Skip main navigation
×
Cookies Notification
We use cookies on this site to enhance your user experience. By continuing to browse the site, you consent to the use of our cookies.
Learn More
 |
System Upgrade on Tue, May 28th, 2024 at 2am (EDT)
Existing users will be able to log into the site and access content. However, E-commerce and registration of new users may not be available for up to 12 hours.For online purchase, please visit us again. Contact us at customercare@wspc.com for any enquiries.
Lectures on Organic Chemistry
Purchase
Save for later
Item saved, go to cart
ISBN: 978-1-86094-053-8 (hardcover)
USD 54.00
Add to cart
ISBN: 978-1-911298-72-4 (ebook)
USD 22.00
Add to cart
ISBN: 978-1-86094-053-8 (hardcover)
Checkout
ISBN: 978-1-911298-72-4 (ebook)
Checkout
IMPORTANT!
This ebook can only be accessed online and cannot be downloaded. See further usage restrictions.
This ebook can only be accessed online and cannot be downloaded. See further usage restrictions.
One of the challenges faced by a student beginning a university course in organic chemistry is that of focussing on the basic material. The central aim of Lectures on Organic Chemistry is to provide all first year students with a clear and concise guide to the important general reactions of organic chemistry, which form the foundation to all later work. They should find this to be a valuable text, enabling them to better understand organic reactions and the inter-relationship between various classes of organic compounds. It should also be of value as a convenient reference and review guide to those who have completed their formal training in organic chemistry.
Sample Chapter(s)
Chapter 1: Introduction (2,424 KB)
Contents:
- The Alkanes
- The Alkenes
- The Alkynes
- The Arenes
- Halo-Alkanes
- Grignard and Alkyllithium Reagents
- Hydroxyl Compounds
- Ethers
- Epoxides
- Thiols and Thioethers
- The Carbonyl Group
- Unsaturated Carbonyl Compounds
- Amines
- Carbohydrates
- Carboxylic Acids
- Carboxylic Esters
- Amides
- Acyl Halides
- Acid Anhydrides
- Cyanides (Nitriles)
- Bifunctional Acids and Esters
- Amino Acid and Peptides
- Carbonic Acids and Their Derivatives
- Sulphoxides and Sulphones
- Sulphonic Acids and Their Derivatives
- Nitro Compounds
- Carbon-Nitroso Compounds
- Heterocyclic Compounds
- Basic Organic Photochemistry
- Appendices: Some Approximate Chemical Shift Ranges for Different Groups
- NMR Data for Some Common Deuterated Solvents
- Some Typical Values for I.R. Vibrational Frequencies
Readership: First year undergraduates in chemistry, biology and medicine.
Free Access
FRONT MATTER
- Pages:i–xiv
https://doi.org/10.1142/9781848160903_fmatter
Preview Abstract
The following sections are included:
- PREFACE
- CONTENTS
- ABBREVIATIONS
Free Access
Introduction
- Pages:1–33
https://doi.org/10.1142/9781848160903_0001
Preview Abstract
The following sections are included:
- Review Of Basic Atomic And Molecular Orbital Theory
- Stereochemistry - Isomerism
- Stereochemistry - Conformation
- A Quick Review of Reaction And Reagent Types
- Acid And Base Concepts
No Access
The Alkanes
- Pages:35–44
https://doi.org/10.1142/9781848160903_0002
Preview Abstract
The following sections are included:
- General
- Synthesis
- Catalytic Hydrogenation of Alkenes and Alkynes
- Reduction of RX
- Hydrolysis of Grignard Reagents
- Wurtz Coupling
- Reduction of Carbonyl Compounds
- The Clemmensen Reduction
- The Wolff-Kishner Method
- Thermal Decarboxylation of Acid or Salt
- Catalytic Thermal Decarbonylation of Aldehydes
- Reactions of Alkanes
- Pyrolysis
- Oxidation - Combustion
- Halogenation (esp. Chlorination)
No Access
The Alkenes
- Pages:45–59
https://doi.org/10.1142/9781848160903_0003
Preview Abstract
The following sections are included:
- General
- Synthesis
- From Alkyl Halides - Elimination of HX
- Dehydration of Alcohols
- Dehalogenation of 1,2-Dihalides With Zinc
- Semi-hydrogenation of Alkynes - Dissolving Metal Reductions
- Semi-hydrogenation of Alkynes - Use of a Lindlar Catalyst
- Reactions of Alkenes
- Hydrogenation
- Addition of HX
- With Hydrogen Halides
- Hydration of Alkenes - Formation of Alcohols
- Addition of Hal2
- In Inert Solvents
- In Water - Addition of HOX
- Reaction With Mercury(II) Acetate
- Hydroboration/Oxidation
- Oxidation Reactions
- KMnO4 and OsO4
- Ozonolysis
- Epoxide Formation
- Radical Reactions
- Nucleophilic Additions
No Access
The Alkynes
- Pages:61–67
https://doi.org/10.1142/9781848160903_0004
Preview Abstract
The following sections are included:
- General
- Synthesis
- Double Dehydrohalogenation of Alkyl Dihalides
- Dehalogenation
- From Hydrazones
- Alkylation of Terminal Alkynes
- Reactions of Alkynes
- Addition Reactions
- Electrophilic Additions
- Nucleophilic Additions
- Catalytic Hydrogenation
- Acidity of Terminal Alkynes
- Oxidative Coupling Reactions of 1-Alkynes
- Addition Reactions
No Access
The Arenes
- Pages:69–86
https://doi.org/10.1142/9781848160903_0005
Preview Abstract
The following sections are included:
- General
- Reactions of Arenes
- Electrophilic Aromatic Substitution
- Reactions
- Halogenation
- Nitration
- Sulphonation - Formation of Arylsulphonic Acids
- Friedel-Crafts Alkylations
- Friedel-Crafts Acylation - Formation of Aryl Ketones
- Chloromethylation - Formation of Benzyl Chloride
- Some Controlling Factors
- Type of Substituents on the Ring
- Substituents With a Lone Pair on the Atom Bonded to the Ring
- Substituents With Positive Charge or Electronegative Atoms
- Alkyl and Aryl Groups
- Factors Affecting the Ratio of Meta to Para Substitution
- Factors Affecting the Ration of Ortho to Para Substitution
- Direction of Substitution in Compounds With Both Electron-Donating and - Withdrawing Groups
- Type of Substituents on the Ring
- Reactions
- Reactions at the Side Chain
- Halogenation of Side Chain Groups
- Oxidation
- Reduction of Arenes
- Catalytic Hydrogenation
- Dissolving Metal Reduction to the Diene - The Birch Reduction
- Aromatic Nucleophilic Substitution
- The SN1 Pathway
- The SN(AR)2 Mechanism
- The Cine (or Benzyne) Mechanism
- Electrophilic Aromatic Substitution
No Access
Halo-Alkanes
- Pages:87–105
https://doi.org/10.1142/9781848160903_0006
Preview Abstract
The following sections are included:
- General
- Synthesis
- Direct Halogenation of Alkanes
- Additions to Alkenes and Alkynes
- Of Halogens
- Of HX
- From Alcohols
- With PX3
- With Thionyl Chloride
- With HX
- From Terminal Alkynes - Formation of 1-Haloalkynes
- Reaction With HOX
- Reaction of Acetylide With X2
- By Elimination of HX From 1,2-Dihaloalkanes - Formation of Mono-halo Alkenes
- Aryl Halides
- Halogenation of Arenes
- Reaction of Copper(I) Halides and Aryl Diazonium Salts - The Sandmeyer Reaction
- Reactions of Haloalkanes
- Nucleophilic Substitution of X
- The SN2 Mechanism
- Nucleophilicity versus Basicity of Nucleophile
- Structure of the Alkyl Group
- Leaving Group Effects
- Solvent Effects
- The SN1 Mechanism
- Other Less Common Mechanisms for Aliphatic Nucleophilic Substitution
- The SN2' Mechanism
- The SN1' Mechanism
- The SNi Mechanism
- The SN2 Mechanism
- Elimination Reactions - Loss of HX
- The E2 Mechanism
- The E1 Mechanism
- The E1cB Mechanism
- Hofmann versus Saytzeff Elimination
- Summary of Factors Affecting the Substitution: Elimination Ratio
- Nucleophilic Substitution of X
No Access
Grignard and Alkyllithium Reagents
- Pages:107–110
https://doi.org/10.1142/9781848160903_0007
Preview Abstract
The following sections are included:
- General
- Synthesis
- Oxidative Addition - Direct Reaction of RX and M
- Metal Hydrogen Exchange
- Metal Halide Exchange for Aryl Lithium Species
- Reactions of Grignard and Organolithium Reagents
- Hydrolysis
- Halogenation
- With Carbonyl Compounds
- With Acid Derivatives
- With Nitrites
- With N,N-Dialkyl Formamides - The Bouveault Reaction
- Reaction With Cyclic Ethers
- With O2 and S8
No Access
Hydroxyl Compounds
- Pages:111–132
https://doi.org/10.1142/9781848160903_0008
Preview Abstract
The following sections are included:
- Alcohols
- General
- Synthesis
- Hydrolysis of Alkyl Halides
- Hydrolysis of Esters
- Hydration of Alkenes
- Hydroboration-Oxidation of Alkenes
- Dihydroxylation ofAlkenes - Formation of cis 1,2-Diols (cis vie Diols)
- From Epoxides
- Acid Hydrolysis - Formation of trans 1,2-Diols
- Reaction With Metal Hydrides - SN2 Ring Opening
- With Organometallic Reagents (& other carbanions)
- Reduction of Carbonyl Compounds
- With Metal Hydrides
- Catalytic Reduction With Propan-2-ol - the Meerwein-Pondorf Reaction
- Catalytic Hydrogenation
- Reaction of Organometallic Species With Carbonyls
- With Methanal - Formation of Primary Alcohols
- With Aldehydes - Formation of Secondary Alcohols
- With Ketones - Formation of Tertiary Alcohols
- Reactions of Alcohols
- Acidic Reactions
- With Alkali Metals
- Basic Reactions
- Nucleophilic Reactions
- With Carboxylic Acids - Ester Formation 1
- With Acid Chlorides - Ester Formation 2
- Displacement Reactions
- With HBr
- With Thionyl Chloride - Conversion to Alkyl Chloride With Stereo-retention
- With Thionyl Chloride and Pyridine - Conversion to RCl With Stereo-inversion
- With Phosphorus Halides
- Conversion to RX via Sulphonate Esters
- Other C-O Bond Fragmentation Reactions
- Dehydration Reactions
- Conversion of a 1,2-Diol to a Ketone - The Pinacol-Pinacolone Rearrangement
- Oxidation Reactions
- Primary Alcohols
- Secondary Alcohols
- Tertiary Alcohols
- Acidic Reactions
- Phenols
- General
- Synthesis
- From Diazonium Salts
- Industrial Preparation of Phenol
- Reactions of Phenols
- O-Alkylation and O-Acylation
- Reaction With Diazomethane - Formation of Methyl Ethers
- Electrophilic Substitutions
- Oxidation of Phenols
- Mono-hydroxylic Species
- Chromic Acid
- Other Oxidants - Free Radical Processes
- Oxidation of Dihydroxyarenes
- 1,4-Dihydroxyarenes
- 1,2-Dihydroxyarenes (Catechols)
- Mono-hydroxylic Species
- Coupling With Aromatic Diazonium Compounds
No Access
Ethers
- Pages:133–136
https://doi.org/10.1142/9781848160903_0009
Preview Abstract
The following sections are included:
- Synthesis
- From Alkoxides and Alkyl Halides - The Williamson Synttesis
- From Alkyl Halides and Alcohols With Silver(I) Oxide - The Purdie Synttesis
- Addition of ROH to Alkenes
- Reaction of a Primary Alcohol With Acid
- Reactions of Ethers
- Cleavage Reactions
- Large Ring (Crown) Ethers
No Access
Epoxides
- Pages:137–140
https://doi.org/10.1142/9781848160903_0010
Preview Abstract
The following sections are included:
- Synthesis
- Athene and Peracid
- From DMSO, NaH and Carbonyl Compounds
- Reaction of Halohydrin and Base
- Reaction of gem Dihalide, a Carbonyl Compound and BuLi
- Reaction of a Carbonyl Compound Withα-Halo Ester to Form α,β-Epoxy Ester - The Darzen's Condensation
- Reactions of Epoxides
- Reduction With LiAlH4
- Reactions With HX
No Access
Thiols And Thioethers
- Pages:141–144
https://doi.org/10.1142/9781848160903_0011
Preview Abstract
The following sections are included:
- Thiols
- Synthesis
- From Alkyl Halides
- From RI and NaSH
- From RX and Thiourea
- From Alkyl Halides
- Reactions of Thiols
- Oxidation
- Reduction - Desulphurization
- Acylation - Formation of Thiol Esters
- Reactions With Carbonyl Compounds
- Synthesis
- Thioethers (Sulphides)
- Synthesis
- From RS-
- Reactions of Thioethers
- Alkylation Reactions
- Oxidation
- Reduction to Hydrocarbon
- Synthesis
No Access
The Carbonyl Group
- Pages:145–183
https://doi.org/10.1142/9781848160903_0012
Preview Abstract
The following sections are included:
- General
- Aldehydes and Ketones
- Synthesis of Aldehydes
- Ozonolysis of Alkenes via Ozonide
- Oxidation of Primary Alcohols
- Pyridinium Chlorochromate (PCC, C5H5NH+ CrO3Cl-)
- Pyridinium Dichromate (PDC, (C5H5NH)2Cr2O7)
- Manganese Dioxide
- Silver(I) Carbonate
- Hydration of Alkynes
- From Primary Alkyl Iodides or Tosylates and DMSO
- Catalytic Hydrogenation of Acyl Chlorides - The Rosenmund Reduction
- Reduction of Nitriles - The Stephen Reduction
- Aromatic Aldehydes - The Reimer-Tiemann Reaction
- Aromatic Aldehydes - The Gattermann-Koch Reaction
- Industrial Oxidation of Alkenes - The Wacker Process
- Synthesis of Ketones
- Ozonolysis of Alkenes
- Oxidation of Secondary Alcohols
- Pfitzner-Moffatt Oxidation
- The Swern Oxidation
- Oxidation of 1,2-Diols
- Rearrangement of a Strained 1,2-Diol - The Pinacol-Pinacolone Rearrangement
- Hydration of Alkynes - Formation of Methyl Ketones
- Thermolysis of Calcium and Barium Dicarboxylates - Formation of Cyclopentanones and Cyclohexanones
- Aromatic Ketones - The Friedel-Crafts Acylation
- Reactions of the Carbonyl Group
- Reactions Of Carbonyl Compounds Without Enolisation
- Addition Reactions
- With HCN
- With Organometallics
- Formation of β-Hydroxy Esters - The Reformatsky Reaction
- The Stobbe Condensation
- Reaction of Ketones and Diazomethane
- With Amines
- Primary Amines - Imine Formation
- Secondary Amines - Formation of Enamines
- Special Cases - Other Amines
- Hydrazine - Formation of Hydrazones
- Semicarbazide
- Hydroxylamine - Formation of Oximes
- Amine Formation Reactions
- Reductive Amination
- Formation of β-Amino Carbonyls - The Mannich Reaction
- With Alcohols - Formation of Hemiacetals and Acetals
- With Thiols - Formation of Thioacetals
- Reduction Reactions With Metal Hydrides
- Reactions With Phosphorus Ylids - The Wittig Reaction
- Reaction With Dimsyl Sodium: a Sulphur Ylid
- Addition of Bisulphite
- Oxidation Reactions
- Of Aldehydes
- Of Ketones
- Peracid Oxidation to Esters - The Baeyer-Villiger Oxidation
- Oxidation to 1,2-Diones With SeO2
- Reduction Reactions
- Metal Hydrides
- Reduction to 1,2-Diols With Metals - The Pinacol Reaction
- Reduction to Alkanes
- The Clemmensen Reduction
- Reduction via the Hydrazone - the Wolff-Kishner Reaction
- Reductton via Thioacetals
- Reduction of Aldehydes With No α-Hydrogens - The Cannizzaro Reaction
- Miscellaneous Reactions
- With PCl5
- Conversion of a Strained 1,2-Dione to an α-Hydroxyacid - The Benzilic Acid Rearrangement
- Conversion of Aldehydes to Nitrites
- Addition Reactions
- Reactions Of The Carbonyl Group via Enols
- Conversion of a Methyl Ketone to a Carboxylic Acid - The Haloform Reaction
- Formation of α-Hydroxy Carbonyls - The Aldol Condensation
- Base Catalysed Reaction
- Acid Catalysed Reaction
- Use in Synthesis
- Formation of Carbocyclic Rings
- Mixed Aldol Reactions - General
- Mixed Aldol Reactions of Aldehydes - The Claisen-Schmidt Reaction
- Alkylation of Enolates - O vs. C Attack
- Special Condensation Reactions
- The Benzoin Condensation
- Reactions Of Carbonyl Compounds Without Enolisation
No Access
Unsaturated Carbonyl Compounds
- Pages:185–193
https://doi.org/10.1142/9781848160903_0013
Preview Abstract
The following sections are included:
- α,β-Unsaturated Aldehydes and Ketones
- Quinones
- Reactions of Quinones
- Reduction
- Addition Reactions
- With HX
- With Amines
- Reactions With Dienes - Diets-Alder Reactions
- Reactions of Quinones
- Ketenes
- Synthesis
- From α-Bromo Acyl Bromides and Zinc
- From Diketenes
- Reactions of Ketenes
- Hydrolysis
- Alcoholysis
- With Amines
- With Carboxylic Acids
- Dichloroketene
- Synthesis
No Access
Amines
- Pages:195–216
https://doi.org/10.1142/9781848160903_0014
Preview Abstract
The following sections are included:
- General
- Synthesis
- Aliphatic Amines
- Alkylation Reactions
- Of Ammonia
- Primary Amines - The Gabriel Synthesis
- Secondary Amines From Trifluoromethanesulphonamides
- Tertiary Amines
- Reductive Methods
- Of Amides
- Of Nitro Compounds
- Of Azides
- Of Nitriles, Oximes
- Reduction of Imines
- The Eschweiler-Clark Reaction
- Use of B(CN)H3- as Hydride Source
- Hydrolytic Methods
- Rearrangements
- The Hofmann Elimination for RCONH2 Species
- The Curtius Rearrangement
- The Lossen Rearrangement
- The Schmidt Rearrangement
- The Beckmann Rearrangement
- Alkylation Reactions
- Aliphatic Amines
- Reactions of Amines
- Basicity and Nucleophilicity
- Alkylation
- Acylation - Formation of Amides
- Halogenation
- Aliphatic Amines
- Aromatic Amines
- Nitrosation
- Primary Amines
- R = Aryl
- R = Alkyl
- Secondary Amines
- Alkyl Amines
- Aryl Amines
- Tertiary Amines
- Primary Amines
- Reactions With Carbonyl Compounds
- Primary Amines
- Secondary Amines
- Tertiary Amines
- Reaction of 1° Amines With Dichlorocarbene - Formation of Isonitriles
- Oxidation Reactions
- Oxidation Only at Nitrogen - Use of Peracids
- Primary Amines
- Secondary Amines
- Tertiary Amines
- Oxidation at the α-Carbon - Dehydrogenation
- Oxidation Only at Nitrogen - Use of Peracids
- Deprotonation
- Basicity and Nucleophilicity
No Access
Carbohydrates
- Pages:217–236
https://doi.org/10.1142/9781848160903_0015
Preview Abstract
The following sections are included:
- General
- Structure and Nomenclature of Simple Sugars
- Structural Conventions for Carbohydrates
- Reactions and Derivatives of the Simple Sugars
- Hemiacetal and Acetal Formation etc.
- Alkylation of Hydroxyl Groups
- Acylation of the Hydroxyl Groups
- Reduction of Carbohydrates
- Oxidation of carbohydrates
- Oxidation with bromine water - formation of aldonic acids
- Oxidation with nitric acid - formation of aldaric acids
- Oxidation with copper and silver salts - reducing sugars
- Oxidation with phenylhydrazine - osazone formation
- Periodate oxidation - C-C bond cleavage
- Reactions Altering Chain Length - Ascent or Descent of Sugar Series
- Fischer-Kiliani Sequence - Chain lengthening
- The Ruff Degradation - Chain Shortening
No Access
Carboxylic Acids
- Pages:237–250
https://doi.org/10.1142/9781848160903_0016
Preview Abstract
The following sections are included:
- General
- Synthesis of Carboxylic Acids
- Hydrolysis Reactions
- Nitriles
- Esters, Amides and Trihalides
- Carboxylation Reactions
- Oxidation Reactions
- Oxidation of Primary Alcohols
- Oxidation of Aldehydes
- Oxidation of Alkyl Benzenes
- Oxidation of Methyl Ketones - The Haloform Reaction
- The Arndt-Eister Reaction - Ascension of The Carboxylic Acid Series
- Hydrolysis Reactions
- Reactions of Carboxylic Acids
- Nucleophilic Displacement of OH
- Ester Formation
- Amide Formation
- Reactions With Metal Hydrides -Reduction Reactions
- Formation of Other Acid Derivatives
- α-Hydrogen Substitution
- α-Bromination - The Hell-Volhard-Zelinsky Reaction
- Removal of CO2 - Decarboxylation Reactions
- Conversion of Acid to Alkyl Halide - The Hunsdieker Reaction
- Thermolysis of Salts
- Nucleophilic Displacement of OH
No Access
Carboxylic Esters
- Pages:251–259
https://doi.org/10.1142/9781848160903_0017
Preview Abstract
The following sections are included:
- General
- Synthesis
- From Acids (or a Derivative) and Alcohols
- Formation of Methyl Esters with Diazomethane
- Alkylation of Acids with Alkyl Halides
- Reactions of Esters
- Nucleophitic Attack at C=O
- Hydrolysis
- Reaction with Metal Hydrides - Reduction
- With Grignard Reagents
- With Amines
- α-Hydrogen Abstraction - including The Claisen Condensation
- Pyrolysis
- Reduction With Metals - The Acyloin Condensation
- Nucleophitic Attack at C=O
No Access
Amides
- Pages:261–269
https://doi.org/10.1142/9781848160903_0018
Preview Abstract
The following sections are included:
- General
- Synthesis
- Pyrolysis of Ammonium Carboxylates
- From Acyl Compounds
- From Oximes - The Beckmann Rearrangement
- Aldoximes
- α-Keto Oximes
- α-Amino Species
- Reactions of Amides
- Attack by Nucleophiles at Carbonyl Group
- Hydrolysis
- Reaction With Metal Hydrides
- Dissolving Metal Reduction
- Dehydration
- Conversion to Amine With One Carbon Less - The Hoftnann Degradation
- Attack by Nucleophiles at Carbonyl Group
No Access
Acyl Halides
- Pages:271–272
https://doi.org/10.1142/9781848160903_0019
Preview Abstract
The following sections are included:
- General
- Synthesis
- From the Acid
- Reactions of Acyl Halides
- Nucleophilic Substitution
- Reduction to Aldehyde - The Rosenmund Reduction
- Reduction to Alcohol
- Acylation of Arenes - The Friedel Crafts Acylation Reaction
No Access
Acid Anhydrides
- Pages:273–276
https://doi.org/10.1142/9781848160903_0020
Preview Abstract
The following sections are included:
- General
- Synthesis
- From Acyl Halides
- From Carboxylic Acids - Trans-acylation Reactions
- Dehydration of a Dicarboxylic Acid (Cyclic Anhydrides only)
- Reactions of Acid Anhydrides
- Nucleophilic Attack
- Condensation With Aromatic Aldehydes - The Perkin Reaction
No Access
Cyanides (Nitriles)
- Pages:277–283
https://doi.org/10.1142/9781848160903_0021
Preview Abstract
The following sections are included:
- General
- Synthesis
- From Alkyl Halides
- Dehydration of Primary Amide
- From Oximes - The Abnormal Beckmann Rearrangement
- Reactions of Nitriles
- Nucleophilic Attack
- Hydrolysis
- Alcoholysis
- General
- Formation of Amides - The Ritter Reaction
- Metal Hydride Reductions
- With Grignard Reagents
- Formation of Aryl Ketones - The Hoesch Reaction
- Reduction to Aldehyde With SnCl2/HCl - The Stephen Reduction
- Acidic Reactions of α-Hydrogens
- Alkylation
- Nucleophilic Attack
No Access
Bifunctional Acids And Esters
- Pages:285–312
https://doi.org/10.1142/9781848160903_0022
Preview Abstract
The following sections are included:
- Dicarboxylic Acids
- General
- Synthesis
- Dicarboxylation of 1,1-Dimetalaalkanes
- Oxidative Cleavage of Cyclic Ketones
- Reactions of Diacids
- Thermolysis
- Thermolysis of Malonates
- Thermolysis of Oxalic Acid
- Thermolysis of Larger Diacids
- Reaction With Acetic Anhydride
- With Ammonia
- Thermolysis
- Hydroxy Acids
- General
- Synthesis
- α-Hydroxy Acids
- Hydrolysis of α-Halo-acids
- From Cyanohydrins
- Base Induced Rearrangement of 1,2-Diketone - The Benzilic Acid Rearrangement
- β-Hydroxy Acids
- Reaction of Carbanion of Ester With Aldehyde
- General Method For Other Hydroxy Acids
- α-Hydroxy Acids
- Reactions of Hydroxy Acids
- Internal Esterification - Formation of Lactones
- Formation of Lactides From α-Hydroxy Acids
- β-Substituted Esters - An Overview
- Ready Carbanion Formation
- Easy Mono-decarboxylation
- Dialkyl Malonates
- Synthesis
- From α–Halo-acids
- Reactions of Malonate Esters
- Reaction of Anion With Alkyl Halide
- Reaction of Anion With α,ω-Dihalides
- Reactions of Anion With Aldehydes and Ketones - The Knoevenagel Condensation (with aldol condensation)
- 1,4-Addition With α,β-Unsaturated Carbonyls - Michael Addition
- Synthesis
- Unsaturated Carboxvlic Acids
- General
- Synthesis
- Hydrolysis of Allyl Nitrites
- Acid Hydrolysis
- Hydrolysis With Base
- Hypohalite Oxidation of Unsaturated Methyl Ketone - The Haloform Reaction
- Hydrolysis of Allyl Nitrites
- Reactions of Unsaturated Carboxylic Acids
- General Reactions
- Reactions of the Double Bond
- Migration of The Double Bond
- 1,4- Conjugate Additions (inch Michael Additions)
- Lactone Formation
- Butenedioic Acids
- Thermolysis
- Addition of Br2
- Maleic Acid
- Fumaric Acid
- With Dienes - Diels Alder Reactions
- General Reactions
- β–Keto Esters
- Synthesis
- From Esters
- The Claisen Condensation
- The Dieckmann Condensation
- From Malonate Esters and Acyl Chlorides
- By Alcoholysis of Diketene
- From Esters
- Reactions of β-Keto Esters
- With Alkyl Halides - Alkylation of β-Keto Esters
- Acidic Work-up
- Basic Work-up
- With Acyl Halides
- Reaction With α,β-Unsaturated Carbonyl Compounds - Michael Addition
- With Alkyl Halides - Alkylation of β-Keto Esters
- Synthesis
No Access
Amino Acids and Peptides
- Pages:313–327
https://doi.org/10.1142/9781848160903_0023
Preview Abstract
The following sections are included:
- Introduction
- Structure and Classification
- Synthesis of Amino Acids
- From an α-Bromo Acid
- From Addition of HCN to an Aldehyde
- Via Malonic Esters
- Peptide Synthesis
- Peptide Synthesis - Blocking Groups on Amino Acids
- Protection of amino groups
- Protection of carboxyl groups
- Protection of -SH groups
- Protection of hydroxyl groups
- Peptide Synthesis - Coupling Amino Acid Residues
- Acid chloride method
- Mixed anhydride method
- Active ester method
- Coupling reagent method
No Access
Carbonic Acids and Their Derivatives
- Pages:329–340
https://doi.org/10.1142/9781848160903_0024
Preview Abstract
The following sections are included:
- General
- Alkyl Carbonates
- Synthesis
- From Phosgene and Alcohols
- From Silver Carbonate and Alkyl Iodides
- Reactions of Alkyl Carbonates
- With Ketones
- With Alkyl Nitriles
- Synthesis
- Phosgene
- Synthesis
- From Sulphur Trioxide and Carbon Tetrachloride
- Reactions of Phosgene
- With Water - Hydrolysis
- With Alcohols
- With Amines
- Synthesis
- Chloroformates
- Reactions of Chloroformates
- With Amines
- With Grignard Reagents
- Reactions of Chloroformates
- Urethanes
- Synthesis
- From Chloroformate and an Amine (including Ammonia)
- From Urea
- From an Isocyanate and an Alcohol
- Reactions of Urethanes
- With Amines
- Hydrolysis
- Synthesis
- Urea
- Synthesis
- From Phosgene
- From Alkyl Carbonates
- Industrial Preparation From Cyanamides
- Industrially From Ammonia and Carbon Dioxide
- Reactions of Urea
- With Chlorine and Sodium Hydroxide (OCl-)
- Hydrolysis
- Thermolysis
- With Malonate Esters
- Synthesis
- Alkyl Carbonates
No Access
Sulphoxides and Sulphones
- Pages:341–350
https://doi.org/10.1142/9781848160903_0025
Preview Abstract
The following sections are included:
- General
- Sulphoxides
- Synthesis of Sulphoxides
- From Sulphides by Oxidation
- Aryl Sulphoxides
- Reactions of Sulphoxides
- Reactions at the α-Carbon
- General
- Alkylation Reactions
- Reactions With Carbonyl Compounds
- Halogenation
- Reactions Involving Oxygen
- Removal of Oxygen - The Pummerer Rearrangement
- Reduction of Sulphoxides to Sulphides
- Loss of Sulphur and Oxygen
- Simple Desulphurization - Alkane Formation
- By Elimination - Alkene Formation
- Thermolysis
- Applications of Elimination Reactions to Synthesis
- Formation of α,β-Unsaturated Carbonyls
- Conversion of Aldehyde to Methyl Ketone
- Reactions at the α-Carbon
- Synthesis of Sulphoxides
- Sulphones
- Synthesis of Sulphones
- By Oxidation of Sulphides and Sulphoxides
- For Mixed Alkyl Sulphones
- Aromatic Sulphones
- Reactions of Sulphones
- Deprotonation
- Reactions at Oxygen
- Other Points
- Reduction to Alkanes
- Elimination Reactions - Formation of Alkenes
- Synthesis of Sulphones
- Sulphoxides
No Access
Sulphonic Acids and Their Derivatives
- Pages:351–356
https://doi.org/10.1142/9781848160903_0026
Preview Abstract
The following sections are included:
- General
- Synthesis
- The Acids
- Aliphatic Sulphonic Acids
- From Alkyl Halides
- By Peracid Oxidation of Thiols
- Aromatic Sulphonic Acids
- Aliphatic Sulphonic Acids
- Acid Chlorides
- Commercial Preparation
- Aromatic Sulphonyl Chlorides
- Esters
- Sulphonamides
- The Acids
- Reactions of Sulphonic Acids and Their Derivatives
- Sulphonic Acids
- Acid Chlorides
- Esters
- Nucleophilic Substitution Reactions
- Reductions
- Primary Tosylates
- Secondary and Tertiary Tosylates
- Amides
No Access
Nitro Compounds
- Pages:357–365
https://doi.org/10.1142/9781848160903_0027
Preview Abstract
The following sections are included:
- General
- Synthesis
- Aliphatic Nitro Compounds
- Commercial Synthesis
- Nitration of "Active" Methylenes
- From Primary and Secondary Halides With No Active Methylenes
- By Peracid Oxidation of Amines
- Aromatic Nitro Compounds
- Aliphatic Nitro Compounds
- Reactions of Nitro Compounds
- Reactions of the Anion
- With Magnesium Methylcarbonate - Formation of α-Nitro Carboxylic Acids
- With Aldehydes - The Henry Reaction
- With α,β-Unsaturated Carbonyls - Michael Additions
- With Halogens - α-Halogenation
- Conversion to Carbonyl Compounds - The Nef Reaction
- Reduction Reactions
- Reduction to Nitroso Compounds
- Reduction to Hydroxylamines
- With Zinc and Aqueous Ammonium Chloride
- With the Borane. THF Complex
- Reduction to Amines
- Metal Reductions
- Metal-Hydrogen Reductions
- NaSH, Na2S2, (NH4)2S
- Metal Hydrides
- Reactions of the Anion
No Access
Carbon-Nitroso Compounds
- Pages:367–373
https://doi.org/10.1142/9781848160903_0028
Preview Abstract
The following sections are included:
- General
- Synthesis
- Aromatic Nitroso Compounds
- Nitrosation of Arenes
- From Nitro-Arenes
- Aliphatic Nitroso Compounds
- Nitrosation of "Active" Methylenes
- Acid Reactions - For Base Labile R Groups
- Base Reactions - For Acid Labile R Groups
- Neutral Reactions - For Acid and Base Sensitive R Groups
- Addition of NOX Reagents to Alkenes
- Nitrosation of "Active" Methylenes
- Aromatic Nitroso Compounds
- Reactions of Nitroso Compounds
- With Amines
- With α-Carbanions of Malonates, etc.
- With Grignard Reagents
- Reduction
- Oxidation
- Spin Trapping
No Access
Heterocyclic Compounds
- Pages:375–394
https://doi.org/10.1142/9781848160903_0029
Preview Abstract
The following sections are included:
- Introduction
- Reactivity in Aromatic Heterocycles
- Reaction at the heteroatom
- Reaction of the aromatic π system
- Nucleophilic attack at the C-X "double bond"
- Pyridine
- Condensation of Ammonia and 1,5-Dicarbonyl Compounds
- Pyrylium Salts
- Pyrrole, Furan, Thiophen
- Introduction
- Indoles
- Five Membered Rings Containing Two Heteroatoms
- IMIDAZOLES
- OXAZOLES
- THIAZOLES
- From thioamides and α halocarbonyl compounds
- From ammonium dithiocarbamate and α halocarbonyl compounds
- From an α-acylamino carbonyl compound and phosphorus pentasulphide
No Access
Basic Organic Photochemistry
- Pages:395–407
https://doi.org/10.1142/9781848160903_0030
Preview Abstract
The following sections are included:
- Introduction
- Photolysis of Carbonyl Compounds
- Photolysis of Diazo Compounds
- Diazoalkanes
- Alkyl azides
- Photoreduction
- Photo-Addition
- Photoaddition of Alkenes to Carbonyl Compounds - the Paterno-Büchi Reaction
- Photoaddition of Alkenes to Aromatic Compounds
- Photo-Rearrangement
- Cis-trans Isomerisation
- Intramolecular Photocyclisations
- Photoisomerisation of Benzenoid Compounds
- Photo-Oxidation
- Formation of Peroxy Compounds
Free Access
BACK MATTER
- Pages:409–423
https://doi.org/10.1142/9781848160903_bmatter
Preview Abstract
The following sections are included:
- APPENDIX 1: Some Approximate Chemical Shift Ranges For Different Groups
- APPENDIX 2: NMR Data for Some Common Deuterated Solvents
- APPENDIX 3: Some Typical Values For I.R. Vibrational Frequencies
- INDEX
Sample Chapter(s)
Chapter 1: Introduction (2,424 KB)
