Organic Flashcards

CIE Chemistry A-Level
Topic 14 - An Introduction to Organic

Chemistry
Flashcards
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What is a functional group?
What is a functional group?
The group of atoms responsible for the

characteristic reactions of a compound.
What is a homologous series?
What is a homologous series?
A series of organic compounds with the

same functional group with successive
members differing by -CH2.
What is an alkane? Include the general
formula
What is an alkane? Include the general formula
A saturated hydrocarbon with general

formula CnH2n+2.
Suffix: -ane.
State the molecular, displayed and
skeletal formulae of butane
State the molecular, displayed and skeletal formulae
of butane
Molecular: C4H10
Displayed:
Skeletal:
What is an alkene? Include the general
formula
What is an alkene? Include the general formula
An unsaturated hydrocarbon with the

general formula CnH2n.
Suffix: -ene.
Write the molecular, displayed and
skeletal formulae of but-2-ene
Write the molecular and skeletal formulae of
but-2-ene
Molecular: C4H8
Skeletal:
The number 2 in but-2-ene signifies that the double bond is between the
2nd and 3rd carbon.
What is an arene?
(A level only)
What is an arene? (A level only)
● An aromatic hydrocarbon.
● Aromatic means that it contains a
benzene ring.
● Prefix: phenoyl- OR suffix: -benzene.
What is a halogenoalkane?
What is a halogenoalkane?
An alkane where a hydrogen atom has
been replaced by a halogen atom.
Prefix: fluoro-/ chloro-/ bromo-/ iodo-.
Write the molecular, displayed and
skeletal formulae of 1-chloropropane.
Write the molecular, displayed and skeletal formulae
of 1-chloropropane
Molecular: C3H7Cl
Displayed: The ‘1’ refers to the
carbon the halogen
atom is bonded to.
Skeletal:
What is a halogenoarene?
(A level only)
What is a halogenoarene? (A level only)
● An aromatic hydrocarbon whereby one or more hydrogen
atoms bonded to the aromatic ring are replaced by a
halogen atom.
● E.g. Chlorobenzene:
Naming: [fluoro-/ chloro-/ bromo-/ iodo-] - benzene

What is an alcohol? Include the general
formula
What is an alcohol? Include the general formula
An organic compound with a lone hydroxyl group
(-OH) attached to an alkyl group. The general
formula is CnH2n+1OH.
Suffix: -ol.
Write the molecular and skeletal
formulae of propan-2-ol
Write the molecular and skeletal formulae of
propan-2-ol
Molecular: C3H8O
The ‘2’ refers to

the position of the
Skeletal: hydroxyl group.
How are alcohols classified?
(R group - any alkyl chain)
● Primary, 1° - The carbon bonded to the hydroxyl group is

bonded to one R group only.
● Secondary, 2° - The carbon bonded to the hydroxyl group
is bonded to two R groups.
● Tertiary, 3° - The carbon bonded to the hydroxyl group is
bonded to three R groups.
What is a phenol?
(A level only)
What is a phenol? (A level only)
A phenyl group (-C6H5) bonded

to a hydroxyl group (-OH).
Phenol = C6H5OH.
Suffix: -phenol / -benzenol.
What is an aldehyde? Draw the
functional group
What is an aldehyde? Draw the functional group
An organic compound with the -CHO

functional group.
Suffix: -al.
What is a ketone? Draw the functional
group
What is a ketone? Draw the functional group
An organic compound with the RCOR functional

group.
Suffix: -one.
E.g. propanone, more commonly known as
acetone.
What is a carboxylic acid? Draw the
functional group
What is a carboxylic acid? Draw the functional group
An organic compound with the -COOH

functional group.
Suffix: -oic acid.
E.g. ethanoic acid, a key component of vinegar.
What is an ester? Draw the functional
group
What is an ester? Draw the functional group
An organic compound commonly formed

from a condensation reaction between
alcohol and carboxylic acid functional
groups.
Name the ester shown below
Name the ester shown below
This part of the molecule is
derived from the alcohol,
This part of the
methanol.
molecule is
derived from the
carboxylic acid,
ethanoic acid.
Methyl ethanoate
What is an acyl chloride? Draw the
functional group
(A level only)
What is an acyl chloride? Draw the functional group
(A level only)
A carboxylic acid derivative where
the -OH group in -COOH has
been replaced with a chlorine
atom to form a -COCl group.
Suffix: -oyl chloride.
What is a primary amine? Draw the
functional group
What is a primary amine? Draw the functional group
● An amine is a derivative of
ammonia.
● In a primary amine, one
hydrogen atom in ammonia is
substituted with an alkyl group.
● Suffix: -amine.
What is a nitrile? Draw the displayed
formula of ethanenitrile
What is a nitrile? Draw the displayed formula of
ethanenitrile
● An organic compound with a -CN
functional group.
● Prefix: cyano- OR suffix: -nitrile.
● Ethanenitrile:
What is an amide?
(A level only)
What is an amide? (A level only)
Formed from the condensation

reaction between a carboxylic
acid and an amine functional
group.
Suffix: -amide
What is an amino acid?
(A level only)
What is an amino acid? (A level only)
● An organic compound that
has both a carboxylic acid and
amine functional group.
● In an alpha-amino acid, both
groups are attached to the
same carbon atom.
● Naming: Amino- -oic acid.
What is an aliphatic hydrocarbon?
What is an aliphatic hydrocarbon?
A compound containing only carbon and

hydrogen atoms in which the carbon
atoms are arranged in a linear or
branched structure.
What is benzene?
What is benzene?
Benzene is an aromatic hydrocarbon/

arene.
Molecular formula: C6H6
Describe how to name an organic
compound.
Describe how to name an organic compound
● Identify the longest carbon chain that contains the functional
group (this is the stem).
● Identify the functional group (this is the prefix / suffix).
● Count the number of carbon atoms so that the functional group
has the lowest number.
● Add any side chains or less important functional as prefixes (in
alphabetical order).
● If there are 2 or more identical groups, use the prefixes di-/ tri-/
tetra- before that part of the name.
Draw and name the different structural
isomers of dimethylbenzene
(A level only)
Draw and name the different structural isomers of
dimethylbenzene (A level only)
1,2-Dimethylbenzene 1,3-Dimethylbenzene 1,4-Dimethylbenzene
Draw and name the structural isomers of
the aliphatic hydrocarbon C5H12
Draw and name the structural isomers of the
aliphatic hydrocarbon C5H12
What is the molecular formula of the
compound below?
What is the molecular formula of the compound
below?
C 4H 6O 2
What is homolytic fission?
What is homolytic fission?
A covalent bond breaks. Each bonding atom
receives an electron from the bonding pair, forming
two radicals (highly reactive, neutral species).
What is heterolytic fission?
What is heterolytic fission?
A covalent bond breaks. One bonding atom receives
both electrons from the bonding pair.
Jürgen Martens, CC BY-SA 3.0
What is a free radical?
What is a free radical?
A highly reactive neutral species with an

unpaired electron.
What are the three steps in a free radical
substitution mechanism?
What are the three steps in a free radical substitution
mechanism?
1. Initiation
2. Propagation
3. Termination
What is an electrophile?
What is an electrophile?
An electron pair acceptor
What is an nucleophile?
What is an nucleophile?
An electron pair donor
What is an addition reaction?
What is an addition reaction?
An addition reaction is a reaction where

two reactants react to form one product.
The atom economy is 100%.
What is a substitution reaction?
What is a substitution reaction?
A substitution reaction is a reaction

where an atom/ group is replaced by
another atom/ group.
Atom economy is less than 100%.
What is an elimination reaction?
What is an elimination reaction?
● An elimination reaction is a reaction where 2

substituents are removed from a molecule.
● E.g. a dehydration reaction (a molecule of
water is produced).
What is a hydrolysis reaction?
What is a hydrolysis reaction?
The splitting of a compound/ molecule

using water.
What is a condensation reaction?
What is a condensation reaction?
The formation of a compound with the

release of water.
What is oxidation?
What is oxidation?
Loss of electrons / increase in oxidation

number.
What is reduction?
What is reduction?
Gain of electrons / decrease in oxidation

number.
In organic redox reactions, how can
oxidising and reducing agents be
represented?
In organic redox reactions, how can oxidising and
reducing agents be represented?
● Oxidising reagents: [O]

● Reducing reagents: [H]
What is electron repulsion theory?
What is electron repulsion theory?
● Electron pairs are areas of negative charge

that repel each other.
● Lone pairs of electrons offer more repulsion
than bonding pairs.
Describe the shape and bond angles of
ethene
Describe the shape and bond angles of ethene
● Bond shape: Trigonal Planar

● Bond angle: 120°
Describe the shape and bond angles in
ethane
Describe the shape and bond angles in ethane
● Bond shape: Tetrahedral

● Bond angle: 109.5°
Explain the bond shape and angle in an
ethane molecule.
Explain the bond shape and angle in an ethane
molecule.
● Both carbon atoms promote an electron from the 2s orbital to the 2p
orbital to form four identical sp3 hybrid orbitals.
● These sp3 orbitals arrange themselves as far apart as possible from each
other.
● Each carbon atom then forms sigma bonds with the three hydrogen
atoms. A sigma bond also forms between the two carbon atoms when the
sp3 orbitals overlap end-to-end.
● There are 4 bonding pairs of electrons which causes a tetrahedral bond
shape and a bond angle of 109.5°.
Explain the bond shape and angle in an
ethene molecule.
Explain the bond shape and angle in an ethene molecule.
● Both carbon atoms promote an electron from the 2s orbital to the 2p orbital
to form three identical sp2 hybrid orbitals. (The other 2p orbital is
unchanged).
● The three sp2 orbitals arrange themselves as far apart as possible from
each other.
● 2 sp2 orbitals forms a sigma bond with a hydrogen. A sigma bond forms
between the carbon atoms when the sp2 orbitals overlap end-to-end,
followed by a pi bond when the p-orbitals overlap sideways.
● There are 3 areas of electron density, creating a trigonal planar shape and
a bond angle of 120°.
Describe the shape and bond angle of
benzene
(A level only)
Describe the shape and bond angle of benzene
(A level only)
Planar, 120°
Describe the bonding in benzene
(A level only)
Describe the bonding in benzene (A level only)
Delocalised structure of benzene:
● Each carbon atom uses two electrons form sigma
bonds with the adjacent carbon atoms. One electron
is used to form a sigma bond with a hydrogen atom.
● The remaining electron on each carbon atom is
delocalised to form a delocalised 𝛑 system (an area
of electron density).
Predict the shape and bond angle
around carbon in RCOOH
Predict the shape and bond angle around carbon in
RCOOH
● 3 areas of electron density like ethene
● Bond shape: Trigonal planar
● Bond angle: 120°
What is structural isomerism?
What is structural isomerism?
Compounds with the same molecular

formula but different structural formulae.
What are the 3 divisions of structural
isomerism?
What are the 3 divisions of structural isomerism?
1. Positional
2. Chain
3. Functional group
Why are propan-1-ol and propan-2-ol
structural isomers?
Why are propan-1-ol and propan-2-ol structural
isomers?
Positional isomerism
The position of the functional group has
changed.
Why are pentane and 2-methylbutane
structural isomers?
Why are pentane and 2-methylbutane structural
isomers?
Chain isomerism
Branching changes the structural formula of a
compound.
Why are propanal and propanone
structural isomers?
Why are propanal and propanone structural
isomers?
Functional group isomerism
The functional group has changed
(molecular formula stays the same).
What is stereoisomerism?
What is stereoisomerism?
Compounds with the same molecular

and structural formulae but a different
arrangement of atoms in space.
What causes geometrical (cis-trans)
stereoisomerism?
What causes geometrical (cis-trans)
stereoisomerism? What do cis and trans mean?
Cause by the limited rotation around the
carbon-carbon pi bond. Aany groups
bonded to the carbon are fixed in
position.
How do you determine whether an
stereoisomer is cis or trans?
How do you determine whether an stereoisomer is
cis or trans?
● In trans (or E) isomers, high priority groups are
on opposite sides of the C=C (above and
below).
● In cis (or Z) isomers, high priority groups are on
the same side of the C=C (above or below).
How can you identify the highest priority
group?
How can you identify the highest priority group?
● For molecules where only single atoms are attached to the carbons in the
C=C, the highest priority group has the highest atomic mass.
● For non-complex small groups such as -CH3, look at the atomic mass of
the atom attached directly to the C=C (in -CH3 this would be the carbon
atom- ignore the hydrogen atoms). The one with the greatest atomic
mass is the high priority group.
● For more complex groups (i.e. CH3CH2Cl), don’t just observe the atomic
mass of the carbon as it is directly attached to the C=C, look at what the
carbon is directly attached to etc.
Draw the cis and trans isomers of
2-chloropent-2-ene
Draw the cis and trans isomers of 2-chloropent-2-ene
trans-2-Chloropent-2-ene cis-2-chloropent-2-ene
The high priority groups are on The high priority groups are
opposite sides of C=C. on the same side of C=C.
What causes optical isomerism? What
are optical isomers?
What causes optical isomerism? What are optical
isomers?
● Optical isomerism is a type of
stereoisomerism found in molecules that
contain a chiral centre.
● Optical isomers or enantiomers are
non-superimposable, mirror images of each
other.
What is a chiral centre?
What is a chiral centre?
In organic chemistry, a chiral centre is in

the form of a carbon atom bonded to four
different groups. Compounds may
contain more than 1 chiral centre.
Draw diagrams to show the optical
isomers of butan-2-ol. Why can
butan-2-ol form optical isomers?
Draw diagrams to show the optical isomers of
butan-2-ol. Why can butan-2-ol form optical
isomers?
Optical isomers:
The central carbon in the diagrams is chiral because it is attached

to four different groups: -OH, -CH3, -H, and -CH2CH3. The two
isomers are non-superimposable mirror images of each other.
Identify the chiral centre in the molecule
below
Identify the chiral centre in the molecule below
This carbon is chiral as it is
bonded to 4 different groups:
-H, -OH, -COOH, -CH2COOH
Topic 15 - Hydrocarbons
Flashcards

Why are alkanes generally unreactive?
Why are alkanes generally unreactive?
● C-C and C-H bonds have a fairly high bond

enthalpy and therefore require a lot of energy
to overcome.
● The difference in electronegativities of C and
H is so small, making it very resistant to
reactions with polar reagents.
Write the chemical equation for the
complete combustion of ethane
Write the chemical equation for the complete
combustion of ethane
C2H6 + 3½O2 → 2CO2 + 3H2O
Write an overall equation for the
substitution reaction of ethane with
chlorine. Include any conditions.
Write an overall equation for the substitution reaction
of ethane with chlorine. Include any conditions.
UV light
C2H6 + Cl2 → C2H5Cl + HCl
What are the three steps of free radical
substitution?
What are the three steps of free radical substitution?
1. Initiation
2. Propagation
3. Termination
Write the mechanism for the free radical
substitution of ethane with chlorine
Write the mechanism for the free radical substitution of
ethane with chlorine
Initiation: Cl2 → 2Cl•
Propagation: C2H6 + •Cl → •C2H5 + HCl
•C2H5 + Cl2 → C2H5Cl + •Cl
Termination: •Cl + •Cl → Cl2
•C2H5 + •Cl → C2H5Cl
•C2H5 + •C2H5 → C4H10
What is crude oil a source of?
What is crude oil a source of?
Aliphatic and aromatic alkanes
What is cracking?
What is cracking?
The process in which complex organic

molecules are broken down into smaller
organic molecules, such as simple
alkanes.
Why is cracking used?
Why is cracking used?
To obtain more useful and smaller

alkanes and alkenes
What are the conditions and reagents for
the hydrogenation of alkenes. Write an
equation for the hydration of ethene
What are the conditions and reagents for the
hydrogenation of alkenes. Write an equation for the
hydration of ethene
● Hydrogen gas
● Nickel catalyst
● 150℃
C 2H 4 + H 2 → C 2H 6
What are the conditions and reagents for
the hydration of alkenes? Write an
equation for the hydration of ethene
What are the conditions and reagents for the
hydration of alkenes? Write an equation for the
hydration of ethene
● Steam
● H3PO4 catalyst
● 300℃ degrees
● 60-70 atm
C2H4 + H2O → C2H5OH
What are the conditions for the reactions
between alkenes and halogens? Write
an equation for the reaction between
ethene and bromine
What are the conditions for the reactions between
alkenes and halogens? Write an equation for the
reaction between ethene and bromine
● Room temperature
C2H4 + Br2 → C2H4Br2
What are the conditions for the reactions
between alkenes and hydrogen halides?
Write an equation for the reaction
between ethene and hydrogen bromide
What are the conditions for the reactions between
alkenes and hydrogen halides? Write an equation for
the reaction between ethene and hydrogen bromide
● Room temperature
C2H4 + HBr → C2H5Br
What is Markovnikov’s rule?
What is Markovnikov’s rule?
In the electrophilic addition of a hydrogen

halide to an asymmetric alkene, the
hydrogen atom will bond to the carbon
that is already bonded to the most
hydrogens.
Draw the mechanism for the electrophilic
addition reaction between ethene and
bromine
Draw the mechanism for the electrophilic addition
reaction between ethene and bromine
This leaves a (positive)

carbocation that is attracted
The electron dense carbon-carbon double
to the negative bromide ion
bond induces a dipole in the Br2 molecule.
The 𝜋 bond breaks and a carbon atom forms and hence forms a covalent
a bond with a bromine atom. bond with it.
Draw the mechanism for the electrophilic
addition reaction between propene and
hydrogen bromide (forming the minor
product)
Draw the mechanism for the electrophilic addition
reaction between propene and hydrogen bromide
(forming the minor product)
Br is more
electronegative than H. This leaves a (positive)
carbocation that is attracted
The electron dense C=C double bond is attracted to
to the negative bromide ion
the slightly positive hydrogen, causing the 𝜋 bond to
break and a covalent bond to form between the and hence forms a covalent
carbon and hydrogen atom. bond with it.
How are carbocations classified?
How are carbocations classified?
Primary Secondary Tertiary
Carbocation is bonded Carbocation is bonded Carbocation is bonded

to one alkyl group. to two alkyl groups. to three alkyl groups.
What is the trend in carbocation stability?
What is the trend in carbocation stability?
Primary → Secondary → Tertiary

Stability increases →
The more alkyl groups attached to the carbocation, the

more the positive charge is spread out, increasing stability.
In terms of carbocation stability, what will
be the major product in the addition
reaction between a hydrogen halide and
an unsymmetrical alkene?
In terms of carbocation stability, what will be the
major product in the addition reaction between a
hydrogen halide and an unsymmetrical alkene?
The major product will be the one whose
carbocation intermediate has the greater
stability i.e. a secondary carbocation is more
likely to form than a primary carbocation.
How can alkenes be oxidised to form a
diol? Write an equation for the oxidation
of ethene
How can alkenes be oxidised to form a diol? Write
an equation for the oxidation of ethene
● Manganate(VII) ions are a strong oxidising agent.
● When cold, dilute and acidified, the ions
experience a colour change from purple to
colourless as they are reduced.
C2H4 + H2O + [O] → (CH2OH)2
What happens when an alkene is
oxidised with hot, concentrated acidified
potassium manganate solution?
What happens when an alkene is oxidised with hot, concentrated acidified
potassium manganate solution?
The C=C double bond is broken and replaced with 2 x

C=O bonds (forming 2 carbonyl compounds):
What occurs next is based on whether the R groups are

alkyl groups or hydrogen atoms
After an alkene has been oxidised using
hot, concentrated H+/Cr2O72-, both R
groups of one of the products are alkyl
groups. What happens to this product?
After an alkene has been oxidised using hot, concentrated
H+/Cr2O72-, both R groups of one of the products are alkyl
groups. What happens to this product?
● The alkene was split into a ketone (where both
R groups are alkyl groups) and another
carbonyl
● Ketones cannot be oxidised further so
no further reaction occurs.
hot, concentrated H+/Cr2O72-, one of the
products has the following R groups: an
alkyl chain and a hydrogen atom. What
happens to this product?
After an alkene has been oxidised using hot,
concentrated H+/Cr2O72-, one of the products has the
following R groups: an alkyl chain and a hydrogen atom.
What happens to this product?
● The alkene was split into an aldehyde (with an alkyl group and
a hydrogen atom as the R groups) and another carbonyl
● The aldehyde is further oxidised to form a carboxylic acid:
hot, concentrated H+/Cr2O72-, both R
groups of one of the products are
hydrogen atoms. What happens to this
product?
After an alkene has been oxidised using hot,
concentrated H+/Cr2O72-, both R groups of one of the
products are hydrogen atoms. What happens to this
product?
● The alkene was oxidised to form methanal (with 2 hydrogen
atoms as R groups) and another carbonyl
● Methanal will be completely oxidised to form carbon dioxide
and water:
What is addition polymerisation?
What is addition polymerisation?
The joining together of unsaturated

alkene monomers to form a polymer. No
other products are formed (atom
economy is 100%).
How do alkenes undergo addition
polymerisation?
How do alkenes undergo addition polymerisation?
The 𝛑 bond breaks and each electron

goes towards forming a 𝝈 bond with an
adjacent monomer unit.
Deduce the repeat unit of the addition
polymer formed from the monomer
below
Deduce the repeat unit of the addition polymer formed
from the monomer below
● Turn the double C=C into a single C-C.

● Add and extend bonds out from the sides of the carbon
atoms.
● Add in square brackets around the molecule.
Identify the monomer that formed the
addition polymer below
Identify the monomer that formed the addition polymer
below
Propene
Why are polymers difficult to dispose of?
Why are polymers difficult to dispose of?
● They are non-biodegradable.

● The combustion of polymers can often form
harmful compounds (such as HCl for
chlorinated polymers)
Why are alkanes suitable for use as
fuels?
Why are alkanes suitable for use as fuels?
High standard enthalpy changes of

combustion (releases a lot of energy
upon combustion)
What are the problems with carbon
monoxide?
What are the problems with carbon monoxide?
● Carbon monoxide is poisonous.

● It irreversibly binds to haemoglobin, reducing the
amount of oxygen that can be carried in the blood.
● Cells may become deoxygenated, leading to cell death.
● If too much CO is inhaled, this could lead to death.
Why are atmospheric oxides of nitrogen
pollutants?
Why are atmospheric oxides of nitrogen pollutants?
● Nitrogen monoxide can react with

chemicals that cause acid rain.
● Nitrogen dioxide can also contribute to
photochemical smog.
Describe how a catalytic converter works
Describe how a catalytic converter works
● Nitrogen monoxide is formed in car engines:
N2(g) + O2(g) → 2NO(g)
● A catalytic converter removes a majority of NO so it
isn’t released into the atmosphere:
2NO(g) + 2CO(g) → N2(g) + CO2(g)
● A ceramic honeycomb structure is coated in a thin
layer of metal catalysts (such as platinum and
rhodium) https://bit.ly/pmt-cc
What are the environmental
consequences of unburnt hydrocarbons?
What are the environmental consequences of
unburnt hydrocarbons?
Hydrocarbons in the atmosphere can

absorb infrared radiation, causing the
greenhouse effect.
What are the environmental
consequences of the emission of
greenhouse gases?
What are the environmental consequences of the emission of
greenhouse gases?
Greenhouse gases cause the greenhouse effect which contributes to climate
change:
● Electromagnetic radiation from the sun passes through the atmosphere.

Some radiation is absorbed by Earth so temperature increases.
● Heat is radiated from the Earth as infrared radiation which is absorbed by
greenhouse gases in the atmosphere. This causes the bonds in these
molecules to vibrate before this energy is re-emitted.
● As a result, the atmosphere warms up even further, contributing to global
warming.
How is infrared spectroscopy used to
monitor air pollution?
How is infrared spectroscopy used to monitor air
pollution?
● IR spectroscopy identifies particular bonds in a
molecule.
● Different pollutants will have different patterns of
absorption as they contain different bonds.
● It is also possible to measure the concentration of
each pollutant.
Describe the halogenation of benzene
(A level only)
Describe the halogenation of benzene (A level only)
● E.g. Bromination:
● Benzene only reacts with bromine if a hydrogen
carrier, FeBr3 or AlBr3, is present.
● This forms bromobenzene and hydrogen bromide:
● C6H6 + Br2 → C6H5Br + HBr
What is the role of the halogen carrier in
the halogenation of benzene?
(A level only)
What is the role of the halogen carrier in the
halogenation of benzene? (A level only)
● To generate the electrophile:
● Br2 + FeBr3 → FeBr4- + Br+
● FeBr4- then reacts with the proton expelled from
the intermediate to regenerate the halogen
carrier:
● FeBr4- + H+ → FeBr3 + HBr
Draw and name the mechanism for the
bromination of benzene (A level only)
Draw and name the mechanism for the bromination of
benzene (A level only)
Electrophilic substitution.
The Br+ ion accepts a pair of The intermediate is so unstable that it

electrons from the ring of breaks down, releasing a hydrogen ion.
delocalisation. This forms the product, bromobenzene.
How does benzene undergo nitration?
(A level only)
How does benzene undergo nitration? (A level only)
Benzene reacts with conc. nitric acid at a
temperature of 50℃ - 60℃ with a conc.
sulfuric acid catalyst to from nitrobenzene
and water:
C6H6 + HNO3 → C6H5NO2 + H2O
How does sulfuric acid act as a catalyst
in the nitration of benzene?
(A level only)
How does sulfuric acid act as a catalyst in the
nitration of benzene? (A level only)
● Generation of electrophile:
● H2SO4 + HNO3 → NO2+ + HSO4- + H2O
● Sulfuric acid is regenerated when the
hydrogensulfate ion reacts with the proton that
is expelled from the intermediate:
● HSO4- + H+ → H2SO4
Draw and name the mechanism for the
nitration of benzene (A level only)
Draw and name the mechanism for the nitration of
benzene (A level only)
Electrophilic substitution
The NO2+ ion accepts a pair of The intermediate is so unstable that it

electrons from the delocalised breaks down, releasing a hydrogen ion.
pi system. This forms the product, nitrobenzene.
How does benzene undergo an
alkylation reaction? Write an equation for
the reaction between benzene and
chloroethane (A level only)
How does benzene undergo an alkylation reaction?
Write an equation for the reaction between benzene
and chloroethane (A level only)
React benzene with a haloalkane in the
presence of a halogen carrier (e.g. AlCl3):
C6H6 + C2H5Cl → C6H5(C2H5)+ HCl
How does the halogen carrier generate
the electrophile when benzene reacts
with a haloalkane?
How does the halogen carrier generate the
electrophile when benzene reacts with a haloalkane?
● Halogen carrier reacts with haloalkane to generate

electrophile:
● AlCl3 + C2H5Cl → AlCl4- + C2H5+
● AlCl4- reacts with the proton expelled from the
intermediate to regenerate the halogen carrier:
● AlCl4- + H+ → AlCl3 + HCl
How does benzene undergo an acylation
reaction? Write an equation for the
reaction between benzene and ethanoyl
chloride (A level only)
How does benzene undergo an acylation reaction?
Write an equation for the reaction between benzene
and ethanoyl chloride (A level only)
Reflux benzene with an acyl chloride in
the presence of a halogen carrier (i.e.
AlCl3):
C6H6 + CH3COCl → C6H5COCH3+ HCl
How does the halogen carrier generate
the electrophile when benzene reacts
with an acyl chloride? (A level only)
How does the halogen carrier generate the
electrophile when benzene reacts with an acyl
chloride? (A level only)
● Halogen carrier reacts with acyl chloride to generate
electrophile:
● AlCl3 + CH3COCl → AlCl4- + CH3CO+
● AlCl4- reacts with the proton expelled from the
intermediate to regenerate the halogen carrier:
● AlCl4- + H+ → AlCl3 + HCl
How does benzene undergo addition
reactions with hydrogen? (A level only)
How does benzene undergo addition reactions with
hydrogen? (A level only)
C6H6 + 3H2 → C6H12
● Nickel catalyst
● Heated to around 150℃
● High pressure
● These conditions are required because this reaction has a
high activation energy.
How is the side chain of methylbenzene
completely oxidised to give benzoic
acid? (A level only)
How is the side chain of methylbenzene completely
oxidised to give benzoic acid? (A level only)
● Alkyl groups attached to a benzene ring are
oxidised fairly easily when heated under reflux with
alkaline potassium manganate solution.
● Purple solution → Dark brown precipitate of MnO2
● Dilute sulfuric acid is then added.
● Overall, methylbenzene is oxidised to benzoic acid.
How does the ring of delocalisation affect
the reactions of benzene? (A level only)
How does the ring of delocalisation affect the
reactions of benzene? (A level only)
● Electron density is relatively low so there is weak attraction to
electrophiles.
● This means benzene is unable to undergo electrophilic addition
reactions and will slowly undergo electrophilic substitution
reactions.
● If benzene was to undergo addition reactions it would
permanently break the delocalisation- energetics would be
against this happening.
Compare the reactivity of chlorobenzene
to chloroalkanes (A level only)
Compare the reactivity of chlorobenzene to
chloroalkanes (A level only)
● The C-Cl bond in chlorobenzene is stronger than expected.
One of the lone pairs on the chlorine atom interacts with the
delocalised ring electrons, strengthening the bond.
● This means the bond is harder to break and hence requires
more energy to overcome.
● This means chlorobenzene is less reactive than
chloroalkanes.
How can you tell whether a substitution
reaction by a halogen will occur in the
benzene ring or on the side chain?
(A level only)
How can you tell whether a substitution reaction by a
halogen will occur in the benzene ring or on the side
chain? (A level only)
For the substitution by a halogen:
● If UV light is present and a catalyst is absent:
substitution takes place on the side chain.
● If a catalyst is present and UV light is absent:
substitution takes place in the ring.
Topic 16 - Halogen Derivatives
Flashcards

What are halogenoalkanes?
What are halogenoalkanes?
Halogenoalkanes are organic

compounds where the hydrogen atom on
an alkane has been replaced by a
halogen.
How do halogenoalkanes undergo
hydrolysis reactions?
How do halogenoalkanes undergo hydrolysis
reactions?
CH3CH2Br + H2O → CH3CH2OH + HBr

- Reaction is fairly slow.
- Resulting solution can be tested with
AgNO3 to determine the halogen present.
How do halogenoalkanes undergo a
nucleophilic substitution reaction to form
a nitrile?
How do halogenoalkanes undergo a nucleophilic
substitution reaction to form a nitrile?
CH3CH2Br + KCN → CH3CH2CN + KBr

- Heat under reflux.
- Ethanol is used as the solvent.
How do halogenoalkanes react with
ammonia to form a primary amine?
How do halogenoalkanes react with ammonia to
form a primary amine?
First the halogenoalkane reacts with ammonia to form an alkyl
ammonium salt:
● CH3CH2Br + NH3 → CH3CH2NH3Br
If the ammonia is in excess, the salt reacts to form a primary

amine:
● CH3CH2NH3Br + NH3 → CH3CH2NH2 + NH4Br

How does 2-bromopropane react to form
an alkene?
How does 2-bromopropane react to form an alkene?
Elimination reaction:
Reflux with KOH in ethanol (or conc. NaOH
solution).
CH3CHBrCH3 + KOH → CH2=CHCH3 + KBr + H2O
Describe the SN1 nucleophilic
substitution mechanism
Describe the SN1 nucleophilic substitution
mechanism
E.g. (CH3)3CCl + OH- → (CH3)3COH + Cl-
In the first stage, the halogenoalkane ionises to form the

carbocation intermediate (CH3)3C+ and Cl-.
The (CH3)3C+ intermediate then immediately reacts with

the hydroxide ion to form the product.
What does the SN1 mechanism look
like?
What does the SN1 mechanism look like?
Step 1
Step 2
Describe the SN2 nucleophilic
substitution mechanism
Describe the SN2 nucleophilic substitution mechanism
E.g. CH3CH2Br + OH- → CH3CH2OH + Br-
- These reactions are a one step mechanism.
- The nucleophile attacks the substrate at the same time as the
leaving group leaves the substrate.
- The nucleophile attacks the carbon atom from the back side,
causing an inversion of the groups in the product.
- The nucleophile attacks from the backside because the large
halogen atom prevents the attack from the other direction.
What does a SN2 mechanism look like?
What does a SN2 mechanism look like?
E.g. CH3Cl + OH- → CH3OH + Cl-
What are the inductive effects of alkyl
groups?
What are the inductive effects of alkyl groups?
Alkyl groups are electron-donating groups.

They push electrons away, making the alkyl
group have a slight positive charge and the
carbon it is bonded with to have a slight negative
charge. This is called the positive inductive
effect.
What mechanism (SN1 or SN2) do
primary, secondary and tertiary
haloalkanes react via?
What mechanism (SN1 or SN2) do primary,
secondary and tertiary haloalkanes react via?
Primary halogenoalkanes tend to react via the SN2
mechanism.
Tertiary halogenoalkanes tend to react via the SN1

mechanism.
Secondary halogenoalkanes react via a mixture of the two,

depending on the structure.
What are the relative strengths of
carbon-halogen bonds?
What are the relative strengths of carbon-halogen
bonds?
As you go down Group 7, the carbon-halogen
bond strength decreases.
C-F > C-Cl > C-Br > C-I
Hence what is the trend in the rate of
hydrolysis of carbon-halogen bonds?
Hence what is the trend in the rate of hydrolysis of
carbon-halogen bonds?
As you go down the group, the rate of
hydrolysis of carbon-halogen bonds increases
as less energy is required to break the bond
since bond strength weakens down the group.
What are the uses of fluoroalkanes and
fluorohalogenoalkanes?
What are the uses of fluoroalkanes and
fluorohalogenoalkanes?
- Refrigerants
- Used in aerosols
- Used in making foamed plastics
They are very chemically inert and will not react
with anything.
What is the environmental problem with
the use of CFCs (chlorofluorocarbons)?
What is the environmental problem with the use of
CFCs (chlorofluorocarbons)?
CFCs damage the ozone layer. The ozone is in the upper
atmosphere and it absorbs a lot of UV radiation.
CFCs are broken down by UV light, releasing a chlorine

radical. This chlorine radical react with ozone and breaks it
down to oxygen. This means there is less protection from
UV radiation.
Give the equations for the reactions that
take place between a chlorine free
radical and ozone
Give the equations for the reactions that take place
between a chlorine free radical and ozone
Cl. + O3 → O2 + ClO.
. .
ClO + O3 → 2O2 + Cl
Overall: 2O3 → 3O2
Topic 17 - Hydroxy Compounds
Flashcards

What is the chemical equation for the
complete combustion of ethanol?
What is the chemical equation for the complete
combustion of ethanol?
CH3CH2OH + 3O2 ⟶ 2CO2 + 3H2O
What condition is required to ensure
complete combustion takes place?
What condition is required to ensure complete
combustion takes place?
Excess oxygen
incomplete combustion of ethanol to
produce carbon monoxide?
What is the chemical equation for the incomplete
combustion of ethanol to produce carbon monoxide?
C2H5OH + 2O2→ 3H2O + 2CO
How do alcohols react to form
halogenoalkanes?
How do alcohols react to form halogenoalkanes?
There are multiple ways alcohols can react to

form halogenoalkanes:
- React with sodium halides and sulfuric acid.
- React with sodium or potassium iodide and
concentrated phosphoric (V) acid.
How do alcohols react with sodium?
How do alcohols react with sodium?
2CH3CH2OH + 2Na → 2CH3CH2ONa + H2

Ethanol reacts with sodium to form hydrogen gas
and sodium ethoxide (an alkoxide).
If the solution is evaporated, sodium ethoxide
remains as a white solid.
How are primary alcohols oxidised to
aldehydes?
How are primary alcohols oxidised to aldehydes?
If you heat a primary alcohol with acidified potassium
dichromate(VI), the alcohol will be oxidised to form an
aldehyde:
CH3CH2OH + [O] → CH3CHO + H2O
The acidified potassium dichromate(VI) will change
colour from orange to green.
carboxylic acids?
How are primary alcohols oxidised to carboxylic
acids?
If a primary alcohol is heated under reflux with acidified
potassium dichromate(VI), the alcohol will be oxidised form a
carboxylic acid.
CH3CH2OH + 2[O] → CH3COOH + H2O
The acidified potassium dichromate(VI) will change colour

from orange to green.
How are secondary alcohols oxidised to
ketones?
How are secondary alcohols oxidised to ketones?
If a secondary alcohol is heated under reflux with
acidified potassium dichromate (VI), the alcohol will be
oxidised to form a ketone:
CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O
How do alcohols undergo dehydration
reactions?
How do alcohols undergo dehydration reactions?
Alcohols undergo dehydration reactions to form
an alkene and a water molecule.
Two options to carry out dehydration:
- Heat with strong acid catalyst.
- Pass alcohol vapour over Al2O3 powder.
dehydration of propan-2-ol to form
prop-2-ene?
What is the chemical equation for the dehydration of
propan-2-ol to form prop-2-ene?
CH3CH(OH)CH3 → CH2CHCH3 + H2O
How do alcohols react with carboxylic
acids?
How do alcohols react with carboxylic acids?
Alcohols react with carboxylic acids to

form esters. This process is called
esterification and requires heating with a
sulfuric acid catalyst.
reaction between methanol and ethanoic
acid? Give the name of the ester formed
What is the chemical equation for the reaction
between methanol and ethanoic acid? Give the
name of the ester formed
CH3OH + CH3COOH → CH3COOCH3 + H2O
Product CH3COOCH3 is methyl ethanoate.
How do acyl chlorides react to form an
ester? (A-Level only)
How do acyl chlorides react to form an ester?
(A-Level only)
Acyl chlorides react with primary alcohols to
form esters. Hydrogen chloride is also
produced during the reaction.
CH3COCl + CH3OH → CH3COOCH3 + HCl
reaction between ethanol and propanoyl
chloride? Give the name of the ester
formed
(A-Level only)
between ethanol and propanoyl chloride? Give the
name of the ester formed (A-Level only)
CH3CH2COCl + CH3CH2OH → CH3CH2COOCH2CH3 +
HCl
The product CH3CH2COOCH2CH3 is ethyl propanoate.
- Primary, 1° - The carbon bonded to the alcohol group is

bonded to one R (alkyl) group only.
- Secondary, 2° - The carbon bonded to the alcohol group is
bonded to two R groups.
- Tertiary, 3° - The carbon bonded to the alcohol group is
bonded to three other R groups.
How can you distinguish between
primary, secondary and tertiary alcohols?
How can you distinguish between primary, secondary and
tertiary alcohols?
- Tertiary cannot be oxidised and therefore there’s no colour
change (remains orange) when heated with acidified potassium
dichromate (VI).
- Primary and secondary alcohols are able to be oxidised and so
there would be a colour change from orange to green.
- You could run further tests on the resulting solutions from
primary and secondary alcohols by using Fehling’s or Tollens’
reagent.
How can you deduce the presence of a
CH3CH(OH)– group in an alcohol?
How can you deduce the presence of a
CH3CH(OH)– group in an alcohol?
- Iodine is added to a small volume of alcohol.
- Some sodium hydroxide is then added to decolourise
the iodine.
- The presence of a CH3CH(OH)- group is indicated by
a very pale yellow precipitate known as
tri-iodomethane, CH3I.
How does phenol react with bases, e.g.
NaOH? (A-Level only)
How does phenol react with bases, e.g. NaOH?
(A-Level only)
Phenol reacts with sodium hydroxide to
form sodium phenoxide and water.
reaction of phenol with sodium
hydroxide?
(A-Level only)
What is the chemical equation for the reaction of
phenol with sodium hydroxide? (A-Level only)
- +
C6H5OH + NaOH → C6H5O Na + H2O
How does phenol react with sodium?
(A-Level only)
How does phenol react with sodium? (A-Level only)
Phenol reacts with sodium to form

sodium phenoxide and hydrogen gas.
reaction of phenol with sodium?
(A-Level only)
phenol with sodium? (A-Level only)
C6H5OH + Na → C6H5O-Na+ + ½H2
How does phenol react with diazonium
salts?
(A-Level only)
How does phenol react with diazonium salts?
(A-Level only)
In a coupling reaction:
C6H5OH + NaOH → C6H5O-Na+ + H2O
The sodium phenoxide solution reacts with a

benzenediazonium salt solution:
How does phenol react with dilute nitric
acid?
(A-Level only)
How does phenol react with dilute nitric acid?
(A-Level only)
Phenol reacts readily with dilute nitric acid at room temperature
to form a mixture of 2-nitrophenol and 4-nitrophenol.
How does phenol react with
concentrated nitric acid?
(A-Level only)
How does phenol react with concentrated nitric acid?
(A-Level only)
Phenol reacts with concentrated nitric acid to form
2,4,6-trinitrophenol.
How does the bromination of phenol
occur?
(A-Level only)
How does the bromination of phenol occur?
(A-Level only)
Phenol reacts with bromine to form a white
precipitate of 2,4,6-tribromophenol.
What are the relative acidities of water,
phenol and ethanol?
(A-Level only)
What are the relative acidities of water, phenol and
ethanol? (A-Level only)
Phenol > water > ethanol

Phenol is the most acidic.
Ethanol is the least acidic.
Explain the relative acidities of water,
phenol and ethanol
(A-Level only)
Explain the relative acidities of water, phenol and
ethanol (A-Level only)
- Phenol is the most acidic because the phenoxide ion is relatively stable. The
lone pair on the oxygen atom is delocalised into the pi system meaning the
negative charge is dispersed among the carbon atoms so phenol is most likely
to donate a hydrogen ion.
- Ethanol and water have similar acidities but ethanol is the least acidic. This is
because of the positive inductive effect. The alkyl group in the ethoxide ion
“pushes” electrons away from itself. This increases the electron density of the
oxygen, making it more likely to bond to a hydrogen ion and reform ethanol.
Topic 18 - Carbonyl Compounds
Flashcards

aldehydes?
How are primary alcohols oxidised to aldehydes?
If a primary alcohol is heated with acidified potassium
dichromate(VI), the alcohol will be oxidised to form an
aldehyde.
CH3CH2OH + [O] → CH3CHO + H2O
How are secondary alcohols oxidised to
ketones?
How are secondary alcohols oxidised to ketones?
If a secondary alcohol is heated under reflux with

acidified potassium dichromate(VI), the alcohol will be
oxidised to form a ketone:
CH3CH(OH)CH3 + [O] → CH3COCH3 + H2O
How are aldehydes and ketones reduced
using cyanide ions?
How are aldehydes and ketones reduced using
cyanide ions?
By using HCN in ethanol or NaCN solution:

CH3CHO + HCN → CH3CH(OH)CN
CH3COCH3 + HCN → CH3C(OH)CNCH3
How are aldehydes and ketones reduced
using NaBH4 or LiAlH4 ions?
How are aldehydes and ketones reduced using
NaBH4 or LiAlH4 ions?
NaBH4 and LiAlH4 are reducing agents

and can both be represented as [H] in
chemical equations:
CH3CHO + 2[H] → CH3CH2OH
What is the mechanism for the reaction
between HCN and aldehydes and
ketones?
What is the mechanism for the reaction between
HCN and aldehydes and ketones?
Nucleophilic addition
What is the test for a carbonyl
compound?
What is the test for a carbonyl compound?
Brady’s reagent / 2,4-dinitrophenylhydrazine
(2,4-DNPH):
- Add a few drops of the unknown sample to 5 cm3 of
Brady’s reagent.
- The presence of a carbonyl compound is indicated by
a yellow/orange precipitate.
How can you test for an aldehyde using
Fehling’s solution?
How can you test for an aldehyde using Fehling’s
solution?
Warm the sample with Fehling’s solution.

If an aldehyde is present, the blue
solution will form a brick red precipitate.
How can you test for an aldehyde using
Tollens’ reagent?
How can you test for an aldehyde using Tollens’
reagent?
Add Tollens’ reagent to the sample and warm in a
water bath.
The presence of a silver mirror on the test tube
indicates that the sample contains an aldehyde
functional group.
How do CH3CO- compounds react with
alkaline aqueous iodine?
How do CH3CO- compounds react with alkaline
aqueous iodine?
Iodine is added to the aldehyde or ketone
solution. Just enough NaOH is added until the
iodine is decolourised.
A pale yellow precipitate of tri-iodomethane,
CH3I, is formed.
Topic 19 - Carboxylic Acids and
Derivatives
Flashcards

carboxylic acids?
How are primary alcohols oxidised to carboxylic
acids?
If a primary alcohol is heated under reflux with acidified
potassium dichromate(VI), the alcohol will be oxidised to form
a carboxylic acid.
CH3CH2OH + 2[O] → CH3COOH + H2O

How are aldehydes oxidised to
carboxylic acids?
How are aldehydes oxidised to carboxylic acids?
If an aldehyde is heated under reflux with acidified potassium

dichromate(VI), the aldehyde will be oxidised to form a
carboxylic acid.
CH3CHO + [O] → CH3COOH

How do nitriles react to form carboxylic
acids?
How do nitriles react to form carboxylic acids?
Nitriles react via acid hydrolysis to form carboxylic

acids.
Heat the nitrile under reflux with a strong acid
catalyst:
CH3CN + 2H2O + HCl → CH3COOH + NH4Cl
How do carboxylic acids react with
metals?
How do carboxylic acids react with metals?
Carboxylic acids react with metals to

form a salt and hydrogen gas.
reaction of ethanoic acid with sodium?
ethanoic acid with sodium?
2CH3COOH + 2Na → 2CH3COO-Na+ + H2
carbonates?
How do carboxylic acids react with carbonates?
Carboxylic acids react with carbonates to

form a salt, carbon dioxide and water.
reaction of ethanoic acid with sodium
carbonate?
ethanoic acid with sodium carbonate?
2CH3COOH + Na2CO3 → 2CH3COO-Na+ + CO2 + H2O
alkalis?
How do carboxylic acids react with alkalis?
Carboxylic acids react with alkalis to

form a salt and water:
- +
CH3COOH + NaOH → CH3COO Na + H2O
How do alcohols react with carboxylic
acids?
How do alcohols react with carboxylic acids?
Alcohols react with carboxylic acids to

form esters. This process is called
esterification and requires heating with a
sulfuric acid catalyst.
reaction between methanol and ethanoic
acid? Give the name of the ester formed
between methanol and ethanoic acid? Give the
name of the ester formed
CH3OH + CH3COOH → CH3COOCH3 + H2O
Product CH3COOCH3 is methyl ethanoate.
How do carboxylic acids form alcohols?
How do carboxylic acids form alcohols?
Reduction with LiAlH4
reduction of ethanoic acid?
What is the chemical equation for the reduction of
ethanoic acid?
CH3COOH + 4[H] → CH3CH2OH + H2O
How do carboxylic acids react to form
acyl chlorides?
(A-Level only)
How do carboxylic acids react to form acyl
chlorides? (A-Level only)
Carboxylic acids react with sulfur dichloride
oxide to form an acyl chloride, sulfur dioxide
and hydrogen chloride.
CH3COOH + SOCl2 → CH3COCl + SO2 + HCl
reaction between ethanoic acid and
sulfur dichloride oxide?
(A-Level only)
between ethanoic acid and sulfur dichloride oxide?
(A-Level only)
CH3COOH + SOCl2 → CH3COCl + SO2 + HCl
How is methanoic acid further oxidised?
(A-Level only)
How is methanoic acid further oxidised?
(A-Level only) Although methanoic acid is a carboxylic
acid, it also has an aldehyde functional
group. This means the aldehyde group
can be oxidised further by using Tollens’
reagent or Fehling’s solution.
The methanoic acid is oxidised to carbon
dioxide and water.
oxidation of methanoic acid?
(A-Level only)
What is the chemical equation for the oxidation of
methanoic acid? (A-Level only)
HCOOH + [O] → CO2 + H2O
How is ethanedioic acid oxidised further?
(A-Level only)
How is ethanedioic acid oxidised further?
(A-Level only)
Ethanedioic acid is oxidised to carbon

dioxide and water using warm acidified
potassium manganate(VII) solution.
oxidation of ethanedioic acid?
(A-Level only)
What is the chemical equation for the oxidation of
ethanedioic acid? (A-Level only)
(COOH)2 + [O] → 2CO2 + H2O
State the relative acidities of carboxylic
acids, alcohols and phenols
(A-Level only)
State the relative acidities of carboxylic acids,
alcohols and phenols (A-Level only)
Carboxylic acids → Phenol → Alcohols

→ Decreasing acidity →
Explain the relative acidities of carboxylic
acids, alcohols and phenols
(A-Level only)
Explain the relative acidities of carboxylic acids,
alcohols and phenols (A-Level only)
● Carboxylic acids are the most acidic as the carboxylate ion has a delocalised pi system
that develops over the -COO- group. This distributes the negative charge, making the
carboxylate ion more stable.
● Phenols are more acidic than alcohols because the the phenoxide ion is relatively stable.
The lone pair on the oxygen is delocalised into the pi system so the negative charge is
dispersed. This makes phenol more likely to donate a hydrogen ion compared with
alcohols.
● Alcohols are the least acidic because of the positive inductive effect. In the alkoxide ion,
the alkyl groups “push” electrons away from themselves, increasing the electron density
of the oxygen, making it more likely to bond to a hydrogen ion and reform an alcohol.
What determines the acidity of chlorine
substituted ethanoic acids?
(A-Level only)
What determines the acidity of chlorine substituted
ethanoic acids? (A-Level only)
- You can strengthen an acid by pulling charge away
from the -COO- end. This can be done by adding a
chlorine atom to the chain.
- Chlorine is very electronegative and so will have a
tendency to attract electrons towards itself.
- The more chlorines bonded, the stronger the acid.
How do acyl chlorides react with water?
(A-Level only)
How do acyl chlorides react with water?
(A-Level only)
Hydrolysis reaction:
The acyl chloride reacts with water to form a
carboxylic acid and hydrochloric acid.
hydrolysis of ethanoyl chloride?
(A-Level only)
What is the chemical equation for the hydrolysis of
ethanoyl chloride? (A-Level only)
CH3COCl + H2O → CH3COOH + HCl
How do acyl chlorides react with
alcohols? (A-Level only)
How do acyl chlorides react with alcohols?
(A-Level only)
Acyl chlorides react with alcohols to form
an ester and hydrochloric acid:
CH3COCl + CH3OH → CH3COOCH3 + HCl
How do acyl chlorides react with phenol?
(A-Level only)
How do acyl chlorides react with phenol?
(A-Level only)
An acyl chloride reacts with phenol to

form an ester and hydrochloric acid.
CH3COCl + C6H5OH → CH3COOC6H5 + HCl
How do acyl chlorides react with
ammonia?
(A-Level only)
How do acyl chlorides react with ammonia?
(A-Level only)
Acyl chlorides react with ammonia to
form a primary amide and hydrochloric
acid:
CH3COCl + NH3 → CH3CONH2 + HCl
How do acyl chlorides react with a
primary amine?
(A-Level only)
How do acyl chlorides react with a primary amine?
(A-Level only)
Acyl chlorides react with a primary amine
to form a secondary amide and
hydrochloric acid:
CH3COCl + CH3NH2 → CH3CONHCH3 +
HCl https://bit.ly/pmt-edu
Compare the relative ease of hydrolysis
of acyl chlorides, alkyl chlorides and aryl
chlorides
(A-Level only)
Compare the relative ease of hydrolysis of acyl
chlorides, alkyl chlorides and aryl chlorides
(A-Level only)
- Acyl chlorides react vigorously with cold water to
produce a carboxylic acid and hydrogen chloride gas.
E.g. CH3COCl + H2O → CH3COOH + HCl
- Alkyl chlorides have almost no reaction with water.
- Aryl chlorides have no reaction with water.
How do esters undergo acid hydrolysis?
How do esters undergo acid hydrolysis?
Heat the ester under reflux with dilute aqueous

acid. The ester will be hydrolysed into a
carboxylic acid and alcohol.
The reaction is slow and reversible.
CH3COOCH3 + H2O ⇌ CH3COOH + CH3OH
How do esters undergo base hydrolysis?
How do esters undergo base hydrolysis?
Heat the ester under reflux with a dilute alkali.
The ester will be hydrolysed into the salt of the
carboxylic acid, and the alcohol. The reaction is
one-way and faster than acid hydrolysis.
CH3COOCH3 + NaOH → CH3COO-Na+ + CH3OH
State the major commercial uses of
esters
State the major commercial uses of esters
- Perfumes
- Solvents
- Flavourings

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CIE Chemistry A-Level

Topic 14 - An Introduction to Organic

PMT Education is licensed under https://bit.ly/pmt-cc

The group of atoms responsible for the

A series of organic compounds with the

A saturated hydrocarbon with general

An unsaturated hydrocarbon with the

Naming: [fluoro-/ chloro-/ bromo-/ iodo-] - benzene

The ‘2’ refers to

● Primary, 1° - The carbon bonded to the hydroxyl group is

A phenyl group (-C6H5) bonded

An organic compound with the -CHO

An organic compound with the RCOR functional

An organic compound with the -COOH

E.g. ethanoic acid, a key component of vinegar.

An organic compound commonly formed

Formed from the condensation

A compound containing only carbon and

Benzene is an aromatic hydrocarbon/

1,2-Dimethylbenzene 1,3-Dimethylbenzene 1,4-Dimethylbenzene

Jürgen Martens, CC BY-SA 3.0

A highly reactive neutral species with an

An electron pair acceptor

An electron pair donor

An addition reaction is a reaction where

A substitution reaction is a reaction

● An elimination reaction is a reaction where 2

The splitting of a compound/ molecule

The formation of a compound with the

Loss of electrons / increase in oxidation

Gain of electrons / decrease in oxidation

● Oxidising reagents: [O]

● Electron pairs are areas of negative charge

● Bond shape: Trigonal Planar

● Bond shape: Tetrahedral

Compounds with the same molecular

Compounds with the same molecular

In organic chemistry, a chiral centre is in

The central carbon in the diagrams is chiral because it is attached

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● C-C and C-H bonds have a fairly high bond

C2H6 + 3½O2 → 2CO2 + 3H2O

Propagation: C2H6 + •Cl → •C2H5 + HCl

•C2H5 + Cl2 → C2H5Cl + •Cl

Termination: •Cl + •Cl → Cl2

•C2H5 + •Cl → C2H5Cl

•C2H5 + •C2H5 → C4H10

Aliphatic and aromatic alkanes

The process in which complex organic

To obtain more useful and smaller

In the electrophilic addition of a hydrogen

This leaves a (positive)

Primary Secondary Tertiary

Carbocation is bonded Carbocation is bonded Carbocation is bonded

Primary → Secondary → Tertiary

The more alkyl groups attached to the carbocation, the

The C=C double bond is broken and replaced with 2 x

What occurs next is based on whether the R groups are

The joining together of unsaturated