You are on page 1of 88

AS-LEVEL

AS-LEVEL
CHEMISTRY

CHEMISTRY
NOTES

snaprevise.co.uk
I have designed and compiled
these beautiful notes to
provide a detailed but concise
summary of this module.
I have spent a lot of time
perfecting the content as
well as the presentation to
make your learning as easy as
possible and less daunting.

A-LEVEL REVISION & EXAM


PREP IN A SNAP

Concise & exam High quality notes Created by A*


board specific videos and summaries students

Visit snaprevise.co.uk to find out more


DISCLAIMER
The information presented is no way produced
or endorsed by any exam board.
INDEX

MODULE 2: FOUNDATIONS IN CHEMISTRY. . . . . . . . . 5


TOPIC 1: ATOMS AND REACTIONS . . . . . . . . . . . . . . . . . . . 6

Section 1: Atoms & Reactions . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 7

Section 2: Compounds, Formulae & Equations . . . . . . . . . . . . . . . . . . . . . . . . . . 9

Section 3: Amount of a Substance. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 10

Section 4: Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13

Section 5: Redox . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15

TOPIC 2: ELECTRONS, BONDING AND STRUCTURE. . . . . . . . . 18

Section 1: Electron Structure. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19

Section 2: Bonding & Structure . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22

MODULE 3: THE PERIODIC TABLE AND ENERGY. . . . . . 31


TOPIC 1: THE PERIODIC TABLE . . . . . . . . . . . . . . . . . . . . . 32

Section 1: Periodicity. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33

Section 2: Group 2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38

Section 3: Halogens. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40

Section 4: Qualitative analysis . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42

3
TOPIC 2: PHYSICAL CHEMISTRY. . . . . . . . . . . . . . . . . . . . 43

Section 1: Enthalpy changes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 44

Section 2: Reaction Rates. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49

Section 3: Chemical equilibrium. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 53

MODULE 4: CORE ORGANIC CHEMISTRY . . . . . . . . . . 56


TOPIC 1: BASIC CONCEPTS AND HYDROCARBONS. . . . . . . . . 57

Section 1: Basic Concepts of Organic Chemistry. . . . . . . . . . . . . . . . . . . . . . . . . 58

Section 2: Alkanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64

Section 3: Alkenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67

TOPIC 2: ALCOHOLS, HALOALKANES AND ANALYSIS . . . . . . . . 74

Section 1: Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75

Section 2: Haloalkanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78

Section 3: Organic Synthesis. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 80

Section 4: Analytical techniques. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 84

4
MODULE 2

FOUNDATIONS
IN
CHEMISTRY
TOPIC 1

Atoms
and
Reactions
SECTION 1:
Atoms & Reactions
1 Atomic structure & Isotopes
•• Atoms are made up of protons, electrons and neutrons
•• Neutral atoms have the same number of protons and electrons
•• You can work out numbers of protons, electrons and neutrons from the element symbol
•• To find the total number of electrons for positive ions take away the same number of electrons
from the atom (e.g. 3 from a 3+ ion) and for negative ions add the same number of electrons

Particle Position Relative Mass Charge


Proton Nucleus 1.0 +1
Neutron Nucleus 1.0 0
Electron Shells around nucleus 1/2000 -1

2 Isotopes
•• Isotopes are atoms of an element with the same number of protons, but different numbers
of neutrons
•• They have the same numbers of electrons and identical chemical reactions as a result
•• The atomic number is often omitted because it stays the same and the element symbol
indicates how many protons there are

snaprevise.co.uk 7
3 Relative Masses
•• The relative isotopic mass is the mass of an atom of an isotope compared with the mass of
1/12th an atom of 12C
•• The relative atomic mass, Ar, is the weighted mean mass of an atom compared with 1/12th of
the mass of an atom of 12C

4 Mass spectrometry
•• Mass spectrometry allows the masses of individual molecules or isotopes to be determined
by turning substances into positive ions and measuring their mass/charge (m/z) ratio
•• Mass spectra plot m/z against percentage abundance

•• Number of isotopes can be identified by number of peaks


•• Each peak represents an isotope
•• To find the relative atomic mass multiply each isotopic mass by percentage abundance, add
the results together and divide by 100

5 Relative molecular mass


•• Relative molecular mass, Mr, is the mass of all the atoms in a molecule of a simple molecular
substance
•• It’s found by adding up the relative atomic masses of all atoms in a molecule
•• Relative formula mass is the mass of one formula unit of a compound that forms a giant
structure e.g. NaCl
•• It’s found in exactly the same way as Mr

snaprevise.co.uk 8
SECTION 2:
Compounds, Formulae
& Equations
1 Ionic formulae
•• The formulae of ionic compounds can be found by balancing the charges of the individual
ions that make it up
•• You need to know the charges of the specific ions and groups of the periodic table shown below
•• Find the charges of the ions in a compound and multiply up the number of moles of positive
and negative ions until they balance
+1 +2 +3 -3 -2 -1
Group 1 Group 2 Group 3 Group 5 Group 6 Group 7
Silver Zinc Iron (III) Phosphate Sulfate (SO42-) Nitrate (NO3-)
Gold Tin (PO43-) Carbonate Hydroxide
Hydrogen Lead (CO32-) (OH-)
Ammonium Iron (II)
(NH4+) Copper (II)

EXAM TIP
Brackets in a formula, like Ca(OH)2, mean the thing in brackets is one ion, and there may be
more than one of them

2 Balancing equations
•• Match the number of moles of each element on each side
•• To write the ionic equation for reactions involving ions write out just the ions that react
•• Leave out all the spectator ions (the ones that don’t change oxidation number or state)
•• For ionic equations the charges also need to balance
•• Unbalanced, no state symbols: Cu2+ + OH- Cu(OH)
•• Balanced, state symbols: Cu2+(aq) + 2OH-(aq) Cu(OH)2(s)

EXAM TIP
It’s really easy to forget to put state symbols on during an exam, but you can lose marks for
not including them so add them if you’re ever in doubt

snaprevise.co.uk 9
SECTION 3:
Amount of a Substance
1 Moles
•• A mole is a measurement of an amount of substance, with the symbol ‘mol’
•• It is the amount of any substance containing as many particles as there are carbon atoms in
12g of carbon-12
•• Avogadro’s constant, NA, is the number of atoms per mole of any substance and is equal to
6.02 x 1023
•• The molar mass is the mass per mole of substance in g/mol
•• The molar volume is the volume per mole of gas. At room temperature and pressure it is
24.0 dm3/mol

EXAM TIP
The molar volume and NA are in the data sheet, you don’t need to remember them

2 Empirical and molecular formulae


•• The empirical formula is the simplest whole number ratio of elements in a compound
•• The molecular formula is the formula that’s used and is the actual ratio of elements in a
compound

3 Finding empirical and molecular formulae


•• You can find empirical and molecular formulae for a compound from experimental data
•• For the empirical formula, divide the mass of each element by the Ar to find the number of
moles of each element present
•• Divide by the smallest number
•• Multiply up to get whole numbers for each element
•• To find the molecular formula, divide the molecular mass (Mr) by the mass of the empirical
formula, and multiply the empirical formula by the result

snaprevise.co.uk 10
4 Hydrated salts and water of crystallisation
•• A hydrated salt is one which contains water of crystallisation e.g. MgSO4·7H2O. An anhydrous
salt is one with no water of crystallisation e.g. MgSO4.
•• To work out the amount of water of crystallisation in a salt:
○○ From the Mr - Find the Mr of the anhydrous salt and subtract it from the hydrated Mr then
divide the remainder by the Mr of water
○○ From experimental results — Find the moles of water lost when a hydrated salt is heated
in a crucible and the number of moles of anhydrous salt left at the end

5 Mole calculations
•• You convert moles, mass and formula mass using

•• All gases take up 24 dm3/mol at RTP, so mol if V is in dm3

•• Divide by 24000 instead if V is in cm3


•• For solutions,

EXAM TIP
Sometimes mol/dm3 is abbreviated to ‘M’, they mean exactly the same thing

6 The ideal gas equation


•• Links pressure, P, volume, V, temperature, T, the gas constant, R, and the number of moles of
gas present, n.
•• pV = nRT
•• Use the molar volume to convert masses of gas to volumes

EXAM TIP
All the quantities in the ideal gas equation need to be in SI units, (p: Pa, V: m3, T:K) so you’ve
got to remember to convert any data you’re given. R is in the data book.

snaprevise.co.uk 11
7 Stoichiometric relationships
•• The ratios of moles in chemical equations shows how many moles of a product will give how
many moles of a reactant and vice versa
•• Work out the number of moles of reactants
•• Use the ratio to find number of moles of products
•• Also works the other way round

8 Percentage yield and atom economy


•• Percentage yield =

•• Percentage yield may be low due to the reaction not going to completion, impurities or side
reactions for example

•• Atom economy =

•• Atom economy will be low if more than one product is formed

9 Sustainability and atom economy


•• Processes with high atom economies are more sustainable
•• They can be productive without depleting resources, as they reduce the amount of raw
materials required and reduce waste.
•• Addition reaction have atom economies of 100%
•• Substitution and elimination reactions have lower atom economies.

snaprevise.co.uk 12
SECTION 4:
Acids
1 Acids and bases
•• Acids release H+ ions into solution and bases take up H+ ions.
•• Alkalis are soluble bases that release OH- ions into solution.
•• Common ones you need to know are in the table.

Acid Formula Salt Alkali Formula


Sulfuric H2SO4 Sulfate Potassium KOH
Hydroxide
Hydrochloric HCl Chloride Sodium NaOH
Hydroxide
Nitric HNO3 Nitrate Ammonia NH3
Ethanoic/acetic CH3COOH Acetate

2 Strong acids
•• Completely dissociate (give up H+ ions) in solution, weak acids only partially dissociate

3 When an acid reacts with a base


there is a neutralisation reaction
•• In a neutralisation reaction H+ + OH-(aq) H2O(l)
•• Acid + Base Salt + Water
•• A salt is an acid with the hydrogen replaced by a metal
•• Common bases are carbonates, metal oxides and alkalis e.g. KOH
•• Acid + Carbonate Salt + Water + CO2
•• 2HCl + CaCO3 CaCl2 + CO2 + H2O
•• Acid + Metal Oxide Salt + Water
•• 2HCl(aq) + MgO(s) MgCl2(aq) + H2O(l)
•• Acid + Alkali Salt + Water
•• HCl(aq) + NaOH(aq) HCl(aq) + H2O(l)

snaprevise.co.uk 13
4 Acid-Base Titrations
•• These allow you to find out exactly how much acid is needed to neutralize a quantity of alkali
•• Measure alkali into a flask using a pipette
•• Add indicator
•• Fill burette with known quantity of acid
•• Conduct a rough titration to approximate amount
○○ Add acid form burette
○○ Swirl flask
○○ The alkali will be neutralized when the indicator changes colour
•• Conduct accurate titration
○○ Run acid within 2cm3 of the end point
○○ Slowly add more and record the amount of acid used to neutralize the alkali
•• Conduct experiment 2/3 times
•• Take an average value

5 Titration calculations
•• If you know the balanced equation, you can use the results of the titration to find out how
much of the unknown alkali (or acid if you’re adding known alkali) is present
•• Work out how much acid was added from the volume and concentration
•• Use the equation to find the corresponding number of moles of alkali
•• Use the number of moles of alkali and the volume to find concentration, or whatever other
quantity you need to determine

snaprevise.co.uk 14
SECTION 5:
Redox

1 Oxidation number
•• The oxidation number is the number of electrons an atom uses to bond to atoms of other
elements, and is the charge the atom would have if it were fully ionic
•• There are a set of rules for working out oxidation number
•• Elements bonded to identical atoms have an oxidation number of 0
•• The rest are in the table

Species Oxidation Number Examples


Uncombined Element 0 S, N2, K
Combined Oxygen -2 H2O, Na2O
Combined Oxygen in -1 H2O2
Peroxides
Combined Hydrogen +1 H2O, NH3
Combined Hydrogen in -1 NaH
Hydrides
Simple Ion Ionic charge Mg2+, 2+; Na+, 1+; Br-, 1-
Combined Fluorine -1 NaF, MgF2, HF

2 Oxidation numbers
in compounds and ions
•• There are also rules about oxidation numbers for atoms in compounds and ions
•• For a complex ion, the sum for each atom must equal overall charge on the ion
•• For compounds (ions with a charge of 0), the sum must be 0
•• To find the oxidation number for any atom in a compound
○○ Write out all the oxidation numbers you know, and multiply up by the number of atoms
of each type and add them all together
○○ The remaining unknown oxidation number, when added to the number you just worked
out, should equal the overall charge

snaprevise.co.uk 15
3 Writing oxidation numbers
in compounds
•• Some compounds have the same names, but different compositions and oxidation numbers
•• Write the oxidation number of the key species as a roman numeral in brackets to make it
clear
•• For transition metal compounds write the oxidation number of the metal
•• FeCl2 = Iron (II) Chloride
•• FeCl3 = Iron (III) Chloride
•• FeO = Iron (II) Oxide
•• Fe2O3 = Iron (III) Oxide
•• An oxyanion is an anion that contains an element and oxygen
•• Write the oxidation number of the element in the anion that isn’t oxygen
•• NaNO2 = Na+ + NO2- = Sodium Nitrate (III)
•• NaNO3 = Na+ + NO3- = Sodium Nitrate (V)
•• SO32- = Sulfate (IV)
•• SO42- = Sulfate (VI)

EXAM TIP
If you’re asked to write down the name of one of these compounds from the formula, you
need to put the oxidation number in or you could lose marks

4 Redox reactions
•• Redox reactions are where one species is reduced and another is oxidised
•• Oxidation is loss of electrons
•• Reduction is gain of electrons
•• The species that is reduced takes electrons from the one that is oxidised
•• Redox can also be understood in terms of oxidation number changes
•• If something is oxidised its oxidation number increases by 1 for each electron lost
•• If something is reduced its oxidation number decreases by 1 for each electron gained
•• Metals tend to get oxidised, while non-metals tend to get reduced

snaprevise.co.uk 16
5 Redox reactions with metals and acids
•• Metal + Acid Salt + Hydrogen
•• Mg(s) + 2HCl MgCl2(aq) + H2(g)
•• Assign oxidation numbers to each species in the reaction to work out what’s being reduced
or oxidised

Mg(s) + 2HCl MgCl2(aq) + H2(g)


0 +1 -1 +2 -1 0
+1 -1 -1 0

•• Mg has gone from 0 +2 so is oxidised


•• H has gone from +1 0 so is reduced

6 Unfamiliar redox equations


•• Put in the oxidation numbers for all the species on both sides of the equations first
•• Find the species that change oxidation number
•• Assign them as reduction if it’s decreased and oxidation if it’s increased

EXAM TIP
The total change in oxidation number will always be zero, so you can add up all the changes
you’ve found to check if you’ve got everything.

snaprevise.co.uk 17
TOPIC 2

Electrons,
Bonding
and Structure
SECTION 1:
Electron Structure
1 Electron shells
•• Electrons in an atom are arranged into shells, or energy levels.
•• The shells are numbered with the principal quantum number, n.
•• Higher quantum numbers are further from the nucleus and higher in energy

n Max number of electrons Sub-shells


1 2 1s
2 8 2s, 2p
3 18 3s, 3p, 3d
4 32 4s, 4p ,4d, 4f

2 Orbitals
•• Each shell is split into a set of sub-shells, or sub-levels, called orbitals
•• An orbital is a region around the nucleus that can hold up to two electrons, with opposite
spins
•• The first four sets of sub-shell are the s-, p-, d- and f-orbitals

Number of orbitals Maximum number


Shape of orbital in
Sub-shell of electrons in sub-
sub-shell In sub-shell level
S Spherical 1 2
P Dumbell 3 6
D — 5 10

•• S orbitals have the lowest possible energy in a shell


○○ Spherical shape
○○ As distance from nucleus increases, electron density decreases
•• P orbitals have the second lowest energy
○○ They have a node (region of zero electron density) at the nucleus of each atom
○○ ‘Dumbbell’ shape
○○ 2 opposite lobes

snaprevise.co.uk 19
EXAM TIP
The fourth set of sub-shells are called the f-orbitals. You don’t need to know about them,
but there are 7 f-orbitals, so it can hold a total of 14 electrons.

3 Filling orbitals
•• Electrons fill up orbitals from the lowest energy first
•• The order of energies from lowest to highest is:
•• 1s 2s 2p 3s 3p 4s 3d 4p
•• The 4s orbital is lower in energy than the 3d, so it gets filled first
•• Orbitals can be represented with box notation
•• Each orbital holds two electrons with opposite spins
•• Spin is represented by an up or a down arrow
•• The diagram represents an atom with 10 electrons

•• Electrons prefer to occupy orbitals on their own


•• Only pair up when no empty orbitals of the same energy are available
•• There are only four electrons in the 2p orbitals below
○○ Singly fill all three
○○ Add the remaining electron with an opposite spin

snaprevise.co.uk 20
EXAM TIP
You don’t need to be able to explain spin, because it’s so difficult to do, just know that
electrons in the same orbital have different spins. They’re called spin up and spin down

4 Writing electron configurations


•• We can write out the electronic configuration (which electrons are in which orbitals) for an
atom using sub-shell notation
•• Write out the orbitals that have electrons in them in increasing energy order
•• Add the number of electrons in each set of orbitals as a subscript next to it
•• Sulphur has 16 electrons: 1s2, 2s2, , 2p6, 3s2 ,3p4
•• Know up to krypton, 36 electrons: 1s2, 2s2, 2p6, 3s2, 3p6, 4s2, 3d10,4p6
•• For ions, the highest energy electrons are lost first, so add or take electrons away from the
right of the electron configuration for the atom
•• Mg: 1s2, 2s2, 2p6, 3s2
•• Mg2+: 1s2, 2s2, 2p6, 3s2
•• The electron configuration can also be represented as a box diagram
•• These are often done with energy increasing upwards

snaprevise.co.uk 21
SECTION 2:
Bonding & Structure
1 Ionic bonding
•• The most stable electron configurations have a full outer shell
•• This is also known as a noble gas configuration, because it’s the same electron configuration
that an atom of a noble gas element will have
•• Atoms bond with each other and form ions to achieve this
•• Ionic materials are made up solely of ions, ionically bonded to each other
•• An ionic bond is the electrostatic attraction between oppositely charged ions
•• The strength of ionic bonding is determined by
○○ Charges on the ion
○○ Radii of ions
○○ Smaller ions form stronger ionic bonds
•• Use dot and cross diagrams to show gain and loss of electrons to form ions

EXAM TIP
Ionic materials are normally made up of a metal that can give up electrons to get a full
outer shell and a non-metal that can accept electrons to get a full outer shell

snaprevise.co.uk 22
2 Giant ionic lattices
•• All ionic compounds have extended structures called giant ionic lattices
•• The lattice structure extends in all directions
•• Forces exerted by the ions on each other act equally in all directions
•• This keeps each individual ion in its place

3 Physical properties of ionic compounds


•• The giant lattice structure of ions and the bonding between ions explains the physical
properties of ionic compounds
•• High melting and boiling points are explained by ions that are strongly held together by the
attraction between positive and negative charges
•• The electrical conductivity of ionic compounds is explained by whether the ions can move or
not
○○ In solid state the ions are fixed, so ionic compounds don’t conduct
○○ In liquid and aqueous states the ions can move, so the compounds conduct
•• Ionic compounds dissolve in polar solvents
•• A polar solvent is one where each solvent molecule has small negative and positive charges
on it
•• Ionic compounds are soluble in polar solvents because the charges on the solvent can attract
ions from the lattice with opposite charge
•• This pulls ions out of the lattice into solution

snaprevise.co.uk 23
4 Covalent bonds
•• Another way atoms achieve full outer shells
•• The strong electrostatic attraction between a shared pair of electrons and the nuclei of the
atoms involved in the bond
•• All bonds except for those between atoms of the same element are a mix of ionic and
covalent

5 Dot and cross diagrams


•• Covalent bonds between two atoms are normally represented using dot and cross diagrams
•• Normally just draw the outer shell of electrons by drawing one circe around each element
•• Use dots to represent electrons from one atom, and crosses for the other
•• Overlap the circles of the two bonding atoms and draw the shared electrons in the
overlapped part
•• Covalent bonds are often drawn as lines between atoms, with double bonds as double lines
and triple bonds as triple lines
•• Pairs of electrons that aren’t involved in bonding are called lone pairs
•• Just drawn on the outer shell of electrons

snaprevise.co.uk 24
•• Atoms can bond to more than one other atoms
•• Atoms can also form dative bonds
○○ One atom donates both the electrons in a bond
○○ Drawn as a line going from the atom donating electrons to the one receiving them
○○ Exactly the same as a normal covalent bond once it has formed

•• Some elements don’t have enough electrons to form covalent bonds to get a full outer shell
e.g. boron in BF3
•• Elements in groups 15-17 from period 3 down have outer shells that can hold more than
eight electrons
•• These can form more than 4 covalent bonds e.g. SF6, PCl5

6 Average bond enthalpy


•• Measures how much energy is required to break a covalent bond
•• The higher the bond enthalpy the stronger the bond

snaprevise.co.uk 25
7 Shapes of molecules and ions
•• The shape of a molecule or ion can be predicted by electron pair
repulsions theory
•• Electron pairs have the same charge so repel other electron pairs
•• Arrange electron pairs so they’re as far away from each other as
possible
•• Lone pairs are more electron dense than bonding pairs so repel more
•• So the angle between bonding pairs in CH4 is 109.5o, but in NH3 is 107o,
and is only 104.5o in H2O

•• The shapes of ions can be found in exactly the same way


○○ Put brackets round the whole ion and add the charge in the top right
•• When drawing 3D shapes use bold and dotted wedges to show bonds going towards and
away from you

snaprevise.co.uk 26
8 Electronegativity
•• Covalent bonds can have a degree of ionic character
•• Electronegativity is the ability of an atom to attract the bonding electrons in a covalent bond
•• Increases going up and to the right on the periodic table
•• Measured using the Pauling scale
•• The higher an element’s electronegativity, the more strongly it attracts electrons
•• Bonds between atoms with the same electronegativity are non-polar
•• Bonds between atoms with different electronegativities are polar
•• Polar bonds have more of the electron density closer to the more electronegative atom
•• The charge difference creates a permanent dipole
•• This is shown using δ+ (small positive charge) and δ- (small negative charge)
•• H has an electronegativity of 2.20, and Cl 3.16

•• If a molecule has polar bonds it may be polar


•• This is when the permanent dipoles of the polar bonds add up to give an overall dipole e.g. CHCl3
•• If the molecule is symmetrical they may cancel out e.g. CCl4

9 Intermolecular forces
•• Two kinds: weak van der Waals’ forces and stronger hydrogen bonding
•• Van der Waals’ forces include quite weak permanent dipole-induced dipole and permanent
dipole-permanent-dipole and weaker London (dispersion) forces
•• Permanent dipole-induced dipole is where a molecule with a permanent dipole causes
a dipole in a non-polar molecule, the two molecules then attract
•• Permanent dipole-permanent dipole is where opposite charges on two molecules with
permanent dipoles attract

snaprevise.co.uk 27
•• London (dispersion) is where electrons in atoms constantly moving
•• They become unevenly spread which gives atoms a temporary dipole
•• This induces a temporary dipole moment in the neighboring atom, repelling or attracting its cloud
•• Attraction is relatively weak, increases with increasing number of electrons

10 Hydrogen bonding
•• Occur when H is bonded to N, O or F
•• The bond is the attraction between a lone pair on one N, O or F to a δ+ H attached to N, O or
F on a nearby molecule
•• F, N and O are all very electronegative
•• Draw covalent bonding pair of electrons away from the hydrogen
•• Bond is polarized
•• δ+ hydrogen forms weak bonds with the lone pairs on the other F, N and O
•• Stronger than van der Waals’ forces but much weaker than covalent/ionic bonds
•• Bond drawn as dashed line

EXAM TIP
Hydrogen bonding occurs in any molecule with N, O or F bonded to H, so remember it for
organic molecules like alcohols e.g. CH3CH2OH (ethanol)

snaprevise.co.uk 28
11 Properties of water
•• Hydrogen bonding gives water unusual properties
•• Low density
○○ In ice molecules are fixed
○○ Form a fixed lattice of hydrogen bonded molecules
○○ Hydrogen bonds hold molecules apart
○○ In liquid water molecules move past each other often
○○ Form hydrogen bonds less often so less held apart and move closer together
○○ So ice is less dense than water
•• High melting and boiling point
○○ Hydrogen bonds are stronger than van der Waals’ forces
○○ Extra strength has to be overcome to melt or boil water
○○ So the melting and boiling points are much higher than other compounds like it
•• Also causes things like high surface tension that allows insects to walk on water

12 Simple covalent lattices


•• Made up of molecules where the atoms in one molecule are bonded together by strong
covalent bonds
•• Different molecules are bonded by weak intermolecular forces e.g. van der Waals’ forces or
hydrogen bonding
•• Solid structures have molecules fixed in place by intermolecular forces
•• When these change state the forces break

snaprevise.co.uk 29
13 Physical properties
of simple covalent lattices
•• Low melting and boiling points due to weak intermolecular forces
•• Non-conductors as there are no free ions
•• Mostly soluble in non-polar solvents
○○ Molecules that form simple covalent lattices are often non-polar
○○ Like dissolves like
○○ So they’re soluble in non-polar solvents
○○ Things like ice that are polar will dissolve in polar solvents

snaprevise.co.uk 30
MODULE 3

THE PERIODIC
TABLE
AND ENERGY
TOPIC 1

The Periodic
Table
SECTION 1:
Periodicity
1 The periodic table
•• Arranges elements in three ways
•• By increasing atomic number
•• In periods that show repeating trends in properties across the period
○○ The repeating pattern of trends is called periodicity
•• In vertical columns called groups
○○ Groups have similar chemical properties
○○ There are also trends in properties going down groups

EXAM TIP
People don’t like periodicity because it looks like it’s a load of fact learning, but all of the
trends you need to know are based on electron configurations. If you can use the periodic
table to work out what electron configuration everything has, and remember a couple of
important rules, then a lot of the time you’ll be able to work out the answer

2 Periodic trends in electron


configurations
•• Configuration of electrons in outer shell determines reactivity
•• Elements within the same group of the periodic table have the same electron configuration
in their outer shell
•• This means the same number of electrons in the same type of orbitals
•• This explains why they have the similar reactivity
•• Elements are broadly organised into s-, p- and d-blocks depending on what type of orbital is
being filled
•• S Block
○○ Elements from Groups 1 and 2
○○ Outermost electrons lie in s orbitals

snaprevise.co.uk 33
○○ Electrons easily lost to form ions
○○ Reactive metals
○○ Generally have low melting and boiling temperatures
•• P Block
○○ Elements in groups 3,4,5,6,7
○○ Outermost electron in p orbital
○○ Contains all non-metals and metalloids
•• D Block
○○ Lies between groups 2 and 3
○○ Much less reactive than other metals
○○ Outer s orbital is full and inner d orbitals are being filled

3 First Ionisation Energy


•• The energy required to remove 1 mol of electrons from 1 mol of gaseous ions
•• Successive ionisation energies involve removing further electrons
•• Down a group
○○ Decreases
○○ More shielding by increased number of shells inside outer shell
○○ Also means the electron is further away (greater atomic radius)
○○ So weaker attraction between nucleus and electron
○○ So easier to lose an electron
•• Across periods 2 and 3
○○ Increases
○○ Increase in nuclear charge
○○ So atomic radius decreases
○○ No addition of new shells to shield outer electrons
○○ Stronger attraction between nucleus and electron so harder to remove

snaprevise.co.uk 34
•• There are smaller trends within a period because full sets of s- and p- orbitals are also stable
•• P-orbitals are higher in energy than s-orbitals so are further from the nucleus
•• Further away means lower attraction, so taking an electron from a p-orbital needs less
energy
•• This can be seen going from s- to p-orbitals e.g. Be B, Mg Al
•• Putting an electron into a p-orbital with an electron already in it takes more energy
•• This can be seen for N O

•• Successive ionisation energies can be used to work out the electron configuration of an
unknown element
•• A big increase means electrons are being lost from a shell closer to the nucleus

4 Metallic bonding
•• Metals consist of giant lattices of fixed positive metal ions
•• These are surrounded by delocalised electrons shared between all the metal ions that can
move through the structure
•• Metallic bonding is the strong attraction between the metal ions and the ‘sea’ of delocalized
electrons

snaprevise.co.uk 35
5 Giant covalent lattices
•• Giant networks of atoms all bonded covalently together e.g. carbon and silicon
•• Electrons localised in bonds
•• Three forms of carbon, which forms up to four bonds
•• Diamond
○○ Each carbon atom forms a single covalent bond to 4 other carbon atoms in a tetrahedral
shape
○○ Extremely hard because of all the bonds
•• Graphite
○○ 2-Dimensional layers of carbon covalently bonded in hexagonal rings, one on top of
another
○○ Layers extend over huge numbers of atoms
○○ Can slide over each other, which makes graphite very soft
•• Graphene
○○ One layer of graphite with carbon arranged in hexagonal rings
○○ Each carbon only forms three bonds so has a spare electron
○○ This allows it to conduct electricity
•• Silicon as an element has the same structure as diamond
•• Silicon forms silicon dioxide, SiO2 (which is sand), which has a similar structure to diamond
•• The silicon atoms are where carbon is
•• One oxygen lies between each silicon atom

6 Properties of giant metal


and covalent lattices
•• Metal lattices
•• High melting and boiling point
○○ Closely packed atoms with strong attractive forces between ions and electrons
○○ Lots of energy required to move fixed ions from position to melt
○○ Even more energy required to separate ions and boil
•• Good Conductor of Electricity
○○ Delocalized electrons free to move and carry current even in solid state
•• Metals aren’t soluble, they react with water instead
•• Covalent lattices
•• High melting and boiling boint

snaprevise.co.uk 36
○○ Very strong covalent bonds throughout structure need to be broken before melting or
boiling occurs
•• Variable conductors of electricity
○○ If there are free electrons not in covalent bonds (graphite, graphene) they can conduct
○○ If there are no free electrons (diamond) they can’t conduct
○○ Silicon poorly conducts electricity because it’s electrons are in covalent bonds, but can be
made to move
•• Insoluble, as there are no ions to be solvated

7 Melting points across period 2 and 3


•• Metallic elements
○○ Bigger atoms have weaker forces of attraction and lower boiling points
○○ Where there are more delocalized electrons per ion, the attractive forces are stronger
○○ So going to the right melting and boiling points increase
•• Covalent elements
○○ If they form giant covalent lattices elements with more electrons form more bonds
○○ So melting and boiling points increase
○○ If they form simple covalent molecules (N and P onwards) they have low melting and
boiling points because molecules are only linked by weak intermolecular forces

Period 2 Li Be B C N2 O2 F2 Ne
Period 3 Na Mg Al Si P4 S8 Cl2 Ar
Giant Giant Simple
Structure
metallic Covalent molecular
Strong
forces
between Strong
Weak
Forces positive covalent
intermolecular
ions and bonds
delocalised
electrons

snaprevise.co.uk 37
SECTION 2:
Group 2
1 Group 2 redox reactions
•• All group 2 elements have 2 electrons in their outer shell
•• They all lose these to form 2+ ions in redox reactions
•• M M+ + e-
•• M+ M2+ + e-

2 Group 2 reactivities
•• Reactivities shown by reactions with oxygen, water and dilute acids
•• Oxygen
○○ All group 2 metals react to form ionic, basic oxides
○○ 2Mg(g) + O2(g) 2MgO(s)
○○ Mg has been oxidised from 0 +2
•• Water
○○ All react apart from Be
○○ Shows that Be is least reactive
○○ Reactivity increases down the group
○○ Reduce water to form hydroxides and hydrogen gas
○○ Ca(s) + 2H2O(l) Ca(OH)2(aq) + H2(g)
•• Dilute acids
○○ All react apart from Be
○○ Reactivity increases down the group
○○ React to form a salt and H2(g)
○○ Mg(s) + H2SO4(aq) MgSO4(aq) + H2(g)

EXAM TIP
You don’t need to know any reactions with acids that don’t produce only a salt and hydrogen

snaprevise.co.uk 38
3 Reactivity and ionization energy
•• First and second ionization energy decreases down the group
•• Atomic radius increases down the group (although effective nuclear charge does so too)
•• Electrons are further from nucleus
•• Experience the nuclear charge less strongly
•• Shielding also increases
•• Because electrons become easier to lose, group 2 elements undergo oxidation more easily
•• So reactivity increases

4 Reactions of group 2 oxides and water


•• Group 2 oxides react with water to form soluble hydroxides
•• Soluble hydroxides release OH- to form alkaline solutions, roughly pH 10-12
•• MO(s) + H2O(l) M(OH)2(aq)
•• Group 2 oxides and hydroxides aren’t all soluble in water
•• Solubility increases down the group, BeO isn’t soluble so doesn’t react
•• More soluble hydroxides release more OH- ions into solution so are more alkaline
•• Mg(OH)2 is slightly soluble so weakly alkaline
•• Ba(OH)2 is very soluble and more alkaline

5 Uses of group 2 compounds


•• Group 2 oxides, hydroxides and carbonates are basic
•• They are used as bases commercially
•• Calcium hydroxide used to reduce acidity levels in acidic soils
•• Indigestion remedy
○○ Stomachs contain HCl
○○ Too much causes indigestion
○○ Magnesium hydroxide (milk of magnesia) or calcium carbonate used to neutralise it
○○ Mg(OH)2 + 2HCl MgCl2 + H2O
•• Calcium carbonate also used as a building material
○○ Limestone and marble mostly CaCO3
○○ Major drawback is it reacts with acid rain
○○ CaCO3(s) + 2HCl(aq) CaCl2aq) + H2O(l) + CO2(g)

snaprevise.co.uk 39
SECTION 3:
Halogens
1 Physical properties
•• Exist as diatomics
•• Have low melting and boiling points as only weak intermolecular forces exist
•• Boiling point increases down the group due to increasing London forces
Colour in
Halogen State at RTP Colour Colour in water
cyclohexane
Chlorine Gas Green/yellow Pale green Pale green
Bromine Liquid Dark red/brown Orange Orange
Iodine Solid Grey/black Brown Violet

2 Electron configuration
•• All have s2p5 configuration
•• Highly electronegative and very reactive
•• Want to gain one electron to have a full outer shell (noble gas configuration)
•• Form 1- ions during reactions

3 Reactivity
•• Oxidizing power decreases down the group
•• Higher halogens will oxidise lower halogens
•• Can be seen by the colour of two halogens in solution
•• The more reactive halogen will be a 1- ion, the less reactive one will be a diatomic element
•• Colour will be of the less reactive halogen

4 Reactivity in terms of ease of forming 1- ions


•• Outer shell of halogens gets further from the nucleus down the group
•• Electrostatic attraction with the nucleus is lower
•• Electron shielding due to inner shells is higher

snaprevise.co.uk 40
•• Weaker attraction to electrons
•• Worse oxidising agents
•• Less likely to form 1- ion

5 Disproportionation
•• Oxidation and reduction of the same element during a redox reaction
•• Chlorine with Water
○○ React irreversibly to form HCl (Cl reduced) and HClO (Cl oxidised)
○○ Cl2(aq) + H2O(l) HCl(aq) + HClO(aq)
•• Chlorine with cold dilute NaOH(aq)
○○ React to from NaCl (Cl reduced) and NaClO (Cl oxidised)
○○ Cl2(aq) + 2NaOH(aq) NaCl(aq) + NaClO(aq) + H2O(l)
•• Also occurs with other halogens

6 Chlorine as a disinfectant
•• Added to drinking water to kill bacteria
•• Benefits of killing bacteria are weighed against risks of adding Cl2
○○ Cl2 is a toxic gas
○○ Cl2 can react with hydrocarbons in water to form chlorohydrocarbons which are
carcinogenic

7 Characterising halides
•• Chlorine, bromine and iodine produce different coloured precipitates when they react with
silver nitrate and ammonia
•• Dissolve halide in water
•• Add aqueous silver nitrate
•• Note colour of precipitate
○○ If colour is hard to distinguish add dilute then concentrated aqueous ammonia
○○ Note solubility of precipitate in aqueous ammonia

Colour of AgX Soluble in dilute Soluble in conc.


Halide
precipitate aqueous ammonia aqueous ammonia
Cl- White Yes Yes
Br- Cream No Yes
I- Yellow No No

snaprevise.co.uk 41
SECTION 4:
Qualitative analysis
1 Tests for ions
•• Tests show whether something is present or not, not how much there is
•• Anions: Carbonate (CO32-) and sulfate (SO42-), also halides from the last section
•• Carbonate reacts with acid to form CO2: CO32-(aq) + 2H+(aq) H2O(l) + CO2(g)
•• To test for carbonate
○○ Add a strong dilute acid
○○ Pass any gas formed through limewater
○○ If it goes cloudy carbonate is present
•• Sulfate reacts with barium ions to form an insoluble salt
•• Ba2+(aq) + SO42-(aq) BaSO4(s)
•• To test for sulfate ions
○○ Add HCl and barium sulfate
○○ If a white precipitate forms barium ions are present
•• Cations: NH4+
•• Ammonium ions react with hydroxide to form ammonia and water
•• NH4+(aq) + OH-(aq) NH3(g) + H2O(l)
•• To test for ammonium
○○ Add NaOH solution and warm gently
○○ Test any gas evolved with litmus paper
○○ If it goes blue and the gas smells like ammonia when wafted gently towards your nose,
ammonia is present

EXAM TIP
You need to know the ionic equations for all the test reactions. Using the ionic equations
means you can include only the ions that are reacting during the test (like NH4+ and OH-)
and ignore the others (like the counter ion for ammonium and Na+)

snaprevise.co.uk 42
TOPIC 2

Physical
Chemistry
SECTION 1:
Enthalpy changes
1 Enthalpy changes in reactions
•• Enthalpy, H, is the amount of thermal energy in a system in kJ
•• Can’t measure H, but in some reactions there is a change of enthalpy, ΔH
•• ΔH is the heat exchanged between system (atoms and bonds involved) and surroundings
(everything else)
•• Normally kJmol-1
•• ΔH = Hproducts - Hreactants, can be positive or negative
•• Negative = Exothermic
○○ Heat flows from the system to the surroundings (energy is released)
○○ Energy of system has decreased
•• Positive = Endothermic
○○ Heat flows from the surroundings into the system (energy is absorbed)
○○ Energy of system has increased

EXAM TIP
Exothermic reactions give out heat and endothermic reactions take it up, so an exothermic
reaction in a test-tube will feel warm and an endothermic one will feel cold. It seems weird
that an exothermic reaction should have a negative ΔH because it’s giving out heat, but it’s
just the way that ΔH is defined as Hproducts - Hreactants

2 Energy profile diagrams


•• Change in enthalpy can be shown on a diagram

snaprevise.co.uk 44
3 Activation energy, Ea
•• Minimum amount of energy that the particles need to react during a reaction
•• Looks like a hump on an energy profile diagram
•• Even though energy comes out of an exothermic reaction still need energy to overcome the
activation energy to make the reaction happen

EXAM TIP
You need to remember to show enthalpy change and activation energy with arrows
pointing the right way. Learn the ways they’re drawn in the diagrams. Exothermic arrows
go down, endothermic go up, activation energy arrows always go up and are shown going
from reactants to products.

4 Important terms
•• Standard conditions: 100kPa and 298K
•• Standard states: physical state an atom or molecule is in at standard conditions
•• All enthalpy changes measured in kJmol-1 and under standard conditions
•• Enthalpy change of reaction, ΔrH: Energy change of a reaction
•• Enthalpy change of formation, ΔfH: The enthalpy change when one mole of the compound is
formed from its elements
•• Enthalpy change of combustion, ΔcH: The enthalpy change that occurs when one mole of a
substance is completely burned in oxygen
•• Enthalpy change of neutralisation, ΔneutH: The energy change when an acid and a base react
to form 1 mole of water

snaprevise.co.uk 45
5 Determining enthalpy changes from
experiment
•• Measure enthalpy change from experiment by measuring change in temperature
•• Use the relationship q = mcΔT to find enthalpy change
○○ q = heat exchanged with surroundings, normally in J
○○ m = mass of substance changing temperature, normally in g
○○ c = specific heat capacity, energy required to raise the temperature of a gram of
substance by 1K, normally in Jg-1K-1
○○ ΔT = temperature change in K
•• Three experimental methods: coffee cup calorimeter, copper calorimeter and spirit burner,
bomb calorimeter
•• All heat up water and help minimise amount of heat lost to surroundings
•• Coffee cup calorimeter
○○ Add one liquid to coffee cup, take temperature every minute until it stabilises (4 minutes)
○○ Add second liquid to cup, measure temperature every minute from 6 minutes onward
○○ Use graph to work out max ΔT during reaction (at 5 minutes)
○○ Polystyrene is excellent insulator, minimizes heat loss to surroundings
○○ Allows us to find accurate values for ΔH
○○ Usually gives accurate results
•• Copper calorimeter and spirit burner
○○ Useful for enthalpy of combustion of fuels
○○ Heat given out by burning fuel is used to warm a mass of known water
○○ Measure mass of fuel burned and the ΔT of water
○○ Allows you to find approximate value for ΔH
•• Bomb calorimeter
○○ Combusts sample in pure oxygen to burn as completely as possible
○○ Minimises heat loss as much as possible
○○ Measure mass of sample burned and temperature change of water

EXAM TIP
You need to know about the different ways of measuring enthalpy change and how to do them

snaprevise.co.uk 46
6 Average bond enthalpy
•• The average heat needed when one mole of covalent bonds are broken, measured in the
gaseous state
•• Average for one type of bond e.g. C-H over lots of compounds
•• Bond enthalpies for a type of bond don’t vary much between compounds
•• Bond enthalpies for a specific molecule may vary from the average
•• Reactions often modelled in three parts
○○ Bonds of reactants broken
○○ Atoms rearrange to form products
○○ Bonds of products form
•• In exothermic reactions, bond enthalpies of products is higher than reactants
•• Energy is released
•• In endothermic reactions, bond enthalpies of products is lower than reactants
•• Energy is taken in
•• Can use average bond enthalpy data to predict enthalpy change
•• ΔH = Σ(bond enthalpies of reactants) - Σ(bond enthalpies of products)

7 Hess’ Law
•• The enthalpy change of a reaction depends only on the enthalpy of reactants/products
•• Doesn’t depend on the route taken
•• Can be shown using an enthalpy cycle

•• If you know ΔH and ΔH1 for example you can find ΔH2
•• Each corner of the cycle has to have the same number of each atom
•• Enthalpy changes from enthalpies of combustion
○○ Given enthalpies of combustion of two substances
○○ Put them at two corners of the triangle

snaprevise.co.uk 47
○○ Multiply up to have the same number of atoms
○○ Find the enthalpy change to go from one substance to the other
•• Enthalpy changes from enthalpies of formation
○○ Put elements at one corner
○○ Put compounds of the elements at other corners
○○ Multiply up to have the same number of atoms
○○ Add enthalpies of formation and work out enthalpy change from one substance to
another
•• For enthalpy changes for unknown reactions you’ll be given the cycle and just need to work
out the enthalpy changes

snaprevise.co.uk 48
SECTION 2:
Reaction Rates
1 Concentration and collision theory
•• Collision theory used to explain rates in terms of successful collisions between atoms/molecules
•• Atoms/molecules need to collide in the right orientation with enough energy to overcome
the activation energy
•• As concentration increases there are more particles of reactant per unit volume in solution
•• The more particles there are in a solution per unit volume, the greater the chance of
collisions between reactants
•• So there will be more effective collisions per second with energy in excess of the activation energy
•• Same is true for pressure in gases

2 Finding rates from gradients


•• Can plot concentration, gas volume of products or mass of substances formed or any other
physical quantity that changes during a reaction against time
•• Rate at any time is equivalent to the gradient of the graph at that point
•• Measure by taking a tangent to the curve

EXAM TIP
Remember that you find gradient at a point by drawing a flat line against the curved graph,
then finding rise over run

snaprevise.co.uk 49
3 Catalysts
•• Catalysts offer an alternative route by which the reaction can happen
•• This often means that less energy is required to allow the reaction to take place
•• This means that the rate of reaction is faster because more collision occur with energy in
excess of the activation energy
•• The catalyst itself is not used up in the reaction, it only speeds up the reaction

4 Types of catalyst
and their importance in society
•• There are homogeneous and heterogeneous catalysts
•• Homogeneous
○○ Same phase as reactants (solid/liquid/gas)
○○ Enzymes are homogeneous biological catalysts
•• Heterogeneous
○○ Different phase from reactants
○○ Catalysts in immiscible liquid phases also count as heterogeneous
○○ Catalytic converters in cars are heterogeneous (solid catalyst, gaseous reactants)
•• Industrial processes strive to have 100% atom economy
•• New catalysts developed to improve efficiency
○○ The industrial production of ethanoic acid has become much more sustainable by the
use of a cobalt catalyst
○○ A process was developed using methanol and carbon monoxide which has an atom
economy of 100%
○○ Scientists then develop a rhodium catalyst, which required lower pressure and temperature
○○ This has improved yield to around 98% and reduced CO2 emissions
•• Catalysts save energy by allowing lower temperatures and pressures to be used reducing
CO2 emissions

snaprevise.co.uk 50
5 Investigating reaction rates experimentally
•• Lots of variable that can be measured over time to follow reaction rate
•• Volume of gas produced using a gas syringe
•• Measuring mass of a reaction by performing on a balance
•• Recording time take for a change to occur e.g. precipitate forming
•• Using a colourimeter to measure changes in concentration of a coloured reactant or product

6 The Boltzmann distribution


•• Distribution of energies (and speeds) of molecules at a particular temperature
•• Some molecules are fast with high energy, some are slow with low energy
•• Only molecules above the activation energy will react when they collide
•• No molecules with zero energy
•• No upper limit on energy, just very unlikely for molecules to have really high energy
•• Area under the curve represents total number of molecules, doesn’t change with changing
conditions

7 Effects of temperature and catalysts


on the Boltzmann distribution
•• Temperature shifts the graph to the right and flattens it
•• More molecules are above the activation energy so rate increases
•• As molecules are moving faster more collisions also occur

snaprevise.co.uk 51
•• Catalysts provide another pathway with a lower activation energy
•• Boltzmann curve shows that there are the same number of particles with the same energy
•• But more particles per second have energy in excess of the new, lower activation energy, so
the reaction is faster

snaprevise.co.uk 52
SECTION 3:
Chemical equilibrium
1 Dynamic equilibrium
•• Some reactions are reversible
•• This is represented by the symbol �� ��
��

•• Reactions go both ways


•• In dynamic equilibrium the rate of forward (right) reaction is the same as the backward (left)
reaction
•• Concentrations of products and reactants stay the same
•• Dynamic equilibrium can only happen in a closed system

2 Le Chatelier’s principle
•• Position of equilibrium affected by:
○○ Concentrations of reactants and products
○○ Pressure of gases
○○ Temperature
•• Effects of changes in conditions predicted by Le Chatelier’s principle
•• When a dynamic equilibrium is subjected to change, equilibrium shifts to minimise the change
•• Rate of forward or backward increases to minimise change
•• Concentration
○○ Increasing concentration of one species increases the rate of the reaction that consumes
that species
○○ N2(g) + 3H2(g) �� ��
�� 2NH3(g)
○○ Increasing H2 concentration increases the forward reaction rate
○○ Equilibrium shifts to the right
•• Pressure
○○ Only affects equilibrium if gases are present
○○ When we increase the pressure, the system responds by trying to reduce the pressure
○○ It does so by moving to the side with fewer particles
○○ In the reaction above increasing pressure would move to the right
○○ Increasing pressure of one gas is the same as increasing concentration
•• Temperature
○○ Increasing temperature causes reaction to take in heat

snaprevise.co.uk 53
○○ Rate of endothermic reaction increases
○○ N2(g) + 3H2(g) �� ��
�� 2NH3(g)
○○ The forward reaction is exothermic
○○ This means that as result of forward reaction, heat is given out and temperature rises
○○ If we raise temperature at which equilibrium is established then equilibrium will move to
the left
○○ System is opposing change and trying to lower the temperature with the endothermic reaction

3 Catalysts and equilibrium


•• Speeds up rates of reaction
•• In an equilibrium reaction both forward and reverse rates are speeded up equally
•• NO effect on the yield
•• We get no more product, we just get it faster

4 Investigating the effects of changing


temperature and concentration
•• Lots of different methods
•• If coloured compounds are involved colourimeters can be used to measure concentrations
•• Titrations can be used to measure concentrations of acids and bases
○○ Remove samples at set intervals and titrate against known solutions
•• Measure pressure of system if gases are involved
○○ E.g. 2NO2(g) �� ��
�� N2O4(g)
○○ NO2 brown, N2O4 colourless
○○ Mixture of N2O4 and NO2 is put in a syringe
○○ If compressed, first solution will get darker as concentration increases
○○ The it will get paler as NO2 is converted into colourless N2O4
○○ Equilibrium moves to the side with the fewest moles of gas to reduce pressure
•• Concentration, this is an example, don’t need to know it specifically
○○ E.g. ICl + Cl2 �� ��
�� ICl3
○○ Iodine chloride can be put in a u-tube
○○ Chlorine gas is passed over it
○○ Iodine (III) chlorine, a yellow solid forms
○○ If more chlorine is added, the concentration is increased
○○ More yellow solid will form

snaprevise.co.uk 54
5 Equilibrium vs yield in industry
•• Want to get high yield in industry but need to do it in reasonable time
•• Haber process good example N2(g) + 3H2(g) �� ��
�� 2NH3(g)
•• Forward reaction is exothermic
•• Favoured by high pressure and low temperature
•• Low temperature would give low rate so compromise used that balances rate and yield
•• High pressure difficult to do industrially
•• Requires lots of energy to maintain and can be dangerous so again a compromise pressure is
used
•• Iron catalyst also used
•• Compromise conditions mean only 15% yield achieved by unreacted reactants are fed back
into the reaction

6 The equilibrium constant, Kc


•• Measure of where an equilibrium lies
•• For the reaction mA + nB �� ��
�� pC + qD:

7 Estimating the position


of equilibrium with Kc
•• Kc > 1 means equilibrium lies to the right, more products formed
•• Kc < 1 means equilibrium lies to the left, more reactants formed

snaprevise.co.uk 55
MODULE 4

CORE ORGANIC
CHEMISTRY
TOPIC 1

Basic Concepts
and
Hydrocarbons
SECTION 1:
Basic Concepts
of Organic Chemistry
1 IUPAC nomenclature
for systematic naming of compounds
•• Specific naming system used to give unambiguous names to compounds
•• Three parts to a name: stem, suffix and prefix
•• Stem: main part, depends on the longest carbon chain in a molecule
•• Based on name of the alkane that corresponds to the longest carbon chain

Alkane Number of C atoms in the main carbon chain


Methane 1
Ethane 2
Propane 3
Butane 4
Pentane 5
Hexane 6
Heptane 7
Octane 8
Nonane 9
Decane 10

•• Suffix: end of the name, identifies the most important functional group
•• If a suffix starts with a vowel the -e at the end of the alkane stem is dropped
•• Prefix: start of the name, identifies any other functional groups and the carbons they’re attached to

Functional group Formula Prefix Suffix


Alkanes C-C -ane
Alkenes C=C -ene
Haloalkanes -F fluoro-
-Cl chloro-
-Br bromo-
-I iodo-

snaprevise.co.uk 58
Functional group Formula Prefix Suffix
Alcohols -OH hydroxy- -ol
Carboxylic Acid -COOH -oic acid
Aldehydes -CHO -al
Ketones C-CO-C -one

•• Numbers are used to indicate the location of a carbon side chain or functional group on the
main chain
•• Dashes separate numbers from words
•• Commas separate numbers
•• To name a compound
○○ Identify the longest carbon chain and the right alkane stem
○○ Identify the most important functional group and which carbon on the carbon chain it is
attached to
○○ Attach the suffix to the stem with number of the carbon it’s on before it, removing the -e
from the stem if needed
○○ Identify any other functional groups and add them as prefixes
○○ Prefixes are written in alphabetical order, numbering the carbons so that the smallest
numbers possible are used
○○ di- indicates two identical functional groups, tri- three and tetra- four
•• Aldehydes and carboxylic acids don’t need numbers because they’re always at the end of a
chain
•• Alkanes with a hydrogen removed are called alkyl groups
•• They’re added as prefixes when attached to the main carbon chain

Alkyl group Number of C atoms in the side carbon chain


Methyl 1
Ethyl 2
Propyl 3
Butyl 4
Pentyl 5
Hexyl 6
Heptyl 7
Octyl 8
Nonyl 9
Decyl 10

snaprevise.co.uk 59
2 Interpreting structures
•• General formula: the simplest algebraic formula of a member of a homologous series,
represents the actual number of atoms in each molecule e.g. C4H10
•• Structural formula: shows number of atoms present and way in which they are arranged
relative to each other
•• Displayed formula: shows actual places of the atoms and nature of the bonds between them
•• Skeletal formula: carbon and hydrogen atoms omitted with carbon atoms represented by
junctions between bonds

3 Functional groups and homologous series


•• Functional group: a group of atoms responsible for the characteristic reactions of a compound
•• Homologous series: a series of organic compounds having the same functional group but
with each successive member differing by CH2
•• Homologous series generally have similar chemical properties
•• Their physical properties change as each unit of CH2 is added
•• Their molecular formula can be worked out from a basic formula for the series
•• Alkyl group: an alkane missing a single hydrogen, can be a side chain on other carbon chains
•• Formula CnH2n+1 e.g. propyl CH3CH2CH2 (C3H7)
•• Aliphatic: a compound containing carbon and hydrogen joined together in straight chains,
branched chains or non-aromatic rings e.g. 2,3-dimethylpentane
•• Alicyclic: an aliphatic compound arranged in non-aromatic rings with or without side chains
e.g. cyclohexane
•• Aromatic: a compound containing a benzene ring
•• Saturated: a compound with single carbon–carbon bonds only
•• Unsaturated: the presence of multiple carbon–carbon bonds, including C = C, triple bonds
and aromatic rings

snaprevise.co.uk 60
4 Formulae for homologous series
•• Each homologous series has a general formula that lets you work out the molecular formula
for a given number of carbons
•• E.g. alkanes CnH2n+2, alkenes CnH2n, alcohols CnH2n+1OH

5 Isomerism
•• Compounds can have the same molecular formulas, but different structural formulas
•• These are structural isomers
•• Three ways for isomers to be different
○○ Alkyl groups in different places
○○ Functional groups in different places
○○ Functional groups rearranged into different functional groups

6 Reaction mechanisms
•• Covalent bond fission (breaking) can happen in two ways
•• Heterolytic Fission
○○ Bond breaks unevenly
○○ Both electrons from shared pair move to one atom
•• This forms two species:
○○ Positively charged cation (electrohpile)
○○ Negatively charged anion (nucleophile)
•• Homolytic Fission
○○ Bond breaks evenly
○○ One electron moves to each atom
○○ This forms two electrically uncharged radicals

snaprevise.co.uk 61
7 Radicals
•• Formed in homolytic fission
•• Have an unpaired electron
•• Because of the unpaired electron, radicals are very reactive
•• Represented in reaction mechanisms by a single dot next to the radical

EXAM TIP
In drawn out reaction mechanisms, radical unpaired electron movements are shown by a
half curly arrow with only one ‘hook’, but you don’t need to know how to do these because
all the examples you’ll come across will just be equations like the one above

8 Curly arrows
•• Used to show the movement of a pair of electrons in a reaction mechanism
•• Happens in either heterolytic fission (going to the atom that becomes negatively charged) or
covalent bond making
•• Start from a bond, a lone pair or a negative charge
•• Point to exactly where the electrons are going

snaprevise.co.uk 62
9 Reaction mechanisms
•• Models of how electrons move during a reaction
•• Curly arrows show movement of electrons in each step
•• Show actual charges with small plus or minus signs next to the atom that has the charge like
carbon in the mechanism above
•• Show dipoles on important bonds where the two atoms have different electronegativities
•• Use δ+ for a small positive charge and δ- for a small negative charge

snaprevise.co.uk 63
SECTION 2:
Alkanes
1 Alkanes
•• Alkanes are saturated hydrocarbons
•• This means that they contain only carbon to carbon single bonds
•• Carbon has four electrons in the outer shell (group 14) so forms four bonds
•• General formula of CnH2n + 2
•• Each C-C or C-H bond is formed from direct overlap of orbitals of bonding atoms
•• This is called a sigma (σ) bond
•• These can freely rotate around the axis of the bond

2 Bonding in alkanes
•• The carbon 2s and three 2p orbitals combine to form four hybrid sp3 orbitals
•• These are what overlap to form sigma bonds
•• They are shaped like lopsided p orbitals
•• Arranged in a tetrahedral formation 109.5o away from each other
•• So carbon atoms in alkanes have the atoms they’re bonded to arranged in a tetrahedral
formation
•• This is explained by electron pair repulsion theory as it allows the electrons in the bonds to
be as far away from each other as possible

snaprevise.co.uk 64
3 Boiling/melting points in alkanes
•• Alkanes have covalent bonds inside molecules
•• They have London forces between molecules, holding them together
•• The longer the carbon chain, the stronger the forces
•• There is more molecular surface area and each molecule has more electrons that can
interact
•• So short chain alkanes have lower boiling points than long chain alkanes
•• Effect of branching
○○ Branched-chain alkanes have smaller molecular surface areas
○○ They are not as closely packed
○○ London forces are reduced
○○ Branched chain alkanes have lower boiling points than straight chain alkanes

4 The low reactivity of alkanes


•• All covalent sigma bonds have high enthalpies so are hard to break
•• Carbon and hydrogen have very similar electronegativities so the bonds have very low
polarities
•• This means they aren’t reactive to electrophiles/nucleophiles either

5 Combustion of alkanes
•• Combustion (burning) is a rapid oxidation reaction which combines oxygen with another
substance
•• All hydrocarbons undergo complete combustion when plenty of O2 is present with a clean
blue flame to give CO2 and H2O
•• High numbers of carbon and hydrogen atoms mean hydrocarbons burn well and release lots
of heat energy
•• E.g. burning methane (used in domestic cooking and heating)
•• CH4 + 2O2 CO2 + 2H2O
•• Methane is the main gas used in domestic heating and cooking
•• If there is insufficient oxygen, then the alkanes undergo incomplete combustion
•• This produces colourless, odourless carbon monoxide, CO, and soot, C, with a yellow flame
•• Lots of different reactions e.g.
○○ 2CH4 + 2½O2 CO + C + 4H2O
○○ 2CH4 + 3½ O2 CO2 + CO + 4H2O

snaprevise.co.uk 65
•• Carbon monoxide is toxic, because it reduces the capacity of blood to carry oxygen
•• If appliances are not properly maintained, then insufficient oxygen may be supplied to the
burners
•• This may cause carbon monoxide to be produced

6 Radical substitution
•• Alkanes react with halogens in UV light to form haloalkanes
•• Reaction process proceeds by a free radical mechanism with three stages
•• Initiation — formation of radicals
○○ Cl2 2Cl·
○○ Needs UV or ~300oc
•• Propagation — two repeated steps that build up product in a side reaction
○○ CH4 + Cl· ·CH3 + HCl (making alkyl radical)
○○ ·CH3 + Cl2 CH3Cl + Cl·(forming haloalkane)
•• Termination — two radicals react to form a stable product
○○ Lots of possible reactions
○○ 2Cl· Cl2
○○ 2·CH3 C2H6
○○ ·CH3 + Cl· CH3Cl

EXAM TIP
You need to know radical substitution reactions and their three stages for both chlorine
and bromine, but they both happen in exactly the same way

7 Limitations of radical substitutions


•• Because so many different radicals can be formed in the propagation and termination steps,
there are lots of different possible products
•• Further products can be formed if the products of one chain are involved in more
propagation steps
•• Therefore there’s a low atom economy and yield with lots of undesired side products

snaprevise.co.uk 66
SECTION 3:
Alkenes
1 Alkenes
•• Alkenes are a homologous series of unsaturated hydrocarbons
•• General formula of CnH2n
•• Unsaturated means that they contain double carbon to carbon bonds
•• Made up of one sigma and one pi (π) bond
•• π-bond is formed by sideways overlap of p-orbitals compared to head on overlap for σ-bonds
•• π-bonds have 2 regions of electron density, above and below the internuclear axis
•• They prevent rotation about the bond because the two p-orbitals have to be parallel to each other
•• This means the alkene is flat in the region of the double bond

2 Trigonal planar carbon atoms in alkenes


•• Each carbon has three other atoms bonded to it around it
•• Two hydrogens σ-bonded to it
•• One carbon σ- and π-bonded to it
•• The σ-bonds stay 120o apart to keep the electrons in the bonds as far away from each other
as possible (electron pair repulsion theory)
•• So the carbons have a trigonal planar geometry around them

snaprevise.co.uk 67
3 Stereoisomerism in alkenes
•• Stereoisomers are compounds with the same structural formula but with a different
arrangement of the atoms in space
•• There can be stereoisomers of alkenes because the double bond can’t rotate
•• Rotation would require the breaking of the pi bond, which requires a great deal of energy
•• For an alkene to show geometric isomerism, there must be two different types of atoms
attached to each carbon in the double bond
•• Alkenes have E and Z isomers
○○ Look at one carbon atom of a double bond and assign priority using Cahn-Ingold-Prelog
rules to the substituents
○○ The highest molecular weight substituent has the highest priority and so on
○○ Do the same for the other carbon atom
○○ If the highest priority substituents for each carbon are on the same side of the double
bond it’s the Z-isomer
○○ If they’re on opposite sides it’s the E-isomer

•• Cis-trans naming is appropriate if each carbon has two identical groups attached to it
○○ Split the alkene along the line of the carbon-carbon double bond
○○ If both sides have the same group it’s the cis-isomer
○○ If both sides have one of each group it’s the trans-isomer

snaprevise.co.uk 68
4 Stereoisomers from structural formulas
•• Given a structural formula with a double bond, work out which isomer it is
•• Then swap constituents at the double bond to get the other isomer

5 Reactivity and the π-bond


•• The π-bond has a lower bond enthalpy than the σ-bond
•• This means it’s easier to break
•• So alkenes are more reactive than alkanes

6 Electrophiles
•• Species that are electron-pair acceptors
•• Could be because it’s a positive ion or has a δ+ region
•• Attracted to the high electron density in π-bonds

7 Addition reactions of alkenes


•• A reaction where the π-bond breaks and a small molecule is added across the two carbon
atoms
•• Gives a saturated organic product
•• Hydrogenation is the addition of an H2 molecule across the double bond
○○ Suitable catalyst e.g. nickel
○○ H2 and the alkene are passed over the catalyst at 150oc

•• Halogenation is the addition of a halogen (Cl2, Br2 etc) across the double bond
○○ Reactions proceed at room temperature
○○ No UV light required
○○ Forms di-substituted haloalkanes

snaprevise.co.uk 69
○○ In the first step a dipole is induced in Br2 as it approaches the electron rich double bond
○○ Makes the closer Br δ+
○○ This then attracts electrons from the double bond

•• Test for saturation


•• If an organic compound decolourises bromine or iodine solution a double bond is present
•• Hydration is the addition reaction of water across the double bond of a gaseous alkene to
make an alcohol
○○ Temperature of 300oc
○○ Pressure of 65 atm
○○ H3PO4 catalyst

•• Hydrogen halides, HX, (HCl, HBr etc) add across the double bond to give haloalkanes
○○ Hydrogen halides are gases
○○ Bubbled through alkenes to give a reaction

EXAM TIP
You need to know the mechanisms for all these addition reactions

snaprevise.co.uk 70
8 HX adding to unsymmetrical haloalkanes
•• If the alkene is unsymmetrical two products can form
•• Use Markownikoff’s rule to work out the major product
•• The major product is the molecule in which hydrogen adds to the carbon with the greatest
number of hydrogens already attached to it
•• This is related to the stability of the carbocation intermediate formed
•• Stability: tertiary carbocation > secondary carbocation > primary carbocation
•• More alkyl groups attached to a carbon make the carbocation more stable

9 Addition polymerisation of alkenes


•• Polymers are large molecules made from smaller monomer units
•• The double bond in alkenes ‘opens up’ to form polymers
•• π-bond breaks and the carbon atoms form σ-bonds to other monomers
•• Polymers can be millions of monomers long so we draw a repeating unit
•• To make a repeat unit from a monomer
○○ Draw the individual monomer in square brackets
○○ Turn the double bond into a single bond
○○ Add bonds on either side extending out of the square brackets
○○ Add subscript n, this shows how many monomers are in a polymer molecule (can be very large)

snaprevise.co.uk 71
•• To find a monomer from a polymer
○○ Choose a group of atoms and find where it repeats
○○ The section between the two repeat points is the repeat unit
○○ Make sure it’s as small as possible i.e. one monomer not two
○○ Do the above steps in reverse to get the monomer molecule

EXAM TIP
You need to be able to find monomers from polymers and create polymers from monomers

10 Sustainability and processing


waste polymers
•• Plastics and synthetic polymers are non-biodegradable
•• Cannot be broken down by living organisms in the way that natural compounds are
•• Waste plastics that are sent to landfill and remain there for many years as they only
decompose slowly
•• Plastics are mainly hydrocarbon so can be burned
○○ This allows some of the energy used to make them to be recovered
○○ But this also produces CO2
○○ Some plastics produce toxic waste products e.g. HCl when burned
○○ These can be removed using gas scrubbers
•• Plastics can be recycled by being melted down and reshaped into new things
•• Plastics can also be broken down to small organic molecules to be used in other polymers or
industrial reaction
•• This reduces the need for plastic disposal and the demand for the production of plastics
•• Recycling polymers saves the energy that would be used making new polymers
•• Only uses the energy needed for the process of recycling
•• But:
○○ The plastics need to be sorted to be recycled
○○ This takes time or expensive equipment
○○ There’s a small market for recycled plastic because companies are concerned about
quality and contamination from previous use

snaprevise.co.uk 72
11 Biodegradable polymers
•• Polymers that can be attacked by microorganisms and environmental conditions and broken
down into harmless or useful substance
•• Should break down in the same amount of time as normal green waste
•• Biodegradable polymers can be mixed with addition polymers like polyethene
•• The biodegradable polymer can break down allowing the material to biodegrade
•• This leaves small pieces of plastic which can also be dangerous
•• If just biodegradable polymers are used it’s a bioplastic
•• These fully degrade so don’t create landfill or need energy to be recycled
•• They can be carbon neutral if they’re made with sustainable farming methods
•• Photodegradable polymers break down in sunlight
•• This reduces the chance they damage the environment
•• Once exposed to light it’s not possible to stop this process
•• They might not get exposed to enough light in a landfill for this to happen

snaprevise.co.uk 73
TOPIC 2

Alcohols,
haloalkanes
and analysis
SECTION 1:
Alcohols
1 Properties of alcohols
•• Saturated, homologous series with formula CnH2n+1OH
•• Can be primary (1 C attached to OH C), secondary (2 Cs attached to OH C) or tertiary (3 Cs
attached to OH C)

•• Are polar because the oxygen atom is more electronegative than carbon
•• Have relatively low volatility
•• Volatility is a measure of how easily molecules can escape from a liquid
•• A volatile liquid loses molecules from the surface very easily and so it will have a low boiling
temperature
•• Branching generally decreases boiling point, and so increases volatility
•• Alkanes have a much lower boiling point than an alcohol with the same number of carbons
•• In alkanes the intermolecular forces are only weak induced dipoles (London Forces)
•• In alcohols, the OH group can form hydrogen bonds, which are much stronger
•• These hydrogen bonds require much more energy to be broken
•• So boiling points are higher

•• Alcohols are covalent but dissolve in water


•• Polar OH group in alcohol forms hydrogen bonds with polar OH group in water
•• Carbon chain can’t form hydrogen bonds to water
•• The longer the carbon chain, the less soluble the alcohol is

snaprevise.co.uk 75
2 Combustion of alcohols
•• Happens in the same way as for alkanes producing CO2 and water
•• e.g. C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(l)

3 Oxidation of alcohols
•• Oxidation of the –OH group to C=O (carbonyl) group
•• Acidified potassium dichromate (VI) usually used as oxidising agent (H+/K2Cr2O7)
•• Represented by [O] in equations
•• Cr (VI) is reduced to Cr3+ ions
•• Colour change from orange to green
•• Functional group of product depends on whether it is a primary, secondary or tertiary
alcohol
•• Primary
○○ Oxidised to form aldehydes
○○ Reaction stops if aldehyde is distilled off straight away
○○ Reaction will continue if heated under reflux
○○ These are then oxidized to form carboxylic acids
•• Secondary
○○ Heat under reflux
○○ Oxidised to form ketones
•• Tertiary
○○ These cannot be oxidised
○○ No reaction occurs

snaprevise.co.uk 76
4 Dehydration of alcohols
•• H2O can be eliminated from alcohols to give alkenes
•• Heat under reflux with a strong acid e.g. H2SO4/H3PO4
•• The acid is a catalyst for the reaction

EXAM TIP
An elimination is a reaction where one molecule forms two products, and normally one is
small. A dehydration is an elimination where water is one of the products

5 Substitution with halide ions


•• Alcohols undergo a nucleophillic substitution reaction with halide ions
•• -OH group replaced by Cl-/Br-/I-
•• ROH + HX RX + H2O
•• An acid catalyst is added along with the halide source and the mixture is warmed
•• To form a chloroalkane, HCl is added
•• To form a bromoalkane, normally NaBr is added with H2SO4 to make HBr in situ
•• This doesn’t work for iodine as it’s oxidized by H2SO4 to give I2 so the yield is poor
•• Phosphoric acid is used instead

EXAM TIP
You don’t need to know a mechanism for this

snaprevise.co.uk 77
SECTION 2:
Haloalkanes
1 Nucleophiles
•• Electron pair donors (and also Lewis bases)
•• Have partial (δ-) or full negative charges
•• Attracted to positive charges or δ+
•• E.g. H2O, NH3, OH-

2 Hydrolysis of haloalkanes
•• Haloalkanes are alkanes with one or more hydrogen replaced by a halogen
•• There’s a large difference in electronegativity between carbon and the halogens
•• So the bond is polar, carbon is δ+ and the halogen δ-
•• Haloalkanes undergo hydrolysis
•• This is a substitution reaction with water as a nucleophile (nucleophilic substitution)
•• Hydrolysis with aqueous alkali to form alcohols
•• CX + OH- COH + X-
○○ -OH group substituted for the halogen
○○ NaOH or KOH used
○○ Done under reflux conditions
•• Haloalkanes can also react with AgNO3 and water
•• Halide ion leaves during the reaction
•• This reacts with Ag+ to give a precipitate
•• Can use how long the precipitate takes to appear to determine how fast reactions of
different haloalkanes are
○○ Add 1cm3 of each haloalkane to different test tubes in a water bath at 50oc
○○ Put test tubes with ethanol, water and aqueous silver nitrate in the water bath
○○ Allow them to come to the same temperature
○○ Add 1cm3 of ethanol, water and aqueous silver nitrate to each haloalkane
○○ See how long it takes for precipitate to appear
•• Use this to determine bond strengths of different C-X bonds
•• Stronger bonds will lead to a slower reaction so precipitate will take longer to appear
•• Fluoroalkanes can’t be used because FNO3 is soluble, not a precipitate
Haloalkane Halide Colour of AgX precipitate
chloroalkane Cl- White
bromoalkane Br- Cream
iodoalkane I- Yellow

snaprevise.co.uk 78
3 The mechanism of nucleophilic substitution
•• Electrophilic OH- attacks δ+ carbon
•• Reaction shows bromine but could be any halogen

4 Hydrolysis rates of primary haloalkanes


•• Explained by C-X bond enthalpies
•• Going down halogens atoms increase in size
•• Bonding electrons are further from nucleus so more shielded
•• This gives lower C-X bond enthalpies
•• Easier to break the bond so reaction happen faster
•• Electronegativity increases up the group
•• C-F bonds are most polar so attract nucleophiles more
•• But bond enthalpies are very high so hardest to break and react slowest

5 Haloalkanes and the environment


•• Haloalkanes used in industry as CFCs
•• CFCs are gases and eventually escape into the atmosphere
•• Exposed to UV light in the stratosphere
•• C-X bonds break in UV light
•• Undergo homolytic fission to form radicals
•• E.g. CHFCl2 CHFCl·+ Cl·
•• Ozone (O3) is present in the stratosphere as the ozone layer (20km up)
•• Protects earth from UV which causes cell mutations responsible for cancer and cataracts by absorbing it
•• Radicals including from CFCs catalytically destroy ozone e.g.
○○ Propagation: Cl· + O3 ·ClO + O2
○○ Propagation: ·ClO + O3 Cl· + O2
○○ Overall: 2O3 3O2
•• Also happens with other radicals e.g. ·NO
○○ Propagation: ·NO + O3 ·NO2 + O2
○○ Propagation: ·NO2 + O ·NO + O2
○○ Overall: O3 + O 2O2

snaprevise.co.uk 79
SECTION 3:
Organic Synthesis
1 Practical skills
•• Quickfit apparatus used in practical organic chemistry
•• Grease joints with petroleum jelly to get a good fit or use plastic connectors
•• Distillation is a separating technique used to collect product from an organic synthesis reaction
•• Equipment
○○ Round bottom flask for reaction mixture
○○ Heating mantle
○○ Thermometer and holder
○○ Condenser and connector to join it to the round bottom flask
○○ Collecting flask
•• Set up using clamp stands and bosses to hold equipment
•• Connect bottom of condenser to tap with rubber hose and run rubber hose from top of
condenser to sink and turn on gentle flow of water
•• Pour reaction mixture into flask with anti bumping granules
•• Heat and note temperature that products starts evaporating and being collected
•• This is its boiling point and helps to identify it

snaprevise.co.uk 80
•• Heating under reflux is a technique used to ensure a reaction mixture doesn’t boil away
•• Equipment
○○ Pear shaped flask
○○ Heating mantle
○○ Condenser

2 Preparing and purifying organic liquids


•• Many organic liquids are immiscible in water
•• Can use a separating funnel to separate organic product from an aqueous solvent
•• Mount an iron ring on a clamp stand and put separating funnel in it
•• Ensure tap is closed and add reaction mixture until no more than half full
•• Wash reaction vessel with water, add to funnel and put stopper on
•• Take funnel out of ring and invert, open tap to equalise pressure, close tap
•• Gently shake mixture, opening tap every now and then while inverted to release pressure
•• Carry on until no longer hear ‘whistle’ when opening the tap
•• Put funnel in iron ring and allow layers to seperate
•• Remove stopper, put a beaker under the spout and open tap
•• Collect the lower water layer in the beaker and turn off the tap

snaprevise.co.uk 81
•• Aqueous layer can be discarded as it has no product in it
•• Place fresh beaker under tap and collect product
•• Shake with drying agent and pour product into fresh container
•• Drying agents are anhydrous inorganic salts like MgSO4 and CaCl2
•• They absorb water so can dry other liquids
○○ Add a few spatulas of drying agent to wet organic product
○○ If the drying agent clumps add more
○○ When the drying agent remains free moving the organic product is dry
○○ Use gravity filtration to remove drying agent and leave dry product
•• Redistillation purifies product through multiple distillations
•• Keep repeating a distillation, keeping only the product each time, until desired purity is achieved

3 Identifying functional groups


and predicting properties
•• Need to be able to recognise double bonds, haloalkanes, carbonyls (C=O), carboxylic acids
and alcohols

Functional group Reagents to test for Observations


unsaturated hydrocarbon Add a few drops of Bromine water decolourises
(C=C) bromine water and shake
haloalkane Silver nitrate, ethanol, White precipitate = chloro-
water Cream precipitate = bromo-
Yellow precipitate = iodo-
carbonyl Acidified potassium Ketones — no change
dichromate (VI) Aldehydes — orange green
Fehling’s solution Ketones — no change
Aldehydes — dark red
Tollens’ reagent precipitate
Ketones — no silver mirror
Aldehydes — silver mirror
carboxylic acid Universal indicator or pH pH of a weak acid
probe
Reactive metal e.g. Ca Hydrogen effervesced
Carbonate e.g. MgCO3 CO2 effervesced
alcohol Warm with equal volume Sweet smell of an ester after a
of carboxylic acid and a short time
few drops of H2SO4

snaprevise.co.uk 82
•• Many compounds have more than one functional group
•• These can all be identified individually
•• Properties will all be dependent on what functional groups are present, and can be predicted
from the properties of simple examples of the functional groups shown

4 Synthetic routes
•• Need to be able to give two step reactions that generate one compound from another

snaprevise.co.uk 83
SECTION 4:
Analytical techniques
1 Infrared radiation
•• Different bonds in covalent molecules absorb radiation at particular frequencies
•• Frequency of infrared radiation depends on the energy required to cause the bond to stretch or bend
•• Amount of vibration depends on:
○○ Bond strength
○○ Bond length
○○ Mass of each atom involved in the bond
•• Infrared spectra usually have a range from 300 to 4000cm-1

2 Absorption of IR radiation
by atmospheric gases
•• IR absorption happens everywhere, not just inside spectrometers
•• C=O, O-H and C-H bonds are very good at absorbing IR
•• These bonds are found in common greenhouse gases like CO2, H2O, CH4
•• These gases absorb IR radiation leaving the earth and emit it back towards the earth
•• This is the greenhouse effect
•• These gases are suspected of causing global warming
•• So governments have introduced policies to limit their emissions and encourage
technologies and energy resources that don’t emit them

3 Identifying functional groups


in IR spectra
•• O-H bond in alcohols has a broad absorption at 3200-3550cm-1
•• If this peak is present the compound being analysed has an alcohol group
•• Most organic compounds have an absorption at ~3000cm-1 due to C-H bonds
•• Don’t confuse this with a broad O-H peak
•• In the spectra below these are the peaks just to the right of the O-H peak

snaprevise.co.uk 84
•• C=O bond in aldehydes, ketones and carboxylic acids absorbs from 1640-1750cm-1
•• If no OH peak is present, the compound is an aldehyde/ketone
•• If an OH peak is present, the compound is a carboxylic acid

EXAM TIP
Infrared absorption data is given in the data sheet, this will tell you what bonds absorb at
what frequencies

4 Interpretation of spectra
•• If you’re given a spectra, identify what clear peaks are present
•• Match these up with the known absorptions of functional groups
•• Use these to work out what functional groups are in the molecule

snaprevise.co.uk 85
5 Uses of IR spectroscopy
•• Used in monitoring air pollution
•• Pollutants like CO and NO have specific absorptions that allow their concentrations to be monitored
•• This can be used to study the effect of traffic on air quality
•• Also used in breathalyzers
•• The strength of the absorption peak of alcohols in breath depends on the concentration in
the blood
•• This phenomenon is described by the Beer-Lambert law
•• So IR spectra can be used to determine blood alcohol levels
•• Commonly used alongside other technologies like fuel cells that react with alcohols or
chemical reactions that show the presence of alcohols to identify alcohol

6 Mass spectrometry
•• Mass spectrometers only detect ions
•• Organic compounds vapourized and ionized when driven through a mass spectrometer
•• Some form a molecular ion, M+
•• This is when the molecule loses an electron
•• The mass of the electron is negligible, so this has the same mass as the relative molecular
mass of the original molecule
•• Mass spectra show the mass to charge (m/z) ratio of ions that are put into it
•• The molecular ion will have the highest m/z value with reasonable intensity
•• There may be a peak 1 unit higher due to 13C being 1.11% naturally abundant
•• This is the M+1 peak, don’t confuse it for the molecular ion
•• If a molecule includes a 13C atom instead of a 12C atom it will have an m/z value one higher
than normal

snaprevise.co.uk 86
7 Fragmentation patterns
•• Excess energy given in forming the molecular ion may cause the molecule to fragment and
split into pieces
•• Fragmentation can happen anywhere in a molecule, and fragments can break into further fragments
•• So lots of different m/z ratios due to different fragments are seen in spectra
•• This allows them to be used to identify different molecules
○○ Two isomers will have the same molecular ion peak, but different fragmentation patterns
○○ Organic compounds have unique mass spectra, which can be used as a fingerprint for identification
•• When an ion fragments, one fragment is charged, while the other is neutral
•• This can be reversed, so one fragmentation gives two possible fragments that can be detected
•• If you get a mass spectrum of an unknown compound it helps to draw out the compound
and look at what could fragment off to help explain the m/z peaks
•• Table shows some common fragments

m/z value Possible fragment ion identity


15 CH3+
17 OH+ from alcohols
29 C2H5+
43 C3H7+
57 C4H9+

EXAM TIP
Different fragments can have the same m/z value, so a peak in a spectrum at 43 from a
molecule that you don’t think can fragment to give C3H7+ may well not be that

snaprevise.co.uk 87
8 Finding structures
from different analytical data
•• Different analytical provide different information so they are used together to work out what
compound is being studied
•• Elemental analysis gives the percentage of each element in a compound
•• Use percentages and Ar values to work out number of moles of each element and empirical/
molecular formula
•• Mass spectrometry is destructive — the sample can’t be retrieved after analysis
•• But it works on very small quantities, is quite cheap and very accurate
•• Helps to find relative molecular mass from molecular ion peak
•• Fragmentation pattern gives an idea of structure
•• IR is non-destructive
•• When given data from the three techniques and asked to determine what molecule is present
○○ Use elemental analysis to find the empirical/molecular formula
○○ Use mass spec. To find the Mr if not found from elemental analysis
○○ Also use mass spec. to work out what fragments form
○○ Use this to find a plausible structure and choose between isomers
○○ Use IR to determine what functional groups are present and incorporate them into the
molecule

EXAM TIP
You’ll only need to be able to work out spectra and data relating to compounds with the
functional groups covered in this module

snaprevise.co.uk 88

You might also like