Key term
CCEA A-Level Chemistry 1110
Formulae, Equations and Amounts of Substance
Atomic Structure
Topic overviewProtons, neutrons and electronsAtomic number, mass number and the composition of ionsIsotopes and relative isotopic massRelative atomic, molecular and formula massMass spectra and relative atomic mass calculationsMass spectra of diatomic elementsElectronic configuration and the building up principleOrbitals, electron spin and orbital shapesThe s-, p-, d- and f-blocks of the Periodic TableIonisation energies and their equationsTrends in ionisation energy as evidence for shells and subshells
Bonding
Topic overviewIonic bonding and electron transferDot and cross diagrams for ionic compoundsCovalent bonding and the shared pairLone pairs and co-ordinate bondingDot and cross diagrams for covalent molecules and ionsThe octet rule and its limitationsElectronegativity and bond polarityMetallic bonding
Intermolecular Forces and Structure
Shapes of Molecules and Ions
Redox
The Halogens
Acid-Base Titrations
Qualitative Tests
Formulae and Amounts of a Substance
Nomenclature and Isomerism in Organic Chemistry
Alkanes
Topic overviewAlkanes as saturated hydrocarbonsBoiling points of alkanes and van der Waals' forcesBoiling points of branched isomersComplete and incomplete combustion of alkanesPollutants from alkane fuels and the atmosphereCatalytic convertersRadicals, homolytic fission and heterolytic fissionFree radical substitution of alkanes
Alkenes
Topic overviewUnsaturated hydrocarbons and the bromine water testSigma and pi bonds in the carbon–carbon double bondElectron density at C=C, reactivity and catalytic hydrogenationAddition of chlorine and bromine to alkenesAddition of hydrogen chloride and hydrogen bromideElectrophiles, heterolytic fission and the addition mechanismCarbocation stability and Markovnikov additionAddition polymerisation of alkenes
Halogenoalkanes
Topic overviewClassification and boiling points of halogenoalkanesLaboratory preparation of a halogenoalkane from an alcoholNucleophiles and hydrolysis with aqueous alkaliReactions with ammonia and with potassium cyanideRelative rates of hydrolysis and carbon–halogen bond enthalpyElimination using ethanolic potassium hydroxideCFCs and the ozone layer
Alcohols
Infrared Spectroscopy
Energetics
Topic overviewExothermic and endothermic changesStandard conditions and the standard enthalpy changeEnthalpy level diagramsStandard enthalpies of combustion and formationStandard enthalpy of neutralisationMeasuring enthalpy changes by experimentEnthalpy calculations using q = mcΔTHess's Law and enthalpy cyclesIndirect enthalpy calculations using Hess's LawAverage bond enthalpies and their limitations
Kinetics
Equilibrium
Group II Elements and Their Compounds
Topic overviews-block character and electronic configurationTrends in atomic radius and first ionisation energyReactions of the elements with oxygen, water and dilute acidsThe oxides and their reactions with water and dilute acidsThermal stability of the carbonates and hydroxidesUses of magnesium oxide, calcium carbonate and limeSolubility trends and solubility curves
Lattice Enthalpy, Entropy and Free Energy
Topic overviewLattice enthalpy and the factors that control itBorn–Haber cycles for Group I halidesBorn–Haber cycles for Group II halides and oxidesEnthalpy of hydration and enthalpy of solutionCalculations on dissolving ionic compoundsEntropy and the limits of enthalpy changeStandard entropy change calculationsFree energy and the temperature of feasibility
Rates of Reaction
Equilibrium and Acid-Base Equilibria
Topic overviewEquilibrium concentrations from initial amountsKc expressions, values and unitsBrønsted–Lowry acids, bases and conjugate pairsKw, pH and the pH of strong acids and basesKa, pKa and the pH of weak acidsBuffer solutions and how they resist pH changeCalculating the pH of a buffer solutionTitration curves, indicators and the pH of salt solutions
Isomerism
Aldehydes and Ketones
Topic overviewStructure and naming of aldehydes and ketonesBoiling points and solubility of carbonyl compoundsPreparation from primary and secondary alcoholsReaction with hydrogen cyanide and the nucleophilic addition mechanismRacemic mixtures from nucleophilic addition2,4-dinitrophenylhydrazine and the identification of carbonylsDistinguishing aldehydes from ketones, and reduction with lithal
Carboxylic Acids
Derivatives of Carboxylic Acids
Topic overviewEsters and acyl chlorides: structure and namingBoiling points and solubility of monoestersMaking esters from alcohols with carboxylic acids or acyl chloridesThe laboratory preparation of a liquid esterFats and oils as esters of glycerolTransesterification, biodiesel and margarineReactions of acyl chlorides with water and alcohols
Aromatic Chemistry
Spectroscopy and Chromatography
Topic overviewThe mass spectrum: molecular ion and base peakFragmentation and the formulae of fragment ionsHigh resolution mass spectrometryNuclear magnetic resonance and the TMS standardChemically equivalent hydrogens and chemical shiftIntegration curvesSpin–spin splitting and the n+1 ruleDeducing a structure from an nmr spectrumPaper and thin-layer chromatographyGas–liquid chromatography
Volumetric Analysis
Transition Metals
Topic overviewThe characteristic properties of the transition metalsElectronic configurations of the metals and their ionsComplexes, ligands and coordination numberOxidation number, redox and disproportionationMonodentate, bidentate and polydentate ligandsLigand strength and the entropy of ligand replacementLigand replacement in copper(II) complexesThe colours of the aqueous transition metal ionsHydroxide precipitates with sodium hydroxidePrecipitates with aqueous ammonia and their dissolutionVanadium and the interconversion of its oxidation states
Electrode Potentials
Amines
Amides and Polymers
Amino Acids and Proteins
Amides and Polymers
The basicity of amides
- 3 things to know
- Unit A2 2
Overview
Recall questions on why an amide would be expected to be basic and why it is not, what delocalisation of the nitrogen lone pair means, the bond length and planarity evidence for it, ranking ammonia, ethylamine and ethanamide, why the planarity matters to proteins, and the order of reactivity of acyl chloride, ester and amide.
What you need to know
Answer each one before you reveal it.
Your recallNot started
Key term
Give one piece of structural evidence that the nitrogen lone pair in an amide is delocalised
Key term
Besides the bond length, give one piece of structural evidence that the amide lone pair is delocalised.
Questions from this subtopic
Each one with the model answer underneath.
- 1
Are amides basic?
Model answer
They are far less basic than amines and in practice are effectively neutral.
- 2
Why would an amide be expected to be basic?
Model answer
Its nitrogen atom carries a lone pair, which could accept a proton as an amine's does.
- 3
Why is an amide much less basic than an amine?
Model answer
The nitrogen lone pair is delocalised into the adjacent carbonyl group, so it is much less available to accept a proton.
- 4
What does delocalisation of the lone pair mean here?
Model answer
The lone pair overlaps with the π system of the carbon–oxygen double bond and is spread over the nitrogen, the carbon and the oxygen.
- 5
Give one piece of structural evidence for that delocalisation.
Model answer
The carbon–nitrogen bond in an amide is shorter than an ordinary single bond, which shows it has partial double bond character.
- 6
Besides the bond length, give one piece of structural evidence that the amide lone pair is delocalised.
Model answer
The amide group is planar, with the nitrogen and its substituents in the same plane as the carbonyl, which a fully single-bonded nitrogen would not require.
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