• 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
• 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
• 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
• 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
• 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
• Enantioselective conjugate addition

•Introduction
• Pyridine - Structure
  - Nucleophilic Substitution
  - Acts as a Nucleophilic Catalyst
• Pyridine N-Oxide - Structure
  - Nucleophilic Substitution
  - Cleavage of N-oxide bond
• Hydroxy Pyridine - Tautomerism
• Pyrrole - Structure
  - The Vilsmeier Reaction
  - The Mannich Reaction
  - Pyrrole - conjugate alkylation
  - Olefin metathesis - pyrrole formation
• The Ritter reaction
• Hantsch pyridine synthesis
• DDQ oxidation of dihydropyridine

• Endo v Exo
• Diels Alder: orbital explanation for the endo rule
• Regioselectivity in Diels-Alder
• Dienophile stereochemistry
• Diene stereochemistry
• Auxiliary-controlled Diels-Alder

• 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