Organic Chemistry 3720 Mechanisms

The sequence of mechanisms here matches the chapters found in Organic Chemistry by Klein (3rd Edition). If you have the 1st or 2nd editions, old Chapter 13 is now Chapter 12, old Chapter 14 is now Chapter 13, and so on.

Chapter 12 - Alcohols and Phenols

[12.04] Reduction with NaBH4

[12.04] Reduction with LiAlH4

[12.04] Reduction of ester with LiAlH4

[12.05] Anti-dihydroxylation (Ch. 8 review)

[12.05] Syn-dihydroxylation (Ch. 8 review)

[12.06] Aldehyde/ketone with Grignard

[12.06] Ester with Grignard reagent

[12.09] Reaction of alcohol with SOCl2

[12.09] Reaction of alcohol with PBr3

[12.10] Oxidation with chromic acid

Chapter 13 - Ethers & Epoxides ; Thiols & Sulfides

[13.05] Acid-catalyzed etherification

[13.05] Williamson ether synthesis

[13.06] Acidic cleavage of ether

[13.06] Autooxidation of ether

[13.08] Epoxidation of alkene

[13.08] Epoxide from halohydrin

[13.10] Ring-opening of epoxides

[13.11] Oxidation of thiols

[13.11] Alkylation of thiols

Chapter 14 - Infrared Spectroscopy & Mass Spectrometry

No new mechanisms

Chapter 15 - Nuclear Magnetic Resonance Spectroscopy

No new mechanisms

Chapter 16 - Conjugated Pi Systems & Pericyclic Reactions

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

[16.07] Diels-Alder cycloaddition

Chapter 17 - Aromatic Compounds

[17.06] Bromination at benzylic carbon

[17.06] SN1 at benzylic carbon

[17.06] E1 at benzylic carbon

[17.06] Electrophilic addition at benzylic carbon

Chapter 18 - Aromatic Substitution Reactions

[18.02] Bromination of benzene

[18.02] Chlorination of benzene

[18.02] General Mechanism for EAS

[18.03] Sulfonation of benzene

[18.04] Nitration of benzene

[18.05] Friedel-Crafts alkylation of benzene

[18.06] Friedel-Crafts acylation of benzene

[18.07] Bromination of phenol; activating group

[18.07] Bromination of phenol acetate; activating group

[18.08] Nitration of benzoic acid; deactivating group

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

[18.13] Nucleophilic aromatic substitution (SNAr)

[18.14] Elimination-addition; benzyne

Chapter 19 - Aldehydes and Ketones

[19.04] Nucleophilic addition in basic conditions

[19.04] Nucleophilic addition in acidic conditions

[19.05] Base-catalyzed hydration

[19.05] Acid-catalyzed hydration

[19.05] Acid-catalyzed acetal formation

[19.06] Imine formation

[19.06] Enamine formation

[19.06] The Wolf-Kischner reduction

[19.07] Acetal hydrolysis

[19.08] Dithioacetal formation

[19.09] Reduction of carbonyl with hydride

[19.10] Addition of Grignard to aldehyde

[19.10] Cyanohydrin formation

[19.10] Wittig reaction with ketone

[19.11] Baeyer-Villager reaction

Chapter 20 - Carboxylic Acids and Their Derivatives

[20.04] Acid-catalyzed nitrile hydrolysis

[20.04] Base-catalyzed nitrile hydrolysis

[20.04] Carboxylation of Grignard reagent

[20.04] Nucleophilic acyl substitution

[20.07] Ester to amide conversion

[20.10] Fischer esterification reaction

[20.11] Base-promoted saponification

[20.11] Acid-catalyzed ester hydrolysis

[20.11] Ester reduction with LAH

[20.11] Ester reacting with Grignard reagent

[20.12] Hydrolysis of amide in acid

[20.12] Hydrolysis of amide in base

[20.13] Acid-catalyzed hydrolysis of nitrile

[20.13] Base-catalyzed hydrolysis of nitrile

[20.13] Grignard addition to nitrile

Chapter 21 - Alpha Carbon Chemistry : Enols & Enolates

[22.02] Acid-catalyzed halogenation of ketone

[21.02] The Hell-Volhardt-Zelinsky reaction

[21.03] The aldol condensation

[21.03] The crossed aldol reaction

[21.03] The intramolecular aldol reaction

[21.04] The Claisen condensation

[21.04] The Dieckmann cyclization

[21.05] Alkylation of an enolizable ketone

[21.05] The malonic ester synthesis

[21.05] The acetoacetic ester synthesis

[21.05] Decarboxylation of beta-oxo carboxylic acids

[21.06] The Michael reaction

[21.06] Conjugate addition of organocuprate

[21.06] The Robinson annulation

Chapter 22 - Amines

[22.05] The Gabriel synthesis

[22.06] Reductive amination

Copyright Peter Norris 2015-2019