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Advanced Higher Chemistry Resource Guide: March 2015

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Advanced Higher Chemistry

Resource Guide
March 2015
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Advanced Higher Chemistry Resources Guide


This resource guide has been produced in response to requests from staff who attended the NQ Sciences events at Hampden Stadium in December 2013.
Those attending felt it would be useful to have a document which helped them navigate to the most relevant resources quickly.

The following pages show the mandatory course key areas table from the SQA Advanced Higher Chemistry Course and Unit Support Notes. An additional
fourth column has been included which contains hyperlinks to useful resources. Please note: Staff are not required to use the resources listed – they
are only included as helpful suggestions. Staff should also refer to the SQA website for the most up-to-date course and unit support notes.

To further assist staff content links to useful SQA documentation have been included at the beginning of each unit along with resources for the Researching
Chemistry Unit.

SQA documents Web link


Course specification http://bit.ly/13xROgY
Course assessment specification http://bit.ly/1vZ38Iw
Course and unit support notes http://bit.ly/1vZ3grF
Assessment overview published June 2014 http://bit.ly/1AbCbaM

Education Scotland learning materials


Higher Sciences website http://bit.ly/HigherSciences

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Inorganic and Physical Chemistry Unit specification http://bit.ly/13ao2hh

Mandatory course key areas Suggested learning activities Exemplification of key areas Useful resources
Electromagnetic radiation Education Scotland produced Electromagnetic radiation and Education Scotland resources – Electronic
and atomic spectra curriculum support staff notes for atomic spectra. structure and the periodic table.
current Electronic Structure and the
Electromagnetic waves Periodic Table, and also for Electromagnetic radiation may be
ChemWiki resources – Electromagnetic
The relationship c = f λ Principles of Chemical Reactions. described in terms of waves and
These booklets have lots of suitable can be characterised in terms of radiation.
extra activities and teaching wavelength and/or frequency. The
applications. relationship between these
quantities is given by c = fλ where c
An internet search on CD or DVD represents the speed of light, f
spectroscope will produce many sites represents the frequency of the
-1
with simple instructions which allow wave (s ) and λ represents the
learners to make individual wavelength (m). When radiation in
spectroscopes from any unwanted the visible part of the
CDs or CD-ROMs. For example, electromagnetic spectrum is being
Arvind Gupta toys spectrascope. described, it is common to specify
An online and printable wavelength in nanometres (nm).
electromagnetic spectrum is
available from the Royal Society of
Chemistry (search RSC learnnet
electromagnetic spectrum printable).
The speed of light can be taken as
-1
3·00 × 108 m s (see Data Booklet).
Frequency is often quoted in Hz,
-1
which is the same as s
.
Dual nature of electromagnetic A video on the dual nature of light When electromagnetic radiation is New Chemistry Teaching resources –
radiation — waves and can be found on the internet (search absorbed or emitted by matter, it Wave particle duality
particles Quantum mechanics: the dual nature appears to behave more like a
of light — YouTube). stream of particles than as a wave.

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

–34
The relationships Use h = 6·63 × 10 J s (see Data These particles are known as PhET animation – Waves on a string
E = hf and E = Lhf Booklet). For Avogadro’s constant, photons. When a photon is
23 –1
use L = 6·02 × 10 mol (see Data absorbed or emitted, energy is PhET animation- Quantum wave
Booklet). gained or lost by electrons within
interference
the substance. The photons in high
-1
To get E, in kJ mol , it is more frequency radiation can transfer
convenient to use E = Lhf/1000 or E greater amounts of energy than
= Lhc/1000. L is the number of photons in low frequency radiation.
formula units in one mole of the The energy associated with a single
substance. (Formula units can be photon is given by E = hf where ‘h’
atoms, molecules or groups of ions represents Planck’s constant. For
depending on how the formula is chemists, it is more convenient to
usually written and on the type of express the energy associated with
bonding structure present.) a mole of photons which is given by
-1
E = Lhf giving the energy in J mol
where L represents Avogadro’s
constant.
Atomic emission Learners can observe atomic When energy is transferred to McGraw-Hill Education animation – Line
Evaluation of evidence for emission by carrying out flame tests. atoms, electrons within the atoms spectra
energy levels in atoms of Methods for this can be found by may be promoted to higher energy
elements searching for RSC flame test. The levels.
Learn Chemistry activity – Flame tests
flames can be looked at through a
spectroscope to show emission To allow the electrons to return to
spectra. The RSC website gives their original levels, energy must be PhET animation – Neon lights and other
more information. lost from the atom. This energy is discharge lamps
released in the form of a photon.
Spectacular demonstration versions The spectrum of light emitted
in which an alcohol spray is used to (atomic emission spectrum) is not
produce coloured flames over a continuous, but consists of a series
metre long could also be used. See of lines at discrete frequencies.
the RSC website and in the RSC
publication ‘Classic Chemistry This phenomenon provides direct
Demonstrations’ No. 34 page 80. evidence for the existence of
Search RSC flame colours — a discrete (quantised) energy levels

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

demonstration. for electrons. An atom can be


considered as emitting a photon of
To view an atomic emission light energy when an electron
spectrum, a simple hand-held moves from a higher energy level to
spectroscope can be used to view a a lower energy level. Each element
vapour discharge lamp or, if good produces a unique pattern of
blackout conditions are available, frequencies of radiation in its
from a flame test. Fluorescent tube emission spectrum.
lamps, commonly used for classroom
lighting, contain mercury vapour. If a
spectroscope is used to view an
illuminated fluorescent lamp, a series
of purple lines from the atomic
emission spectrum of mercury can be
observed.

SSERC activity with filter paper SSERC experiment – Sodium absorption


soaked in brine to observe sodium spectrum with a white Lumiled
spectrum. A useful resource on
spectroscopy and the identification of
elements from emission spectra can
be found on the 800mainstreet.com
website (search spectroscopy
element identification and emission
spectra 800 main street). SSERC is
currently developing an instrument 800mainstreet resources – Spectroscopy:
using a camera or phone with a Element identification and emission spectra
diffraction grating attachment.

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Atomic spectroscopy Resources describing atomic Atomic emission spectroscopy and RSC resource – Atomic absorption
absorption are available from the atomic absorption spectroscopy are spectrometry
Atomic emission spectroscopy RSC (search RSC atomic absorption used to identify and quantify the
and atomic absorption or CHP atomic absorption elements present in a sample. In
Learn Chemistry resources – Measuring
spectroscopy and how they spectroscopy). Interesting anecdotes absorption spectroscopy,
are used to identify and can be provided of the forensic uses electromagnetic radiation is lead levels in hair
quantify the elements present of atomic absorption spectroscopy. directed at an atomised sample.
in a sample For example, the investigation of
toxic levels of heavy metals in Isaac Radiation is absorbed as electrons
Newton’s hair due to his alchemical are promoted to higher energy
pastimes or the high levels of lead in levels. An absorption spectrum can
men’s hair treated with hair products be produced by measuring
to reduce greyness. Search RSC how a sample’s transmission of
learnNet anecdotes lead in hair. light varies with wavelength.
In emission spectroscopy, high
A free science video by ‘Brightstorm’ temperatures are used to excite the
on atomic emission spectra is electrons within atoms. As the YouTube video – Atomic emission spectra
available (search atomic emission electrons drop to lower energy
spectra YouTube brightstorm2). levels, photons are emitted. An University of Oregon animation – Create
Videos on use of spectroscopy in emission spectrum can be absorption or emission spectra for various
astronomy, on the spectrum of stars produced by measuring how much
elements
and on the absorption and emission light is emitted at different
spectra of hydrogen are also wavelengths.
available (search atomic emission
spectra YouTube brightstorm2). Each element produces a
Astronomy-spectroscopy -1/3 characteristic absorption/emission
YouTube (spot the error on spectrum which can be used to
atomic size) Astronomy-spectroscopy identify that element. In atomic
-2/3 YouTube (does show temp spectroscopy, the concentration of
in °K (sic)) an element within a sample is
related to the intensity of light
Spectrum of stars 1of2 YouTube emitted or absorbed.
Forensic ink analysis (search
forensic ink analysis YouTube).

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

A very useful website from


uoregon.edu has an applet which
shows the absorption and emission
spectra of most elements just by
clicking on the appropriate element
on a Periodic Table. Search for
University of Oregon elements.
Light from a sodium lamp passing
through a sodium flame from, say, a
sodium pencil produces a shadow
when projected on to a white screen.
Atomic orbitals, electronic Electrons, behave as standing waves The discrete lines observed in MyRSC animation – Electron orbitals
configurations and the within the atom. atomic emission spectra can be
Periodic Table explained if electrons, like photons,
Wave mechanics tells us that there display the properties of particles
University of Sheffield animation – The
The four quantum numbers are different shapes and sizes of and waves. Within the atom,
Orbitron
used to describe any electron standing waves possible around the electrons behave as waves and
within an atom. nucleus; which are known as orbitals. there are different sizes and shapes
of wave possible around the
The shapes of s, p and d The circumference of the standing nucleus. These are known as
orbitals wave is always equal to an integral orbitals and each can hold a
number of wavelengths. The principal maximum of two electrons. The four
quantum number, n, is the quantum numbers are:
circumference of the orbital in terms
of the number of wavelengths.  the principal quantum number, n
Revised Higher 2(a) atomic orbital  the angular momentum
notes page 28. quantum number, l
 the magnetic quantum number,
The RSC website has pages which m
offer very clear and attractive  the spin magnetic quantum
representations of orbitals with number, s
accompanying text which refers to
the wave nature of the electron. A
free science video by ‘Brightstorm’

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

covers quantum numbers but this is


beyond the level required and would
need some previous teaching or
learning. Search for Quantum
numbers Brightstorm YouTube.

A Sci-Comm video showing 3D


models helping to visualise s, p and d
orbitals is available. The RSC
website has an animation which can
be used to illustrate the absorption
and emission of light by an atom. It
can also be run set at ‘Orbital Model’
and shows a pictorial representation
of the orbitals and labels them using
the "1s" "2p" type of nomenclature,
but search orbital diagrams
Brightstorm YouTube.
Electronic configuration A free science video by ‘Brightstorm’ Any atom can only have a Brightstorm animation – Orbital Diagrams -
including: covers orbital box diagrams and maximum of two electrons within Concept
 aufbau principle covers the aufbau principle, Pauli any single orbital. The aufbau
 Hund’s rule exclusion principle and Hund’s rule. principle states that electrons fill
 Pauli exclusion principle Another free science video by orbitals in order of increasing
‘Brightstorm’ (brightstorm.com) energy. The relative energies
covers electronic configurations. corresponding to each orbital can
Search the aufbau principle. be represented diagrammatically
Teachers/lecturers may wish to for the first four shells of a multi-
introduce only elements 1–20 at first electron atom. In an isolated atom
and return to the remaining elements the orbitals within each subshell are
during the coverage of transition degenerate. Hund’s rule states that
metals. when degenerate orbitals are
available, electrons fill each singly,
keeping their spins parallel before
spin pairing starts.

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

The Pauli exclusion principle states


that no two electrons in the one
atom can have the same set of
four quantum numbers. As a
consequence, no orbital can hold
more than 2 electrons and the 2
electrons must have opposite spins.
Electronic configurations using
spectroscopic notation and orbital
box notation can be written for
elements of atomic numbers 1 to
36.
The Periodic Table is f-orbitals are not assessable The Periodic Table can be
subdivided corresponding to subdivided into four blocks (s, p, d
electron configurations and f) corresponding to the outer
electronic configurations of the
elements within these blocks.
Ionisation energies as A graph of first ionisation energies The variation in first, second and
evidence for electron against atomic number shows blips, subsequent ionisation energies with
Configurations which gives good evidence of s and p increasing atomic number for the
orbitals being filled. first 36 elements can be explained
The relative values of first, in terms of the relative stability of
second and subsequent different electronic configurations,
ionisation energies can be and so provides evidence for these
evaluated in terms of the electronic configurations.
stabilities of different subshell
electron configurations
Shapes of Molecules and Although valence shell electron pair Shapes of Molecules and PhET animations - Molecule shapes
Polyatomic Ions repulsion (VSEPR) theory does not Polyatomic Ions
provide an accurate description of
VSEPR rules the actual molecular orbitals in a The arrangement of electron pairs
molecule, the shapes predicted are is linear, trigonal planar,
Apply VSEPR rules to usually quite accurate. The RSC has tetrahedral, trigonal bipyramidal
determine shapes of links to sites allowing the 3D display and octahedral when the total

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

molecules and polyatomic of molecules with different numbers number of bonding and non-
ions of bonding and non-bonding pairs. bonding electron pairs is 2, 3, 4, 5
Search Cheml Ed home page then and 6, respectively. Electron pair
search for molecular orbitals. repulsions decrease in strength in
Alternatively, search: the order: non-bonding pair/non-
 davidson edu molecular orbitals bonding pair > non-bonding
(both need 3D java) pair/bonding pair > bonding
 chemmy bear shapes of molecules pair/bonding pair. These different
gives animated shapes strengths of electron pair repulsion
 beavon clara orbitals contents is an account for slight deviations from
animation showing molecular expected bond angles in molecules
shapes but has no commentary such as NH3 and H2O.
Transition metals A striking display can be made by Transition metals Brightstorm video – Exceptions to electron
Electronic configuration of creating a set of sample bottles The d-block transition metals are configurations
transition metal atoms and containing salts or compounds of the metals with an incomplete d
ions and the anomalies of the first 30 elements. If these are then subshell in at least one of their ions.
Education Scotland activity – Preparation of
model explained positioned on an A1 or A2 sized The filling of the d orbitals follows,
Periodic Table poster it is striking that with the exception of chromium and potassium trioxolatoferrate(III)
only the dblock compounds are copper atoms. These exceptions
coloured. Learners may also notice are due to a special stability
that zinc compounds are white — associated with the d subshell
indicating that, although lying in the being half filled or completely filled.
central region of the Periodic Table, When atoms from the first row of
zinc is different from the transition the transition elements form ions it
metals. Scandium is also different is the 4s electrons which are lost
since it forms only the 3+ ion which first rather than the 3d electrons.
has no d electrons. A short
‘Brightstorm’ video on ‘Exceptions to
electron configurations’ covers the
electronic configurations of Cr and
Cu.
Oxidation states of transition Zinc is used to reduce a solution of Oxidation states of transition metals RSC experiment – The oxidation states of
Metals yellow ammonium vanadate(V) to a An element is said to be in a vanadium

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

mauve solution containing particular oxidation state when it ChemGuide resources – Oxidation states
Oxidation numbers of vanadium(II) ions. The intermediate has a specific oxidation number.
transition metal ions oxidation states of vanadium(IV) The oxidation number can be
(blue) and vanadium(III) (green) are determined by following certain
Using changes in oxidation also seen. See the RSC website and rules. Transition metals exhibit
number of transition metal also the RSC publication ‘Classic variable oxidation states of differing
ions to determine whether Chemistry Demonstrations’ No. 92 stability. Compounds of the same
oxidation or reduction has page 258. transition metal but in different
occurred oxidation states may have different
Another video resource can be found colours. Oxidation can be
at Chemistry oxidation of vanadium considered as an increase in
YouTube. oxidation number and reduction can
A similar experiment using zinc be considered as a decrease in
amalgam is also shown in a one- oxidation number. Compounds
minute video produced by the Open containing metals in high oxidation
University. states tend to be oxidising agents
whereas compounds with metals in
Can also do similar experiment with low oxidation states are often
oxidation states of Mn. reducing agents.

Bromfield Honors Chemistry video


‘Assigning Oxidation Numbers’
covers all the main points for
assigning oxidation numbers. Search
blinkx.com assigning-oxidation-
numbers.

A website which is a series of


questions and answers on oxidation
numbers is available. It is good but
fast. It is best done as revision after
oxidation numbers have been taught.
Search 9.1.2 assigning Oxidation
Numbers YouTube

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Ligands Instructions for carrying out a Ligands may be negative ions or Learn Chemistry experiment – Reactions of
Bonding of ligands in transition microscale investigation into the molecules with nonbonding pairs of transition elements
metal complexes chemistry of the transition elements, electrons which they donate to the
looking at their redox and central metal atom/ion forming
Classification of ligands precipitation reactions is available dative bonds. Ligands can be
Coordination number from the RSC website. Search RSC - classified as monodentate,
Naming complex ions learn Chemistry – microscale bidentate up to hexadentate. The
according to IUPAC rules chemistry transition elements. total number of bonds from the
ligands to the central transition
metal atom/ion is known as the co-
ordination number. Complexes are
written and named according to
IUPAC rules.
Explanation of colour in An interesting introduction into colour In a complex of a transition metal Learn Chemistry experiment – Making
transition metal complexes in transition metal compounds is the d orbitals are no longer glass
through the production of coloured degenerate. The energy difference
glass. between subsets of d orbitals
RSC experiment – Complexes of nickel(II)
More can be found in the RSC depends on the ligand. Colours
publication ‘Classic Chemistry of many transition metal complexes with ethylenediamine
Experiments’ No.44 page 112 and on can be explained in terms of d-d
the RSC website. This allows transitions. Light is absorbed when
learners to make glass and then electrons in a lower energy d orbital
colour some glass using transition are promoted to a d orbital of higher
metal oxides. RSC publication energy.
‘Classic Chemistry Demonstrations If light of one colour is absorbed,
No. 93 page 261 shows different then the complementary colour will
colours of nickel complexes with be observed.
water and ethylenediamine as
ligands in different ratios.

The chemguide.co.uk website has


pages which cover colours of
transition metal complexes.

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Opportunity for learners to find out


about the spectrochemical series and
investigate how the position of ligand
in the series may affect the colour
and paramagnetism of the complex.
Prepare solutions containing
2+ 2+( 2+(
Cu (aq), Ni aq), Co aq).
(Concentrations are not important but
concentrated enough to have
characteristic colours.) Add conc HCl

to provide Cl ions as ligands and
concentrated NH3(aq) to provide NH3
molecules as ligands. See colour
changes due to differences in energy
levels between d orbitals. Original
solutions have H2O molecules as
ligands.
UV and visible absorption of A UV-visible spectrometer measures Ultra-violet and visible absorption RSC experiment – Investigating commercial
transition metal complexes the intensity of radiation transmitted spectroscopy involve transitions sunscreens
through a sample, and compares this between electron energy levels in
with the intensity of incident radiation. atoms and molecules where the
Chemistry Teaching Resources activity –
Determination of Mn in steel (PPA energy difference corresponds to
from unrevised AH). The wavelength the ultra-violet and visible regions Determination of manganese in steel (Unit
ranges are approximately 200–400 of the electromagnetic spectrum. 1 PPA 2)
nm for ultra-violet and 400– 700 nm
for visible light.
Catalysis by transition metals Hydrogen peroxide oxidises It is believed that the presence of RSC experiment – A visible activated
potassium sodium tartrate (Rochelle unpaired d electrons or unfilled d complex
Transition metals and their salt) to carbon dioxide. The reaction orbitals allows intermediate
compounds can acts as is catalysed by cobalt(II) chloride. complexes to form, providing
Iowa State University animation – Cobalt
catalysts The colour of the cobalt(II) chloride reaction pathways with lower
turns from pink to green (an activated activation energies compared to the chloride catalysis
complex), returning to pink again as uncatalysed reaction. The variability
the reaction dies down. Details of the of oxidation states of transition

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

experiment are available from the metals is an important factor.


RSC publication ‘Classic Chemistry Homogeneous and heterogeneous
Demonstrations’ page 1 and also catalysts should be explained in
from their website. Search for RSC terms of changing oxidation states
Classic Chemistry Demonstrations a with the formation of intermediate
visible activated complex. complexes and the adsorption of
(The experiment may have been reactive molecules onto active sites
done at Higher but at AH discussion respectively.
would involve oxidation states.)
Chemical equilibrium Try to ensure links to organic A chemical reaction is in equilibrium ChemConnections animation – Equilibrium
Equilibrium expressions, chemistry through pKa values and when the composition of the
factors affecting equilibria and buffers are constantly reinforced as reactants and products remains Beckerdemos experiment – pH rainbow
well as links within the Unit itself. constant indefinitely. The
calculation of the composition tube
Nclark.net and beckerdemos contain equilibrium constant (K)
of the equilibrium mixtures lots of good ideas for this Unit and characterises the equilibrium
other levels of Chemistry. They composition of the reaction mixture. Nancy Clark resources – Acids and Bases
contain links to a variety of For the general reaction,
animations, experiments and Learn Chemistry experiment – Challenging
tutorials. Search n clark acids and aA + bB ⇌cC + dD medicines: physiochemical properties
bases website or becker demos (pH K = [C]c[D]d
Rainbow tube).
[A]a[B]b Nuffield Foundation experiments – Dynamic
Strictly speaking, equilibrium
constants are defined in terms of the equilibria
activities of the reactants and where [A], [B], [C] and [D] are the
products, but a good working equilibrium concentrations of A, B, Learn Chemistry resources – Starter for ten
approximation is achieved by using C and D respectively and a, b, equilibria
the concentration of solutions, in mol c and d are the stoichiometric
-1
l , in place of activities. coefficients in the balanced reaction
Quia animation – Rags to riches
Because the concentrations of pure equation.
solids or pure liquids are constant, by
convention they can be given the Equilibrium constants are
value 1 in the equilibrium equation. independent of the concentrations
The website chm.davidson.edu has or pressures of species in a given
an equilibrium animation showing reaction. The numerical value of the

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

the effect of temperature changes. equilibrium constant depends on


Partition coefficients could be the reaction temperature. For
included as a specific example of an endothermic reactions a rise in
equilibrium constant. temperature causes an increase in
K, i.e., the yield of the product is
increased.
For exothermic reactions a rise in
temperature causes a decrease in
K, i.e., the yield of the product is
decreased. The presence of a
catalyst does not affect the value of
the equilibrium constant.
Equilibrium constants have no
units.

Ionic product of water and Point out that the equilibrium does
+
In water and aqueous solutions ChemConnections animation – Equilibrium
calculations of pH not involve free protons but H3O (aq). there is an equilibrium between the
Use Kw to calculate pH of water and it water molecules and hydrogen and Davidson College experiment – Chemical
+ can be used to show that the pH of hydroxide ions.
pH = –log10[H ] equilibrium
water varies with temperature. The
-
chemguide.co.uk website has useful This ionisation of water can be
Kw = [H+ ][OH ] information on the ionic product of represented by:
water, including variation of Kw at
H2O(ℓ) + H2O(ℓ)⇌ H3O (aq) + OH(aq)
+
different temperatures. Unfortunately
Kw has been given units. Search
chemguide ionic product for water Water is amphoteric. The
+
Calculations of [H ] for different pH dissociation constant for the
values. Quiz on calculating pH; quia ionisation of water is known as the
pH pOH game ionic product and is represented by
Kw. The value of the ionic product
A fun equilibrium applet can be found varies with temperature.
here called ChemConnections
equilibrium.

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

At 25 °C the value of Kw is
-14
Some useful Java animations can be approximately 1 × 10 .
found at Davidson virtual chemistry
experiments. A shorthand representation of
+ +
H3O (aq) is H (aq).
Another Equilibrium animation can be
found at Davidson Dr Nut equkin. Stoichiometric equations and
equilibrium expressions can be
+
written using H (aq) instead of
+
H3O (aq) where the meaning is
clear. The relationship between
pH and the hydrogen ion
concentration is given by
+
pH = –log10 [H ]
+
pH = –log10[H ] and
–pH
conversely [H+] = 10 .

In water and aqueous solutions with


a pH value of 7 the concentrations
+ –
of H (aq) and OH (aq) are both
-1
10-7 mol l at 25 °C. If the
+
concentration of H (aq) or the

concentration of OH (aq) is known,
the concentration of the other ion
can be calculated using Kw or by
using pH + pOH = 14.
Bronsted-Lowry acids/bases Video by Mark Rosengarten video The Bronsted-Lowry definitions of YouTube video – Bronsted-Lowry Theory
definitions pH of salt solutions defines Bronsted/Lowry acids and acid and base state that an acid is of acids and bases
Equilibria of the salt solutions bases. Search YouTube chemistry a proton donor and a base is a
tutorial 11.4a Bronsted Lowry. Videos proton acceptor.
University of Nebraska activities –
by Papapodcasts go further, covering
conjugate acids and bases. For every acid there is a conjugate Bronsted/Lowry Acids and bases
base, formed by the loss of a
proton.

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

For every base there is a conjugate YouTube video – Bronsted-Lowry


acid, formed by the gain of a acids/bases.
proton.

A soluble salt of a strong acid and a


strong base dissolves in water to
produce a neutral solution. A
soluble salt of a weak acid and a
strong base dissolves in water to
produce an alkaline solution. A
soluble salt of a strong acid and a
weak base dissolves in water to
produce an acidic solution.

Soaps are salts of weak acids and


strong bases. The acidity, alkalinity
or neutrality of the above kinds of
salt solution can be explained by
reference to the appropriate
equilibria.

Strong and weak acids and For a video of a simple animation Strong and weak acids and bases Iowa State University animation – Solutions
bases showing the difference between the In aqueous solution, strong of acid, base and salt
Properties of strong and weak strong acid, HCl, and the weak acid, acids/bases are completely
acids and bases. HF, in terms of ionisation, search dissociated into ions but weak
Learn Chemistry animation – Strong/weak
the acid dissociation constant, mhhe chemistry demonstrations acids/bases are only partially
Ka or pKa where acid_ionization. dissociated. Examples of strong acids and bases
pKa = –log10Ka acids include hydrochloric acid,
Other Papapodcasts’ videos cover sulfuric acid and nitric acid. RSC resources – Indicators and titration
strong/weak acids and strong/weak Ethanoic, carbonic, and sulfurous curves
bases. Search papapodcasts strong acids are examples of weak acids.
and weak acids. Solutions of metal hydroxides are Nuffield Foundation activities – pH of oxides
strong bases. Ammonia and
amines are examples of weak

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Investigation of pH of strong and bases.


weak acids and bases using pH
meter or indicators. Investigate pH of The weakly acidic nature of
differing metal/non-metal hydroxide solutions of carboxylic acids, sulfur
solutions. dioxide and carbon dioxide can be
explained by reference to equations
Look at titration curves for strong/ showing the equilibria. The weakly
weak acids and bases. alkaline nature of a solution of
Short videos of these are available at ammonia or amines can be
titration curve YouTube. Some good explained by reference to an
reading can be found at: chem guide equation showing the equilibrium.
pH titration curves. The acid dissociation constant is
represented by Ka or by pKa where
A search for iastate greenbowe pH pKa = –log10Ka
meter shows a simple animation
using a pH meter to test pH of Although equimolar solutions of
various acids and alkalis of differing weak and strong acids/bases differ
concentrations. in pH, conductivity, and reaction
rates they do not differ in
Search thinkquest dissociation stoichiometry of reactions.
constant for information on strong
and weak acids and on the acid
dissociation constant.

Calculate acidity/basicity of a given


salt solution and confirm by
measurement of pH. Test pH of
various salt solutions including
sodium carbonate, sodium sulfite,
sodium stearate, ammonium
chloride, ammonium nitrate etc.

The Chem.iastate.edu website also


shows a simple animation using a pH

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

meter to test pH of various salt


solutions of differing concentrations.
Search iastate greenbowe pH_meter.
-1
Calculation of pH for a weak Calculate pH of a 0·1 mol l solution The approximate pH of a weak acid
acid of a weak acid and confirm by can be calculated using pH = ½ pKa
pH = ½ pKa – ½ log10c measurement. Dilute it tenfold to – ½ log10c where c is the nominal
show pH rises by 0·5 rather than by 1 concentration of the acid in the
as it would when diluting a strong solution.
-1
acid such as 0·1 mol l HCl. Good
opportunity for candidates to practise
diluting accurately.
Buffer solutions Prepare buffer solution, measure pH Indicators are weak acids for which McGraw-Hill Education animation – Buffers
Composition of a buffer, how and compare with calculated value. the dissociation can be represented
buffers work and calculation Opportunity to use pH meter and use as: University of Southern California animation
buffer solution to calibrate it.
– Acid base titration
HIn(aq) + H2O(ℓ)⇌H3O (aq) + In (aq)
of the pH of buffers –
pH of blood important. Small change +
pH = pKa – log10 [acid/salt] in pH causes major problems. Need The acid indicator dissociation
to explain to learners that acetic acid ChemCollective animation – Acid Base
constant is represented as KIn and
and acetate are the same as is given by the following chemistry and buffers concept test
ethanoic and ethanoate. Search expression:
mhhe essential chemistry buffer 12 + -
KIn = [H3O ][In ]
for an animation of how a buffer
[HIn]
solution resists change in pH when a
In aqueous solution the colour of
strong acid or a strong base is
the acid indicator is distinctly
added.
different from that of its conjugate
Another animation of a buffer solution
base. The colour of the indicator is
in which learners can prepare a
determined by the ratio of [HIn] to
buffer solution, test its pH, add acid –
[In ].
or alkali and test the pH again can be
found by searching for iastate
The theoretical point at which
greenbowe ph buffer solution. This +
colour change occurs is when [H ]
can also be used to compare
= KIn.
measured pH value of buffer against

19
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

the calculated value. A search for The colour change is assumed to


chemcollective Concept Test be distinguishable when [HIn] and
-
acidbase yields shows an interesting [In ] differ by a factor of 10. The pH
but difficult quiz. range over which a colour change
Unfortunately, answers are not occurs can be estimated by the
provided. An animation showing the expression: pH = pKIn ±1
difference in pH changes when
adding an acid or alkali to a buffer
solution compared with adding acid
or alkali to water can be found by
searching for michele usc acid base
or nred.org titration web.
Reaction feasibility Enthalpy of formation ΔHof = ΣΔHof (products) – ΣΔHof Dartmouth College activity – Enthalpy of
Standard enthalpy of The standard enthalpy of formation, (reactants). formation of magnesium oxide
formation, definitions and ΔHof, is the enthalpy change when
one mole of a substance is formed
relevant calculations Knowledge of standard conditions
from its elements in their standard
ΔHof = ΣΔHof (products) – states. The standard enthalpy of a is important.
ΣΔHo f (reactants). reaction can be calculated from the
standard enthalpies of formation of
the reactants and products.

Entropy and prediction of Investigate simple exothermic and The entropy (S) of a system is a University of Toronto animation – Entropy
value of entropy endothermic reactions. measure of the degree of disorder
Discuss in terms of entropy changes. of the system. The greater the Nuffield Foundation activity – A colourful
Changes of entropy A fun flash animation of entropy can degree of disorder, the greater the
clock reaction
be found by searching utoronto entropy. Entropy increases as
Einstein quote entropy flash. temperature increases. Changes of
state involve changes in entropy.
Second and Third Laws of Experiment/demo of endothermic The change in standard entropy for Leek High School activities – Endothermic
Thermodynamics reaction of Ba(OH)2 with NH4Cl a reaction system can be calculated reactions
Examples of practical work which can from the standard entropies of the
be carried out on spontaneous reactants and products.

20
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

endothermic reactions. Search ΔSo = ΣΔSo (products) – ΣΔSo


leekhigh staffs chemistry Chemical (reactants).
reactions endothermic.
Calculations in changes in Experiment/demo of endothermic The change in standard entropy for Nuffield Foundation activity – Endothermic
standard entropy reaction of Ba(OH)2 with NH4Cl a reaction system can be calculated solid-solid reactions
ΔSo = ΣΔSo (products) – ΣΔSo Examples of practical work which can from the standard entropies of the
(reactants). be carried out on spontaneous reactants and products.
endothermic reactions. Search ΔSo = ΣΔSo (products) – ΣΔSo
leekhigh staffs chemistry Chemical (reactants).
reactions endothermic.
Free energy Former AH PPA, verification of a Applications of the concept of free Education Scotland activity – Verification of
thermodynamic prediction could be energy a thermodynamic prediction (Unit 2 PPA 4)
The concept of free energy carried out here as an example of a
theoretical prediction working out The feasibility of a chemical
fairly closely to the observed reaction under standard conditions
ΔG = ΔH – TΔS
experimental value. Suggest a larger can be predicted from the
Calculation of standard free quantity of NaHCO3(s) be used to calculated value of the change in
energy change for a ensure bulb of thermometer is
o
standard free energy (ΔG ). The
reaction completely covered but this will temperatures at which a reaction
ΔGº = Σ ΔGº (products) – produce a volume of CO2 greater may be feasible can be estimated
Σ ΔGº (reactants). 3
than 100 cm so needs to be from
o o o
monitored carefully and heating ΔG = ΔH – TΔS by considering
stopped and syringe removed from the range of values of T for which
3 o
the barrel before 100 cm reached. ΔG < 0. Under non-standard
Ellingham diagrams can be used to conditions any reaction is feasible if
o
show how G varies with temperature ΔG is negative. At equilibrium, ΔG
and they were useful in predicting = 0.
temperatures at which reductions of
metal oxides became feasible. A reaction will proceed
spontaneously in the forward
direction until the composition is
reached where ΔG = 0.

21
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Kinetics Propanone/iodine reaction PPA from The rate of a chemical reaction Chemistry Teaching Resources activity –
Determination of the order of a current AH. Decolourisation of blue normally depends on the Verification of a thermodynamic prediction
reaction (0, 1, 2, 3) from food dye. See SSERC bulletin No. concentrations of the reactants. (Unit 2 PPA 5)
experimental data and rate 225. Within the body, drug molecules
equations. Calculation of rate are converted into a number of For a first order reaction the rate of
constants and units of k. different molecules that are more reaction is proportional to the SSERC activity – Determining the rate
rate = k[A] easily excreted into the urine. These concentration of one reactant and constant and order of reaction
molecules are called metabolites and the rate can be expressed as: rate
the whole process is called = k[A] where k is the rate constant RSC case study – Horse racing forensic
metabolism. The metabolism of the and [A] is the concentration of laboratory
-1
drug will begin as soon as it is reactant A in mol l .
administered and in many cases the
process follows first order kinetics, The order of a reaction with respect
i.e. the rate of metabolism is to any one reactant is the power to
proportional to the concentration of which the concentration of that
the drug. The RSC have a case reactant is raised in the rate
study from The Horseracing Forensic equation. The overall order of a
Laboratory (HFL). There is a learner reaction is the sum of the powers to
worksheet and additional notes and which the concentrations of the
answers for teachers. Search Royal reactants are raised in the rate
Society of Chemistry, chemistry at equation. The order of a reaction
the races. can only be determined from
experimental data.

The rate constant can be


determined from initial rate data for
a series of reactions in which the
initial concentrations of reactants
are varied.

Integral orders of reaction from zero


order to third order should be
covered.

22
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Reaction mechanisms SN1 and SN2 reaction mechanisms Reaction mechanisms usually Learn Chemistry activity – Iodination of
can be discussed here but will also occur by a series of steps. The rate propanone
The rate determining step in a be covered in the Organic Chemistry of reaction is dependent on the
reaction Unit. slowest step, which is called the
‘rate determining step’.
From the rate equation predict
the rate determining step and Experimentally determined rate
possible mechanism. equations can provide evidence for
a proposed reaction mechanism.

23
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Organic Chemistry and Instrumental Analysis Unit specification: http://bit.ly/1yYkeIX

Mandatory course key areas Suggested learning activities Exemplification of key areas Useful resources
Molecular orbitals Chem.purdue.edu has information When atoms approach each other,
Formation of bonding about atomic orbitals becoming their separate sets of atomic Purdue University resources – Molecular
molecular orbitals molecular orbitals orbitals merge to form a single set orbital theory
of molecular orbitals. Some of the
molecular orbitals, known as University of Sheffield animation – The
‘bonding molecular orbitals’, orbitron
occupy the region between two
nuclei. The attraction of positive
nuclei to negative electrons
occupying bonding molecular
orbitals is the basis of bonding
between atoms. Each molecular
orbital can accommodate a
maximum of two electrons
3 2
Hybridisation sp , sp hybrid mhhe.com has pages which cover Hybridisation is the process of McGraw-Hill Education animation –
orbitals and their role in the hybridisation including an animation. mixing atomic orbitals within an Hybridisation
formation of sigma and pi Consider effect that the different atom to generate a set of new
bonds types of bonds have on the shapes hybrid orbitals. IB Chemistry resources – Orbitals
of molecules, eg shape of CH4 v
C2H4 v C2H2. As an extension, bonding in alkynes
can be described in terms of sp
As an extension, bonding in alkynes hybridisation with both sigma and pi
can be described in terms of sp bonds. The website ibchem.com
hybridisation with both sigma and pi has information on sigma bonds, pi
bonds. The website ibchem.com has bonds and hybridisation.
information on sigma bonds, pi There are also other videos on the
bonds and hybridisation. internet covering hybridisation.

24
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

There are also other videos on the atomic orbitals called hybrid
internet covering hybridisation. orbitals. Bonding in alkanes can be
3
described in terms of sp
hybridisation and sigma bonds.

Bonding in alkenes can be


2
described in terms of sp
hybridisation and both sigma and pi
bonds.

A sigma bond is a covalent bond


formed by end-on overlap of two
atomic orbitals lying along the
axis of the plane.

A pi bond is a covalent bond formed


by the sideways overlap of two
parallel atomic orbitals lying
perpendicular to the axis of the
bond.

The bonding continuum Markrosengarten.com has a fun The bonding continuum PhET animation – Molecule polarity
The symmetry and position of song and video covering covalent, In a non-polar covalent bond, the
bonding orbitals between polar covalent and ionic bonding. bonding molecular orbital is YouTube video – What kind of bonds are
atoms determines types of Useful as revision of Higher bonding. symmetrical about the midpoint these?
bonding - ionic, polar or non- between two atoms. Polar covalent
polar covalent bonding. bonds result from bonding
molecular orbitals which are
asymmetric about the midpoint
between two atoms. Ionic

25
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

compounds represent an extreme


case of asymmetry with the bonding
molecular orbitals being almost
entirely located around just one
atom.
Molecular structure Molecular drawing packages such as Learners should be able to draw
Convertion between ChemSketch can be set to display structural formulae and skeletal ACD resources – ChemSketch
molecular, structural and structures in skeletal representation formulae and to interconvert
skeletal formulae with no more if required. 3D representations of between molecular, structural and Cambridgesoft resources – ChemDraw
than 10 carbon atoms in their relatively small molecules (less than skeletal formulae for organic
longest chain 10 carbon atoms) containing molecules with no more than 10 Chemdoodle resources – Chemdoodle
common functional groups can be carbon atoms in their longest chain.
created and manipulated by learners In a skeletal formula neither the
using molymods or similar. carbon atoms, nor any hydrogens YouTube video – Introduction to line
Wireframe, stick, ball and stick and attached to the carbon atoms, are drawings in organic chemistry
space-filling representations should shown. The presence of a carbon
all be familiar. Learners can rotate atom is implied by a ‘kink’ in the
molecules around the x, y and z axes carbon backbone, and at the end of
to align any chosen bond horizontally a line.
or vertically, to align any three atoms
in a given plane, to zoom in and out,
and to switch on and off atom labels.
Molecules sketched in 2D mode can
be converted into 3D representations
in Chemsketch. CHIME (a free plugin
for web browsers) can also display a
huge range of molecules in 3D.
Extensive free libraries of 3D
molecules are available to be
downloaded from the internet. The

26
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

structures of aliphatic compounds


can be drawn on a Chemsketch type
system. The functional groups -OH, -
COOH, -C=O, -NH2, -CONH-, -COO-
can also be drawn and added to
these compounds using a
Chemsketch type system. A free
alternative to Chemdraw is
Chemsketch, which is available from
ACD labs or ISIS Draw. The
structural formulae of aliphatic
compounds can be represented in
skeletal form using a Chemdraw type
system. Molecular drawing packages
such as ChemSketch can be set to
display structures in skeletal
representation if required. Learners
may learn how to interconvert
between full and shortened structural
formulae and skeletal formulae using
the Chemsketch type system.
Tutorials on using Chemsketch and
drawing skeletal formulae are
available on the internet.
Stereochemistry Videos on different forms of Stereoisomers are molecules with YouTube video – Introduction to
stereoisomerism isomerism by Dr Chris Arthur and the same molecular formula with a stereoisomerism
‘Brightstorm’ are available on the different spatial arrangement of
internet. their atoms.

27
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Geometric isomerism Make molecular models of cis and Geometric isomerism is one type of Boston College activity – Bromination of
cis and trans. trans isomers. The influence of stereoisomerism. It arises due to stilbene
geometric isomerism on chemical the lack of free rotation around a
Physical and chemical properties can be illustrated by the bond, frequently a carbon–carbon Yteach animation – Cis- and trans-isomers
properties of geometric fact that cis-butenedioic acid is more double bond, but not always. of compounds with a double carbon-carbon
isomers. readily dehydrated than trans- bond
butenedioic acid. Geometric isomers are labelled cis
and trans according to whether the Learn Chemistry resources – Chemistry
Melting points and densities of cis- substituent groups are on the same olympiad support booklet
butenedioic and transbutenedioic side or on different sides of the
acid can also be compared. Health carbon-carbon double bond.
issues associated with trans fatty
acids. Also, the cis geometry of Geometric isomers display
combretastatin is crucial to differences in some physical
anticancer activity. Alkenes are often properties.
used to rigidify structures into active
conformations. Geometric isomerism can also
influence chemical properties.
Optical isomerism The Thalidomide story could be Optical isomers are non- YouTube video – Optical isomerism
non-superimposable mirror discussed here. Limonene exists in superimposable mirror images of
image, chiral/ enantiomers two isomeric forms. One has the asymmetric molecules and such Learn Chemistry activity – Extracting
scent of oranges, and the other of molecules can be described as limonene from oranges
Racemic mixture and effect on pine. A microscale investigation of chiral molecules or enantiomers.
polarised light the isomers of limonene is available University of Bristol resources – Optical
from the RSC. Chm.bris.ac.uk has Optical isomerism occurs in isomerism In thalidomide
Physical and chemical more information about limonene. substances in which four different
properties of optical isomers Ibuprofen is normally sold as a substituent groups are arranged YouTube video – Naming enantiomers R
mixture of two optical isomers, one of around a central ‘chiral’ carbon and S
which is an effective pain-killing drug atom. Optical isomers, in general,
and the other of which is inactive. have identical physical and Learn Chemistry activity – Synthesis of

28
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

This gives a low atom economy for chemical properties, except when Nurofen
the desired product. Recent research they are in a chiral environment.
has produced a more efficient However, they have an opposite
synthetic route to produce only the and equal effect on the direction of
desired isomer. More information rotation of plane-polarised light, and
from the RSC. Chiral drugs are often are therefore said to be optically
sold as racemates despite the fact active. Racemic mixtures contain
that activity is due mainly to one of equal amounts of both optical
the enantiomers. However, there are isomers, and are optically inactive.
cases where the pure enantiomer is In biological systems, only one
sold if there is a clear clinical optical isomer of each asymmetric
advantage (for example if the other organic compound is usually
enantiomer has toxic side effects). present.
An example is esomeprazole which
is the active enantiomer of
omeprazole — an antiulcer agent. R-
and S- enantiomers can be
discussed but will not be assessed.
Can discuss chirality in drugs such
as ibuprofen. S-Naproxen is a pain
reliever and its enantiomer R-
Naproxen is a liver toxin. Use a
polarimeter, if one is available, to
demonstrate the rotation of plane
polarised light by optical isomers.
Many links show the number of
synthetic steps involved in making an
asymmetric compound. Enzymes are
now being used to produce
asymmetric compounds in fewer

29
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

synthetic steps. A simple polarimeter


can be made from polaroid sun
glasses using the instructions from
the RSC Classic Chemistry
Demonstrations No.13, page 26
(also available on the internet).
Colby.edu has a video which covers
chirality, stereoisomerism and optical
activity. Also covers R- and S-
enantiomers.
Synthesis It is important that many, varied, real- Recognising and using types of Learn Chemistry animations – Investigate
From given equations identify: life contexts for these reactions are reaction in organic synthesis. Given organic reaction mechanisms
substitution, addition, provided. Similarities/parallels equations, the following reaction
elimination, condensation, between the different reaction types types can be identified: substitution, HKEdCity animations – Reaction
hydrolysis, oxidation, should be constantly reinforced and addition, elimination, condensation, mechanism animation
reduction reactions opportunities to make connections hydrolysis, oxidation, reduction.
Devise synthetic routes, with frequently provided. CompoundChem resources – Explorations
no more than three steps, Learners should be able to devise of everday chemical compounds
from a given reactant to a final RSC website Learn Chemistry has a synthetic routes, with no more than
product. program Investigating Organic three steps, from a given reactant
Deduce possible reactions Reaction Mechanisms which is an to a final product.
from molecular structures online tutorial on reaction
mechanisms. Learners should be able to look at
molecular structures and deduce
the reactions it can undergo.
Bond fission homolytic and Free radical chain reaction When an organic reaction takes ChemGuide resources – Free radical
heterolytic fission mechanism is covered at Higher. place, bonds are broken and mechanisms menu
Chemguide.co.uk has information formed. If, when the bond between
which covers free radical substitution atoms breaks, each atom retains Avogadro resources – Bond fission,
reaction mechanism in more detail one electron from the former radicals and photochemical reactions

30
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

than at Higher. covalent bond, then two free


radicals are formed. This is known
Tutorvista provides more information as homolytic fission. Reactions
on homolytic and heterolytic fission. involving free radicals tend to result
Pi bonds are easier to break than in formation of very complex
sigma due to weaker overlap of mixtures of products, thus making
orbitals. This can be used to explain them unsuitable for synthesis. If,
why carbonyls are important in when the bond between atoms
synthesis (pi bond and polarity). breaks, one atom retains both of
the electrons from the former
covalent bond, then an ion pair is
formed. This is known as heterolytic
fission.

Reactions proceeding via


heterolytic fission tend to produce
far fewer products and are therefore
better suited for synthesis.
Heterolytic fission will be favoured
when the bond between the atoms
is polar.
Electrophiles and nucleophiles Avogadro.co.uk provides definitions Electrophiles and nucleophiles in Avogadro resources – Introducing chemical
Reactions involving heterolytic and examples of nucleophiles and reactions involving heterolytic bond kinetics rate equations
bond fission. electrophiles. fission, attacking groups are
classified as ‘nucleophiles’ or
Nucleophiles or electrophiles ‘electrophiles’. Nucleophiles are
as attacking groups. atoms or groups of atoms which are
attracted towards atoms bearing a
(partial) positive charge.

31
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Nucleophiles are capable of


donating and sharing an electron
pair to form a new bond.

Electrophiles are atoms or groups


of atoms which are attracted
towards atoms bearing a (partial)
negative charge. Electrophiles are
capable of accepting an electron
pair.
Curly arrow notation Chemguide.co.uk has information on Use of double-headed and single- ChemGuide resources – Curly arrow
Use of double-headed and use of curly arrows. headed arrows to show electron mechanisms
single-headed arrows to show movement. The head and tail of
electron movement. The curly the arrow indicates the destination University of Oxford animations –
arrow shows source and and origin of the pair of electrons. Interactive organic reaction mechanisms
destination of the electron (s)
An arrow starting at the middle of a Kirsop Labs animations – How to draw
covalent bond indicates that mechanisms using curly arrows
heterolytic bond fission is occurring.

When an arrow is drawn with the


head pointing to the space between
two atoms, this indicates that a
covalent bond will be formed
between the two atoms.

A double-headed arrow indicates


the movement of an electron pair
and a single-headed arrow
indicates the movement of a single

32
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

electron.
Haloalkanes Alkaline hydrolysis of a bromoalkane. Haloalkanes (alkyl halides) are
Classification of Experiment on nucleophilic named according to IUPAC rules.
monohaloalkanes as primary, substitution reactions of haloalkanes
secondary or tertiary. — See ‘Chemistry in Context Monohaloalkanes can be classified
Monohaloalkanes undergo Laboratory Manual, fifth edition’ by as primary, secondary or tertiary.
nucleophilic substitution Graham Hill and John Holman,
reactions: published by Nelson Thornes. React Monohaloalkanes undergo
 alkalis to form alcohols monohaloalkanes with aqueous nucleophilic substitution reactions.
alcoholic alkoxides to form alkali and test for halide ion using They react with:
ethers silver nitrate solution React  alkalis to form alcohols
 ethanolic cyanide to form monohaloalkanes with ethanolic  alcoholic alkoxides to form ethers
nitriles which can be potassium hydroxide and test for  ethanolic cyanide to form nitriles
hydrolysed to carboxylic alkene produced. Some haloalkanes which can be hydrolysed to
acids are used as anticancer agents and carboxylic acids (chain length
 Monohaloalkanes can also are called alkylating agents. increased by one carbon atom)
undergo elimination Associated with toxic side effects.
reactions to form alkenes Monohaloalkanes can also undergo
elimination reactions to form
alkenes. For example: Ethanolic
KOH.
The reaction mechanism for Not necessary to go into inductive The reaction mechanisms for SN1 University of Surrey animation – SN1
SN1 and SN2 reactions stabilisation in great detail. and SN2 reactions can be mechanism
Mechanisms and animations for SN1 represented using curly arrows.
SN1 and SN2 reactions using and SN2 are available on the internet. The dominance of an SN1 or SN2 University of Surrey animation – SN2
curly arrows and mechanisms Chemguide.co.uk gives information mechanism for a particular mechanism
with particular attention given on nucleophilic substitution haloalkane can be explained in
to the transition state/ reactions. terms of steric hindrance and the Kirsop animations – Looking for Curly
intermediate inductive stabilisation of an Arrows?
intermediate carbocation. An SN2

33
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

reaction proceeds via a single five-


centred transition state, whereas an
SN1 reaction occurs in two steps via
a carbocation.
The preparation properties, Preparation of esters, ethanol Alcohols exhibit hydrogen bonding Learn Chemistry experiment – Preparation
and reactions of alcohols reacting with Na to form sodium and as a result have anomalously of esters
Preparation from alkenes ethoxide, oxidation of ethanol, high boiling points compared to
haloalkanes and reduction of ethanal and propan- 2-ol by acidified many other organic compounds of Education Scotland activity – preparation of
carbonyl compounds using dichromate, etc. Dehydration of comparable relative formula mass benzoic acid by the hydrolysis of ethyl
lithium aluminium hydride ethanol to ethene using aluminium and shape. The shorter chain benzoate
oxide. Alcohol groups present in a alcohols are miscible with water,
Physical properties related to lot of drugs since they are involved in but their solubility in water Learn Chemistry experiment – Microscale
bonding hydrogen bonding with protein decreases as chain length oxidation of alcohols
binding sites (for example blockers increases. Alcohols can be
Dehydration, reaction with and antiasthmatics). prepared from: Education Scotland activity – Preparation of
metals  alkenes by acid-catalysed aspirin
hydration;
Reactions with  haloalkanes by substitution Learn Chemistry experiment – Dehydration
carboxylic acids and acid of ethanol to form ethene
chlorides Alcohols react with some reactive
metals to form alkoxides. Alcohols
can be dehydrated to alkenes.
Alcohols undergo condensation
reactions with carboxylic acids and
react more vigorously with acid
chlorides to form esters. Aldehydes
and ketones can be reduced to
primary and secondary alcohols
respectively, by reaction with lithium
aluminium hydride in ethoxyethane.

34
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Ethers Ethers were the first anaesthetics. Ethers have the general structure
Williamson ether synthesis, eg R'-O-R'' where R' and R'' are alkyl
Naming and general structure synthesis of 1-ethoxy butane from groups. Ethers are named
Boiling point related to 1-bromo butane and ethanol — can according to IUPAC rules. Due to
bonding. also be done as a kinetic experiment. the lack of hydrogen bonding
Ethoxyethane is not fully miscible in between ether molecules, they
Preparation using haloalkanes water, having the same solubility as have lower boiling points than the
with alkoxides. n-butanol. corresponding isomeric alcohols.
Ethers can be prepared by the
Chemical and physical Methoxymethane and ethoxyethane reaction of haloalkanes with
properties of ethers linked to are more soluble in water than alkoxides. Ethers are commonly
molecular size and uses ethoxyethane, but they are not fully used as solvents since they are
miscible. relatively inert chemically and will
dissolve many organic compounds.
This is due to the formation of
hydrogen bonds between the ether The solubility of ethers in water
molecules and water molecules. decreases as the molecular size
Ethers, of low relative molecular increases.
mass are highly flammable and on
exposure to air may form explosive
peroxides. Ether experiment
can be demonstrated.
Alkenes Preparation of cyclohexene from Preparation of alkenes Education Scotland activity – Preparation of
Preparation: cyclohexanol. Alkenes can be prepared in the benzoic acid by the hydrolysis of ethyl
 dehydration of alcohols laboratory by: benzoate
 base-induced elimination  dehydration of alcohols using
of hydrogen halides from aluminium oxide, concentrated Kirsop Labs animations – Looking for Curly
monohaloalkanes sulfuric acid or orthophosphoric Arrows?
acid
 base-induced elimination of

35
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

hydrogen halides from


monohaloalkanes
 Electrophilic addition Chem. covers a variety of reaction Alkenes can undergo the following Kirsop Labs animations – Looking for Curly
reactions: catalytic addition mechanisms including reactions of electrophilic addition reactions: Arrows?
of hydrogen to form alkanes alkenes such as addition of H-X to  catalytic addition of hydrogen to
 addition of halogens to form an alkene and also Markovnikov’s form alkanes
dihaloalkanes rule (with a different spelling).  addition of halogens to form
 addition of hydrogen halides dihaloalkanes
according to Markovnikov’s  addition of hydrogen halides
rule, to form according to Markovnikov’s rule,
monohaloalkanes to form monohaloalkanes
 acid-catalysed addition of  acid-catalysed addition of water
water according to according to Markovnikov’s rule,
Markovnikov’s rule, to form to form alcohols.
alcohols.
The mechanism for both the
addition of hydrogen halides and
the acid-catalysed addition of water
involves a carbocation intermediate.

The mechanism for addition of a


halogen involves a cyclic ion
intermediate.

Both mechanisms can be written


using curly arrows.
Carboxylic acids Preparation of benzoic acid from Preparation and reactions of Education Scotland activity – Preparation of
Preparation by: ethyl benzoate (previously a PPA). carboxylic acids benzoic acid by the hydrolysis of ethyl
 oxidising primary alcohols benzoate
and aldehydes;

36
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

 hydrolysing nitriles, esters, Carboxylic acids are weak acids, Carboxylic acids can be prepared Learn Chemistry resources – Information
amides. neutralisation with alkalis to form by: on carboxylic acids and carboxylic acid
salts, reaction with Mg — covered in  oxidising primary alcohols and derivatives
Physical Chemistry Unit. aldehydes;
 hydrolysing nitriles, esters, McGraw-Hill Education resources –
Reactions: Carboxylic acids are often ionised in amides. Reaction of carboxylic acids
 formation of salts by drugs and form ionic interactions with
reactions with metals or binding sites. Penicillin contains a Reactions of carboxylic acids Learn Chemistry experiment – Synthesis of
bases carboxylate ion that plays a crucial include: nylon
 condensation reactions with binding role. Consider role of  formation of salts by reactions
alcohols to form esters in the carboxyl functional group in with metals or bases
 presence of an acid catalyst polymerisation the formation of  condensation reactions with
reaction with amino groups polyesters, polyamides and proteins. alcohols to form esters in the
to form amide links  presence of an acid catalyst
 reduction with lithium reaction with amino groups to
aluminium hydride to form form amide links
primary alcohols  reduction with lithium aluminium
hydride to form primary alcohols
Amine classification as Solubility of lower amines in water, Amines are organic derivatives of Learn Chemistry resources – Structure and
primary, secondary or tertiary. test pH of solutions formed. ammonia and can be classified as reactions of amines
Compare pH of ethylamine solution primary, secondary or tertiary.
Physical properties related to with pH of ammonia. Neutralise Primary and secondary amines, but ChemGuide resources – Introducing
structure. solutions of amines with mineral not tertiary amines, associate by amines
acids. chem.purdue.edu provides hydrogen bonding.
Amines as weak bases and some information about amines Purdue University resources – Amines,
their use in salt formation. in drugs. Indiana.edu also provides As a result, primary and secondary Alkaloids, and Amides
information about amines and amines have higher boiling points
their salts in medicines. than isomeric tertiary amines. YouTube video – Amines experiment
Amine molecules can hydrogen
bond with water molecules thus

37
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Elmhurst.edu has some homework explaining the appreciable solubility


ideas on amines but need to be of the shorter chain length amines
selective. in water. The nitrogen atom in
amines has a lone pair of electrons
which can accept a proton from
water, producing hydroxide ions.

Amines are weak bases, which


react with aqueous mineral or
carboxylic acids to form salts.
Aromatic hydrocarbons and Many everyday consumer products Aromatic hydrocarbons and Learn Chemistry resources – Substance:
reactions of benzene have very distinctive smells as a reactions of benzene List of aromatic hydrocarbons
Structure, bonding and result of the presence of key Benzene C6H6 is the simplest
stability of the benzene ring. aromatic compounds. A brief interest member of the class of aromatic YTeach animation – Halogenation of a
Substitution reactions of raising activity can be a display of hydrocarbons. The benzene ring benzene ring
benzene (phenyl); alkylation, household products containing these has a distinctive structural formula.
nitration, sulfonation and products. Examples would include The stability of the benzene ring is Learn Chemistry experiment – Organic
halogenation as examples of well known antiseptics and due to the delocalisation of molecules day
electrophilic substitution in disinfectants containing electrons. A benzene ring in which
benzene and other aromatic tricholorophenol or 4-chloro-3,5- one hydrogen atom has been Shell resource – Benzene-containing
feedstocks product stewardship summary
compounds dimethylphenol, permanent markers substituted by another group is
containing xylene or toluene. An known as the phenyl group. The
internet search using these phenyl group has the formula -
compounds as key words will return C6H5. The benzene ring resists
the names of several well known addition reactions. One or more
products. Benzene and its related hydrogen atoms of a benzene
compounds are important as molecule can be substituted to form
feedstocks in the dyes and pigments a range of consumer products.
industry, the pharmaceuticals Bonding in benzene can be
2
industry and the detergents industry. described in terms of sp

38
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Many drugs contain aromatic rings. hybridisation, sigma and pi bonds


They play a crucial role in binding as and electron delocalisation.
a result of their planar shape and
hydrophobic character Mechanism Consider only alkylation, nitration,
not necessary but should be able to sulfonation and halogenation as
work out the product formed from examples of electrophilic
benzene and the electrophile/ substitution in benzene and other
reaction mixture. aromatic compounds.

Experimental determination SnI4 or CuO empirical formula In organic chemistry, a number of Elemental Microanalysis videos – How to
of structure experiment can be done again here experimental techniques are carried videos
Elemental microanalysis but is probably not necessary. out to verify that the correct
Determination of the masses Opportunity to practise empirical chemical structure has been
of C, H, O, S and N in a formula calculations from results of synthesised.
sample of an organic elemental microanalysis
compound in order to experiments. Elemental microanalysis can be
determine its empirical formula Other elements in organic used to determine the masses of C,
compounds can also be determined H, O, S and N in a sample of an
by elemental microanalysis. organic compound in order to
determine its empirical formula.
Spectroscopy The RSC has produced Learn Chemistry resources – Introduction to
‘Spectroscopy in a suitcase’ which spectroscopy
is an outreach activity giving school
students the chance to learn about Learn Chemistry resources – Spectroscopy
spectroscopy through hands-on in a suitcase

39
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

experience. As well as covering the


principles of spectroscopic RSC resources – SpectraSchool
techniques, the activities use real-life
contexts to demonstrate the
applications of the techniques. This
can be used to teach mass
spectrometry, infra-red spectroscopy
and proton NMR spectroscopy.

The RSC ‘SpectraSchool’ is also


very useful and as well as providing
useful background information, it
also gives learners the opportunity to
print their own spectra for a range of
compounds.
Mass spectrometry In mass spectrometry, the sample is Mass spectrometry can be used to RSC animation –Mass Spectrometry
Interpretation of fragmentation first vaporised and ionised, and determine the accurate molecular
data to gain structural fragmentation occurs when mass and structural features of an ChemGuide resources – Information on the
information excessive energy is used to ionise organic compound. Fragmentation workings of a Mass Spectrometer
the molecules. The ion fragments are takes place producing parent ion
separated according to their mass- and ion fragments. A mass
to-charge ratio using an electric or spectrum is obtained showing a plot
magnetic field. Many types of mass of the relative abundance of the
spectrometer will automatically ions detected against the mass-to-
compare the mass spectrum of the charge ratio. The molecular formula
sample against a large database of can be confirmed from a high
known organic compounds to look accuracy determination of the mass
for an exact match and to allow of the parent ion. The fragmentation
identification. The mass spectrum is pattern can also be interpreted to
like a fingerprint for a particular gain structural information.

40
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

compound.
Infra-red spectroscopy IR is still widely used as it is cheaper Infra-red spectroscopy can be used Learn Chemistry resources – Information
Interpretation of spectral data than NMR and can be used to follow to identify certain functional groups on IR Spectroscopy
to gain structural information reaction progress (i.e. carbonyl in an organic compound.
group present or absent). It also has ChemGuide resources – Information on IR
many specialist applications in Infra-red radiation causes parts of a Spectroscopy
forensics, polymer chemistry and molecule to vibrate. The
quality control. Chemguide.co.uk wavelengths that are absorbed to RSC animation –Infra-Red Spectrometer
provides much background cause the vibrations will depend on
information on infra-red the type of chemical bond and the
spectroscopy. groups or atoms at the ends of
these bonds.

In infra-red spectroscopy, infra-red


radiation is passed through a
sample of the organic compound
and then into a detector which
measures the intensity of the
transmitted radiation at different
wavelengths.

Infra-red absorbances are


measured in wavenumbers, the
reciprocal of wavelength, in units of
-1
cm .

41
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

1
Interpretation of H NMR Hydrogen nuclei behave like tiny Proton nuclear magnetic resonance ChemGuide resources – information on
spectra. magnets and in a strong magnetic spectroscopy (proton NMR) can proton NMR
field some are aligned with the field give information about the different
Understand how a proton (lower energy) whilst the rest are environments of hydrogen atoms in Learn Chemistry resources – Spectra
NMR spectrum is produced aligned against it (higher energy). an organic molecule, and about school
Interpretation of spectral data how many hydrogen atoms there
to gain structural information Absorption of radiation in the radio- are in each of these environments. RSC animation – NMR spectrometer
frequency region of the In the proton NMR spectrum the
Draw and analyse low electromagnetic spectrum will cause peak position (chemical shift) is Learn Chemistry activity – Nuclear
resolution proton NMR spectra the hydrogen nuclei to ‘flip’ from the related to the environment of the H Magnetic Resonance
and to analyse high resolution lower to the higher energy alignment. atom. The area under the peak is
proton NMR spectra. As they fall back from the higher to related to the number of H atoms in
the lower level, the emitted radiation that environment.
is detected. The standard reference
substance used in NMR An interaction with H atoms on a
spectroscopy is tetramethylsilane neighbouring carbon atom can
(TMS) which is assigned a chemical result in the splitting of NMR peaks
shift value equal to zero. into 'multiplets'. The number of H
atoms on the neighbouring carbon
will determine the number of lines
The RSC website provides online within a multiplet.
NMR spectroscopy resources with
video, tutorials and spectra Learners would be expected to be
databases. able to draw and analyse low
resolution proton NMR spectra
There is also a large RSC resource and to analyse high resolution
providing background theory for proton NMR spectra.
NMR and simple correlation
information.

42
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Chemguide.co.uk provides
background information on NMR
spectroscopy as well as information
on interpreting both low resolution
and high resolution NMR spectra.

Application of NMR in medical body


scanners can be discussed here.
UV Spectroscopy When ninhydrin reacts with amino Most organic molecules appear ChemGuide resources – UV-Visible
acids, a highly conjugated product is colourless because the energy absorption spectra
Absorption of visible light by formed which absorbs light in the difference between the highest
organic molecules. visible region. An intense purple occupied molecular orbital (HOMO) Learn Chemistry resources –UV Visible
colour (max 750 nm) is observed. and the lowest unoccupied spectroscopy
An explanation of why organic molecular orbital (LUMO) is
compounds are colourless or This is used in the detection of amino relatively large resulting in the YouTube video – How does a
coloured with reference to acids. absorption of light in the ultraviolet spectrophotometer work?
molecular orbital theory or region of the spectrum.
conjugated systems. Students can prepare a variety of Coloured organic compounds Learn Chemistry activity – The microscale
dyes themselves and examine the contain delocalised electrons within synthesis of azo dyes
structures to locate the molecular orbitals which extend
chromophore. across several atoms. This is
known as a conjugated system. The
Examples would include the more atoms the delocalised
preparation of azo dye from molecular orbital spans, the smaller
aminobenzene (aniline), sodium the energy gap between the
nitrite and 2-naphthol at low delocalised orbital and the next
temperatures. unoccupied orbital and hence the
lower the frequency of light (or
The azo dye can be used to dye a longer the wavelength or lower the
piece of cotton. energy of radiation) absorbed by

43
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

the compound. When the


Synthetic indigo can also be wavelength of the light absorbed is
prepared using a microscale method. in the visible region, the organic
substance will appear coloured.
Molecules in which the structural
formula contains alternate double
bonds will exhibit molecular orbitals
containing delocalised electrons
which will extend the conjugated
section of the molecule.
Chromophores For example, a compound in which The chromophore is the group of ChemGuide resources – UV-Visible
the chromophore absorbs blue light atoms within a molecule, which is Absorption Spectra
Describe a chromophore and will appear yellow. Complementary responsible for the absorption of
explain its role in the colour colours can be demonstrated very light in the visible region of the PhysClips animations – Colouring mixing
exhibited by the compound. effectively using online resources spectrum. Light can be absorbed and colour vision
which will allow colour mixing to be when electrons in a chromophore
demonstrated on a computer screen are promoted from one molecular
or interactive whiteboard. An internet orbital to another.
search using ‘RGB colour mixing’ will
produce suitable animations and If the chromophore absorbs light of
animations. one colour, the compound will
exhibit the complementary colour.
Simple spectroscopes made from
DVDs can be used to view light
transmitted or reflected by coloured
compounds.

44
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Pharmaceutical Chemistry Discuss paracetamol which taken Drugs are substances which alter
according to the correct dosage is the biochemical processes in the RSC resources – Breaking the rules
Effect of drugs on the body beneficial but is very dangerous body. Drugs that have beneficial
when taken in larger quantities and effects are used in medicines. A Learn Chemistry activity – Masterminding
Lipinski rule of five may lead to liver failure and death. medicine usually contains the drug Molecules
plus other ingredients.
Most drugs bind to a protein target
by intermolecular binding forces and Lipinski rule of five (multiples of 5).
do not undergo any reaction. An  Molecular mass less than
induced fit normally leads to the 500 amu.
effects observed.  Not more than 5 hydrogen
bond donors.
‘The Design Studio’ is a useful,  Not more than 10 hydrogen
interactive RSC resource to bond acceptors.
introduce the topic of drugs and  An octanol/water partition
medicines. The resource gives coefficient log P not greater
learners the opportunity to learn than 5.
about the causes and effects of
diseases such as cancer, HIV and
asthma using their knowledge of
chemistry. It then challenges the
learner to design an ‘optimal’ drug to
treat one of the diseases using their
knowledge of organic chemistry.

Another interactive resource from the


RSC is the 'Masterminding
Molecules' package. This resource
combines learning with game-play
and involves cracking a code to

45
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

reveal hidden chemical concepts


involved in design of drugs and
medicines. Clinical trials allow safety
and efficacy data to be collected for
new drugs or devices.

Depending on the nature of the


study, healthy volunteers or patients
may be used in a small pilot study. If
the safety and efficacy data is
satisfactory, the scale of the study
will be increased. In randomised
drug trials a group of patients are
divided with some being given the
drug.

RSC learn chemistry has a bank of


resources in challenging medicine.

Not all will be suitable for the AH


course.
Classification of drugs Andanamide (also known as the bliss Many drugs can be classified as The Merck Manual resources – Drug–
molecule) is a recently discovered agonists or as antagonists at receptor interactions
Classification of drugs as messenger molecule that plays a receptors, according to whether
agonists or as antagonists role in pain, depression, appetite, they enhance or block the body’s
memory, and fertility. natural responses. An agonist will Frostburg State University learner resource
produce a response similar to the – Andanamide
Frostburg.edu provides more body’s natural active compound. An
information about Andanamide. The antagonist produces no response University of Bristol resources –
resource also describes the way in but prevents the action of the Andanamide

46
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

which nerve cells communicate, body’s natural active compound.


through molecular keys and
receptors.

There are other drug targets apart


from receptors and enzymes, such
as DNA and RNA.
How drugs work Emphasise importance of shape. Most drugs work by binding to Learn Chemistry resource – Molecules
receptors. Receptors are usually against malaria Design of a structure
Identify the types of interaction Binding of the active molecule to the protein molecules on the surface of activity Relationship study of antimalarial
4-aminoquinolines
between drug functional binding site initiates a series of cells where they interact with small
groups and receptor sites. chemical events which results in a biologically active molecules, or are
change in the cell chemistry. This enzymes that catalyse chemical
RSC quiz – ‘Masterminding molecules’
Recognise the can lead to an observable effect reactions (catalytic receptors).
pharmacophore in drug such as a muscle cell contracting. The structural fragment of a drug
molecules. molecule that confers
YouTube video – Computer Aided Drug
Protein databanks offer a huge pharmacological activity upon it, Discovery Pipeline
number of PDB files containing normally consists of different
examples of proteins with various functional groups correctly
drug molecules bound to a receptor orientated with respect to each
site. Learners can use CHIME, other. The overall shape and size of
PYMOL or Chem3D to explore the the drug has to be such that it fits a
interactions between the functional binding site. The functional groups
group and the receptor site. Some on both the drugs and the receptor
computer packages allow H-bonding are positioned such that the drugs
interactions to be displayed or can interact with and bind to the
electrostatic potential surfaces to be receptor.
examined.
Learners should be able to identify
Design Studio and Masterminding the types of interaction between

47
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Molecules (RSC) can be used to drugs and binding sites.


illustrate these concepts. Excellent
opportunity to investigate structural By comparing the structures of
fragments common to different drugs that have similar effects on
medicines using websites given the body, the structural fragment
above. that is involved in the drug action
can be identified.

Many drugs act as enzyme


inhibitors by binding to the
enzyme’s active site and blocking
the reaction normally catalysed
there.

48
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Researching Chemistry Unit specification: http://bit.ly/1AbDN4p

Mandatory course key areas Suggested learning activities Exemplification of key areas Useful resources
Gravimetric analysis In gravimetric analysis, the mass of
Analytical determination of an element or compound present in
composition of a substance’s a substance is determined by
mass by chemically changing chemically changing that substance
the substance into some other substance of
known chemical composition, which
Understanding of key can be readily isolated, purified and
techniques including ‘weighing weighed to constant mass.
by difference’ and ‘heating to
constant mass’ Learners should be aware of the
techniques of weighing by
difference and heating to constant
mass. Possible experiments
include:
 gravimetric determination of
water in hydrated barium chloride Education Scotland activity – Gravimetric
 gravimetric determination of analysis
water in hydrated magnesium
sulfate
 determination of Ni using
butanedioxime
(dimethylglyoxime)
Volumetric analysis Preparation of a standard solution / Learn Chemistry resources – volumetric
Appreciation of the primary standard / standardising analysis background information and
characteristics of substances solutions experiments
that can be used as a primary
standard

49
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

A solution of accurately known


Good practice in preparation of concentration is known as a
a standard solution and their standard solution. A standard
use in determination of a solution can be prepared directly
unknown solution’s from a primary standard. A primary
concentration standard must have, at least, the
following characteristics:
 high state of purity
 stability in air and in solution
 solubility
 reasonably high formula mass

Examples of primary standards


include:
 sodium carbonate, Na2CO3
 oxalic acid, H2C2O4.2H2O
 potassium hydrogen phthalate,
KH(C8H4O4)
 silver nitrate, AgNO3
 potassium iodate, KIO3
 potassium dichromate, K2Cr2O7

Learners should appreciate why


certain compounds such as sodium
hydroxide are not acceptable as
primary standards. Learners should
also be aware that, where
practicable, titrations should be
repeated until concordant results
are obtained.

50
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Possible experiments include: Learn Chemistry animations – acid/base


 Prepare a standard solution of titration
-1
0·1 mol l
 oxalic acid Education Scotland activity – the purity of
 Standardisation of approx 0·1 mol marble via a back titration
-1
l NaOH(aq)
 Determination of the ethanoic Labskills animation – Titration set up
acid content of vinegar
 Preparation of a standard solution Labskills animation –Titration end points
-1
of 0·1 mol l sodium carbonate
solution
 Standardisation of approximately
-1
0·1 mol l HCl(aq)
 Determination of the purity of
marble by back titration

Animation of titration and titrations


with corresponding calculations can
be found on the internet.
Understanding the role of a Use of a control Learn Chemistry experiment – Aspirin
control in experiments to A control validates a technique and
validate techniques may consist of carrying out a Nuffield Foundation experiment –
determination on a solution of Measuring the vitamin C content of fruit and
known concentration. juices
Possible experiments include:
 Determination of the
percentage acetylsalicylic
acid in a commercial tablet,
using ‘pure’ aspirin as a
control

51
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

 Determination of Vitamin C
in a fruit juice using pure
ascorbic acid as a control
Understanding the use of Complexometric titrations are Education Scotland activity – Gravimetric
complexometric titration in based on reactions in which analysis
quantitative analysis of solutions complexes are formed. EDTA is an
containing a metal ion important complexometric reagent
and can be used to determine the
concentration of metal ions in
solution.

A possible experiment could be the


determination of the percentage of
Ni in a nickel salt using EDTA.
Understanding of back titrations Back titration is used to find the ChemGuide resources – Finding orders of
and associated calculations number of moles of a substance by reaction experimentally
reacting it with an excess volume of
reactant of known concentration. Education Scotland experiment – The purity
of marble via a back titration
The resulting mixture is then titrated
to work out the number of moles of
the reactant in excess. From the
initial number of moles of that
reactant the number of moles used
in the reaction can be determined,
making it possible to work back to
calculate the initial number of moles
of the substance under test. A back
titration is useful when trying to
work out the quantity of substance

52
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

in an insoluble solid.

Possible experiments include:


 Determination of aspirin
 Determination of purity of
marble by back titration
Practical Skills and Colorimetry/accurate dilution Vernier experiment – The synthesis and
Techniques Colorimetry uses the relationship analysis of Aspirin
Preparation of standard between colour intensity of a
solutions using accurate dilution solution and the concentration of Education Scotland activity – determination
technique the coloured species present. A of Mn in steel
Formation and use of calibration calibration curve must be prepared
curves to determine an using solutions of known Education Scotland activity – determination
unknown using solutions of concentrations (standard solutions). of nickel using EDTA
appropriate concentration
The concentration of the ‘unknown’
solution is determined from its
absorbance and by referring to the
calibration curve. The straight line
section of the calibration graph
should cover the dilution range
likely to be used in the
determination.

Possible experiments include:


 Colorimetric determination of
manganese in steel
 Determination of nickel using
colorimetric analysis

53
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Knowledge of the appropriate A video showing simple, fractional In the modern organic chemistry ChemGuide resources – Fractional
use of distillation, reflux, and steam distillation is available laboratory, distillation is a powerful distillation of ideal mixtures and liquids
vacuum filtration, on the internet tool, both for the identification and
recrystallisation and use of a the purification of organic Learn Chemistry experiment – Extracting
separating funnel in the compounds. The boiling point of a limonene form oranges by steam distillation
preparation and purification of compound — determined by
an experimental product distillation — is well-defined and Youtube video – How steam distillation
thus is one of the physical works
properties of a compound by which
it is identified. Education Scotland activity – Preparation of
benzoic acid by hydrolysis of ethyl
Distillation is used to purify a benzoate
compound by separating it from a
non-volatile or less volatile material. OCR A Level Chemistry experiment – The
preparation of ethyl ethanoate
This technique provides
opportunities for learners to Education Scotland activity – preparation of
become familiar with glassware cyclohexene from cyclohexanol (Unit 3 PPA
containing ground glass joints. 1)
Possible experiments include:
 Preparation of benzoic acid
by hydrolysis of ethyl
benzoate
 Preparation of ethyl
ethanoate
 Preparation of cyclohexene
from cyclohexanol

54
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Different videos showing heating Refluxing is a technique used to Learn Chemistry resources – heating under
under reflux are available on the apply heat energy to a chemical reflux
internet. reaction mixture over an extended
period of time. The liquid reaction
mixture is placed in a round-
bottomed flask along with anti-
bumping granules with a condenser
connected at the top. The flask is
heated vigorously over the course
of the chemical reaction; any
vapours given off are immediately
returned to the reaction vessel as
liquids when they reach the
condenser.

This technique provides


opportunities for learners to
become familiar with glassware
containing ground glass joints.
Possible experiments include:
 Preparation of benzoic acid by
hydrolysis of ethyl benzoate
 Preparation of ethyl ethanoate

A video on vacuum filtration Using a Buchner, Hirsch or sintered Learn Chemistry resources – vacuum
showing use of a Buchner funnel glass funnel. These methods are filtration
and a Hirsch funnel is available on carried out under reduced pressure
the internet. and provide a faster means of
separating the precipitate from the
filtrate. The choice of filtering

55
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

medium depends on the quantity


and nature of the precipitate. Education Scotland activity – Preparation of
potassium trioxolatoferrate(III)
Possible experiments include:
 Preparation of potassium Education Scotland activity – Preparation of
trioxolatoferrate(III) aspirin
 Preparation of aspirin
 Preparation of benzoic acid by Education Scotland activity – Preparation of
hydrolysis of ethyl benzoate benzoic acid by hydrolysis of ethyl
 Identification by derivative benzoate
formation
Chemistry teaching resources activity –
Identification by derivative formation (Unit 3
PPA 2)

Videos on recrystallisation are Recrystallisation is a laboratory Learn Chemistry video – Recrystallisation


available on the internet. technique used to purify solids,
based upon solubility.

The solvent for recrystallisation


must be carefully selected such that
the impure compound is insoluble
at lower temperatures, yet
completely soluble at higher
temperatures. The impure
compound is dissolved gently in the
minimum volume of hot solvent
then filtered to remove insoluble
impurities. The filtrate is allowed to
cool slowly to force crystallisation.

56
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

The more soluble impurities are left


behind in the solvent.
Possible experiments include:
 Preparation of benzoic acid by Education Scotland activity – Preparation of
hydrolysis of ethyl benzoate benzoic acid by hydrolysis of ethyl
 Preparation of potassium benzoate
trioxalatoferrate(III)
 Preparation of acetylsalicylic acid Education Scotland activity – Preparation of
potassium trioxolatoferrate(III)

Education Scotland activity – Preparation of


Aspirin
Solvent Extraction For example, supercritical CO2 is Use of a separating funnel ChemGuide learner resources – Partition
used in the preparation of Solvent extraction can be an
decaffeinated coffee. application of the partition of a
solute between two liquids. It is
Videos on solvent extraction are based on the relative solubility of a
available on the internet. compound in two different
immiscible liquids, usually water
and an organic solvent.

The partition coefficient is


expressed as the concentration of a
solute in the organic layer over that
in the aqueous layer.

The two solvents form two separate


layers in the separating funnel and
the lower layer is run off into one
container and the upper layer is

57
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

poured out into another container.


The quantity of solute extracted
depends on the partition coefficient
and on the number of times that the
process is repeated.

Selection of suitable solvents can


be discussed.

Possible experiments include: OCR A Level Chemistry experiment – The


 Preparation of ethyl ethanoate preparation of ethyl ethanoate
 Extraction of caffeine from tea
Nuffield Foundation experiment – extraction
of caffeine
Knowledge of the appropriate Videos of thin-layer Use of thin-layer chromatography to Learn Chemistry video – Thin Layer
uses of thin layer chromatography are available on assess product purity Chromatography (TLC)
chromatograph, melting point the internet.
and mixed melting point Instead of chromatography paper,
determination in evaluating the thin-layer chromatography (TLC)
purity of an experimental uses a fine film of silica or
products aluminium oxide spread over glass
or plastic.

Rf values can be calculated and


under similar conditions a
compound will always have the
same Rf value within experimental
error.

Since a pure substance will show

58
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

up as only one spot on the


developed chromatogram, TLC can
be used to assess the purity of a
product prepared in the lab.
Calculation of Rf values from Possible experiments include: Education Scotland activity – Preparation of
relevant data and its use in  Preparation of aspirin benzoic acid by hydrolysis of ethyl
following the course of a  Hydrolysis of ethyl benzoate benzoate (Unit 3 PPA 3)
reaction.
Education Scotland activity – Preparation of
Aspirin

NCSEC experiment –Plant pigments


activity
Videos on melting point Determination of melting point and Learn Chemistry resources – Melting point
determination are available on the mixed melting point determination
internet.
The melting point of an organic
compound is one of several
physical properties by which it can
be identified. A crystalline
substance has a sharp melting
point falling within a very small
temperature range. Determination
of the melting point can also give
an indication of the purity of an
organic compound, as the presence
of impurities lowers the melting
point and extends its melting
temperature range.

59
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

Since impurities lower the melting


point, the technique of mixed
melting point determination can be
used as a means of identifying the
product of a reaction
Possible experiments include:
 Preparation of benzoic acid by Education Scotland activity – Preparation of
hydrolysis of ethyl benzoate benzoic acid by hydrolysis of ethyl
 Identification by derivative benzoate
formation
 Preparation of aspirin Education Scotland activity – Identification
by derivative formation

Education Scotland activity – Preparation of


aspirin

Stoichiometric Calculations Stoichiometry is the study of ChemGuide resources – What does


Calculations from balanced quantitative relationships involved "stoichiometry" mean?
equations, including multistep in chemical reactions. The ability to
reactions, reactant excess, and balance and interpret equations
empirical formulae from given enabling calculations to be carried
data. out involving any of the above
skills/techniques is an important
Calculations and explanations part of chemistry at this level and is

60
ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

comparing theoretical and examinable in the course


actual yield assessment.

Experimental determination of
percentage yield and atom
economy.

Theoretical percentage yields can


be calculated and compared with
actual yield. Mass transfer or
mechanical losses, purification of
product, side reactions, equilibrium
position and purity of reactants,
inevitably lowers the percentage
yield.
Education Scotland activity – Preparation of
Possible experiments include: aspirin
 Preparation of aspirin
 Preparation of potassium Education Scotland activity – Preparation of
trioxolatoferrate(III) potassium trioxolatoferrate(III)

Education Scotland activity – Preparation of


 Preparation of benzoic acid by benzoic acid by hydrolysis of ethyl
hydrolysis of ethyl benzoate benzoate
 Preparation of ethyl ethanoate
OCR A Level Chemistry experiment –
Preparation of ethyl ethanoate

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ADVANCED HIGHER CHEMISTRY RESOURCES GUIDE

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