Practical Synthetic Organic Chemistry: Reactions; Principles; and Techniques (2nd Edition)

Download Practical Synthetic Organic Chemistry: Reactions; Principles; and Techniques (2nd Edition) written by Stephane Caron in PDF format. This book is under the category Chemistry and bearing the isbn/isbn13 number 1119448859/9781119448853. You may reffer the table below for additional details of the book.


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Stephane Caron


Wiley; 2nd edition




848 pages









Book Description

This electronic book serves as a practical guide for organic chemists. The second edition of Practical Synthetic Organic Chemistry (PDF), which places an emphasis on the most reliable and useful reactions, provides the information necessary for a chemist to not only strategically plan a synthesis, but also to repeat the procedures in the laboratory. This edition of the book was published in 2013.

This comprehensive ebook covers the most essential reactions in organic chemistry, including additions, eliminations, substitutions, rearrangements, oxidations, and reductions, and brings together all of the most relevant advancements and concepts in an one location.

  • Rewrites several portions in order to incorporate fresh and extra examples of chemistry that have been demonstrated on a larger scale.
  • New information on recent developments in CH activation, photoredox and electrochemistry, continuous chemistry, and the application of biocatalysis in the synthesis are included in this publication.
  • Highlights the most essential reactions while discussing fundamental principles, mechanisms, as well as the pros and limitations of the approach and procedures that are used to achieve success in the laboratory.

NOTE: This product only comes with the PDF version of the ebook, “Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques 2nd Edition.” There are no access codes contained within.

Table of contents

Table of contents :
Practical Synthetic Organic Chemistry: Reactions, Principles, and Techniques
List of Contributors
1 Aliphatic Nucleophilic Substitution
1.1 Introduction
1.2 Oxygen Nucleophiles
1.3 Phosphorus Nucleophiles
1.4 Sulfur Nucleophiles
1.5 Nitrogen Nucleophiles
1.6 Halogen Nucleophiles
1.7 Carbon Nucleophiles
1.8 Nucleophilic Substitution at a Sulfonyl Sulfur Atom
2 Addition to Carbon-Heteroatom Multiple Bonds
2.1 Introduction
2.2 Addition of Water to Aldehydes and Ketones: Formation of Hydrates
2.3 Addition of Bisulfite to Aldehydes and Ketones
2.4 The Addition of Alcohols to Aldehydes and Ketones: Acetal Formation
2.5 The Addition of Thiols to Aldehydes and Ketones: S,S-Acetal Formation
2.6 Reductive Etherification
2.7 Addition of NH3, RNH2, and R2NH
2.8 Formation of Hydrazones
2.9 Formation of Oximes
2.10 The Formation of gem-Dihalides from Aldehydes and Ketones
2.11 The Aldol Reaction
2.12 Allylorganometallics: Stannane, Borane, and Silane
2.13 The Nozaki–Hiyama–Kishi Reaction
2.14 Addition of Transition Metal Alkynylides to Carbonyl Compounds
2.15 Addition of Organometallic Reagents to Carbonyls
2.16 Addition of Conjugated Alkenes to Aldehydes: the Baylis–Hillman Reaction
2.17 The Reformatsky Reaction
2.18 The Wittig Reaction
2.19 Horner–Wadsworth–Emmons Reaction
2.20 Peterson Olefination
2.21 Julia–Lythgoe Olefination
2.22 Tebbe Methylenation
2.23 The Mannich Reaction
2.24 The Strecker Reaction
2.25 Hydrolysis of Carbon–Nitrogen Double Bonds
2.26 Conversion of Carboxylic Acids to Acyl Chlorides
2.27 Synthesis of Acyl Fluorides from Carboxylic Acids
2.28 Formation of Amides from Carboxylic Acids
2.29 Formation of Amides from Esters
2.30 Hydrolysis of Acyl Halides
2.31 Conversion of Carboxylic Acids to Esters
2.32 Hydrolysis of Amides
2.33 Conversion of N-Acyloxazolidinones to Other Carboxyl Derivatives
2.34 Alcoholysis of Amides
2.35 Hydrolysis of Esters
2.36 Transesterification
2.37 Alkyl Thiol Addition to Esters
2.38 Addition of Organometallic Reagents to Carboxylic Acid Derivatives
2.39 The Kulinkovich Cyclopropanation
2.40 Synthesis of Acyl Cyanides
2.41 The Ritter Reaction
2.42 Thorpe Reaction
2.43 Addition of Organometallic Reagents to Nitriles
2.44 Conversion of Nitriles to Amides, Esters, and Carboxylic Acids
2.45 Conversion of Nitriles to Thioamides
2.46 The Addition of Ammonia or Amines to Nitriles
2.47 The Addition of Alcohol to Nitriles
2.48 Alkyl Thiol Addition to Nitriles
2.49 The Blaise Reaction
2.50 The Addition of Alcohols to Isocyanates
2.51 The Addition of Amines and Amides to Isocyanates
2.52 The Formation of Xanthates
2.53 The Addition of Amines to Carbon Dioxide
2.54 The Addition of Amines to Carbon Disulfide
2.55 Addition of Organometallic Reagents to Carbon Dioxide
3 Addition to Carbon–Carbon Multiple Bonds
3.1 Introduction
3.2 Hydrogen–Halogen Addition (Hydrohalogenation)
3.3 Hydrogen–Oxygen Addition
3.4 Hydrogen–Nitrogen Addition (Hydroamination)
3.5 Hydrogen–Carbon Addition (Hydroalkylation)
3.6 Halogen–Halogen Addition
3.7 Hydroxy–Halogen Addition
3.8 Amino–Halogen Addition
3.9 Carbon–Halogen Addition
3.10 Oxygen–Oxygen Addition
3.11 Oxygen–Nitrogen Addition
3.12 Nitrogen–Nitrogen Addition
3.13 Carbon–Oxygen Addition
3.14 Carbon–Nitrogen Addition
3.15 Carbon–Carbon Addition
4 Nucleophilic Aromatic Substitution
4.1 Introduction
4.2 Oxygen Nucleophiles
4.3 Sulfur Nucleophiles
4.4 Nitrogen Nucleophiles
4.5 Halogen Nucleophiles
4.6 Carbon Nucleophiles
4.7 ortho-Arynes
5 Electrophilic Aromatic Substitution
5.1 Introduction
5.2 Nitrogen Electrophiles
5.3 Sulfur Electrophiles
5.4 Halogenation
5.5 Carbon Electrophiles
6 Selected Catalytic Reactions
6.1 Introduction
6.2 Organoboron Reagents: The Suzuki–Miyaura Coupling
6.3 Organomagnesium Reagents: Kumada–Corriu Coupling
6.4 Organozinc Reagents: Negishi Coupling
6.5 Cross-Electrophile Coupling
6.6 Organotin Reagents: The Stille Coupling (Migita-Stille Reaction)
6.7 Cross-Coupling Reactions with Organosilicon Compounds
6.8 Metal-catalyzed Coupling of Alkynes (Sonogashira Coupling)
6.9 Metal-Catalyzed Coupling of Alkenes (Heck Coupling)
6.10 Enolate Arylations
6.11 Pd- and Cu-Catalyzed Aryl C—N Bond Formation
6.12 Pd- and Cu-Catalyzed Aryl C—O Bond Formation
6.13 Pd- and Cu-Catalyzed Aryl C—S Bond Formation
6.14 Aryl C—B Bond Formation
6.15 Pd-Catalyzed Aryl C—CN Bond Formation
6.16 Metal-Catalyzed Allylic Substitution
6.17 CatalyticMetal-Mediated Methods for Fluorination
6.18 Selected Metal-Mediated C—H Functionalization
6.19 C—X Bond Forming Reactions via Borrowed Hydrogen Methodologies
6.20 Alkene and Alkyne Metathesis Reactions
6.21 Organocatalysis
7 Rearrangements
7.1 Introduction
7.2 [1,2]-Rearrangements
7.3 Other Rearrangements
7.4 Miscellaneous Migrations
8 Eliminations
8.1 Introduction
8.2 Formation of Alkenes
8.3 Formation of Dienes
8.4 Formation of Alkynes
8.5 Formation of C=N bonds
8.6 Formation of Nitriles
8.7 Formation of Ketenes and Related Compounds
8.8 Fragmentations
8.9 Dehydrating Reagents
9 Reductions
9.1 Introduction
9.2 Reduction of C—C Bonds
9.3 Reduction of C—N Bonds
9.4 Reduction of C—O Bonds
9.5 Reduction of C—S Bonds
9.6 Reduction of C—X Bonds
9.7 Reduction of Heteroatom–Heteroatom Bonds
10 Oxidations
10.1 Introduction
10.2 Oxidation of C—C Single and Double Bonds
10.3 Oxidation of C—H Bonds
10.4 Oxidation of Carbon–Oxygen Bonds and at Carbon Bearing an Oxygen Substituent
10.5 Oxidation of Aldehydes to Carboxylic Acids and Derivatives
10.6 Oxidation of Carbon–Nitrogen Bonds and at Carbon Bearing a Nitrogen Substituent
10.7 Oxidation of Nitrogen Functionalities
10.8 Oxidation of Sulfur and at Carbon Adjacent to Sulfur
10.9 Oxidation of Other Functionality
11 Selected Free Radical Reactions
11.1 Introduction
11.2 Radical Reactions via Chemical Initiation
11.3 Photoredox Catalysis
11.4 Electrochemical Methods
12 Synthesis of “Nucleophilic” Organometallic Reagents
12.1 Introduction
12.2 Synthesis of “Nucleophilic” Organometallic Reagents
12.3 Strategies for Metalating Heterocycles
12.4 Reactions of “Nucleophilic” Organometallic Reagents
13 Synthesis of Common Aromatic Heterocycles
13.1 Introduction
13.2 Pyrroles
13.3 Indoles
13.4 2-Indolinones (Oxindoles)
13.5 Isatins (2,3-Indolindiones)
13.6 Carbazoles
13.7 Pyrazoles
13.8 Indazoles
13.9 Imidazoles and Benzimidazoles
13.10 1,2,3-Triazoles and Benzotriazole
13.11 1,2,4-Triazoles
13.12 Tetrazoles
13.13 Dihydropyridines
13.14 Pyridines
13.15 Quinolines
13.16 Quinolinones and 2-Hydroxyquinolines
13.17 Isoquinolines
13.18 Isoquinolinones
13.19 Quinolones (4-Hydroxyquinolines)
13.20 Pyrimidines and Pyrimidones
13.21 Quinazolines and Quinazolinones
13.22 Pyrazines and Quinoxalines
13.23 Pyridazines, Phtalazines, and Cinnolines
13.24 1,2,4-Triazines
13.25 Furans and Benzofurans
13.26 Benzopyran-4-One (Chromen-4-One, Flavone) and Xanthone
13.27 Coumarins
13.28 Thiophenes and Benzothiophenes
13.29 Isoxazoles and Benzisoxazoles
13.30 Oxazoles and Benzoxazoles
13.31 Isothiazoles and Benzisothiazoles
13.32 Thiazoles and Benzothiazoles
13.33 1,2,4-Oxadiazoles
13.34 1,3,4-Oxadiazoles
14 Access to Chirality
14.1 Introduction
14.2 Using the Chiral Pool
14.3 Classical Resolutions
14.4 Dynamic Kinetic Resolutions
14.5 Desymmetrization of Meso Compounds
14.6 Chiral Chromatography
15 Biocatalysis
15.1 Introduction
15.2 Group Transfer Reactions
15.3 Reductions
15.4 Oxidations
15.5 C—C Bond Forming Reactions
15.6 Future Developments
16 Green Chemistry
16.1 Introduction
16.2 Green Chemistry Metrics
16.3 Solvent and Reagent Selection
16.4 Green Reactions/Reagents
16.5 Examples of Green Methods and Reagents for Common Reaction Types
16.6 Predictive Tools to Design for Green Chemistry
16.7 Green Chemistry Improvements in Process Development
17 Continuous Chemistry
17.1 Introduction
17.2 Aliphatic Nucleophilic Substitutions
17.3 Additions to C—Het Multiple Bonds
17.4 Addition to C—C Multiple Bonds
17.5 Nucleophilic Aromatic Substitutions
17.6 Electrophilic Aromatic Substitution
17.7 Catalysis
17.8 Rearrangements
17.9 Eliminations
17.10 Reductions
17.11 Oxidations
17.12 Free Radical Reactions
17.13 Syntheses of Organometallic Reagents
17.14 Synthesis of Aromatic Heterocycles
17.15 Access to Chirality
17.16 Biotransformations
18 General Solvent Properties
18.1 Introduction
18.2 Definitions and Acronyms
18.3 Solvent Properties
18.4 Mutual Solubility of Water and Organic Solvents
18.5 Other Useful Information on Solvents
18.6 Solvent Safety
18.7 Risk Phrases Used in the Countries of EU
19 Practical Chemistry Concepts Tips for the Practicing Chemist or Things They Don’t Teach You in School
19.1 Introduction
19.2 Reaction Execution
19.3 Solvents and Reagents
19.4 Isolation
19.5 Analysis
Subject Index
Combo Index

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