Organic Chemistry Mechanisms

The sequence of mechanisms here matches the chapters found in Organic Chemistry by Klein (2nd Edition)

Chapter 7 - Substitution Reactions

[7.4] Stereospecificity of SN2 reactions

[7.5] Stereochemistry of SN1 reactions

[7.6] SN1 mechanism with alcohol substrate

[7.6] SN1 reaction of alkyl halide with water

[7.6] SN1 mechanism with rearrangement

[7.7] SN2 mechanism with alcohol substrate

[7.7] SN2 reaction with OTs leaving group

Chapter 8 Alkenes : Structure and Preparation

[8.7] The E2 mechanism of elimination

[8.9] The E1 mechanism of elimination

[8.9] Carbocation rearrangement during E1

Chapter 9 - Addition Reactions of Alkenes

[9.3] Electrophilic addition of HX to alkene

[9.3] Addition of HX to alkene with rearrangement

[9.4] Acid-catalyzed addition of H2O

[9.5] Oxymercuration-demurcuration

[9.6] Hydroboration-oxidation of Alkenes

[9.8] Addition of Br2 in Inert Solvent

[9.8] Addition of Br2 in Participating Solvent

[9.9] Anti dihydroxylation

[9.10] Syn hydroxylation

[9.11] Ozonolytic cleavage of alkene

Chapter 10 - Alkynes

[10.4] Elimination from dibromide

[10.7] Alkyne hydration

[10.7] Acid- and base-catalyzed tautomerism

[10.10] Alkylation of terminal akyne

Chapter 11 - Radical Reactions

[11.3] Chlorination of methane

[11.7] Allylic bromination

[11.10] Radical addition of HBr

[11.11] Radical polymerization

Chapter 12 - Synthesis

No new mechanisms

Chapter 13 - Alcohols and Phenols

[13.4] Reduction with NaBH4

[13.4] Reduction with LiAlH4

[13.4] Reduction of ester with LiAlH4

[13.5] Anti-dihydroxylation (Ch. 9 review)

[13.5] Syn-dihydroxylation (Ch. 9 review)

[13.6] Aldehyde/ketone with Grignard

[13.6] Ester with Grignard reagent

[13.9] Reaction of alcohol with SOCl2

[13.9] Reaction of alcohol with PBr3

[13.9] Oxidation with chromic acid

Chapter 14 - Ethers & Epoxides ; Thiols & Sulfides

[14.5] Acid-catalyzed etherification

[14.5] Williamson ether synthesis

[14.6] Acidic cleavage of ether

[14.6] Autooxidation of ether

[14.8] Epoxidation of alkene

[14.8] Epoxide from halohydrin

[14.10] Ring-opening of epoxides

[14.11] Oxidation of thiols

[14.11] Alkylation of thiols

Chapter 15 - Infrared Spectroscopy & Mass Spectrometry

No new mechanisms

Chapter 16 - Nuclear Magnetic Resonance Spectroscopy

No new mechanisms

Chapter 17 - Conjugated Pi Systems & Pericyclic Reactions

[17.4] Addition of HBr to 1,3-butadiene

[17.4] Diels-Alder cycloaddition

Chapter 18 - Aromatic Compounds

[18.6] Bromination at benzylic carbon

[18.6] SN1 at benzylic carbon

[18.6] E1 at benzylic carbon

[18.6] Electrophilic addition at benzylic carbon

Chapter 19 - Aromatic Substitution Reactions

[19.2] Bromination of benzene

[19.2] Chlorination of benzene

[19.2] General Mechanism for EAS

[19.3] Sulfonation of benzene

[19.4] Nitration of benzene

[19.5] Friedel-Crafts alkylation of benzene

[19.6] Friedel-Crafts acylation of benzene

[19.7] Bromination of phenol; activating group

[19.7] Bromination of phenol acetate; activating group

[19.8] Nitration of benzoic acid; deactivating group

[19.9] Nitration of chlorobenzene; deactivating o/p director

[19.13] Nucleophilic aromatic substitution (SNAr)

[19.14] Elimination-addition; benzyne

Chapter 20 - Aldehydes and Ketones

[20.4] Nucleophilic addition in basic conditions

[20.4] Nucleophilic addition in acidic conditions

[20.5] Base-catalyzed hydration

[20.5] Acid-catalyzed hydration

[20.5] Acid-catalyzed acetal formation

[20.6] Imine formation

[20.6] Enamine formation

[20.6] The Wolf-Kischner reduction

[20.7] Acetal hydrolysis

[20.8] Dithioacetal formation

[20.9] Reduction of carbonyl with hydride

[20.10] Addition of Grignard to aldehyde

[20.10] Cyanohydrin formation

[20.10] Wittig reaction with ketone

[20.13] Baeyer-Villager reaction

Chapter 21 - Carboxylic Acids and Their Derivatives

[21.4] Acid-catalyzed nitrile hydrolysis

[21.4] Base-catalyzed nitrile hydrolysis

[21.4] Carboxylation of Grignard reagent

[21.4] Nucleophilic acyl substitution

[21.7] Ester to amide conversion

[21.10] Fischer esterification reaction

[21.11] Base-promoted saponification

[21.11] Acid-catalyzed ester hydrolysis

[21.11] Ester reduction with LAH

[21.11] Ester reacting with Grignard reagent

[21.12] Hydrolysis of amide in acid

[21.12] Hydrolysis of amide in base

[21.13] Acid-catalyzed hydrolysis of nitrile

[21.13] Base-catalyzed hydrolysis of nitrile

[21.13] Grignard addition to nitrile

Chapter 22 - Alpha Carbon Chemistry : Enols & Enolates

[22.2] Acid-catalyzed halogenation of ketone

[22.2] The Hell-Volhardt-Zelinsky reaction

[22.3] The aldol condensation

[22.3] The crossed aldol reaction

[22.3] The intramolecular aldol reaction

[22.4] The Claisen condensation

[22.4] The Dieckmann cyclization

[22.5] Alkylation of an enolizable ketone

[22.5] The malonic ester synthesis

[22.5] The acetoacetic ester synthesis

[22.5] Decarboxylation of beta-oxo carboxylic acids

[22.6] The Michael reaction

[22.6] Conjugate addition of organocuprate

[22.6] The Robinson annulation

Chapter 23 - Amines

[23.5] The Gabriel synthesis

[23.6] Reductive amination

Copyright Peter Norris 2015