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AS-LEVEL
CHEMISTRY
CHEMISTRY
NOTES
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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.
Section 4: Acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 13
Section 5: Redox . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 15
Section 1: Periodicity. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 33
Section 2: Group 2. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 38
Section 3: Halogens. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 40
3
TOPIC 2: PHYSICAL CHEMISTRY. . . . . . . . . . . . . . . . . . . . 43
Section 2: Alkanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
Section 3: Alkenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67
Section 1: Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 75
Section 2: Haloalkanes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 78
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
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
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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
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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
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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
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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
EXAM TIP
Sometimes mol/dm3 is abbreviated to ‘M’, they mean exactly the same thing
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.
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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
•• Percentage yield may be low due to the reaction not going to completion, impurities or side
reactions for example
•• Atom economy =
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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.
2 Strong acids
•• Completely dissociate (give up H+ ions) in solution, weak acids only partially dissociate
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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
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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
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
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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
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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
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.
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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
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
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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
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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
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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
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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
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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
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•• 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
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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
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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
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
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•• 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)
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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
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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
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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
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○○ 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
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•• 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
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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
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○○ 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
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
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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
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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
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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
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•• 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
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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+)
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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
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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
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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
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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
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○○ 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
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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
EXAM TIP
Remember that you find gradient at a point by drawing a flat line against the curved graph,
then finding rise over run
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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
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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
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•• 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
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SECTION 3:
Chemical equilibrium
1 Dynamic equilibrium
•• Some reactions are reversible
•• This is represented by the symbol �� ��
��
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
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○○ 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
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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
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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
•• 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
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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
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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
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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
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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
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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
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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
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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
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
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•• 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
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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
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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
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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
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
•• 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
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○○ 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
•• 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
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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
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•• 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
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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
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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
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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
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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
EXAM TIP
You don’t need to know a mechanism for this
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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
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3 The mechanism of nucleophilic substitution
•• Electrophilic OH- attacks δ+ carbon
•• Reaction shows bromine but could be any halogen
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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
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•• Heating under reflux is a technique used to ensure a reaction mixture doesn’t boil away
•• Equipment
○○ Pear shaped flask
○○ Heating mantle
○○ Condenser
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•• 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
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•• 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
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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
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•• 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
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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
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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
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
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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
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