• Borohydride reduction
• Cyanide addition
• Hemiacetal formation
• Grignard and organolithium addition

• Ester hydrolysis/formation - acid catalysis
• Amide formation from acid chloride
• Acid chloride formation from carboxylic acid-SOCl₂
• Acid chloride formation from carboxylic acid-PCl₅

• Acetal formation
• Cyclic acetal formation
• Spiroketal formation
• Enamine formation
• Wittig reaction
• Imine formation
• Oxime formation
• Hydrazone formation
• Wolff-Kishner reduction
• Reduction with LiAlH₄

• Introduction
• Configuration
• Chirality R and S
• Chiral or achiral?
• Planes of Symmetry
• Chiral Allenes
• Chiral BINAP
• Centre of Symmetry
• Chiral spiroamides
• Feist's Acid Structures
• Diastereoisomers
• Symmetry of Epoxide Diastereoisomers
• Conformations
• Multiple conformations
• Newman Projections
• Tartaric acid and Newman Projections
• Cyclohexane conformations
• Decalin conformations

• Simple S_N2 reaction
• S_N1 and S_N2
• Carbocation structure and stability
• More S_N2 reactions
• Mitsunobu reaction

E2 bimolecular examples
• E2 to form diene
• E2 Stereoselective for E
• E2 Stereospecific Acyclic
• E2 Cyclohexyl Diast A
• E2 Cyclohexyl Diast B
E1 unimolecular examples
• E1 unimolecular
• E1cb unimolecular conjugate base
• Nitrile oxide synthesis via oxime

• Ethylene and Bromine
• Stereospecific addition
• Epoxidation peracid
• Epoxidation of E-Allyl silane
• Unsymmetrical alkenes HBr
• Regioselective addition
• Diene bromination
• Stereoisomers

• Nitration of benzene
• Friedel-Crafts alkylation
• Friedel-Crafts acylation
• Sulfonation of benzene

• Benzyne mechanism
• S_NAr Addition-elimination
• S_NAr two nitro groups
• Formation of nitrosonium ion
• Formation of diazonium salt

• Jones Oxidation
• SeO₂ allylic oxidation
• Swern Oxidation
• Oxidation of dihydropyridine
• NaIO₄ diol cleavage
• Pb(OAc)₄ diol cleavage

• Cyclopentanone Aldol - acid cat
• Intramolecular aldol reactions
• Knoevenagel condensation
• Lithium enolates
• Mannich reaction
• Enolate alkyation - Allylic strain
• Enolate acylation - Claisen condensation
• Enamine acylation
• Wittig reaction
• Acid-catalysed Bromination
• Base-catalysed Bromination
• Anti Aldol Formation
• Syn Aldol Formation
• Stereoselective Anti Aldol
• Stereoselective Syn Aldol

• How conjugation changes the reactivity of carbonyl groups
• Enolisation
• Direct conjugate addition with enols
• Conjugate addition reactions
• Conjugate addition of enolates
• Robinson annelation
• Dimedone synthesis
• Conjugate Peroxide addition-Epoxidation
• Baylis-Hilman reaction
• Enantioselective conjugate addition

Introduction
• Pyrrole structure
• Pyridine structure
• Pyridine N-oxide structure
• Hydroxy Pyridine - Tautomerism
Synthesis of heterocycles
• Hantsch pyridine synthesis
• Paal-Knorr pyrrole
• Paal-Knorr pyrrole 2
• Knorr pyrrole synthesis
• Thiophene synthesis
• Thionation of a ketone
• Lawesson's reagent
• Thiazole synthesis
• Pyridazine synthesis
• Pyrazole synthesis
• Pyrimidine synthesis
• Olefin metathesis - pyrrole formation
• Triazole formation
• Tetrazole formation
Reactions of heterocycles
• Pyridine Nucleophilic Substitution
• Pyridine Nucleophilic Catalyst
• Vilsmeier reaction
• Mannich reaction
• Pyrrole - conjugate alkylation
• Ritter reaction
• DDQ oxidation of dihydropyridine
• Furan hydrolysis
• Indole alkylation
• Indole Mannich-Substitution
• Pyridine N-oxides benzylic oxidation
• Pyrrole decarboxylation

• Diels-Alder Introduction
• Identifying a Diels-Alder product
• s-cis versus s-trans dienes
• Regioselectivity - how to determine the product
• Regioselectivity explained
Stereochemistry
• Stereochemistry of diene Z,Z
• Stereochemistry of diene Z,E
• Stereochemistry of diene E,E
• Dienophile stereochemistry
• Stereochemistry of the dienophile - working out product structure
Endo v Exo Stereoselectivity
• Endo/Exo Maleic anhydride-cyclopentadiene
• Endo/Exo Methyl Vinyl ketone -cyclopentadiene
• Orbital explanation for the endo rule
• Woodward-Hoffman rules
• Intramolecular DA endo rule
• Endo/Exo in intramolecular
Reaction Gallery
• DA 2,3-Dimethylbutadiene-Acrolein
• DA diene-quinone
• Intramolecular Methyl-2,7,9-decatrienoate
• Auxiliary-controlled DA
• DA 1,1-dimethylbutadiene-methyl methacrylate
• DA 2-methoxybuta-1,3-diene-acrylonitrile
• DA hexa-2,4-diene-acrolein
• DA benzyne-anthracene
• Pyrone Diels-Alder reaction

• Overview
Cycloadditions
• Ozonolysis 1,3-dipolar
• Nitrone 1,3-dipolar
• Isoxazole 1,3-dipolar
• [4+3]-Allyl cycloaddition
• [6+4]-Thermal cycloaddition
• Triazole formation
• Tetrazole formation
• Intramolecular carbonyl ene
• Dihydroxylation using OsO₄
• Periodate diol cleavage
Sigmatropic rearrangements
• [3,3]-Claisen rearrangement aromatic
• [3,3]-Claisen rearrangement acyclic
• [3,3]-Ireland-Claisen
• [2.3]-shift sulfoxide
• [1,5]-H shift cyclopentadiene
• [1,7]-H sigmatropic shift
• [3,3]-Fischer Indole
Electrocyclic reactions
• Stereospecificity
• Conrotatory - cyclobutene
• Disrotatory - hexatriene
Cheleotropic reactions
• Stereospecific diene-SO₂

• Benzilic acid
• Neighbouring group migration
• Pinacol
• Semipinacol rearrangements of diazonium salts
• Ring expansion
• Wagner-Meerwein rearrangements
• Payne rearrangement
• Beckmann rearrangement
• Favorskii rearrangement
• Tiffeneau-Demjanov rearrangement
• Rearrangement using different nucleophiles
• Stereochemistry can indicate NGP
• Which group migrates?
• Baeyer-Villiger
• Neighbouring group participation

• HBr addition to isobutene
• Termination steps
• Chlorination of alkanes
• Conjugate addition to acrylonitrile
• Bu₃SnH reduction of C-Br
• Cyclisations exo/endo
• Cyclisation tin hydride
• Pinacol coupling
• Julia Olefination

• Bond polarization
• Ring expansion
• Beckmann fragmentation
• Fragmentations are controlled by stereochemistry
• Fragmentation of diastereoisomers
• Juvenile hormone synthesis

• Photolysis of diazomethane to produce a carbene
• Methylation of carboxylic acid using diazomethane
• Formation of carbenes
• Reactions of carbenes
• Bamford-Stevens reaction
• Simmons-Smith reaction

• Wittig reaction
• Cyclopropanation
• Felkin-Anh reduction-LiAlH₄
• Chelated reduction ZnBH₄
• Intramolecular carbonyl ene reaction
• Beta-keto sulfoxide reduction
• Cyclohexene epoxide axial opening
• Anti Aldol Formation
• Syn Aldol Formation
• Stereoselective Anti Aldol
• Stereoselective Syn Aldol
• Allylic strain enolate
• Energy Profile of beta-silyl enolate
• Epoxidation of Z-Allyl silane
• Epoxidation of E-Allyl silane
• Axial cyclohexanone alkylation-enamine
• Energy Profile of Z-allyl silane
• Energy Profile of E-allyl silane

• Baldwin's rules - Classes of cyclization
• Baldwin's rules - Endo-trig reactions

Sulfur
• Asymmetric Sulfoxidation
• Sulfonium ylids
• Sulfoxonium ylids
• Pummerer rearrangement
• Sulfoxide elimination
• Swern Oxidation
• Julia Olefination
Boron
• Hydroboration of alkenes
• Hydroboration of cyclopentadiene
• Crotyl boranes react stereospecifically with aldehydes
• Reduction of a ketone using Alpine borane
Silicon
• Vinyl silanes react with electrophiles
• The Peterson reaction
• Stereospecific Peterson olefination
• Silicon alpha anion stabilisation
• Epoxidation of Z-Allyl silane
• Epoxidation of E-Allyl silane

Palladium
• Stille Coupling Reaction
• Mizoroki-Heck Reaction
• Carbonylative Stille Coupling Reaction
• Carbonylation Of A Vinyl Bromide
• Nucleophilic allylic substitution
• TMM cycloaddition
• Suzuki Reaction
Ruthenium
• Hydrogenation Ru cat.
• Hydroformylation Ru cat.
• Olefin metathesis - unsaturated pyrrole
• Olefin metathesis - macrocycle

• Methylation of an enolate
• Benzylation of an enolate
• Evans oxazolidinone syn Aldol
• Evans ent-oxazolidinone syn Aldol
• Evans oxazolidinone Diels-Alder
• Phenylmenthol Diels-Alder
• Alkylation of SAMP hydrazone
• Conjugate addition Oppolzer sultam
• Meyers enolate alkylation
• Schöllkopf amino acid synthesis

• Sparteine controlled deprotonation
• Hydroboration of cyclopentadiene-IPC borane
• Ketone reduction with BINAL-H
• Acetylenic ketone reduction with Alpine borane

• Sharpless asymmetric epoxidation
• Direct Sulfoxidation
• Hydrogenation catalysed by Ru
• Cyclopropanation allylic alcohol
• Et₂Zn addition to aldehydes

• Ketone reduction with CBS
• Intermolecular aldol - proline
• Intramolecular aldol - proline
• Aldol dimerisation - proline
• Intermolecular aldol with a trans substrate
• Intramolecular S_N2 Me-proline
• Indole alkylation - imidazolidinone
• Pyrrole - Friedel-Crafts alkylation
• Carbonyl-ene phosphoramide
• Imine hydrophosphonylation phosphate