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Topic 1. Atoms, Molecules and Stoichiometry Content Relative masses of atoms and molecules The The mole, calculation the of and Avogadro constant empirical
Learning Outcomes:
(a) define atomic,
12
Remarks
the
terms
relative molecular
isotopic,
molecular formulae Reacting masses and volumes (of solutions and gases)
(b) define the term mole in terms of the Avogadro constant (c) calculate the relative atomic mass of an element given the relative abundances of its isotopes (d) define the terms empirical and molecular formula (e) calculate molecular Educational Technology Division Ministry of Education, Singapore July 2006 empirical formulae and using 1
http://www.wwnorton.com/chemistry/overview/ ch4.htm
combustion
data
or
composition by mass (f) write and/or construct http://www.wwnorton.com/chemistry/overview/ ch4.htm Animated tutorial.
including use of the mole concept, involving: (i) reacting masses (from formulae and equations) (ii) volumes of gases (e.g. in the (iii) volumes concentrations solutions (h) deduce relationships (g) 2. Atomic Structure The nucleus of the atom: neutrons and protons, isotopes, proton and nucleon Educational Technology Division Ministry of Education, Singapore July 2006 (a) identify and describe protons, neutrons and electrons in terms of their relative charges and relative masses 2 http://www.chemguide.co.uk/atoms/properties /gcse.html#top Notes. stoichiometric from burning of and of hydrocarbons)
extranuclear structure
(b) deduce
the
behaviour
of
http://lectureonline.cl.msu.edu/%7Emmp/kap2 1/cd533capp.htm
beams of protons, neutrons and electrons in both electric and magnetic fields (c) describe the distribution of mass and charges within an atom (d) deduce protons, electrons the numbers in of and both
neutrons present
atoms and ions given proton and nucleon numbers (and charge) (e) (i) describe the contribution of protons and neutrons to atomic nuclei in terms Educational Technology Division Ministry of Education, Singapore July 2006 3
of proton number and nucleon number (ii) distinguish different between numbers of isotopes on the basis of neutrons present (f) describe the number and http://www.colby.edu/chemistry/OChem/DEM OS/Orbitals.html http://chemmovies.unl.edu/ChemAnime/ECO NFIG/ECONFIG.html Energy simulation. level Animated slide show
relative energies of the s, p and d orbitals for the principal quantum numbers 1, 2 and 3 and also the 4s and 4p orbitals (g) describe the shapes of s and p orbitals (h) state the electronic
http://winter.group.shef.ac.uk/orbitron/
3D visualisations.
http://lectureonline.cl.msu.edu/~mmp/period/e lectron.htm
configuration of atoms and ions given the proton number (and charge) (i) (i) explain energies (ii) explain Educational Technology Division Ministry of Education, Singapore July 2006 the of the factors elements trends in 4
ionisation across a
down a Group of the Periodic Table (see also Section 9) (j) deduce from the of electronic elements ionisation
successive
ionisation energy data of an position of that element within the Periodic Table 3. Chemical Bonding Ionic bonding Covalent bonding and co-ordinate (i) The (ii) Bond bond (dative of covalent) bonding shapes simple molecules energies, and lengths (electrovalent) (a) describe ionic (electrovalent) bonding, chloride as and in sodium magnesium http://www.chemguide.co.uk/atoms/bonding/io nic.html Notes.
bond polarities Educational Technology Division Ministry of Education, Singapore July 2006 5
Intermolecular forces, including bonding Metallic bonding Bonding and physical properties The solid state hydrogen
(b) describe, including the use of dot-and-cross diagrams, (i) covalent bonding, as in hydrogen; nitrogen; hydrogen ethene (ii) co-ordinate formation of (dative the covalent) bonding, as in ammonium ion and in the Al2Cl6 molecule. (c) explain the shapes of, and bond angles in, molecules such as BF3 (trigonal planar); CO2 Educational Technology Division Ministry of Education, Singapore July 2006 (linear); CH4 6 oxygen; chlorine; chloride;
Notes.
Notes.
Notes.
3D models
(tetrahedral);
the
Chime
pyramidal); H2O (non-linear); SF6 (octahedral) by using the Valence Shell Electron Pair Repulsion theory (d) describe covalent bonding in terms of orbital overlap, giving and bonds (see also Section 10.1) (e) predict the shapes of, and bond angles in, molecules analogous to those specified in (c) (f) describe hydrogen bonding, using ammonia and water as examples containing groups (g) explain energy, the bond terms length bond and of -NH molecules and -OH
exercise
on
molecular shapes.
Tutorial models.
with
3D
bond polarity and use them to compare the reactivities of covalent bonds Educational Technology Division Ministry of Education, Singapore July 2006 7
(i) describe metallic bonding in terms of a lattice of positive ions surrounded by mobile electrons (j) describe, types of interpret bonding bonding; bonding) on and/or (ionic other the of
predict the effect of different bonding; covalent bonding; hydrogen metallic physical substances (k) deduce the type of bonding present information (l) show understanding of from given intermolecular interactions;
properties
chemical reactions in terms of energy transfers associated with the breaking and making of chemical bonds (m) describe, in simple terms, the Educational Technology Division Ministry of Education, Singapore July 2006 8
structure as in
of
(ii) simple molecular, as in iodine (iii) giant molecular, as in graphite; diamond (iv) hydrogen-bonded, as in ice (v) metallic, as in copper [the concept of the unit cell is not required] (n) outline physical water (o) suggest from quoted physical data the type of structure and bonding substance (p) recognise that materials are a Educational Technology Division Ministry of Education, Singapore July 2006 9 present in a the importance to properties of the of
hydrogen
bonding
finite
resource of
and
the
importance processes 4. The State gaseous Ideal gas behaviour and deviations from it pV = nRT and its use in determining a value for Mr
recycling
(a) state the basic assumptions of the kinetic theory as applied to an ideal gas
http://www.chm.davidson.edu/ChemistryApple ts/KineticMolecularTheory/BasicConcepts.htm l
Notes
with
Java
simulation.
(b) explain qualitatively in terms of intermolecular forces and molecular size: (i) the conditions necessary for a gas to approach ideal behaviour (ii) the limitations of ideality at very high pressures and very low temperatures (c) state and use the general gas equation pV = nRT in the calculations, including
Notes.
Notes.
Animated tutorial.
http://jersey.uoregon.edu/Piston/index.html
Simulated experiment.
5. Chemical Energetics
(a) explain that some chemical reactions are accompanied by energy changes, principally in the form of heat energy; the energy changes can be exothermic or (H, negative) endothermic
neutralisation; atomisation; electron affinity Hess Law, including Born-Haber cycles Entropy Energy and Free energy; lattice energy;
(H, positive)
(b) explain and use the terms: (i) enthalpy reaction change and of standard
http://chemmovies.unl.edu/ChemAnime/LATH 20ED/LATH20ED.html
Animated tutorial.
conditions, with particular reference to: formation; combustion; solution; atomisation (ii) bond positive, breaking) (iii) lattice Educational Technology Division Ministry of Education, Singapore July 2006 energy (H 11 energy i.e. (H bond hydration; neutralisation;
negative,
i.e.
gaseous
ions to solid lattice) (c) calculate enthalpy changes from experimental including the use relationship enthalpy change = mcT (d) explain, in qualitative terms, the effect of ionic charge and of ionic radius on the numerical magnitude of a lattice energy (e) apply Hess Law to construct simple energy cycles, e.g. Born-Haber cycle, and carry out such energy ionisation electron calculations cycles and energy affinity), terms involving relevant (including and with enthalpy http://www.wwnorton.com/chemistry/overview/ ch11.htm Animated tutorial. http://www.dartmouth.edu/%7echemlab/info/r esources/deltah/deltah.html Energy level diagram Java simulation. appropriate results, of the http://www.chm.davidson.edu/ChemistryApple ts/calorimetry/HeatOFCombustionOfMethane. html http://chemmovies.unl.edu/ChemAnime/IONSI ZED/IONSIZED.html Animation. http://www.chm.davidson.edu/ChemistryApple ts/calorimetry/HeatOFNeutralization.html Java simulations.
particular reference to: (i) determining changes that cannot be Educational Technology Division Ministry of Education, Singapore July 2006 12
by e.g. change
direct an of
formation from enthalpy changes of combustion (ii) the formation of a simple ionic solid and of its aqueous solution (iii) average bond energies (f) construct and interpret a http://bcs.whfreeman.com/chemicalprinciples3 e/content/simulations/gc14ax02.htm On-line reaction diagram. Animation narration. (g) explain and use the term entropy (h) discuss the effects on the entropy of a chemical system by the following: (i) change in temperature (ii) change in phase (iii) change in the number of particles (especially for Educational Technology Division Ministry of Education, Singapore July 2006 13 http://www.wwnorton.com/chemistry/overview/ ch13.htm Animated tutorial. with exercise on
reaction pathway diagram, in terms of the enthalpy change of the reaction and of the activation energy
pathway
gaseous systems) (iv) mixing of particles [quantitative treatment is not required] (i) predict whether the entropy change for a given process or reaction negative (j) define standard Gibbs free energy change of reaction by means of the equation G = H TS (k) calculate G for a reaction using the equation G = H TS http://mc2.cchem.berkeley.edu/Java/Gibbs/Gi bbs.html Java applet showing relationship between G, H, S and T. [the calculation of standard entropy change, S, for a reaction using standard entropies, S, is not required] (l) state whether a reaction or process will be spontaneous by using the sign of G http://www.wwnorton.com/chemistry/overview/ ch13.htm Animated tutorial. is positive or
14
(m) predict
the
effect
of
temperature change on the spontaneity of a reaction, given standard enthalpy and entropy changes 6. Electrochemistry Redox processes: (a) describe and explain redox processes in terms of electron transfer and/or of changes in oxidation number (oxidation state) Animation of an electrochemical cell. http://www.chemguide.co.uk/inorganic/redoxm enu.html#top%20 Notes.
electron transfer and changes in oxidation number state) Electrode potentials (i) Standard electrode (redox) potentials, E; the redox series (ii) Standard potentials, and their uses (iii) Batteries and fuel cells Electrolysis (i) Factors the substance liberated electrolysis (ii) The Educational Technology Division Ministry of Education, Singapore July 2006 Faraday during affecting of amount cell Ecell, (oxidation
15
the their
(iii) Industrial uses of electrolysis (b) define the terms: (i) standard (redox) potential (ii) standard cell potential (c) describe the standard electrode
hydrogen electrode (d) describe methods used to measure the standard electrode potentials of: (i) metals or non-metals in contact with their ions in aqueous solution (ii) ions of the same element in different oxidation http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/animations/SHECu.ht ml Simulation. states http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/animations/SHEZnV7. html Simulation. http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/flashfiles/electroChem /voltaicCell20.html Simulation.
16
(e) calculate
standard
cell
http://www.wwnorton.com/chemistry/tutorials/ ch17.htm
Animated tutorial.
potential by combining two standard electrode potentials (f) use standard cell potentials to: (i) explain/deduce from a simple cell (ii) predict the feasibility of a reaction (g) understand the limitations in the use of standard cell to predict the potentials the direction of electron flow
feasibility of a reaction (h) construct using 9.4) (i) predict qualitatively how the value potential ion Educational Technology Division Ministry of Education, Singapore July 2006 17 of an varies electrode with the http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/flashfiles/electroChem /voltaicCellEMF.html Simulation. the redox equations half-
relevant
(j) state the possible advantages of developing other types of cell, e.g. the H2/O2 fuel cell and improved batteries (as in electric vehicles) in terms of smaller size, lower mass and higher voltage (k) state the relationship, F = Le, between constant, the electron (l) predict the identity of the substance electrolyte aqueous), redox liberated (molten position in during or the electrolysis from the state of the the Faraday Avogadro
http://www.wwnorton.com/chemistry/tutorials/ ch17.htm
Animated tutorial.
series
(electrode
potential) and concentration (m) calculate: (i) the quantity of charge passed electrolysis Educational Technology Division Ministry of Education, Singapore July 2006 18 during http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/flashfiles/electroChem /electrolysis10.html Simulation.
including those in the electrolysis of H2SO4(aq); Na2SO4 (aq) (n) explain, electrode (i) the (ii) the in terms of the the of
reactions, anodising
industrial processes of: aluminium electrolytic purification of copper [technical details are not required] 7. Equilibria Chemical reversible (i) Factors equilibria: reactions; affecting (a) explain, in terms of rates of the forward and reaction reverse and reactions, what is meant by a reversible dynamic equilibrium http://www.chemguide.co.uk/physical/equilibri a/introduction.html#top Notes.
dynamic equilibrium chemical equilibria (ii) Equilibrium constants (iii) The Haber process Ionic equilibria (i) Bronsted-Lowry Educational Technology Division Ministry of Education, Singapore July 2006
19
theory of acids and bases (ii) Acid dissociation constants, Ka and the use of pKa (iii) Base dissociation constants, Kb and the use of pKb (iv) The ionic product of water, Kw (v) pH: choice of pH indicators (vi) Buffer solutions (vii) Solubility product; the common ion effect (b) state Le Chateliers Principle and apply it to deduce qualitatively (from appropriate information) the effects of changes in concentration, pressure or temperature, on a system at equilibrium http://www.chm.davidson.edu/ChemistryApple ts/equilibria/Temperature.html http://www.chm.davidson.edu/ChemistryApple Educational Technology Division Ministry of Education, Singapore July 2006 20 Simulation. Simulation. http://www.chm.davidson.edu/ChemistryApple ts/equilibria/LeChatelier.html Notes. http://www.chemguide.co.uk/physical/equilibri a/lechatelier.html#top Notes.
ts/equilibria/Volume.html
(c) deduce whether changes in concentration, pressure or temperature or the presence of a catalyst affect the value of the equilibrium constant for a reaction (d) deduce expressions for
http://www.chemguide.co.uk/physical/equilibri a/change.html#top
Notes.
Notes.
equilibrium constants in terms of concentrations, Kc, and partial pressures, Kp [treatment of the relationship between Kp and Kc is not required]
Notes.
Simulation.
Animated tutorial.
(e) calculate
the
values
of
equilibrium constants in terms of concentrations or partial pressures from appropriate Educational Technology Division Ministry of Education, Singapore July 2006 21
data (f) calculate appropriate the solving the data of quantities (such quadratic http://www.wwnorton.com/chemistry/overview/ ch14.htm Animated tutorial.
present at equilibrium, given calculations will not require equations) (g) describe and explain the
http://www.chemguide.co.uk/physical/equilibri a/haber.html#top
Notes.
conditions used in the Haber process, as an example of the importance of of an understanding industry (h) show understanding of, and apply the Bronsted-Lowry the concept acids of and theory of acids and bases, including conjugate chemical
Notes.
Animation.
http://www.chemguide.co.uk/physical/acidbas eeqia/theories.html#top
Notes.
behaviour
between strong and weak Educational Technology Division Ministry of Education, Singapore July 2006 22
http://www.chemguide.co.uk/physical/acidbas eeqia/bases.html#top
Notes.
(j) explain the terms pH; Ka; pKa; Kb; pKb; Kw and apply them in calculations, including the relationship Kw = KaKb
+
http://www.chemguide.co.uk/physical/acidbas eeqia/kw.html#top
Notes.
(k) calculate [H (aq)] and pH values for strong acids, weak monobasic acids, strong (monoprotic) bases, and
pH meter simulation.
weak monoacidic bases (l) explain the choice of suitable indicators data (m) describe the changes in pH during acid-base titrations and explain these changes in terms of the strengths of the acids and bases http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/flashfiles/stoichiometr y/a_b_phtitr.html Educational Technology Division Ministry of Education, Singapore July 2006 23 Titration simulation. http://www.chemguide.co.uk/physical/acidbas eeqia/phcurves.html#top Notes. for acid-base titrations, given appropriate http://www.chemguide.co.uk/physical/acidbas eeqia/indicators.html#top Notes.
Titration simulation.
simulation
how
buffer
Notes.
solutions control pH (ii) describe and explain their uses, including the role of H2CO3/HCO3
-
Animated tutorial.
in
controlling pH in blood
(o) calculate the pH of buffer solutions, given appropriate data (p) show understanding of, and apply, the concept of solubility product, Ksp (q) calculate Ksp from
Buffer simulation.
solution
concentrations and vice versa (r) show understanding of the Educational Technology Division Ministry of Education, Singapore July 2006 24
common ion effect 8. Reaction Kinetics Simple reaction; constants Concept of activation energy Effect concentration, temperature, rate Homogeneous heterogeneous catalysis Enzymes biological catalysts as and and catalysts on reaction of rate rate (a) explain and use the terms: rate of reaction; rate equation; order of reaction; rate constant; half-life of a reaction; step; catalysis rate-determining activation energy; http://www.chm.davidson.edu/ChemistryApple ts/kinetics/ReactionRates.html Simulation.
equations; orders of
(b) construct
m n
and
use
rate
Simulation.
cases of single-step reactions and of multi-step processes with a rate-determining step, for which m and n are 0, 1 or Educational Technology Division Ministry of Education, Singapore July 2006
Simulation.
Simulation.
ts/kinetics/MethodOfInitialRates.html http://www.wwnorton.com/chemistry/overview/ ch14.htm http://www.chem.iastate.edu/group/Greenbow e/sections/projectfolder/flashfiles/kinetics2/kin etics.html Simulation rate method. on initial Animated tutorial.
rates method (ii) justifying, for zero- and first-order reactions, the order of reaction from concentration-time graphs (iii) verifying that a suggested reaction consistent mechanism with is the
observed kinetics (iv) predicting the order that would result from a given reaction mechanism (v) calculating an initial rate using concentration data [integrated forms of rate equations required] (c) (i) show understanding that the half-life of a first-order reaction is independent of concentration (ii) use the half-life of a first Educational Technology Division Ministry of Education, Singapore July 2006 26 are not
using the initial rates method (e) devise experimental studying reaction, information (f) explain qualitatively, in terms of collisions, the effect of concentration changes on the rate of a reaction (g) show Boltzmann understanding, distribution, of http://www.chemguide.co.uk/physical/basicrat es/introduction.html#top Notes. the a rate suitable technique of from for a
given
including reference to the what is meant by the term activation energy (h) explain qualitatively, in terms both of the the Boltzmann effect of distribution and of collision frequency, temperature change on a rate Educational Technology Division Ministry of Education, Singapore July 2006
http://www.chm.davidson.edu/ChemistryApple ts/KineticMolecularTheory/Maxwell.html
of speed
http://www.scrolla.hw.ac.uk/talks/shock03/che 27
Simulation.
constant (and, hence, on the rate) of a reaction (i) (i) explain that, in the
mweb/sqa-ucles/exploratory/generic1.html
http://www.wwnorton.com/chemistry/overview/ ch14.htm
Animated tutorial.
presence of a catalyst, a reaction has a different mechanism, i.e. one of lower activation energy, giving constant (ii) interpret this catalytic effect on a rate constant in terms of the Boltzmann distribution (j) outline the different modes of action of homogeneous and heterogeneous including: (i) the Haber process (ii) the catalytic removal of oxides of nitrogen in the exhaust gases from car engines (see also Section 10.2) (iii) the catalytic role oxides of of atmospheric Educational Technology Division Ministry of Education, Singapore July 2006 catalysis, a larger rate
28
nitrogen in the oxidation of atmospheric sulphur dioxide (iv) catalytic role of Fe the /S2O8 reaction (k) describe biological enzymes catalysts as which
23+
in
may have specific activity (l) explain between an reaction systems 9 Inorganic Chemistry http://pearl1.lanl.gov/periodic/ http://www.chemicool.com/ http://chemlab.pc.maricopa.edu/periodic/perio dic.html http://pearl1.lanl.gov/periodic/ On-line periodic tables. the relationship substrate enzyme-catalysed in biochemical http://www.bbc.co.uk/education/asguru/biolog y/02biologicalmolecules/01proteins/11enzyme s/03enzymes_b/index.shtml Animated tutorial.
29
http://www.chemicalelements.com/ 9.1 The Tavle: Chemical Periodicity Periodic Periodicity of physical properties elements: across Period argon) of: (i) atomic radius and ionic radius (ii) melting point (iii) electrical conductivity (iv) ionisation energy Periodicity chemical third Period (i) Reaction elements oxygen chlorine (ii) Variation oxidation of the in number oxides of the with and of properties of the variation the (sodium third to (a) describe qualitatively (and http://www.chem.uoa.gr/Applets/AppletPerTa ble/Appl_PerTable2.html Periodic table with
indicate the periodicity in) the variations in atomic radius, ionic radius, melting point and electrical conductivity of the elements Booklet) (see the Data
correlation plots.
(sodium to sulphur Educational Technology Division Ministry of Education, Singapore July 2006 30
only) and of the chlorides (sodium to only) (iii) Reactions of these oxides chlorides water (iv) Acid/base behaviour of these oxides and the corresponding hydroxides (b) explain qualitatively the http://www.chemguide.co.uk/atoms/properties /atradius.html Notes. and with phosphorus
variation in atomic radius and ionic radius (c) interpret the variation in
melting point and in electrical conductivity in terms of the presence metallic elements (d) explain the variation in first Educational Technology Division Ministry of Education, Singapore July 2006 http://www.chemguide.co.uk/atoms/properties /ies.html 31 Notes. of bonding simple in the molecular, giant molecular or
ionisation energy (e) describe the reactions, if any, of the elements with oxygen (to give Na2O; MgO; Al2O3; P4O10; SO2; SO3), and chlorine (to give NaCl; MgCl2; AlCl3; SiCl4; PCl5) (f) state and explain the
variation in oxidation number of the oxides and chlorides (g) describe the reactions of the oxides with water [treatment of peroxides and superoxides is not required] (h) describe and and explain the
acid/base behaviour of oxides hydroxides, including, where relevant, amphoteric behaviour in reaction with sodium hydroxide (only) and acids (i) describe Educational Technology Division Ministry of Education, Singapore July 2006 and explain the 32
reactions of the chlorides with water (j) interpret the variations and trends in (f), (g), (h), and (i) in terms of bonding and electronegativity (k) suggest the types of chemical bonding present in chlorides and oxides from observations of their chemical and physical properties (l) predict given the Group of characteristic by using
properties of an element in a knowledge periodicity (m) deduce the nature, possible position in the Periodic Table, and identity of from unknown given elements chemical
33
9.2
Group II
(a) describe the reactions of the elements with oxygen and water
Notes.
(b) describe the behaviour of the oxides with water (c) interpret thermal and stability explain of the http://www.chemguide.co.uk/inorganic/group2 /thermstab.html Notes.
qualitatively the trend in the nitrates in terms of the charge density of the cation and the polarisability anion (d) interpret, physical and and make chemical of the large
predictions from, the trends in properties of the elements and their compounds 9.3 GROUP VII The similarities and trends in the physical Educational Technology Division Ministry of Education, Singapore July 2006 (a) describe volatility the and trends colour in of 34 http://www.chemguide. co.uk/inorganic/group7
and
chemical
menu.html#top
properties of chlorine, bromine and iodine (i) Characteristic physical properties (ii) The reactivity elements oxidising agents (iii) Some reactions of the halide ions (iv) The reactions of chlorine aqueous hydroxide (b) analyse the volatility of the elements in terms of van der Waals forces (c) describe and deduce from E values the relative reactivity of the elements as oxidising agents (e) (i) describe and explain the relative thermal stabilities Educational Technology Division Ministry of Education, Singapore July 2006 35 with sodium relative of the as
bond energies (f) describe and explain silver by the ions http://www.chemguide.co.uk/inorganic/group7 /testing.html Notes.
reactions of halide ions with: (i) aqueous followed ammonia, (ii) concentrated acid (g) describe number hot, and the analyse reaction in of sulphuric aqueous
terms of changes of oxidation chlorine with cold, and with aqueous sodium hydroxide 9.4 An Introduction to the Chemistry of Transition Elements General physical and characteristic chemical transition properties elements, of the first set of titanium to copper Colour of complexes Educational Technology Division Ministry of Education, Singapore July 2006 36 (a) explain what is meant by a transition element, in terms of d-block elements forming one or more stable ions with incomplete d orbitals
(b) state
the
electronic
configuration of a first row transition element and of its ions (c) state that the atomic radii, ionic radii and first ionisation energies elements invariant (d) contrast, radius; qualitatively, ionic radius; energy with those the first and of of the are transition relatively
melting point; density; atomic ionisation elements element (e) describe the tendency of
transition elements to have variable oxidation states (f) predict Educational Technology Division Ministry of Education, Singapore July 2006 from a given http://winter.group.shef.ac.uk/chemputer/oxid 37 Oxidation state
electronic configuration, the likely oxidation states of a transition element (g) describe and explain the use of Fe /Fe , MnO4 /Mn Cr2O7 /Cr redox
23+ 3+ 2+ 2+
ation-number.html
calculator.
http://neon.chem.ox.ac.uk/vrchemistry/LiveCh em/transitionmetals_content.html
on
the
and
reactions of transition
systems
Section 6) (h) (i) explain the reactions of transition elements with ligands to form complexes, including the complexes of copper() ions with water and ammonia (ii) describe the formation, and state the colour of, these complexes (i) predict, using E values, the likelihood of redox reactions (j) explain qualitatively that
ligand exchange may occur, Educational Technology Division Ministry of Education, Singapore July 2006 38
including haemoglobin
CO/O2
in
(k) explain how some transition elements compounds and/or can act their as
catalysts (see also 8(j)) (l) explain, in terms of d orbital splitting, element why transition are complexes
usually coloured 10 Organic Chemistry 10.1 Introductory Topics Molecular, and formulae Functional groups and the naming of organic compounds Characteristic organic reactions Shapes bonds Educational Technology Division Ministry of Education, Singapore July 2006 of organic molecules; and structural empirical (a) interpret, formulae formulae and and of the use the http://www.chem.qmw.ac.uk/iupac/ IUPAC website. http://www.sciencegeek.net/APchemistry/orga nic/ochem.shtml and and Notes. nomenclature
nomenclature,
classes of compound: (i) alkanes, arenes (ii) halogenoalkanes halogenoarenes (iii) alcohols (including primary, secondary and alkenes
39
tertiary) and phenols (iv) aldehydes and ketones (v) carboxylic (vi) amines nitriles (b) interpret, following associated reactions: (i) functional group (ii) homolytic and heterolytic fission (iii) free radical, initiation, propagation, termination (iv) nucleophile, electrophile (v) addition, substitution, elimination, hydrolysis (vi) oxidation and reduction [in equations for organic redox reactions, the symbols [O] and [H] are acceptable]
3
acids,
acyl only),
and with
use
the
terminology organic
Animation
on
free
radical substitution.
(c) describe sp hybridisation, as Educational Technology Division Ministry of Education, Singapore July 2006
http://www.chemguide.co.uk/basicorg/bonding /methane.html 40
Notes.
in
ethane
molecule,
sp
hybridisation, as in ethene and benzene molecules, and sp hybridisation, as in ethyne molecule (d) explain the shapes of, and bond angles in, the ethane, ethene, benzene, and ethyne molecules in relation to and carbon-carbon bonds http://www.chemguide.co.uk/basicorg/bonding /ethene.html http://www.chemguide.co.uk/basicorg/bonding /ethyne.html http://www.bluffton.edu/~bergerd/Models/CS/s tructure.html Notes. Notes. Notes with 3D models.
(e) predict the shapes of, and bond angles in, molecules analogous to those specified in (d) (f) describe structural isomerism (g) describe geometrical http://www.creativechemistry.org.uk/molecules/geometrical.htm http://www.bluffton.edu/~bergerd/Models/CS/s truc6.html Notes with 3D models. Notes with 3D models.
isomerism in alkenes, and explain its origin in terms of restricted rotation due to the presence of bonds [use of E, Z nomenclature is not required] Educational Technology Division Ministry of Education, Singapore July 2006
41
Animated tutorial.
Notes.
(i) deduce
whether
given
molecule is optically active based on the presence or absence of chiral centres and/or a plane of symmetry (j) recognise that optical isomers have identical except physical in the properties
direction in which they rotate plane-polarised light (k) recognise that optical isomers have identical except with chemical in their another properties interactions
chiral molecule Educational Technology Division Ministry of Education, Singapore July 2006 42
(l) recognise
that
different exhibit
stereoisomers
different biological properties, for example in drug action (m) deduce the possible isomers for an organic molecule of known molecular formula (n) identify chiral centres and/or geometrical isomerism in a molecule of given structural formula 10.2 Hydrocarbons Alkanes (exemplified by ethane) (i) Free-radical reactions Alkenes (exemplified by ethene) (i) Addition oxidation reactions Arenes by (exemplified and benzene and (a) recognise unreactivity including reagents the of towards general alkanes, polar
(i) Influence delocalised electrons structure properties (ii) Substitution reactions electrophiles
of on and
with
(b) describe the chemistry of alkanes as exemplified by the following reactions of ethane: (i) combustion (ii) substitution by chlorine and by bromine (c) describe the mechanism of free-radical substitution at methyl groups with particular reference to the initiation, propagation and termination reactions Educational Technology Division Ministry of Education, Singapore July 2006 44 http://www.chemhelper.com/frhalog.html Notes.
following reactions of ethene: (i) addition hydrogen, steam, hydrogen halides and halogens (ii) oxidation by cold, dilute manganate(VII) ions to form the diol (iii) oxidation concentrated manganate(VII) the ions leading to the rupture of carbon-to-carbon double bond in order to determine the position of alkene linkages in larger molecules (e) describe the mechanism of electrophilic alkenes, bromine/ethene example as addition in using an by hot,
45
(f) describe the chemistry of arenes as exemplified by the following reactions of benzene and methylbenzene: (i) substitution reactions with chlorine and with bromine (ii) nitration (iii) oxidation acid (g) (i) describe the mechanism of substitution of electrophilic in arenes, of the sidechain to give a carboxylic
http://www.wbateman.demon.co.uk/asa2sums /sum5.3/electsub.htm
using the mono-nitration benzene as an example (ii) describe the effect of the delocalisation of electrons in arenes in such reactions (h) predict whether halogenation will occur in the side-chain or aromatic nucleus in arenes depending conditions Educational Technology Division Ministry of Education, Singapore July 2006 on reaction
46
(i) apply
the
knowledge
of
positions of substitution in the electrophilic arenes (j) recognise the environmental consequences and unburnt from of carbon monoxide, oxides of nitrogen hydrocarbons the internal arising substitution reactions of mono-substituted
combustion engine and of their catalytic removal 10.3 HALOGEN DERIVATIVE S Halogenoalkanes and halogenoarenes (i) Nucleophilic substitution (ii) Elimination Relative strength of the C-Hal bond (a) recall the chemistry of as http://chemistry.boisestate.edu/rbanks/organic /halides.html http://www.cem.msu.edu/~reusch/VirtualText/ alhalrx2.htm#hal4 Notes. Notes with animation (require plugin). the
halogenoalkanes exemplified by
(i) the following nucleophilic substitution reactions of bromoethane: hydrolysis; formation formation ammonia (ii) the elimination of hydrogen bromide from of of nitriles; primary
Chime
47
2-bromopropane (b) describe the mechanism of nucleophilic substitution in halogenoalkanes http://www.rod.beavon.clara.net/SN1.htm http://www.rod.beavon.clara.net/SN2a.htm Animation. Animation. http://www.colby.edu/chemistry/OChem/DEM OS/Substitution.html Animated tutorial.
the
different of and
halogenoalkanes
chlorobenzene with particular reference to hydrolysis and to the relative strengths of the C-Hal bonds (d) explain the uses of and in their relative
(e) recognise the concern about the effect of (CFCs) chlorofluoroalkanes Educational Technology Division Ministry of Education, Singapore July 2006
http://www.atmosphere.mpg.de/enid/1z2.html http://www.nas.nasa.gov/About/Education/Oz 48
Notes. Notes.
on the ozone layer [the mechanistic details of how CFCs deplete the ozone layer are not required] 10.4 Hydroxy Compounds Alcohols (exemplified by ethanol) (i) Formation of with halogenoalkanes (ii) Reaction sodium; oxidation; dehydration (iii) The Phenol (i) Its reaction sodium (ii) Nitration of, and bromination of, the aromatic ring (b) classify hydroxy compounds into primary, secondary and tertiary alcohols acidity; with triiodomethane test (a) recall ethanol: (i) combustion (ii) substitution to give halogenoalkanes (iii) reaction with sodium (iv) oxidation compounds carboxylic acids (v) dehydration to alkenes to carbonyl and the chemistry exemplified of by
one/
alcohols,
Notes. Animation
dehydration of alcohol.
49
characteristic
(d) deduce the presence of a CH3CH(OH) group in an alcohol from its reaction with alkaline aqueous iodine to form tri-iodomethane (e) recall the chemistry of
phenol, as exemplified by the following reactions: (i) with bases (ii) with sodium (iii) nitration bromination aromatic ring (f) explain the relative acidities of water, phenol and ethanol 10.5 Carbonyl Compounds Aldehydes (exemplified ethanal) (i) Oxidation carboxylic acid Educational Technology Division Ministry of Education, Singapore July 2006 to by (a) describe and the formation reduction and of to, Animation. of, of, and the
alcohols respectively 50
with
hydrogen cyanide (ii) Characteristic tests for ketones (b) describe the mechanism of the nucleophilic of addition hydrogen reactions ketones (c) describe the use of 2,4dinitrophenylhydrazine DNPH) presence compounds (d) deduce the nature (aldehyde Educational Technology Division Ministry of Education, Singapore July 2006 51 to of detect (2,4the http://www.demochem.de/D-DNPH-e.htm Notes with video
(RealPlayer needed).
carbonyl
or ketone) of an unknown carbonyl compound from the results of simple tests (i.e. Fehlings and Tollens reagents; ease of oxidation) (e) describe CH3CO the reaction of with http://www.demochem.de/D-Jodof-e.htm Notes with video
compounds
(RealPlayer needed).
alkaline aqueous iodine to give tri-iodomethane 10.6 Carboxylic Acids and Derivatives Carboxylic (exemplified ethanoic acid benzoic acid) (i) Formation and nitriles (ii) Salt, acyl formation Acyl (exemplified ethanoyl chloride) (i) Ease hydrolysis compared Educational Technology Division Ministry of Education, Singapore July 2006 with 52 of chlorides by ester and chloride from primary alcohols acids by and (a) describe carboxylic alcohols, nitriles the formation acids aldehydes of and
from
alkyl (ii)
and
chlorides Reaction alcohols, phenols Esters by (i) ethyl primary amines (exemplified ethanoate from acids acyl
and phenyl benzoate) Formation carboxylic and from chlorides (ii) Hydrolysis (under acidic and under basic conditions) (b) describe carboxylic formation of (i) salts (ii) esters on reaction with alcohols, (iii) acyl using ethyl using ethanoate as an example chlorides, ethanoyl chloride as an example Educational Technology Division Ministry of Education, Singapore July 2006 53 the reactions in of the
acids
the
acidity and of
of of their
acids terms
chlorine-substituted ethanoic structures (d) describe the hydrolysis of acyl chlorides (e) describe the reactions of acyl chlorides with alcohols, phenols and primary amines (f) explain the relative ease of hydrolysis of acyl chlorides, alkyl chlorides and aryl chlorides (g) describe the formation of http://chemistry.boisestate.edu/rbanks/organic /acidhalide.html
esters from acyl chlorides, using phenyl benzoate as an example (h) describe the acid and base hydrolyses of esters http://chemistry.boisestate.edu/rbanks/organic /ester+h.gif Animations.
54
http://chemistry.boisestate.edu/rbanks/organic /ester+oh.gif 10.7 Nitrogen Compounds Primary (exemplified ethylamine phenylamine) (i) Their formation reactions (ii) Salt formation (iii) Other of phenylamine Amides (exemplified by ethanamide) (i) Their from chlorides (ii) Their hydrolysis Amino (exemplified (i) Their acid acids by and formation acyl amines by and (a) describe the formation (by of
ethylamine
nitrile
reduction see also Section 10.3) and of phenylamine (by the reduction of nitrobenzene)
aminoethanoic acid) base properties (ii) Zwitterion formation Proteins (i) Protein structure: primary; Educational Technology Division Ministry of Education, Singapore July 2006 55
secondary; tertiary; quaternary structures (ii) The hydrolysis of proteins (iii) Denaturation proteins (b) explain the basicity of amines http://www.colby.edu/chemistry/OChem/DEM OS/Amines.html (c) explain the relative basicities of ammonia, ethylamine and phenylamine in terms of their structures (d) describe bromine (e) describe amides the from formation the of the reaction of Animated tutorial. of
reaction
between RNH2 and R'COCl (f) describe amide hydrolysis on treatment with aqueous alkali Educational Technology Division Ministry of Education, Singapore July 2006 http://chemistry.boisestate.edu/rbanks/organic /amide.html 56 Animations.
properties of amino acids and the formation of zwitterions (h) describe peptide hence, formation (i) list the major functions of proteins in the body (j) describe the hydrolysis of proteins (k) explain the term primary the formation of http://michele.usc.edu/java/pept.html Animation on peptide formation.
(amide) explain
bonds protein
structure of proteins (l) recognise that the twenty amino acids that make up all the proteins in the body are -amino general acids with the formula http://chemmac1.usc.edu/aacids/Aminoacids.htm Notes with 3D models (require the
Chime
RCH(NH2)CO2H, and be able Educational Technology Division Ministry of Education, Singapore July 2006 57
to interpret the properties of -amino acids in terms of the nature of the R group (m) describe the secondary http://www.med.unibs.it/~marchesi/proteins.ht ml#secondary http://webhost.bridgew.edu/fgorga/proteins/de fault.htm http://www.moleculesinmotion.com/SecStrLA/ menu.html (n) state the importance of the tertiary protein structure and explain the stabilisation of the tertiary structure with regard to the R groups in the amino acid residues (ionic linkages, disulphide bridges, hydrogen bonds and van der Waals forces) (o) describe (i) the quaternary structure of proteins (ii) the protein components Educational Technology Division Ministry of Education, Singapore July 2006 http://www.med.unibs.it/~marchesi/haemogl2. 58 http://www.med.unibs.it/~marchesi/hemoglob. html Notes with 3D-model (requires plugin) the Notes with 3D-models (require plugin) the
structure of proteins: -helix and -pleated sheet and the stabilisation structures bonding by of these hydrogen
Chime
Chime
of haemoglobin
(p) explain
denaturation
of
http://www.lewport.wnyric.org/jwanamaker/ani mations/Enzyme%20activity.html
Animated enzyme.
tutorial
of
proteins by heavy metal ions, extremes of temperature and pH changes (q) apply the knowledge of the loss and formation and to of secondary structures common phenomena tertiary interpret everyday
denaturation
59