Course content
- Covalent bonds in organic molecules
Bonding in ethane, ethene, ethyne. - Alkanes
Introduction to alkanes – Cycloalkanes – IUPAC and common nomenclature of alkanes and cycloalkanes – Physical properties – Conformations of acyclic alkanes – Introduction to cycloalkanes – Cyclohexane – Substituted cycloalkanes – Oxidation of alkanes. - Isomers: the arrangement of atoms in space
Cis-trans isomers – Chiral molecules – Stereocentres – Stereocentres in cyclic molecules – Representation of stereocentres with the R or S descriptors – Diastereomers – Meso compounds – R or S assignment in compounds with two or more stereocentres – Disubstituted cycloalkanes – Physical properties of stereoisomers – Chemical properties of enantiomers. - Alkenes
Introduction – Nomenclature – Physical properties – Hydrohalogenation: electrophilic addition of HX – Markovnikov's rule – Stereochemistry of the electrophilic addition of HX – Hydration: electrophilic addition of water and alcohol – Halogenation: addition of halogens to alkenes – Stereochemistry of halogenation – Reduction of alkenes. - Understanding organic reactions
Types of organic reactions – Bond breaking and formation – Bond dissociation energy – Thermodynamics – Enthalpy and entropy – Energy diagrams – Kinetics. - Alkynes
Introduction – Nomenclature – Physical properties – Introduction to the reactions of alkynes – Addition of hydrogen halides – Addition of water – Reactions of acetylide anions – Reduction of alkynes. - Alkyl halides and substitution reactions
Introduction to alkyl halides – Nomenclature – Physical properties – The polar carbon-halogen bond – General features of nucleophilic substitution – Leaving group – Nucleophile – Possible mechanisms for nucleophilic substitution – SN2 mechanism – SN1 mechanism – Stability of carbocations – Distinguishing between the SN2 and SN1 mechanisms. - Alkyl halides and elimination reactions
General features of elimination – Alkenes: the products of elimination reactions – Mechanism of elimination – E2 mechanism – Zaitsev's rule – E1 mechanism – Distinguishing between the E1 and E2 mechanisms – Distinguishing between the SN1, SN2, E1 and E2 mechanisms. - Alcohols, ethers and epoxides
Introduction – Structure and bonding – Nomenclature – Physical properties – Preparation of alcohols, ethers and epoxides – General features: reactions of alcohols, ethers and epoxides – Dehydration of alcohols to alkenes – Conversion of alcohols to alkyl halides with HX – Conversion of alcohols to alkyl halides with SOCl₂ and PBr₃ – Oxidation of alcohols – Reactions of ethers with strong acids – Reactions of epoxides under acidic and neutral conditions – Epoxidation. - Radical reactions
Introduction – General features of radical reactions – Halogenation of alkanes – Mechanism of halogenation – Differences between chlorination and bromination – Radical addition to double bonds. - Conjugation, resonance and dienes
Conjugation – Resonance and allylic carbocations – Common examples of resonance – Resonance hybrid – Electron delocalisation, hybridisation and geometry – Conjugated dienes – Electrophilic addition: 1,2- and 1,4-addition – Kinetically and thermodynamically controlled products. - Benzene and aromatic compounds
Fundamentals – Structure of benzene – Nomenclature of benzene derivatives – The particular stability of benzene – Aromatic, antiaromatic and non-aromatic compounds – Criteria for aromaticity: Hückel's rule – Aromatic ions – Examples of aromatic compounds. - Reactivity of aromatic compounds
Electrophilic aromatic substitution – General mechanism – Halogenation – Nitration and sulfonation – Friedel-Crafts alkylation and acylation – Alkylation of benzene through acylation-reduction – Comparison of alkylation and acylation – Nomenclature of disubstituted and polysubstituted benzenes – Effect of substituents on reactivity: activating and deactivating substituents – Effect of multiple substituents on orientation – Phenol and its reactions. - Aldehydes and ketones
Introduction – Nomenclature – Preparation of aldehydes and ketones – General reactivity of carbonyl compounds – Reactions of aldehydes and ketones: nucleophilic addition reactions, general considerations – Nucleophilic addition of the hydride ion (reduction reactions) – Oxidation reactions – Reactions with carbon nucleophiles: reactions with organometallic reagents, addition of cyanide ions – Reactions with nitrogen nucleophiles: addition of 1° and 2° amines – Reactions with oxygen nucleophiles: addition of water (hydration), addition of alcohols (formation of acetals, cyclic hemiacetals, introduction to carbohydrates) – α,β-unsaturated carbonyl compounds: reactivity. - Carboxylic compounds: carboxylic acids and derivatives
Structure and bonding – Nomenclature – Preparation of carboxylic acids – Reactions of carboxylic acids: general features – Carboxylic acids: strong Brønsted-Lowry acids – Derivatives of carboxylic acids – Structure and bonding of carboxylic acid derivatives – Nomenclature of carboxylic acid derivatives – Reduction of carboxylic acids and their derivatives – Nucleophilic acyl substitution reactions – Reactions of organometallic reagents with carboxylic acid derivatives – Reactions of acyl halides – Reactions of anhydrides – Reactions of carboxylic acids – Reactions of esters – Reactions of amides – Reactions of nitriles. - Carbonyl and carboxylic compounds: α-condensation reactions
Introduction – Enols – Enolates – Racemisation at the α-carbon – Halogenation at the α-carbon – Direct alkylation of enolates – Malonic ester synthesis – Acetoacetic ester synthesis – Aldol reaction – Crossed aldol reactions – Claisen reaction – Michael reaction. - Amines
Introduction – Structure and bonding – Nomenclature – Preparation of amines – Amines reacting as bases – Relative basicity of amines and other compounds – Amines reacting as nucleophiles – Reactions with nitrous acid: diazotisation, N-nitrosamines – Substitution reactions of aryldiazonium salts: replacement of the diazonium group with hydroxide, chloride, bromide, iodide and cyanide (Sandmeyer reactions), fluoride (Schiemann reaction) and hydrogen. - Carbohydrates
Introduction – Monosaccharides – The family of ᴅ-aldoses – The family of ᴅ-ketoses – Cyclic forms of monosaccharides – Glycosides – Reactions of the OH groups of monosaccharides – Reactions of the carbonyl group: oxidation and reduction – Glucose is the most stable of the aldohexoses – Reducing and non-reducing sugars – Disaccharides – Polysaccharides. - Amino acids and peptides
Amino acids – Configuration of amino acids – Acid-base properties of amino acids – The isoelectric point – Methods for the synthesis of amino acids – Peptide synthesis strategies.