9.1

Concept of enthalpy

1.

Explain endothermic and exothermic reaction using the energy profile diagrams

2.

State standard conditions and define enthalpy of reaction

3.

Define enthalpy of:
i. formation
ii. combustion
ii. atomisation
iv. sublimation
v. neutralisation
vi. hydration
vii. solution (dissolution)

4.

Define
i. heat capacity, C
ii. specific heat capacity, c

5.

Calculate heat change in a calorimeter using the equation, q = mcΔT or q = CΔT

1.

State Hess's Law

2.

Apply Hess's law to calculate enthalpy changes using the algebraic method and the energy cycle method.

9.3

Born-Haber cycle

1.

Define lattice energy

2.

Explain the following effects on the magnitude of lattice energy.
i. Ionic charges
ii. Ionic radii

3.

Explain the hydration process of ionic solids

4.

Sketch Born-Haber cycle for simple ionic solids using energy cycle diagram.

5.

Calculate enthalpy changes using Born-Haber cycle.

10.1

Galvanic cell

1.

Define
i. oxidation
ii. reduction
iii. redox reaction

2.

Sketch and describe the components and operation of a Voltaic/ Galvanic cell

3.

Write half-cell equations and the overall cell reaction equation.

4.

Write cell notation for a Galvanic cell.

5.

Exlpain electrode potential for a metal immersed in a correnponding metals ions solutions

6.

Define:
i. standard electrode potential, E°
ii. standard cell potential, E°cell

7.

Draw, label and explain the standard hydrogen electrode (SHE)

8.

Describe the method used to determine standard electrode (reduction) potentials.

9.

Explain the features of the standard electrode (reduction) potential series.

10.

Use the standard electrode potential values to:
i. compare the relative strength of oxidising agents or reducing agents
ii. calculate standard cell potential using the Eo values
iii. predict the spntaneity of a redox reaction.

10.2

Nernst Equation

1.

Use Nernst equation,
E_cell = E^o_cell - RT/nF ln Q
to determine:
i. cell potential (emf)
ii. concentration or partial pressure of a spcecies
iii. equilibrium constant, K when E_cell = 0

10.3

Electrolytic cell

1.

Describe the component and operation of an electrolytic cell

2.

Explain the influence of the following factors on the selective discharge of a species at the electrode:
i. concentration of the species
ii. standard electrode potential of the species (Elctrochemical Series)
iii. types of electrode (active or inert)

3.

Explain the electrolysis of the following electrolytes using inert electrodes:
i. molten NaCl, concentrated and dilute aqueous NaCl
ii. aqueous Na₂SO₄
Write the half-cell equation

4.

Predict the product of electrolysis using appropriate examples.

5.

Define and use Faraday's first law of electrolysis

11.1

Reaction rate

1.

Define reaction rate

2.

Explain the graph of concentration against time in relation to reaction rate

3.

Write differential rate equation. Determine reaction rate based on differential rate equation of a reaction.
aA + bB → cC
Differential rate equation:
rate = - 1/a d[A] / dt = - 1/b d[B] / dt = + 1/c d[C] / dt

4.

Define:
i. rate law
ii. order of reaction
iii. half-life, t_½

5.

Write the intergrated rate equation for zero, first and second order reactions.

6.

Determine the order of reaction involving a single reactant using
i. initial rate method
ii. the units of rate constant, k
iii. half-life based on the graph of concentration againts time
iv. linear graph method based on the intergrated rate equation and rate law

7.

Perform calculations using the intergrated rate equations.

11.2

Collision theory and transition state theory

1.

Collision theory. Explain the requirements for effective collision:
i. minimum energy
ii. correct orientation

2.

Transition state theory
i. Define activation energy of a reaction with reference to the energy profile diagram
ii. define activated complex
iii. State the characteristics of an activated complex.

11.3

Factors affecting reaction rate

1.

Explain the effect of the following factors on the reaction rate:
i. concentration or pressure
ii. temperature
iii. catalyst
iv. particle size

2.

Explain the effect of temperature on reaction rate using Maxwell-Boltzmann distribution curve.

3.

Explain the effect of catalyst on activation energy based on energy profile diagram for exothermic and endothermic reactions.

4.

Relate the constant and activation energy with temperature using Arrhenius equation:
k = Ae ^-Ea/RT or ln k = ln A - E_a/RT

5.

Determine k, E_a, T and A using Arrhenius equation by calculation and graphical method.

12.1

Introduction

1.

List the elements that made up organic compounds C, H, O, N, P, S and halogens.

2.

State the ability of carbon to form 4 covalent bonds with other carbons or elements:
i. single bond (e.g. C-C, C-X)
ii. double bond (e.g. C=C, C=O)
iii. triple bond (e.g. C≡C, C≡N)

3.

Differentiate between saturated and unsaturated organic compounds.

4.

Give examples of organic compounds used in medicine,
engineering, biotechnology and agriculture.

12.2

Molecular and structural formulae

1.

Define strucutral formula

2.

Draw structural formula in the form of expanded, condensed and skeletal structures based on molecular formula.

3.

Explain primary (1°), secondary (2°), tertiary (3°) and quaternary (4°) carbon.

12.3

Functional groups and homologous series

1.

Define functional group

2.

Name functional groups. Classify organic compounds according to their functional gorups:

3.

Define homologous series and explain general characteristics of its members:
i. represented by a general formula
ii. same functional group and chemical properties
iii. gradual change in physical properties with increasing number of carbon atoms
iv. successive member of a series differs by a -CH₂- group

11.4

Isomerism

1.

Define isomerism

2.

Explain constitutional isomerism.
i. chain isomers
ii. positional isomers
iii. functional group isomers

3.

Define stereoisomerism

4.

Describe cis-trans isomerism due to restricted rotation about:
i. C=C bond
ii. C-C bond in cyclic compounds

5.

Identify cis-trans isomerism of a given structural formula.

6.

Define chirality centre and enantiomers. Identify chirality centre in a molecule.

7.

Explain optical activity of a compound.

8.

Draw a pair of enantiomers using 3-dimensional formula e.g.

9.

Define racemate.

10.

State the applications of chiral compounds in daily life.

12.5

Reactions in organic compounds

1.

Explain covalent bond cleavage:
i. homolytic
ii. heterolytic

2.

State the relative stabilities of primary, secondary and tertiary free radicals, carbocations and carbanions. Explain the inductive effect of alkyl group towards the stability of carbocations and carbanions.

3.

Define electrophile and nucleophile.
i. types of electrophiles: Lewis acids, cations and electron deficient sites in organic compounds
ii. types of nucleophiles: Lewis bases, anions and electron rich sites in organic compounds

4.

Explain the main types of organic reactions:
i. addition: electrophilic and nucleophilic
ii. substitution: electrophilic, nucleophilic and free radical
iii. elimination
iv. rearrangement

13.1

Alkanes

1.

Define hydrocarbon compounds.

2.

Classify hydrocarbons into:
i. aliphatic and aromatic
ii. saturated and unsaturated

3.

Describe alkanes as saturated hydrocarbons with the general formula:
i. C_nH_2n+2, n≥1 for straight chain alkanes
ii. C_nH_2n, n≥3 for cycloalkanes

4.

Draw the structures and name the compounds according to the IUPAC nomenclature for:
i. straight chain and branched alkanes (C₁ – C₁₀)
ii. cyclic alkanes (C₃ - C₆)
iii. alkyl groups

5.

Explain the physical properties:
i. compare the boiling points of:
• alkanes based on molecular weight
• isomeric alkanes
• alkanes and cycloalkanes
ii. solubility

6.

State the natural sources of alkanes.

7.

Describe the combustion of alkanes in:
i. excess oxygen
ii. limited oxygen

8.

Explain the unreactivity of alkanes.

9.

Explain the halogenation reaction of alkanes.

10.

Explain the free radical substitution mechanism for methane, ethane and propane.

11.

Explain the monosubstitution of alkane containing equivalent type of hydrogen atoms as in neopentane.

13.2

Alkenes

1.

Describe alkenes as unsaturated hydrocarbon with the general formula
i. C_nH_2n, n≥2 for straight chain alkenes
ii. C_nH_2n-2, n≥4 for cycloalkenes

2.

Draw the structures and name the compounds according to the IUPAC nomenclature for:
i. straight chain (C₂ – C₁₀) and branched alkenes (C₄ – C₁₀)
ii. cyclic alkenes (C₄ – C₆)
iii. simple dienes (C₄ – C₆)

3.

Show the preparation of alkenes through:
i. dehydration of alcohols
ii. dehydrohalogenation of haloalkanes

4.

State Saytzeff’s rule.
Deduce the major product of elimination reaction.

5.

Explain the reactivity of alkenes.

6.

Write equations for the following addition reactions:
i. hydrogen in the presence of catalyst
ii. halogen (Cl₂ or Br₂) in inert solvent (CH₂Cl₂)
iii. halogen (Cl₂ or Br₂) in water
iv. hydrogen halides (HCl or HBr)
v. acidified water
vi. cold concentrated sulphuric acid

7.

Write the mechanism of electrophilic addition of:
i. hydrogen halides
ii. acidified water
Explain the formation of product according to the Markovnikov’s rule.

8.

Determine the product of the reaction between alkene and hydrogen bromide in the presence of peroxide according to anti-Markovnikov’s rule.

9.

Explain the unsaturation tests for alkenes:
i. Baeyer’s test using cold, dilute, alkaline solution of KMnO₄ at room temperature
ii. reaction with bromine in CH₂Cl₂ and bromine water.

10

Determine the position of double bond through:
i. ozonolysis
ii. reaction with hot, acidified KMnO₄

14.1

Introduction to aromatic compounds

1.

Describe the terms aromatic compounds, Kekulé structure and resonance structure.

14.2

Nomenclature of benzene and its derivatives

1.

Draw the structures and name the benzene derivatives according to the IUPAC nomenclature for:
i. monosubstituted benzene

ii. disubstituted benzene by using numbers
iii. tri- and tetrasubstituted benzene

2.

Draw and give example benzene as a substituent: C₆H₅ - phenyl

14.3

Chemical propeties of benzene and its derivatives

1.

Explain the electrophilic aromatic substitution reactions of benzene:
i. nitration
ii. halogenation
iii. Friedel-Crafts alkylation
iv. Friedel-Crafts acylation

2.

Explain the influence of ortho-para and meta directing substituent towards electrophilic aromatic substitution reaction.

3.

Explain the reactions of benzene derivatives:
i. oxidation of alkylbenzene with hot acidified KMnO₄ or K₂Cr₂O₇ to benzoic acid.
ii. halogenation of toluene:
• free radical substitution of side-chain in the presence of light
• electrophilic aromatic substitution in the presence of Lewis acid

4.

Give the uses of aromatic compounds include the carcinogenic effects of aromatic compounds

15.1

Introduction to haloalkanes

1.

Give the general formula of haloalkane.

2.

Draw the structures, classify and name 1°, 2° and 3° haloalkanes according to the IUPAC nomenclature.

3.

Describe haloalkanes: contain polar bond, carbon bearing the halogen is susceptible to nucleophilic attack.

15.2

Chemical properties of haloalkanes

1.

Explain nucleophilic substitution reaction of haloalkanes

2.

Explain S_N1 and S_N2 mechanisms.

3.

Compare the relative reactivities of 1°, 2° and 3° haloalkanes toward hydrolysis.

4.

Explain elimination reaction with reference to dehydrohalogenation of haloalkanes.

5.

Explain the use of haloalkanes in the synthesis of Grignard reagent, RMgX.
Describe the preparation of alkanes, alcohols (1°, 2° and 3°) and carboxylic acids from Grignard reagents.

6.

Describe Wurtz reaction.

7.

Write the importance of haloalkanes as inert substances.

16.1

Introduction of alcohol

16.2

Nomenclature

16.3

Physical properties of alcohol

16.4

Preparation of alcohols

1.

Give the general formula of alcohol, C_nH_2n+1OH , n≥1

2.

Draw the structures, classify and name the hydroxy compounds (C₁ – C₁₀) according to the IUPAC nomenclature.

3.

Explain the physical properties:
i. boiling point
ii. solubility

4.

Explain the preparation of alcohol by:
i. fermentation
ii. hydration of alkenes
iii. hydrolysis of haloalkanes
iv. addition of Grignard reagent to carbonyl compounds.

16.5

Chemical properties of alcohols

1.

Explain the reactions of alcohol with reference to:
i. reaction with sodium
ii. esterification
iii. dehydration
iv. substitution reactions using HX, PX₃, PX₅ or SOCl₂

2.

Oxidation with KMnO₄/H⁺, K₂Cr₂O₇/H⁺, CrO₃/H⁺ and PCC/CH₂Cl₂

3.

Explain the identification tests to distinguish classes of alcohols:
i. Lucas reagent, i.e. concentrated HCl/ZnCl₂ (between 1°, 2° and 3° alcohol )
ii. KMnO₄/H⁺ or K₂Cr₂O₇ /H⁺ (between 1° and 3°, and 2° and 3° alcohols)

4.

Explain iodoform test, i.e. I₂/NaOH(aq) to identify methyl alcohol group.

5.

Describe the industrial preparation of phenol from isopropylbenzene (cumene).

6.

Compare the acidity of phenol, alcohol and water.

7

Explain the chemical properties of phenol with reference to:
i. reaction with sodium
ii. reaction with sodium hydroxide
iii. Electrophilic aromatic substitution reaction (-OH as ortho-para directing subtituent)
iv. Identification tests using
• FeCl₃ solution
• bromine water

8.

Give the common uses of alcohol and phenol.

17.1

Introduction to carbonyl compounds

17.2

Nomenclature of carbonyl compounds

1.

Give the general formula of aldehydes and ketones

2.

Draw the structures and name the carbonyl compounds for aldehyde (C₁ - C₁₀) and (C₃ - C₁₀) for ketones according to the IUPAC nomenclature.

17.3

Peparation of carbonyl compounds

1.

Explain the preparation of carbonyl compounds through:
i. ozonolysis of alkene
ii. Friedel-Crafts acylation to produce aromatic ketone
iii. oxidation of alcohol

17.4

Chemical properties of carbonyl compounds

1.

Explain the chemical properties with reference to:
i. nucleophilic addition with HCN, water, alcohol, sodium bisulphite and Grignard reagent.
ii. reduction to alcohol using LiAlH₄/H⁺, NaBH₄/H⁺ and H₂/catalyst.
iii. condensation with ammonia derivatives such as hydroxylamine, hydrazine, phenylhydrazine and 2,4-dinitrophenylhydrazine (2,4-DNPH) as identification test for carbonyl compounds.
iv. oxidation with KMnO₄/H⁺, K₂Cr₂O₇/H⁺ , Tollens’, Fehling’s and Schiff’s reagents to differentiate aldehydes from ketones.
v. iodoform test to identify methyl ketone group.

2

State the importance of carbonyl compounds.

18.1

Introduction to carboxylic acids

18.2

Nomenclature of carboxylic acids

18.3

Physical properties of carboxylic acids

18.4

Preparation of carboxylic acids

1.

Give the general formula of carboxylic acids:

2.

Draw the structures and name the carboxyl compounds (C₁ - C₁₀ ) according to IUPAC nomenclature. Givecommon names for C₁ - C₅.

3.

Explain the physical properties:
i. boiling point
ii. solubility including dimerization effect.

4.

Explain the acidity of
i. carboxylic acid in comparison with alcohol and phenol
ii. halogenated carboxlyic acids based on the
- number of halogens
- position of halogens

5.

Explain the preparation of carboxylic acid through:
i. oxidation of alkylbenzene, alcohol and aldehyde
ii. hydrolisis of nitrile compound
iii. carbonation of Grignard reagent

18.5

Chemical properties of carboxylic acids

1.

Explain the chemical properties with reference:-
i. neutralisation with a base
ii. reaction with electropositive metals such as Na, Mg or Ca
iii. reduction with LiAlH₄/H⁺
iv. acyl chloride formation
v. anhydride formation
vi. esterification
vii. amide formation

2.

Explain the reducing property of methanoic acid with:
i. KMnO₄/H⁺
ii. Tollens’ reagent

3.

Explain the relative reactivities of carboxylic acid derivatives towards the hydrolysis reaction.

4.

Give the uses of carboxylic acids and its derivatives.

19.1

Introduction to amines

19.2

Nomenclature

1.

Classify primary, secondary and tertiary amines.

2.

Draw the structures and name aliphatic (C₁ – C₁₀) and aromatic amines according to the IUPAC nomenclature. Give common names (C₁- C₅).

19.3

Physical properties of amines

1.

Explain the physical properties.
i. Boiling point.
Compare the boiling points of:
• 1°, 2° and 3° amines
• amine with alkane, haloalkane, alcohol, carbonyl compound and carboxylic acid.
ii. Solubility.
Compare between 1°, 2° and 3° amines

2.

Compare the basicity of ammonia, aliphatic amines and aromatic amines. Explain basicity in terms of:
i. inductive effect
ii. resonance effect

19.4

Peparation of amines

1.

Explain the preparation of:
i. aromatic amines by reduction of nitro compounds using Zn/H⁺ or SnCl₂/H⁺.
ii. primary aliphatic amines by reduction of nitriles using H₂/Pt, LiAlH₄/H⁺ or NaBH₄/H⁺
iii. primary, secondary and tertiary amines by reductions of amides using LiAlH₄/H⁺ or NaBH₄/H⁺.
iv. primary alkyl and aryl amines by Hoffmann’s degradation of primary amides.

19.5

Chemical properties of amines

1.

Explain the chemical properties with reference to the reactions with:
i. acyl chloride
ii. acid anhydride
iii. benzenesulphonyl chloride (Hinsberg’s test)
Hinsberg’s test is used to distinguish between 1°, 2° and 3° amines.
iv. nitrous acid (NaNO₂ + HCl)
Nitrous acid test can be used to distinguish between:
• 1° aliphatic and 1° aromatic amines
• 1° and 2° aliphatic amines
v. bromine water
Bromine water is used as an identification test for aniline.

2.

Explain the formation of dye by the coupling reaction of diazonium salt (benzenediazonium chloride) and phenol.

20.1

Introduction to amino acids

1.

Give the general structure of a-amino acid.

2.

Identify the structures of 20 standard amino acids.

3.

Name a given amino acid according to the IUPAC nomenclature.

4.

Define the terms zwitterion and isoelectric point, pI.

5.

Draw the structures of a given amino acid
i. in acidic medium
ii. in basic medium
iii. at pI

20.2

Chemical properties of amino acids

1.

Explain the reactions of amino acid with:
i. HCl
ii. NaOH
iii. HNO₂
iv. alcohol in the presence of an acid catalyst

2.

Describe the formation of peptide bond in polypeptides.

3.

Give the importance of amino acids (10 essential amino acids) and proteins (e.g. collagen and haemoglobin)

1.

Explain the terms: monomer, polymer, homopolymer, copolymer, straight chain polymer and cross-linked polymer.

2.

Give examples of natural polymers such as proteins, carbohydrates and natural rubber

3.

Explain the preparation of synthetic polymers through:
i. condensation polymerisation to produce polyamides (e.g. kevlar, nylon 6, nylon 6,6) and polyester (e.g. dacron, terylene)
ii. addition polymerisation to produce polyalkenes (e.g. polyethylene, poly(vinyl chloride) and polystyrene).

4.

Write the uses of synthetic polymers.