CIE AS Chemistry

Revision Notes

Halogenoalkanes
Substitution & Elimination Reactions of Halogenoalkanes
 Halogenoalkanes are much more reactive than alkanes due to the presence of
the electronegative halogens
o The halogen-carbon bond is polar causing the carbon to carry a partial
positive and the halogen a partial negative charge
 A nucleophilic substitution reaction is one in which a nucleophile attacks a
carbon atom which carries a partial positive charge
o An atom that has a partial negative charge is replaced by the nucleophile
 In an elimination reaction of halogenoalkanes, a halogen halide is eliminated to
form an alkene
Hydrolysis
 Halogenoalkanes can be broken down under reflux by water to form an alcohol
o The breakdown of a substance by water is also called hydrolysis
 The reaction is classified as a nucleophilic substitution reaction as a water
molecule in the silver nitrate solution acts as a nucleophile and replaces the
halogen
o Eg. bromoethane reacts with aqueous silver nitrate solution to form ethanol
 The halogen is replaced by an hydroxyl group, OH-
 This reaction is similar to the nucleophilic substitution reaction of halogenoalkanes
with aqueous alkali, however the hydrolysis with water is much slower than with the
OH- ion
o The hydroxide ion is a better nucleophile than water as it carries a full formal
negative charge
o In water, the oxygen atom only carries a partial negative charge
 A hydroxide ion is a better nucleophile as it has a full formal negative charge
whereas the oxygen atom in water only carries a partial negative charge; this
causes the nucleophilic substitution reaction with water to be much slower than
with aqueous alkali

 The halogenoalkanes have different rates of hydrolysis, so this reaction can be

used as a test to identify halogens in a halogenoalkane by measuring how long it
takes for the test tubes containing the halogenoalkane and aqueous silver nitrate
solutions to become opaque
Formation of nitriles
 The nucleophile in this reaction is the cyanide, CN- ion
 Ethanolic solution of potassium cyanide (KCN in ethanol)
is heated under reflux with the halogenoalkanes
 The product is a nitrile
o Eg. bromoethane reacts with ethanolic potassium cyanide when heated
under reflux to form propane nitrile

The halogen is replaced by a cyanide group, CN -

 The nucleophilic substitution of halogenoalkanes with KCN adds an extra carbon

atom to the carbon chain
 This reaction can therefore be used by chemists to make a compound with one
more carbon atom than the best available organic starting material
Formation of primary amines by reaction with ammonia
  The nucleophile in this reaction is the ammonia, NH3 molecule
 Ethanolic solution of excess ammonia (NH3 in ethanol) is heated under
pressure with the halogenoalkane
 The product is a primary amine
o Eg. bromoethane reacts with excess ethanolic ammonia when heated
under pressure to form ethylamine

The halogen is replaced by an amine group, NH2

Elimination reaction
 The halogenoalkanes are heated with ethanolic sodium hydroxide causing the
C-X bond to break heterolytically, forming a X- ion and leaving an alkene as
organic product
o Eg. bromoethane reacts with ethanolic sodium hydroxide when heated
to form ethene

Hydrogen bromide is eliminated to form ethene

Halogenoalkanes: SN1 & SN2 Mechanisms
 In nucleophilic substitution reactions involving halogenoalkanes, the halogen atom
is replaced by a nucleophile
 These reactions can occur in two different ways (known as SN2 and SN1 reactions)
depending on the structure of the halogenoalkane involved
SN2 reactions
 In primary halogenoalkanes, the carbon that is attached to the halogen is bonded
to one alkyl group
 These halogenoalkanes undergo nucleophilic substitution by an SN2 mechanism
o ‘S’ stands for ‘substitution’
o ‘N’ stands for ‘nucleophilic’
o ‘2’ means that the rate of the reaction (which is determined by the slowest step
of the reaction) depends on the concentration of both the halogenoalkane and
the nucleophile ions

 The SN2 mechanism is a one-step reaction

o The nucleophile donates a pair of electrons to the δ+ carbon atom to form a
new bond
o At the same time, the C-X bond is breaking and the halogen (X) takes both
electrons in the bond (heterolytic fission)
o The halogen leaves the halogenoalkane as an X- ion
 For example, the nucleophilic substitution of bromoethane by hydroxide ions to form
ethanol
 The mechanism of nucleophilic substitution in bromoethane which is a primary
halogenoalkane
SN1 reactions
 In tertiary halogenoalkanes the carbon that is attached to the halogen is bonded
to three alkyl groups
 These halogenoalkanes undergo nucleophilic substitution by an SN1 mechanism
o ‘S’ stands for ‘substitution’
o ‘N’ stands for ‘nucleophilic’
o ‘1’ means that the rate of the reaction (which is determined by the slowest step
of the reaction) depends on the concentration of only one reagent,
the halogenoalkane
  The SN1 mechanism is a two-step reaction
o In the first step, the C-X bond breaks heterolytically and the halogen leaves
the halogenoalkane as an X- ion (this is the slow and rate-determining step)
o This forms a tertiary carbocation (which is a tertiary carbon atom with a
positive charge)
o In the second step, the tertiary carbocation is attacked by the nucleophile
 For example, the nucleophilic substitution of 2-bromo-2-methylpropane by hydroxide
ions to form 2-methyl-2-propanol

The mechanism of nucleophilic substitution in 2-bromo-2-methylpropane which is a

tertiary halogenoalkane
Carbocations
 In the SN1 mechanism, a tertiary carbocation is formed
 This is not the case for SN2 mechanisms as a primary carbocation would have been
formed which is much less stable than tertiary carbocations
  This has to do with the positive inductive effect of the alkyl groups attached to the
carbon which is bonded to the halogen atom
o The alkyl groups push electron density towards the positively charged carbon,
reducing the charge density
o In tertiary carbocations, there are three alkyl groups stabilising the carbocation
whereas in primary carbocations there is only one alkyl group
o This is why tertiary carbocations are much more stable than primary ones

The diagram shows the trend in stability of primary, secondary and tertiary carbocations

 Secondary halogenoalkanes undergo a mixture of both SN1 and SN2 reactions

depending on their structure

Relative strength of the C–Hal bond

Reactivity of Halogenoalkanes
 The halogenoalkanes have different rates of substitution reactions
 Since substitution reactions involve breaking the carbon-halogen bond
the bond energies can be used to explain their different reactivities
Halogenoalkane Bond Energy Table
  The table above shows that the C-I bond requires the least energy to break, and is
therefore the weakest carbon-halogen bond
 During substitution reactions the C-I bond will therefore heterolytically break as
follows:
R3C-I + OH- → R3C-OH + I-
halogenoalkane alcohol
 The C-F bond, on the other hand, requires the most energy to break and is, therefore,
the strongest carbon-halogen bond
 Fluoroalkanes will therefore be less likely to undergo substitution reactions
Aqueous silver nitrate
 Reacting halogenoalkanes with aqueous silver nitrate solution will result in the
formation of a precipitate
 The rate of formation of these precipitates can also be used to determine the
reactivity of the halogenoalkanes
Halogenoalkane Precipitates Table
 The formation of the pale yellow silver iodide is the fastest (fastest nucleophilic
substitution reaction) whereas the formation of the silver fluoride is the slowest
(slowest nucleophilic substitution reaction)
 This confirms that fluoroalkanes are the least reactive and iodoalkanes are the most
reactive halogenoalkanes
 The trend in reactivity of halogenoalkanes

Fluoroalkanes & Flurohalogenoalkanes

Uses of Fluoroalkanes & Fluorohalogenoalkanes

 Fluoroalkanes and fluorohalogenoalkanes are chemically inert
 The amount of energy required to break the halogen-carbon bond is so high that
fluoroalkanes and fluorohalogenoalkanes are very unreactive
Fluorohalogenoalkanes
 The most common fluorohalogenoalkanes are chlorofluorocarbons (CFCs)
  These compounds contain carbon atoms with chlorine and fluorine atoms attached to
them
o Eg. CCl3F and CCl2F
 CFCs have many uses due to their chemical inertness as they are non-
flammable and non-toxic
o They are used as refrigerators
o Propellants for aerosols
o As solvents for dry cleaning
Fluoroalkanes
 Hydrofluorocarbons (HFCs) are compounds that contain a carbon attached to
hydrogen and fluorine atoms only
o Eg. CH2F-CF3
 As with CFCs, HFCs are chemically inert and are therefore used for a wide range of
purposes
Fluorohalogenoalkanes & the Ozone Layer
 The most common example of Fluorohalogenoalkanes
is chlorofluorocarbons (CFCs)
 Though chlorofluorocarbons (CFCs) have many beneficial uses, they also have
devastating effects on the ozone layer:
o CFCs absorb a lot of UV radiation in the upper atmosphere
o The CFCs are then broken down by the UV light causing the formation of
chlorine radicals
o These radicals react with ozone and break down the ozone layer
 This is why hydrofluorocarbons (HFCs) are often used as an alternative to CFCs
 As these compounds don’t contain any chlorine atoms, they will not have adverse
effects on the ozone layer

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
 Complete combustion of alcohols to produce 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:
o HX (rather than using HBr, KBr is reacted with H2SO4 or H3PO4 to make HBr
that will then react with the alcohol)
o PCl3 and heat
o PCl5 at room temperature
o SOCl2
 Substitution of alcohols to produce 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
o If the excess ethanol is evaporated off after the reaction a white crystalline
solid of sodium alkoxide is left
Alcohol + sodium → sodium alkoxide + hydrogen
 The longer the hydrocarbon chain in the alcohol, the less vigorous the reaction
becomes

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 K2Cr2O7 or acidified KMnO4
 Acidified potassium dichromate(VI), K2Cr2O7, is an orange oxidising agent
o Acidified means that that the potassium dichromate(VI) is in a solution
of dilute acid (such as dilute sulfuric acid)
o For potassium dichromate(VI) to act as an oxidising agent, it itself needs to be
reduced
o This reduction requires hydrogen (H+) ions which are provided by the acidic
medium
 When alcohols are oxidised the orange dichromate ions (Cr2O7 ) are
2-

reduced to green Cr3+ ions

 Acidified potassium manganate(VII), KMnO4, is a purple oxidising agent
o As with acidified K2Cr2O7 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 (MnO4-) 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
 Since ketones cannot be further oxidised, the ketone product does not need to
be distilled off straight away after it has been formed
Oxidation of ethanol by acidified K2Cr2O7 to form an aldehyde by distillation and carboxylic
acid by refluxing

Oxidation of propan-2-ol by acidified K2Cr2O7 to form a ketone by distillation

Dehydration of alcohols
 Alcohols can also undergo dehydration to form alkenes
o Dehydration is a reaction in which a water molecule is removed from a larger
molecule
o A dehydration reaction is a type of elimination reaction
 Alcohol vapour is passed over a hot catalyst of aluminium oxide (Al2O3) powder OR
pieces of porous pot or pumice as well as concentrated acid can be used as catalysts
 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 H2SO4 or H3PO4)
Carboxylic acid + alcohol → ester + water
 The reaction is reversible so an equilibrium mixture can be established with all the
reactants and products
 Esters have sweet, fruity smells

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

.4.2 Classifying and 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)
Classifying primary, secondary and tertiary alcohols and alcohols with more than one
alcohol group
  Only primary and secondary alcohols can get oxidised when mildly oxidised with
acidified K2Cr2O7
o Primary alcohols get mildly oxidised to aldehydes
o Secondary alcohols get mildly oxidized to ketones
 Tertiary alcohols do not undergo oxidation with acidified K2Cr2O7
 Therefore, only the oxidation of primary and secondary alcohols will change the
colour of K2Cr2O7 solution as the orange Cr2O72- ions are reduced to green Cr3+ ions

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
Test for Alcohols
 Tri-iodomethane (also called iodoform) forms a yellow precipitate with methyl
ketones
o Methyl ketones are compounds that have a CH3CO-group
o 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
o In the halogenation step, all three H-atoms in the -CH3 (methyl) group are
replaced for iodine atoms, forming -CI3
o The intermediate compound is hydrolysed by alkaline solution to form a
sodium salt (RCO2- Na+) and a yellow precipitate of CHI3
 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
 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

1 Aldehydes & Ketones

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Production of Aldehydes & Ketones

Formation of aldehydes & ketones
 Aldehydes and compounds are carbonyl compound which contain a C=O group
 They can be prepared from the oxidation of primary and secondary alcohols
 Acidified potassium dichromate (K2Cr2O7) is an orange oxidising agent
 When the alcohols are oxidised the orange dichromate ions (Cr2O72-) are reduced to
green Cr3+ ions
 Secondary alcohols are oxidised to ketones
o To make a ketone, warm secondary alcohol is slowly added to the oxidising
agent
o Since the formed ketone cannot be further oxidised it does not need to
be distilled off straightway after it has been formed
o Eg. Propan-2-ol will get oxidised to propanone.
 Primary alcohols are oxidised to aldehydes
o To make an aldehyde, warm primary alcohol is slowly added to the
oxidising agent
o The formed aldehyde has a lower boiling point than the alcohol and can
therefore be distilled off as soon as it forms
o The aldehyde is then condensed into a liquid and collected
o If the aldehyde formed is not distilled off, further refluxing with excess
oxidising agent will oxidise the aldehyde to a carboxylic acid
o Eg. propan-1-ol will get oxidised to propanal
Reduction of aldehyde & ketones
 Aldehydes and ketones can be reduced by reducing agents such as NaBH4 or LiAlH4
 Aldehydes are reduced to primary alcohols
o Eg. butanal is reduced to butan-1-ol
 Ketones are reduced to secondary alcohols
o Eg. butanone is reduced to butan-2-ol
Reaction of aldehyde & ketones with hydroxynitrile
 Aldehydes and ketones can undergo nucleophilic addition with hydrogen cyanide,
HCN
 The cyanide ion, CN-, acts as a nucleophile and adds across the C-O bond
 Aldehydes and ketones react with HCN and NaCN (or KCN) as the catalyst and heat
to produce hydroxynitriles
o Hydroxynitriles are nitriles containing a hydroxy, -OH, group
o Eg. propanal reacts with HCN to form 2-hydroxybutanenitrile


Reaction with HCN

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Reaction of Hydrogen Cyanide with Aldehydes & Ketones
 The carbonyl group -C=O, in aldehydes and ketones is polarised
 The oxygen atom is more electronegative than carbon drawing electron density
towards itself
 This leaves the carbon atom slightly positively charged and the oxygen
atom slightly negatively charged
 The carbonyl carbon is therefore susceptible to attack by a nucleophile, such as the
cyanide ion
Nucleophilic addition
 The nucleophilic addition of hydrogen cyanide to carbonyl compounds is a two-step
process
 In step 1 the cyanide ion attacks the carbonyl carbon to form a negatively charged
intermediate
 In step 2 the negatively charged oxygen atom in the reactive intermediate quickly
reacts with aqueous H+ (either from HCN, water or dilute acid) to form 2-
hydroxynitrile
 The cyanide ion attacks the carbonyl carbon to form a negatively charged intermediate
which quickly reacts with a proton to form a 2-hydroxynitrile compound
Exam Tip
The actual negative charge on the cyanide ion is on the carbon atom and not on the nitrogen
atom.

Carbonyl Compound Tests

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Testing for Carbonyls: 2,4-DNPH

 2,4-dinitrophenylhydrazine (also known as 2,4-DNPH) is a reagent which detects the
presence of carbonyl compounds (compounds with -C=O group)
 The carbonyl group of aldehydes and ketones undergoes a condensation reaction
with 2,4-dinitrophenylhydrazine
o A condensation reaction is a reaction in which two molecules join together and
a small molecule (such as H2O or HCl) is eliminated
 The product formed when 2,4-DNPH is added to a solution that contains an aldehyde
or ketone is a deep-orange precipitate which can be purified by recrystallization
 The melting point of the formed precipitate can then be measured and compared to
literature values to find out which specific aldehyde or ketone had reacted with 2,4-
DNPH

Ketones and aldehydes react with 2,4-DNPH in a condensation reaction

 The test tube on the left shows a negative 2,4-DNPH test and the tube on the right shows a
positive test
Exam Tip
The 2,4-DNPH is especially useful as other carbonyl compounds such
as carboxylic acids and esters do not give a positive test.
Identifying Carbonyls: Fehling's Solution & Tollens' Reagent
 The presence of an aldehyde group (-CHO) in an unknown compound can be
determined by the oxidising agents Fehling’s and Tollens’ reagents
Fehling’s solution
 Fehling’s solution is an alkaline solution containing copper(II) ions which act as the
oxidising agent
 When warmed with an aldehyde, the aldehyde is oxidised to a carboxylic acid and
the Cu2+ ions are reduced to Cu+ ions
o In the alkaline conditions, the carboxylic acid formed will be neutralised to a
carboxylate ion (the -COOH will lose a proton to become -COO- )
o The carboxylate ion (-COO-) will form a salt with a positively charged metal
ion such as sodium (-COO-Na+)
 The clear blue colour of the solution turns opaque red due to the formation of
a copper(I) oxide precipitate
 Ketones cannot be oxidised and therefore give a negative test when warmed with
Fehling’s solution
The copper(II) ions in Fehling’s solution are oxidising agents, oxidising the aldehyde to a
carboxylic acid and getting reduced themselves to copper(I) ions in the Cu2O precipitate
Tollens’ reagent
 Tollen’s reagent is an aqueous alkaline solution of silver nitrate in excess ammonia
solution
o Tollen’s reagent is also called ammoniacal silver nitrate solution
 When warmed with an aldehyde, the aldehyde is oxidised to a carboxylic acid and
the Ag+ ions are reduced to Ag atoms
o In the alkaline conditions, the carboxylic acid will become a carboxylate ion
and form a salt
 The Ag atoms form a silver ‘mirror’ on the inside of the tube
 Ketones cannot be oxidised and therefore give a negative test when warmed with
Tollens’ reagent
 The Ag+ ions in Tollens’ reagent are oxidising agents, oxidising the aldehyde to a
carboxylic acid and getting reduced themselves to silver atoms

Iodoform Reaction
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Iodoform Reaction
 Tri-iodomethane (also called iodoform) forms a yellow precipitate with methyl ketones
o Methyl ketones are compounds that have a CH3CO-group
o 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
o In the halogenation step, all three H-atoms in the -CH3 (methyl) group are replaced
with iodine atoms, forming a -CI3 group
o The intermediate compound is hydrolysed by an alkaline solution to form a sodium
salt (RCO2- Na+) and a yellow precipitate of CHI3
The reaction of ethanal with iodoform results in the formation of a yellow CHI3 precipitate

Carboxylic Acids

Production of Carboxylic Acids

 Carboxylic acids are compounds with a -COOH functional group
 They can be prepared by a series of different reactions
Oxidation of primary alcohols & aldehydes
 Carboxylic acids can be formed from the oxidation of primary
alcohols and aldehydes by either acidified K2Cr2O7 or acidified KMnO4 and reflux
 The oxidising agents themselves get reduced causing the solutions to change colour
o In K2Cr2O7 the orange dichromate ions (Cr2O72-) are reduced to green Cr3+ ions
o In KMnO4 the purple manganate ions (MnO4-) are reduced to colourless
Mn2+ ions
 Oxidation of primary alcohols (1) and aldehydes (2) gives carboxylic acids
Hydrolysis of nitriles
 Carboxylic acids can also be prepared from the hydrolysis of nitriles using
either dilute acid or dilute alkali followed by acidification
o Hydrolysis by dilute acid results in the formation of a carboxylic acid and
ammonium salt
o Hydrolysis by dilute alkali results in the formation of a sodium carboxylate
salt and ammonia; Acidification is required to change the carboxylate ion into
a carboxylic acid
 The -CN group at the end of the hydrocarbon chain is converted to a -COOH group
Hydrolysis of nitriles by either dilute acid (1) or dilute alkali and acidification (2) will form
a carboxylic acid
Hydrolysis of esters
 Esters are formed from the condensation reaction between an alcohol and carboxylic
acid
 Hydrolysis of esters by dilute acid or dilute alkali and heat followed by
acidification will reform the alcohol and carboxylic acid
o Hydrolysis by dilute acid, is a reversible reaction and an equilibrium is
established
o Hydrolysis by dilute alkali is an irreversible reaction as all the ester is broken
down to form a sodium carboxylate salt and an alcohol; acidification is
required to change the carboxylate ion into a carboxylic acid
Hydrolysis of esters by either dilute acid (1) or dilute alkali and heat followed acidification
(2) will form a carboxylic acid
Reactions of Carboxylic Acids
 Carboxylic acids are weak acids as they do not completely dissociate in water
 This means that the position of the equilibrium lies to the left and that the
concentration of H+ is much smaller than the concentration of the carboxylic acid
 The solution has a pH value of less than 7

Carboxylic acids are weak acids that do not fully dissociate in water, the position of the
equilibrium lies to the left
 Carboxylic acids are reactive compounds which can undergo many types of reactions
including:
o Redox reactions with reactive metals
o Neutralisation reactions with alkali
o Acid-base reactions with carbonates
o Esterification with alcohols
o Reduction by LiAlH4
 Carboxylic acids undergo a wide variety of reactions

Esters
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Hydrolysis of Esters
 Esters can be hydrolysed to reform the carboxylic acid and alcohol by either dilute
acid or dilute alkali and heat
 When an ester is heated under reflux with dilute acid (eg. sulfuric acid) an
equilibrium mixture is established as the reaction is reversible

Ester hydrolysis by dilute acid is a reversible reaction forming carboxylic acid and alcohol
 However, heating the ester under reflux with dilute alkali (eg. sodium hydroxide) is
an irreversible reaction as the ester is fully hydrolysed
 This results in the formation of a sodium carboxylate salt which needs
further acidification to turn into a carboxylic acid
o The sodium carboxylate (-COO-) ion needs to get protonated by an acid (such
as HCl) to form the carboxylic acid (-COOH)
 Ester hydrolysis by dilute alkali is an irreversible reaction forming a sodium carboxylate
salt and alcohol
Commercial Uses of Esters
 Esters have sweet and fruity smells
 They are therefore commercially used in perfumes and flavourings
 The smaller esters such as ethyl acetate are furthermore used as solvents in organic
chemistry as it can dissolve in a wide range of organic compounds
