4Or
Organic Chemistry
Structure, mechanism and synthesis of carbon compounds.
My level
4.1 Foundations
- Alkanes, alkenes and crude oilGCSEA-LevelHomologous series, fractional distillation, cracking and combustion.
- Functional groups and nomenclatureGCSEA-LevelUndergradRecognising and naming functional groups by IUPAC rules.
- Isomerism and stereochemistryA-LevelUndergradStructural isomers, E/Z, chirality, R/S, enantiomers and diastereomers.
- Conformational analysisUndergradNewman projections, ring conformations, A-values and torsional strain.
- Curly arrows and reaction mechanismA-LevelUndergradNucleophiles, electrophiles and drawing electron flow.
- Acidity and basicity of organic compoundsA-LevelUndergradpKa trends, resonance, induction and hybridisation effects.
- Reactive intermediatesUndergradPhDCarbocations, carbanions, radicals, carbenes and their stabilities.
4.2 Core reactions
- Electrophilic addition to alkenesGCSEA-LevelUndergradHalogenation, hydrohalogenation, Markovnikov selectivity and hydration.
- Nucleophilic substitution (SN1 and SN2)A-LevelUndergradMechanisms, kinetics and stereochemical outcomes of substitution at sp3 carbon.
- Elimination (E1, E2, E1cB)A-LevelUndergradForming alkenes, Zaitsev and Hofmann selectivity, anti-periplanar requirements.
- Electrophilic aromatic substitutionA-LevelUndergradAromaticity, nitration, Friedel-Crafts reactions and directing effects.
- Nucleophilic aromatic substitutionUndergradSNAr via Meisenheimer complexes, and arynes.
- Nucleophilic addition to carbonylsA-LevelUndergradAldehydes and ketones: hydride, cyanide, organometallic and water/alcohol additions.
- Carboxylic acid derivativesA-LevelUndergradAcyl chlorides, anhydrides, esters and amides; nucleophilic acyl substitution.
- Enols, enolates, aldol and ClaisenUndergradPhDEnolate formation, alkylation, aldol and Claisen condensations.
- Conjugate additionUndergradMichael additions and 1,2- vs 1,4-selectivity.
- Radical reactionsA-LevelUndergradFree-radical substitution, chain mechanisms and modern radical chemistry.
- Oxidation and reductionA-LevelUndergradOxidising alcohols, reducing carbonyls, hydrogenation and selectivity.
- Pericyclic reactionsUndergradPhDCycloadditions, electrocyclic reactions and sigmatropic shifts; Woodward-Hoffmann rules.
- RearrangementsUndergradPhDCarbocation shifts, Beckmann, Baeyer-Villiger and related migrations.
4.3 Physical organic chemistry
- Linear free-energy relationshipsUndergradPhDHammett plots and what substituent constants reveal about mechanism.
- Kinetic isotope effectsUndergradPhDPrimary and secondary KIEs and their use in mechanistic studies.
- Hammond postulate and Curtin-Hammett principleUndergradPhDRelating transition-state structure to energy, and product ratios from interconverting conformers.
- Frontier molecular orbital theoryUndergradPhDHOMO-LUMO interactions explaining reactivity and selectivity.
4.4 Synthesis
- Retrosynthetic analysisUndergradPhDDisconnections, synthons and planning multistep syntheses.
- Protecting groups and chemoselectivityUndergradMasking reactive groups and orthogonal deprotection.
- Asymmetric synthesisUndergradPhDChiral pool, auxiliaries and asymmetric catalysis.
- PolymerisationGCSEA-LevelUndergradAddition and condensation polymers, step-growth and chain-growth kinetics.
4.5 Structure determination
- Infrared spectroscopy for functional groupsA-LevelUndergradCharacteristic absorption bands and fingerprint regions.
- NMR spectroscopy for structureA-LevelUndergradChemical shift, integration, coupling patterns and 2D NMR.
- Mass spectrometryA-LevelUndergradMolecular ions, fragmentation, isotope patterns and high-resolution mass.
- ChromatographyGCSEA-LevelUndergradTLC, GC and HPLC; retention, resolution and efficiency.
4.6 Biological organic chemistry
- Amino acids, peptides and proteinsA-LevelUndergradZwitterions, peptide bonds, protein structure and isoelectric points.
- CarbohydratesUndergradMonosaccharides, anomers, glycosidic bonds and polysaccharides.
- Nucleic acidsUndergradNucleotides, base pairing and the chemistry of DNA and RNA.