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Atomic structure & bonding

Atomic structure

Atoms have protons (mass 1, charge +1), neutrons (mass 1, charge 0) and electrons (mass 1/1836, charge -1). Atomic number Z = number of protons. Mass number A = protons + neutrons. Isotopes have the same Z but different A, so different numbers of neutrons.

  • Relative atomic mass (Ar) is a weighted average of isotope masses, found from mass spectrometry data.
  • In a time-of-flight (TOF) mass spectrometer, sample is ionised (electrospray or electron impact), accelerated, then separated by time of flight: lighter ions and more highly charged ions travel faster.
  • Ion time is proportional to root(m/z), so use t is proportional to root(mass/charge) when comparing ions.

Electron configuration

  • Sub-shells fill in order: 1s 2s 2p 3s 3p 4s 3d 4p. Note 4s fills before 3d but empties first when forming transition metal ions.
  • Sub-shell capacities: s = 2, p = 6, d = 10, f = 14 electrons.
  • Write configurations like 1s2 2s2 2p6 3s2 3p4 for sulfur (Z=16).
  • Ionisation energy: energy to remove one mole of electrons from one mole of gaseous atoms/ions. Successive ionisation energies show big jumps when a new (lower) shell starts, giving evidence for shell structure. Across a period, IE generally rises but dips at Group 3 (p starts) and Group 6 (electron pairing repulsion).

Bonding

  • Ionic bonding: electrostatic attraction between oppositely charged ions in a giant lattice; strong, high melting points, conducts only when molten or dissolved.
  • Covalent bonding: shared pair of electrons; can be simple molecular (low melting point, weak intermolecular forces) or giant covalent (diamond, graphite, silicon dioxide) with very high melting points.
  • Metallic bonding: delocalised electrons attract a lattice of positive ions; explains conductivity and malleability.
  • Dative (coordinate) bonding: both electrons in the shared pair come from one atom, shown with an arrow, e.g. in NH4+ or Al2Cl6.

Shapes and polarity

  • Use VSEPR: electron pairs repel to be as far apart as possible; lone pairs repel more than bonding pairs (lone-lone > lone-bond > bond-bond), which squeezes bond angles down (e.g. water is 104.5 degrees, not 109.5).
  • Learn the standard shapes: linear (180), trigonal planar (120), tetrahedral (109.5), trigonal bipyramidal (90/120), octahedral (90).
  • Electronegativity differences create bond polarity; symmetric molecules like CO2 can be non-polar overall even with polar bonds because dipoles cancel.

Common mistakes

  • Confusing mass number with atomic mass (Ar).
  • Forgetting that 4s electrons are removed before 3d when transition metals ionise.
  • Missing lone pairs when predicting shape and bond angle.
  • Saying ionic compounds 'conduct electricity' without stating molten or aqueous.
  • Atomic number = number of protons; mass number = protons + neutrons.
  • Isotopes have the same number of protons but different numbers of neutrons.
  • Electron sub-shell capacities: s holds 2, p holds 6, d holds 10, f holds 14.
  • 4s fills before 3d but is removed first when transition metals form ions.
  • In TOF mass spectrometry, time of flight is proportional to root(mass/charge).
  • Successive ionisation energy jumps occur when electrons are removed from a new inner shell, evidencing shell structure.
  • Lone pair-lone pair repulsion is greater than lone pair-bond pair, which is greater than bond pair-bond pair repulsion.
  • Water's bond angle is 104.5 degrees due to two lone pairs on oxygen compressing the tetrahedral angle.
  • Tetrahedral molecules have bond angles of 109.5 degrees; trigonal planar have 120 degrees; linear have 180 degrees.
  • Dative (coordinate) bonds have both shared electrons donated by one atom, shown with an arrow in diagrams.
  • Ionic compounds only conduct electricity when molten or dissolved in water, never as a solid.
  • Giant covalent structures like diamond and silicon dioxide have very high melting points due to many strong covalent bonds.
What is the atomic number of an element?
The number of protons in the nucleus.
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Define isotopes.
Atoms of the same element with the same number of protons but different numbers of neutrons.
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How many electrons can a p sub-shell hold?
6 electrons.
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Which sub-shell empties first when a transition metal forms a positive ion, 4s or 3d?
4s empties first, even though it filled before 3d.
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State the relationship between time of flight and mass/charge in a TOF mass spectrometer.
Time of flight is proportional to the square root of mass divided by charge (root(m/z)).
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Why do successive ionisation energies show a large jump at certain points?
Because the next electron removed comes from a shell closer to the nucleus, which is held much more strongly.
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Order the repulsion strengths of lone pair-lone pair, lone pair-bond pair, and bond pair-bond pair.
Lone pair-lone pair is greatest, then lone pair-bond pair, then bond pair-bond pair is weakest.
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What is the bond angle in water and why is it not 109.5 degrees?
104.5 degrees, because the two lone pairs on oxygen repel more strongly and squeeze the bond angle down from the ideal tetrahedral 109.5 degrees.
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What is a dative (coordinate) bond?
A covalent bond where both shared electrons are provided by just one of the two atoms, shown with an arrow.
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When does an ionic compound conduct electricity?
Only when molten or dissolved in water, so the ions are free to move; not as a solid.
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Why does diamond have a very high melting point?
It is a giant covalent structure with every carbon atom bonded to four others by strong covalent bonds throughout the lattice.
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What causes metallic bonding?
Electrostatic attraction between a lattice of positive metal ions and a sea of delocalised electrons.
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Give the electron configuration of sulfur (Z=16).
1s2 2s2 2p6 3s2 3p4.
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Why can CO2 be non-polar overall despite having polar C=O bonds?
Because the molecule is linear and symmetric, so the two bond dipoles point in opposite directions and cancel out.
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What is relative atomic mass (Ar)?
The weighted average mass of all the isotopes of an element, relative to 1/12th the mass of a carbon-12 atom.
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Energetics, kinetics & equilibria

Enthalpy changes

Enthalpy change (ΔH) is heat energy transferred at constant pressure. Exothermic = ΔH negative, energy released to surroundings, temperature rises. Endothermic = ΔH positive, energy absorbed, temperature falls.

Know the standard definitions exactly: standard enthalpy of formation (ΔHf, one mole of compound from elements in standard states), standard enthalpy of combustion (ΔHc, one mole of substance burned completely in oxygen), and standard enthalpy of reaction (ΔHr). All measured at 298 K and 100 kPa.

Bond enthalpies are always positive (bond breaking absorbs energy, bond making releases it). Use mean bond enthalpies to estimate ΔH: ΔH = sum(bonds broken) minus sum(bonds formed). This only gives an estimate because mean values are averaged across many compounds, not exact for a specific molecule.

Hess's Law: the enthalpy change for a reaction is independent of the route taken, because enthalpy is a state function. Use this to build energy cycles from formation or combustion data.

Kinetics

Rate of reaction depends on collision frequency and the proportion of collisions with energy above the activation energy (Ea), in the correct orientation. Increasing temperature increases both collision frequency and, more importantly, the fraction of molecules with E greater than Ea (shown by a Maxwell-Boltzmann distribution shifting right and flattening).

Catalysts provide an alternative reaction pathway with lower Ea, increasing the proportion of successful collisions without being used up. They do not change ΔH or the position of equilibrium, only the rate of reaching it.

Rate equations are found experimentally, never from stoichiometry. Rate = k[A]^m[B]^n. Order with respect to a reactant is the power it's raised to; overall order is the sum. Units of k depend on overall order (mol dm-3 s-1 for zero order, s-1 for first order, mol-1 dm3 s-1 for second order).

Equilibria

Le Chatelier's Principle: a system at equilibrium shifts to oppose an imposed change. Increasing pressure shifts equilibrium towards the side with fewer gas moles; increasing temperature shifts towards the endothermic direction; a catalyst has no effect on position of equilibrium, only rate.

Kc and Kp are equilibrium constants: Kc uses concentrations (mol dm-3), Kp uses partial pressures (usually atm or Pa), only valid for gas-phase equilibria. Both only change with temperature, never with concentration, pressure or catalyst changes.

Common mistakes

  • Forgetting state symbols in standard enthalpy definitions.
  • Writing bond enthalpy calculations the wrong way round (bonds broken minus bonds formed, not the reverse).
  • Saying a catalyst changes equilibrium position — it only speeds up reaching it.
  • Confusing rate order with stoichiometric coefficients.
  • Standard conditions for enthalpy measurements are 298 K (25°C) and 100 kPa.
  • ΔH = sum of bond enthalpies broken minus sum of bond enthalpies formed.
  • Hess's Law works because enthalpy is a state function, independent of route.
  • Exothermic reactions have negative ΔH; endothermic reactions have positive ΔH.
  • Catalysts lower activation energy but never change ΔH or the equilibrium position.
  • Rate equations and reaction orders must be found experimentally, not from the balanced equation.
  • Units of the rate constant k change with overall order: mol dm-3 s-1 (zero order), s-1 (first order), mol-1 dm3 s-1 (second order).
  • Increasing temperature increases rate mainly by increasing the fraction of molecules exceeding Ea.
  • Le Chatelier: raising pressure shifts equilibrium to the side with fewer gas moles.
  • Kc and Kp only change with temperature, never with concentration, pressure, or a catalyst.
  • Kp is only valid for equilibria involving gases and uses partial pressures.
  • A catalyst provides an alternative pathway with lower activation energy without being consumed.
What are the standard conditions for enthalpy measurements?
298 K (25°C) and 100 kPa.
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Define standard enthalpy of formation.
The enthalpy change when one mole of a compound is formed from its elements in their standard states, under standard conditions.
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How do you calculate ΔH from bond enthalpies?
ΔH = sum(bonds broken) minus sum(bonds formed). Bond breaking is endothermic, bond making is exothermic.
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State Hess's Law.
The total enthalpy change for a reaction is independent of the route taken, because enthalpy is a state function.
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Why are mean bond enthalpy calculations only estimates?
Because mean bond enthalpies are averaged across many different compounds, not exact for the specific molecule involved.
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What does a catalyst do to activation energy and ΔH?
Lowers activation energy by providing an alternative pathway; ΔH is unchanged.
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Does a catalyst affect the position of equilibrium?
No. It only speeds up the rate of reaching equilibrium, not the position.
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How must reaction order be determined?
Experimentally, from rate data — never assumed from the stoichiometric equation.
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What are the units of k for a second-order reaction?
mol-1 dm3 s-1.
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How does temperature increase reaction rate?
Mainly by increasing the fraction of molecules with energy greater than the activation energy, shown by the Maxwell-Boltzmann distribution shifting right.
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What does Le Chatelier's Principle predict for increased pressure on a gas equilibrium?
The equilibrium shifts towards the side with fewer moles of gas.
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What is the difference between Kc and Kp?
Kc uses concentrations (mol dm-3) and applies generally; Kp uses partial pressures and only applies to gas-phase equilibria.
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What is the only factor that changes the value of Kc or Kp?
Temperature.
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What shape is the Maxwell-Boltzmann distribution and what does the area under it represent?
A skewed curve starting at zero, peaking, then tailing off; the area under the curve represents the total number of molecules, with the area beyond Ea representing those able to react.
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Define standard enthalpy of combustion.
The enthalpy change when one mole of a substance is completely burned in oxygen under standard conditions, all reactants and products in standard states.
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Redox & electrochemistry

What is redox?

Redox reactions involve simultaneous oxidation and reduction. Oxidation is loss of electrons, reduction is gain of electrons - remember OIL RIG.

Oxidation numbers help track electron transfer. Free elements are 0, simple ions equal their charge, oxygen is usually -2 (except peroxides, -1, and OF2, +2), hydrogen is usually +1 (except metal hydrides, -1). The sum of oxidation numbers in a neutral compound is 0, and in an ion it equals the ion's charge.

Half-equations and balancing

You must be able to construct half-equations and combine them, balancing electrons so none are left over. For reactions in acidic solution, balance oxygen with water and hydrogen with H+ ions.

Electrochemical cells and electrode potentials

A standard electrode potential (E-standard, in volts) measures the tendency of a half-cell to be reduced, measured against the standard hydrogen electrode (SHE), which is defined as 0.00V. Standard conditions are 298K, 100 kPa, and 1 mol dm-3 solution concentration.

In the electrochemical series, the more positive the E-standard value, the greater the tendency to be reduced (gain electrons) - these are the stronger oxidising agents. The more negative, the greater the tendency to be oxidised - stronger reducing agents.

To work out cell EMF (Ecell): Ecell = E(positive electrode) minus E(negative electrode), using the more positive value as the cathode (reduction) and more negative as the anode (oxidation). A positive Ecell means the reaction is feasible (thermodynamically favourable), though feasibility does not guarantee the reaction happens quickly - kinetics can still make it very slow.

Cell diagrams

Learn the convention: anode (oxidation, negative electrode) on the left, cathode (reduction, positive electrode) on the right, with single vertical lines for phase boundaries and a double vertical line for the salt bridge. Write the more oxidised species furthest from the salt bridge on each side.

Common mistakes

  • Mixing up which electrode is positive and which is negative - it depends on whether it is a cell (producing current) or electrolysis (using current).
  • Forgetting to balance charge as well as atoms in half-equations.
  • Getting Ecell backwards - always positive minus negative electrode potential, not the other way round.
  • Confusing oxidising and reducing agents with the process itself - the oxidising agent is reduced, and the reducing agent is oxidised.
  • Not stating standard conditions when quoting E-standard values in exam answers.

Fuel cells and storage cells

Hydrogen-oxygen fuel cells produce electricity from the reaction of hydrogen and oxygen, with water as the only product, making them cleaner than combustion engines, though hydrogen storage and production remain practical challenges.

  • OIL RIG: Oxidation Is Loss, Reduction Is Gain (of electrons)
  • The standard hydrogen electrode (SHE) is defined as exactly 0.00V under standard conditions
  • Standard conditions for electrode potentials are 298K, 100 kPa, and 1 mol dm-3 solution concentration
  • Ecell = E(positive electrode) minus E(negative electrode)
  • A positive Ecell indicates a feasible reaction, but says nothing about reaction rate
  • Oxygen has oxidation state -2 in almost all compounds except peroxides (-1) and OF2 (+2)
  • Hydrogen has oxidation state +1 except in metal hydrides, where it is -1
  • The sum of oxidation numbers in a neutral compound is always 0
  • More positive E-standard values mean a stronger oxidising agent (greater tendency to be reduced)
  • In a cell diagram, the anode (oxidation) is written on the left and the cathode (reduction) on the right
  • A double vertical line in a cell diagram represents the salt bridge
  • Hydrogen-oxygen fuel cells produce only water as a product from H2 and O2
What does OIL RIG stand for?
Oxidation Is Loss (of electrons), Reduction Is Gain (of electrons)
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What is the value of the standard hydrogen electrode potential?
0.00V, by definition, under standard conditions
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State the standard conditions used for measuring electrode potentials.
298K, 100 kPa, and 1 mol dm-3 solution concentration
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How do you calculate Ecell for an electrochemical cell?
Ecell = E(positive electrode) minus E(negative electrode)
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What does a positive Ecell tell you about a reaction?
The reaction is thermodynamically feasible, though it may still be slow due to kinetics
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What is the oxidation state of oxygen in most compounds?
-2 (exceptions: peroxides are -1, OF2 is +2)
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What is the oxidation state of hydrogen in most compounds?
+1 (exception: metal hydrides, where it is -1)
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What must the sum of oxidation numbers equal in a neutral compound?
Zero
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What does a more positive E-standard value indicate about a species?
It is a stronger oxidising agent, with a greater tendency to be reduced (gain electrons)
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In cell diagram convention, which electrode is written on the left?
The anode, where oxidation occurs (the negative electrode in a cell)
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What does a double vertical line represent in a cell diagram?
The salt bridge, separating the two half-cells
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What is the only product of a hydrogen-oxygen fuel cell?
Water
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What is an oxidising agent, in terms of electron transfer?
A species that accepts electrons from another species, and is itself reduced in the process
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What is a reducing agent, in terms of electron transfer?
A species that donates electrons to another species, and is itself oxidised in the process
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How do you balance a half-equation for a reaction in acidic solution?
Balance oxygen atoms with water molecules, then balance hydrogen atoms with H+ ions, then balance charge with electrons
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Inorganic & periodicity

Periodicity: structure across Period 3

Across Period 3 (Na to Ar), atomic radius decreases because nuclear charge increases while shielding stays roughly constant, pulling electrons in tighter. First ionisation energy generally rises across the period, with small drops at Al (starts filling 3p, lower energy than 3s) and S (first paired electron in 3p, extra repulsion). Melting points rise from Na to Al (metallic bonding gets stronger as more delocalised electrons and smaller ionic radius increase attraction), peak hugely at Si (giant covalent, strong directional bonds), then drop sharply from P to Ar (simple molecular structures, only weak van der Waals forces between molecules, so little energy needed to melt them).

Reactions of Period 3 oxides with water

Na2O and MgO are basic oxides, they form alkaline solutions with water (NaOH pH 13-14, Mg(OH)2 is only slightly soluble so pH is lower, around 9-10). Al2O3 is amphoteric, it does not react with water but reacts with both acids and bases. SiO2 does not react with water (giant covalent, very stable). P4O10, SO2 and SO3 are acidic oxides, they react with water to give acidic solutions (phosphoric, sulfurous and sulfuric acid), pH roughly 0-2 for the sulfur and phosphorus oxides.

Group 2 trends

Going down Group 2 (Be to Ba), reactivity with water increases, Mg reacts very slowly with cold water but readily with steam, while Ca, Sr and Ba react increasingly vigorously with cold water. This is because ionisation energy decreases down the group (atomic radius increases, more shielding, easier to lose the outer electrons), even though this is only a partial explanation examiners want you to state clearly. Solubility trends matter for exams: Group 2 hydroxides become MORE soluble down the group (Mg(OH)2 nearly insoluble, Ba(OH)2 fairly soluble), but Group 2 sulfates become LESS soluble down the group (MgSO4 soluble, BaSO4 essentially insoluble, this is the basis of the test for sulfate ions using BaCl2).

Group 7 (halogens) trends and reactions

Reactivity as oxidising agents decreases down Group 7 (F2 most reactive, I2 least) because atomic radius increases and shielding increases, so incoming electrons are attracted less strongly. Displacement reactions: a more reactive (higher) halogen will displace a less reactive halide ion from solution, e.g. chlorine water added to potassium bromide solution turns the solution orange as Br2 forms.

Common mistakes

  • Don't say Group 2 metals get 'more reactive' without linking it to ionisation energy and shielding.
  • Don't confuse the melting point pattern, remember Si is the giant covalent outlier with the highest melting point in Period 3.
  • Always state observations precisely in halogen displacement (colour changes), not just 'a reaction happens'.
  • Across Period 3, atomic radius decreases due to increasing nuclear charge and near-constant shielding.
  • First ionisation energy drops at Al (3s to 3p) and at S (first paired 3p electron) within Period 3.
  • Silicon dioxide has the highest melting point in Period 3 because it is giant covalent with strong Si-O bonds.
  • Na2O and MgO are basic oxides forming alkaline solutions; Al2O3 is amphoteric; SiO2 does not react with water; P4O10, SO2 and SO3 are acidic oxides.
  • Group 2 reactivity with water increases down the group because ionisation energy decreases (larger atomic radius, more shielding).
  • Group 2 hydroxides increase in solubility down the group (Mg(OH)2 nearly insoluble, Ba(OH)2 soluble).
  • Group 2 sulfates decrease in solubility down the group (MgSO4 soluble, BaSO4 insoluble, used in the sulfate test with BaCl2).
  • Group 7 oxidising power decreases down the group as atomic radius and shielding increase, weakening attraction for incoming electrons.
  • A halogen higher in Group 7 will displace a halide ion lower in the group from solution, e.g. Cl2 displaces Br2 from KBr solution.
  • The sulfate test uses acidified BaCl2 solution, a white precipitate of BaSO4 confirms sulfate ions present.
  • Melting points across Period 3 fall sharply from Si to Ar because bonding changes from giant covalent to simple molecular with weak van der Waals forces.
  • Amphoteric Al2O3 reacts with both acids and bases but not with water.
Why does atomic radius decrease across Period 3?
Nuclear charge increases while shielding stays roughly constant, so electrons are pulled in more tightly.
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Why does first ionisation energy drop from Mg to Al?
Al's outer electron is in the 3p subshell, which is higher energy and further from the nucleus than the 3s subshell, so it is easier to remove.
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Why does first ionisation energy drop from P to S?
In S the first electron pairs up in a 3p orbital, causing extra electron repulsion that makes it easier to remove.
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Which Period 3 element has the highest melting point and why?
Silicon, because it has a giant covalent structure with strong directional covalent bonds throughout.
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Why do melting points fall sharply from P to Ar in Period 3?
These elements exist as simple molecules held together only by weak van der Waals forces, needing little energy to separate.
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Classify Na2O, Al2O3 and SO3 as acidic, basic or amphoteric.
Na2O is basic, Al2O3 is amphoteric, SO3 is acidic.
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What happens when SiO2 is added to water?
Nothing, SiO2 is a giant covalent structure that does not react with water.
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Why does reactivity of Group 2 metals with water increase down the group?
Ionisation energy decreases down the group due to increasing atomic radius and shielding, so electrons are lost more easily.
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How does the solubility of Group 2 hydroxides change down the group?
It increases, Mg(OH)2 is nearly insoluble while Ba(OH)2 is fairly soluble.
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How does the solubility of Group 2 sulfates change down the group?
It decreases, MgSO4 is soluble while BaSO4 is essentially insoluble.
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What is the test for sulfate ions and what is the positive result?
Add dilute HCl then BaCl2 solution, a white precipitate of BaSO4 confirms sulfate ions.
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Why does oxidising power decrease down Group 7?
Atomic radius and shielding increase down the group, so the nucleus attracts an incoming electron less strongly.
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What is observed when chlorine water is added to potassium bromide solution?
The solution turns orange as chlorine displaces bromine (Br2) from the bromide ions.
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Does fluorine or iodine react more vigorously as an oxidising agent?
Fluorine, it is the strongest oxidising agent in Group 7 and reactivity decreases going down the group.
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Organic chemistry I

Nomenclature and formulae

Organic chemistry starts with naming. Use IUPAC rules: find the longest carbon chain containing the principal functional group, number it to give the lowest locants to that group, and name substituents alphabetically with locants. Know the difference between empirical, molecular, general, structural, displayed and skeletal formulae, and be able to convert between them.

Isomerism

Structural isomers have the same molecular formula but different structures: chain, position and functional group isomers. Stereoisomers have the same structural formula but different spatial arrangement. E/Z isomerism arises from restricted rotation around a C=C double bond and needs the CIP priority rules (higher atomic number = higher priority on each carbon) when the groups are not simply cis/trans.

Alkanes

Alkanes are saturated, general formula CnH2n+2, fairly unreactive due to strong, non-polar C-H and C-C bonds. Free-radical substitution with halogens (e.g. CH4 + Cl2 in UV light) proceeds via initiation (homolytic fission), propagation and termination steps. A common mistake is forgetting termination gives multiple possible products, not just the 'expected' one.

Alkenes

Alkenes are unsaturated, general formula CnH2n, and the C=C double bond (one sigma, one pi bond) is the reactive site, undergoing electrophilic addition. Learn the mechanism for addition of hydrogen halides and halogens, including curly arrows starting from the pi bond. Markovnikov's rule: with unsymmetrical alkenes and HX, the major product has H added to the carbon with more hydrogens already attached, because the more stable (more substituted) carbocation intermediate forms preferentially.

Halogenoalkanes

Carbon-halogen bond polarity and bond enthalpy control reactivity: C-I is weakest and most reactive, C-F is strongest and least reactive, despite C-F being most polar. This trips students up constantly - reactivity in nucleophilic substitution depends on bond enthalpy, not polarity. Nucleophilic substitution with OH-, CN- and NH3 produces alcohols, nitriles and amines respectively. Elimination with hot ethanolic OH- produces alkenes.

Alcohols

Classified as primary, secondary or tertiary by the carbon bonded to -OH. Oxidation with acidified potassium dichromate(VI) differs by class: primary alcohols oxidise to aldehydes then carboxylic acids (distil off the aldehyde to stop at that stage; reflux for full oxidation), secondary alcohols oxidise only to ketones, and tertiary alcohols resist oxidation entirely. Common mistake: forgetting tertiary alcohols simply do not react with the oxidising agent.

Mechanisms and safety

Always use curly arrows correctly - they show movement of a pair of electrons, starting from a bond or lone pair and ending at an atom or new bond. Practise drawing full mechanisms for free-radical substitution, electrophilic addition and nucleophilic substitution, as mechanism questions are heavily marked on arrow accuracy.

  • Alkanes follow general formula CnH2n+2 and alkenes follow CnH2n.
  • Free-radical substitution has three stages: initiation, propagation, termination.
  • Electrophilic addition to alkenes proceeds via a carbocation intermediate.
  • Markovnikov's rule: the major product forms via the more stable (more substituted) carbocation.
  • C-I bonds are weakest and most reactive in nucleophilic substitution; C-F bonds are strongest and least reactive.
  • Halogenoalkane reactivity in substitution depends on bond enthalpy, not bond polarity.
  • Primary alcohols oxidise to aldehydes (distillation) then carboxylic acids (reflux) with acidified K2Cr2O7.
  • Secondary alcohols oxidise only as far as ketones.
  • Tertiary alcohols cannot be oxidised by acidified potassium dichromate(VI).
  • E/Z isomerism requires restricted rotation around a C=C bond and is assigned using CIP priority rules.
  • Curly arrows always represent the movement of a pair of electrons.
  • IUPAC naming gives the lowest possible locants to the principal functional group.
What is the general formula for alkanes?
CnH2n+2
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What is the general formula for alkenes?
CnH2n
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Name the three stages of free-radical substitution.
Initiation, propagation, termination
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What type of mechanism do alkenes undergo with hydrogen halides?
Electrophilic addition
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State Markovnikov's rule in one sentence.
With unsymmetrical alkenes, H adds to the carbon already bearing more hydrogens, giving the more stable carbocation intermediate
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Which carbon-halogen bond is most reactive in nucleophilic substitution and why?
C-I, because it has the weakest bond enthalpy despite being the least polar bond
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Which carbon-halogen bond is least reactive in nucleophilic substitution?
C-F, because it has the strongest bond enthalpy despite being the most polar bond
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How do you stop oxidation of a primary alcohol at the aldehyde stage?
Distil off the aldehyde as it forms, using dilute acidified potassium dichromate(VI) and gentle heating
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What product forms when a secondary alcohol is oxidised with acidified dichromate(VI)?
A ketone
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Why do tertiary alcohols resist oxidation by acidified dichromate(VI)?
There is no hydrogen atom on the carbon bearing the -OH group for the oxidising agent to remove
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What conditions favour elimination over substitution in halogenoalkane reactions?
Hot, concentrated ethanolic (not aqueous) hydroxide ions, giving an alkene
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What do curly arrows represent in a mechanism?
The movement of a pair of electrons, from a bond or lone pair to a new bond or atom
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What condition is needed for E/Z isomerism to exist?
Restricted rotation around a C=C double bond, with each carbon bearing two different groups
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What determines priority when assigning E/Z isomers using CIP rules?
The atom directly attached with the higher atomic number gets higher priority
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Define a structural isomer.
A compound with the same molecular formula but a different structural arrangement of atoms
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Organic chemistry II & analysis

Optical isomerism

A chiral carbon has four different groups attached, giving two non-superimposable mirror-image forms called enantiomers.

Enantiomers rotate plane-polarised light in opposite directions and have identical physical properties otherwise.

A racemic mixture (racemate) has equal amounts of both enantiomers and shows no net optical rotation.

Optical isomerism matters in drug synthesis, since only one enantiomer of a drug may be biologically active.

Aldehydes and ketones

Aldehydes are oxidised by both Fehling's solution (blue Cu2+ to brick-red Cu2O precipitate) and Tollens' reagent (silver mirror from Ag+ to Ag).

Ketones give a negative result with both tests, since they cannot be oxidised easily.

2,4-DNP forms an orange precipitate with any carbonyl (aldehyde or ketone), confirming C=O is present, and its melting point identifies the specific compound.

NaBH4 in water or ethanol reduces aldehydes to primary alcohols and ketones to secondary alcohols.

Carboxylic acids and esters

Carboxylic acids react with carbonates to release CO2 (fizzing), a quick positive test distinguishing them from alcohols and phenols.

Esters are made by refluxing a carboxylic acid with an alcohol using concentrated H2SO4 catalyst (Fischer esterification), an equilibrium reaction.

Esters hydrolyse under acid (reflux with dilute acid, reversible) or base (reflux with NaOH, irreversible, forming a carboxylate salt plus alcohol).

Aromatic chemistry

Benzene undergoes electrophilic substitution, not addition, because the delocalised ring of six pi electrons is unusually stable (extra stabilisation ~150 kJ/mol vs a theoretical Kekule structure).

Nitration uses conc. HNO3 with conc. H2SO4 catalyst at 50 degrees C, generating the NO2+ electrophile.

Friedel-Crafts acylation uses an acyl chloride with AlCl3 catalyst under reflux, anhydrous conditions, forming a ketone attached to the ring.

Spectroscopy for structure

Mass spectrometry: the molecular ion peak (M+) gives Mr; fragmentation peaks help identify substructures.

Infrared spectroscopy: O-H (broad, 2500-3300 for acids, 3200-3550 for alcohols), C=O (1680-1750, sharp), N-H (3300-3500).

NMR: 13C gives number of distinct carbon environments; 1H integration gives ratio of protons; splitting patterns follow the n+1 rule; TMS is the reference standard at 0 ppm.

D2O shake removes O-H and N-H peaks from an 1H NMR spectrum, confirming their position by disappearance.

Common mistakes

Don't confuse Fehling's (aldehyde only) with 2,4-DNP (any carbonyl) — 2,4-DNP does NOT distinguish aldehydes from ketones.

Always state conditions for esterification and Friedel-Crafts reactions; examiners award marks for reflux, catalyst, and anhydrous conditions.

Remember base hydrolysis of esters is one-way (not an equilibrium) because the carboxylate ion formed won't re-form the ester.

  • A chiral carbon has four different groups attached and creates two enantiomers that rotate plane-polarised light in opposite directions
  • A racemic mixture is a 50:50 blend of enantiomers showing zero net optical rotation
  • Fehling's solution and Tollens' reagent both oxidise aldehydes but not ketones, giving a positive test only for aldehydes
  • 2,4-DNP gives an orange precipitate with ANY carbonyl compound (aldehyde or ketone), and its melting point identifies the exact compound
  • NaBH4 reduces aldehydes to primary alcohols and ketones to secondary alcohols
  • Carboxylic acids fizz with carbonates, releasing CO2, distinguishing them from alcohols
  • Esterification uses conc. H2SO4 catalyst under reflux and is reversible; base hydrolysis with NaOH is irreversible
  • Benzene undergoes electrophilic substitution due to delocalised ring stability of about 150 kJ/mol extra than a Kekule structure would predict
  • Nitration of benzene needs conc. HNO3 with conc. H2SO4 at 50 degrees C to generate the NO2+ electrophile
  • Friedel-Crafts acylation needs an acyl chloride, AlCl3 catalyst, reflux, and anhydrous conditions
  • In 1H NMR, the n+1 rule predicts splitting patterns and TMS is the zero-ppm reference standard
  • A D2O shake makes O-H and N-H peaks vanish from an 1H NMR spectrum, confirming their identity
What makes a carbon atom chiral?
It has four different groups attached to it
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What is a racemic mixture?
An equal 50:50 mix of both enantiomers, giving zero net optical rotation
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Which carbonyl test distinguishes aldehydes from ketones?
Fehling's solution or Tollens' reagent; aldehydes give a positive result (brick-red precipitate or silver mirror), ketones don't
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Does 2,4-DNP distinguish aldehydes from ketones?
No, it reacts with both, giving an orange precipitate; only the melting point of the derivative identifies the specific compound
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What does NaBH4 do to an aldehyde and to a ketone?
Reduces the aldehyde to a primary alcohol and the ketone to a secondary alcohol
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How do you test for a carboxylic acid using a carbonate?
Add sodium carbonate; a carboxylic acid fizzes, releasing CO2 gas
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What are the conditions for esterification?
Reflux the carboxylic acid with an alcohol using concentrated H2SO4 as catalyst
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Why is base hydrolysis of an ester irreversible while acid hydrolysis is reversible?
Base hydrolysis forms a stable carboxylate ion that cannot re-form the ester, whereas acid hydrolysis is a true equilibrium
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Why does benzene undergo substitution rather than addition?
Its delocalised ring of six pi electrons is unusually stable, about 150 kJ/mol more stable than a theoretical Kekule structure
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What are the conditions for nitrating benzene?
Concentrated HNO3 with concentrated H2SO4 catalyst at 50 degrees C, generating the NO2+ electrophile
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What are the conditions for Friedel-Crafts acylation?
An acyl chloride with AlCl3 catalyst, under reflux, in anhydrous conditions
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What IR absorption range indicates a C=O group?
1680-1750 per cm, appearing as a sharp peak
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What does the n+1 rule predict in 1H NMR?
The number of peaks a proton signal splits into, based on the number of neighbouring, non-equivalent protons (n)
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What happens to O-H and N-H peaks in an 1H NMR spectrum after a D2O shake?
They disappear, because the exchangeable H is replaced by deuterium, confirming their identity
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What is the molecular ion peak (M+) used for in mass spectrometry?
It gives the relative molecular mass (Mr) of the compound
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