manganate(VII), KMnO 4, is a purple oxidising agent
As with acidified K2 Cr2 O 7 the potassium manganate(VII) is in an acidic medium to allow
reduction of potassium manganate(VII) to take place
When alcohols are oxidised, the purple manganate ions (MnO 4-) are reduced to
colourless Mn2+ ions
Warm primary alcohol is added to the oxidising agent
The formed aldehyde has a lower boiling point than the alcohol reactant so it can be distilled off
as soon as it forms
If the aldehyde is not distilled off, further refluxing with excess oxidising agent will oxidise it to a
carboxylic acid

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Since ketones cannot be further oxidised, the ketone product does not need to be distilled off
straight away after it has been formed
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The reflux setup to convert an alcohol to an aldehyde

The oxidation of ethanol by acidified K2Cr2O7 forms ethanal by distillation and ethanoic acid by refluxing

Oxidation of propan-2-ol by acidified K2 Cr 2 O 7

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Your notes

The oxidation of secondary alcohols by acidified K2Cr2O7 forms a ketone, under distillation

Dehydration of alcohols
Alcohols can also undergo dehydration to form alkenes
Dehydration is a reaction in which a water molecule is removed from a larger molecule
A dehydration reaction is a type of elimination reaction
Alcohol vapour is passed over a hot catalyst of aluminium oxide (Al2 O 3 ) powder OR pieces of
porous pot or pumice as well as concentrated acid can be used as catalysts
Dehydration of ethanol

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Your notes

Dehydration of ethanol using aluminium oxide as a catalyst forms ethene gas, which can be collected
over water

Esterification of Alcohols
Esterification is a condensation reaction between a carboxylic acid and an alcohol to form an
ester and a water molecule
For esterification to take place, the carboxylic acid and alcohol are heated under reflux with a
strong acid catalyst (such as H2 SO 4 or H3PO 4)
Carboxylic acid + alcohol → ester + water
The reaction is reversible so an equilibrium mixture can be established with all the reactants and
products

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Esters have sweet, fruity smells

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Example esterification reaction

Esterification of ethanol and ethanoic acid using a strong acid catalyst to form ethyl ethanoate and water

Exam Tip
The first part of an ester’s name comes from the alcohol, whereas the second part comes from
the carboxylic acid
So, if ethanol and propanoic acid react together, this will make the ester ethyl propanoate

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Classifying & Testing for Alcohols

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Classifying Alcohols
Primary alcohols are alcohols in which the carbon atom bonded to the -OH group is attached to
one other carbon atom (or alkyl group)
Secondary alcohols are alcohols in which the carbon atom bonded to the -OH group is attached
to two other carbon atoms (or alkyl groups)
Tertiary alcohols are alcohols in which the carbon atom bonded to the -OH group is attached to
three other carbon atoms (or alkyl groups)
Primary, secondary and tertiary alcohols

Classifying primary, secondary and tertiary alcohols and alcohols with more than one alcohol group

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Only primary and secondary alcohols can get oxidised when mildly oxidised with acidified
K2 Cr2 O 7
Primary alcohols get mildly oxidised to aldehydes Your notes
Secondary alcohols get mildly oxidiz ed to ketones
Tertiary alcohols do not undergo oxidation with acidified K2 Cr2 O 7
Therefore, only the oxidation of primary and secondary alcohols will change the colour of
K2 Cr2 O 7 solution as the orange Cr2 O 72- ions are reduced to green Cr3+ ions
Testing for alcohols

Only propan-1-ol and propan-2-ol, which are primary and secondary alcohols respectively, can get
oxidised, turning the orange solution green; no colour change is observed with 2-methyl-propan-2-ol,
which is a tertiary alcohol

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Test for Alcohols

Tri-iodomethane (also called iodoform) forms a yellow precipitate with methyl ketones Your notes
Methyl ketones are compounds that have a CH3CO-group
Ethanal also contains a CH3CO- group and therefore also forms a yellow precipitate with
iodoform
The reagent is heated with an alkaline solution of iodine
This reaction involves a halogenation and hydrolysis step
In the halogenation step, all three H-atoms in the -CH3 (methyl) group are replaced for iodine
atoms, forming -CI3
The intermediate compound is hydrolysed by alkaline solution to form a sodium salt (RCO 2 -
Na+) and a yellow precipitate of CHI3
The iodoform reaction

The reaction of methyl ketones with iodoform results in the formation of a yellow CHI3 precipitate

Iodoform & alcohols

The position of a secondary alcohol can be deduced by reacting the compound with alkaline I2
If the -OH group is on the carbon atom next to a methyl group, it will firstly get oxidised to
CH3CH(OH)- by the alkaline solution
This will result in the formation of a methyl ketone RCOCH3
The methyl ketone will then first get halogenated and then hydrolysed to form the sodium salt
and the yellow precipitate
If no yellow precipitate is formed, then this means that the secondary alcohol is not on a carbon
next to a methyl group
Using the iodoform test

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Your notes

The secondary alcohol butan-2-ol will firstly get oxidised to the methyl ketone butanone which will form
a yellow precipitate when reacted with alkaline I2

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Acidity of Alcohols
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Acidity of Alcohols
Alcohols have a low degree of dissociation
This means, that when dissolved in water, alcohol molecules do not dissociate (split up) to a
great extent

ROH (aq) ⇌ RO- (aq) + H+ (aq)

Alcohol alkoxide ion

The position of the equilibrium lies to the left, meaning that there are far more alcohol molecules
than RO - and H+ ions
When water dissociates, the position of the equilibrium still lies to the left, but there are more H+
ions compared to the dissociation of alcohols
H2O (l) ⇌ OH– (aq) + H+ (aq)
As alcohols have a lower [H+ (aq)] in solution compared to water, alcohols are weaker acids than
water

The inductive effect in alcohols

Electron-donating species such as alkyl groups push electrons into a covalent bond and are
said to have a positive inductive effect
In alcohols, the oxygen atom in the alkoxide ion is bonded to an electron-donating alkyl group
This means that there is more electron density on the O - atom
The alkoxide ion is, therefore, more likely to accept an H+ ion and form the alcohol again

The inductive effect in alcohols

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Your notes

Alkyl groups in the alkoxide ion donate electron density to the negatively charged oxygen, causing it to
more readily accept a proton and form the alcohol again
When water dissociates, the hydroxide ion only has one other hydrogen atom
There is no extra electron density on the oxygen which is less likely to accept an H+ ion
Water is therefore a stronger acid than alcohols

The equilibrium of water and hydroxide ions

Water is a stronger acid than alcohols as there are no electron-donating groups in the hydroxide ion,
causing the O- to be less likely to accept a proton and reform water

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