Organic Chemistry

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Organic Chemistry Textbook

• 0.1 The Study of Organic Chemistry


• 1 Authors


• 2 Foreword
  
  
  • 2.1 Purpose and mission.
  
  
  • 2.2 Content and Contributions
  
  
  • 2.3 Licensing
  
  
  • 2.4 How to study organic chemistry
  
  
  
  


• 3 Unit 1: Foundational concepts of organic chemistry


• 4 History of organic chemistry
  
  
  • 4.1 Brief History
  
  
  • 4.2 Synthesis of Urea.
  
  
  • 4.3 Organic vs Inorganic Chemistry
  
  
  • 4.4 Major Advances in the Field of Organic Chemistry.
  
  
  
  


• 5 Atomic structure
  
  
  • 5.1 Atomic Structure.
  
  
  • 5.2 Shells and Orbitals.
  
  
  • 5.3 Filling electron shells.
  
  
  • 5.4 Octet rule.
  
  
  • 5.5 Hybridization.
  
  
  
  


• 6 Electronegativity


• 7 Electronegativity content from Wikipedia
  
  
  • 7.1 Pauling scale
  
  
  • 7.2 Mulliken scale
  
  
  • 7.3 Electronegativity trends
  
  
  
  


• 8 Bonding
  
  
  • 8.1 Ionic Bonding.
  
  
  • 8.2 Covalent Bonding
  
  
  • 8.3 Bond Polarity and Dipole Moment
  
  
  • 8.4 Van der Waals Bonding
  
  
  • 8.5 Organometallic Compounds and Bonding
  
  
  
  


• 9 Electron dot structures & formal charge
  
  
  • 9.1 Electron Dot Structures
  
  
  • 9.2 Formal Charge
  
  
  
  


• 10 Resonance Contents
  
  
  • 10.1 Resonance.
  
  
  • 10.2 Resonance Structures
  
  
  • 10.3 Key characteristics.
  
  
  • 10.4 What resonance is not.
  
  
  • 10.5 History
  
  
  • 10.6 Examples
  
  
  • 10.7 See also
  
  
  • 10.8 References.
  
  
  
  


• 11 Acids and bases
  
  
  • 11.1 Arrhenius Definition: Hydroxide and Hydronium Ions
  
  
  • 11.2 Brønsted-Lowry Acids and Bases: Proton donors and acceptors.
  
  
  • 11.3 Lewis Acids and Bases: Electron donors and acceptors.
  
  
  • 11.4 Nucleophiles and Electrophiles
  
  
  • 11.5 pKaand Acidity
  
  
  
  


• 12 Unit 2: Alkanes and cycloalkanes


• 13 Introduction
  
  
  • 13.1 Introductory Definitions.
  
  
  • 13.2 Methane.
  
  
  • 13.3 Ethane
  
  
  
  


• 14 Drawing alkanes
  
  
  • 14.1 Line drawing shorthand
  
  
  
  


• 15 Conformations
  
  
  • 15.1 Newman projections
  
  
  • 15.2 Conformations and energy.
  
  
  • 15.3 Steric effects
  
  
  • 15.4 Entropy
  
  
  
  


• 16 Preparation of Alkanes


• 17 Properties of Alkanes
  
  
  • 17.1 Chemical properties
  
  
  
  


• 18 Introduction to Nomenclature
  
  
  • 18.1 Number of hydrogens to carbons
  
  
  • 18.2 Naming carbon chains up to twelve.
  
  
  • 18.3 Isomerism.
  
  
  • 18.4 Branched chains
  
  
  • 18.5 Constitutional isomers.
  
  
  • 18.6 Naming Alkanes
  
  
  • 18.7 IUPAC naming rules.
  
  
  • 18.8 Branched Substituents.
  
  
  • 18.9 Common system
  
  
  
  


• 19 See also Contents


• 20 Alkanes


• 21 Methane and carbon chains


• 22 Properties of alkanes


• 23 Drawing alkanes
  
  
  • 23.1 Branched alkanes.
  
  
  
  


• 24 Constitutional isomers


• 25 Naming alkanes


• 26 Cycloalkanes
  
  
  • 26.1 Naming cycloalkanes.
  
  
  • 26.2 Substituents
  
  
  • 26.3 Multicyclic alkanes.
  
  
  • 26.4 Stereochemistry
  
  
  • 26.5 Cyclohexane
  
  
  • 26.6 Other cycloalkanes
  
  
  
  


• 27 Newman projections and conformers


• 28 Conformations


• 29 Stereoisomers and chirality


• 30 Stereoisomers
  
  
  • 30.1 Cis-trans Isomerism
  
  
  • 30.2 Optical Isomerism
  
  
  
  


• 31 Unit 3: Stereochemistry


• 32 Chirality
  
  
  • 32.1 Introduction
  
  
  • 32.2 Chiral Compounds With Stereocenters.
  
  
  • 32.3 Naming conventions
  
  
  • 32.4 Chiral Compounds Without Stereocenters
  
  
  • 32.5 Properties of optical isomers
  
  
  • 32.6 Chirality in biology
  
  
  • 32.7 Chirality in inorganic chemistry.
  
  
  • 32.8 More definitions
  
  
  • 32.9 Enantiopure preparations
  
  
  • 32.10 Enantiopure medications
  
  
  • 32.11 See also
  
  
  
  


• 33 Optical activity
  
  
  • 33.1 Optical Activity
  
  
  • 33.2 What Is Plane Polarized Light?. Contents
  
  
  • 33.3 Why Polarized Light Is Affected
  
  
  • 33.4 Enantiomers
  
  
  • 33.5 History
  
  
  
  


• 34 Enantiomers
  
  
  • 34.1 Enantiomers
  
  
  
  


• 35 Meso compounds
  
  
  • 35.1 Meso Compounds
  
  
  • 35.2 Definition of Meso
  
  
  • 35.3 Plane of Symmetry.
  
  
  • 35.4 Example of a Meso Compound
  
  
  
  


• 36 Diastereomers


• 37 Diastereomers
  
  
  • 37.1 Cis-trans Isomerism
  
  
  • 37.2 E/Z notation
  
  
  
  


• 38 Diastereomers with stereocenters
  
  
  • 38.1 Carbohydrates
  
  
  
  


• 39 Diastereoselectivity


• 40 Configurations
  
  
  • 40.1 Configuration and conformation
  
  
  
  


• 41 R-S notational system
  
  
  • 41.1 R and S Notation
  
  
  • 41.2 E-Z notation
  
  
  
  


• 42 Unit 4: Haloalkanes


• 43 Preparation


• 44 Properties
  
  
  • 44.1 Naming Haloalkanes
  
  
  • 44.2 Physical properties.
  
  
  • 44.3 Chemical properties
  
  
  
  


• 45 Reactions
  
  
  • 45.1 Substitution reactions of haloalkanes.
  
  
  • 45.2 Grignard reagents
  
  
  • 45.3 Elimination reactions
  
  
  
  


• 46 Unit 5: Alcohols


• 47 Preparation


• 48 Properties Contents
  
  
  • 48.1 Naming alcohols
  
  
  • 48.2 Acidity
  
  
  • 48.3 Alkoxides
  
  
  
  


• 49 Reactions
  
  
  • 49.1 Conversion of alcohols to haloalkanes
  
  
  • 49.2 Oxidation of alcohols.
  
  
  
  


• 50 Unit 6: Amine


• 51 Unit 7: Alkenes


• 52 Naming Alkenes
  
  
  • 52.1 EZ Notation
  
  
  
  


• 53 Properties
  
  
  • 53.1 Diastereomerism
  
  
  
  


• 54 Relative stability


• 55 Reactions
  
  
  • 55.1 Preparation
  
  
  • 55.2 Markovnikov’s Rule
  
  
  • 55.3 Addition reactions
  
  
  
  


• 56 Substitution and Elimination Reaction Mechanisms
  
  
  • 56.1 Nucleophilic Substitution Reactions
  
  
  • 56.2 Elimination Reactions
  
  
  
  


• 57 References


• 58 Unit 8: Alkynes


• 59 The triple carbon-carbon bond


• 60 Alkyne properties


• 61 Naming alkynes


• 62 Cycloalkynes


• 63 Alkyne reactions


• 64 Unit 9: Dienes


• 65 Kinds of dienes


• 66 Conjugation


• 67 Diene properties and reactions Contents
  
  
  • 67.1 Hydrobromination:.
  
  
  • 67.2 Diels-Alder Reaction.
  
  
  
  


• 68 Unit 10: Aromatics


• 69 History of Aromatics


• 70 Benzene Structure
  
  
  • 70.1 Benzene Properties.
  
  
  • 70.2 Benzene Health Effects
  
  
  
  


• 71 Aromaticity
  
  
  • 71.1 Definition.
  
  
  • 71.2 Theory
  
  
  • 71.3 Characteristics
  
  
  
  


• 72 Monosubstituted Benzenes
  
  
  • 72.1 Effects of Different Substituents
  
  
  • 72.2 Activating Substituents
  
  
  • 72.3 Deactivating Substituents
  
  
  • 72.4 Activation vs. Deactivation and ortho/para vs. meta directing
  
  
  • 72.5 Detailed Effects of Substituents.
  
  
  
  


• 73 Polysubstituted Benzenes
  
  
  • 73.1 Competition Between Functional Groups
  
  
  • 73.2 Naming Conventions.
  
  
  
  


• 74 Aromatics in history


• 75 Benzene structure


• 76 Benzene properties


• 77 Overview of electrophilic aromatic substitution reactions


• 78 Friedel-Crafts alkylation


• 79 Friedel-Crafts acylation


• 80 Aromatic reactions


• 81 Redox
  
  
  • 81.1 Birch reduction.
  
  
  • 81.2 Oxidation of Benzene in the Human Body.
  
  
  
  


• 82 Nucleophilic Aromatic Substitution
  
  
  • 82.1 Leaving Groups.
  
  
  • 82.2 Rate of Reaction
  
  
  • 82.3 Types of Reactions.
  
  
  
  


• 83 Electrophilic Aromatic Substitution Contents
  
  
  • 83.1 Step 1: Formation of aπ-complex
  
  
  • 83.2 Step 2: Formation of aσ-complex
  
  
  • 83.3 Step 3: Formation of a Substituted product
  
  
  
  


• 84 External links


• 85 References


• 86 Unit 11: Ketones and aldehydes
  
  
  • 86.1 Naming Aldehydes and Ketones
  
  
  • 86.2 Boiling Points and Bond Angles
  
  
  • 86.3 Preparing Aldehydes and Ketones
  
  
  • 86.4 Keto-enol tautomerism.
  
  
  • 86.5 Reactions of Aldehydes and Ketones
  
  
  • 86.6 Inductive Effect and Greek letter assignment
  
  
  
  


• 87 Unit 12: Carboxylic acids


• 88 Preparation


• 89 Properties
  
  
  • 89.1 Nomenclature.
  
  
  • 89.2 Acidity
  
  
  
  


• 90 Reactions
  
  
  • 90.1 Acid Chloride Formation
  
  
  • 90.2 Esterification
  
  
  • 90.3 Anhydrides
  
  
  • 90.4 Amides
  
  
  • 90.5 Acid Decarboxylation
  
  
  • 90.6 Ethanoic anhydride
  
  
  • 90.7 Polyester
  
  
  • 90.8 Distinguishing carboxylic acids from phenols
  
  
  
  


• 91 Unit 13: Carboxylic acid derivatives
  
  
  • 91.1 Structure
  
  
  • 91.2 Nomenclature.
  
  
  • 91.3 Structure and Reactivity
  
  
  • 91.4 Reactions of Carboxylic Acids and Their Derivatives
  
  
  
  


• 92 Unit 14: Analytical techniques


• 93 Elemental analysis


• 94 Chromatography


• 95 Theory


• 96 Paper chromatography


• 97 Thin layer chromatography Contents


• 98 Gas chromatography


• 99 Column chromatography


• 100 Detection methods


• 101 Spectroscopy
  
  
  • 101.1 UV/Visible Spectroscopy
  
  
  • 101.2 NMR Spectroscopy.
  
  
  
  


• 102 Mass Spectroscopy


• 103 Infrared spectroscopy.
  
  
  • 103.1 Summary of absorptions of bonds in organic molecules.
  
  
  • 103.2 Typical method.
  
  
  
  


• 104 References & notes


• 105 Unit 15: Organometallics
  
  
  • 105.1 Main group organometallic chemistry
  
  
  • 105.2 Transition-metal organometallic chemistry.
  
  
  • 105.3 Catalysis by organometallic compounds
  
  
  • 105.4 Organometallics in living systems.
  
  
  
  


• 106 Appendix A: Introduction to reactions


• 107 How to write organic reactions
  
  
  • actions 108 Overview of addition, elimination, substitution and rearrangement re-
  
  
  • 108.1 Some basic reaction types
  
  
  • 108.2 Addition reaction.
  
  
  • 108.3 Elimination reaction
  
  
  • 108.4 Substitution reactions
  
  
  • 108.5 Rearrangement reactions
  
  
  
  


• 109 Polar and radical reactions
  
  
  • 109.1 Polar reactions
  
  
  • 109.2 Radical reactions.
  
  
  
  


• 110 Redox reactions


• 111 Functional groups in reactions


• 112 Drawing reactions
  
  
  • 112.1 Drawing reactions
  
  
  • 112.2 Arrows
  
  
  
  


• 113 Rates and equilibria Contents
  
  
  • 113.1 Rate of reaction
  
  
  • 113.2 Equilibrium.
  
  
  
  


• 114 Gibbs free energy


• 115 Bond dissociation energy


• 116 Energy diagrams


• 117 Transition states
  
  
  • 117.1 Transition State
  
  
  • 117.2 Intermediate Molecules
  
  
  • 117.3 Energy Diagrams and Transition States
  
  
  
  


• 118 Carbocations
  
  
  • 118.1 Carbocation Structure
  
  
  • 118.2 Carbocation Stability
  
  
  • 118.3 Formation of Carbocations
  
  
  • 118.4 Reactions of Carbocations.
  
  
  
  


• 119 Electrophilic additions


• 120 Zaitsev’s rule


• 121 Oxidation


• 122 Radicals
  
  
  • 122.1 Radical stability
  
  
  
  


• 123 Rearrangement reactions
  
  
  • 123.1 Sigmatropic arrangements
  
  
  
  


• 124 Pericyclic reactions


• 125 Diels-Alder reaction


• 126 Epoxide


• 127 Appendix B: Index of reactions


• 128 Appendix C: Introduction to functional groups


• 129 Overview of Functional Groups
  
  
  • 129.1 Introduction
  
  
  • 129.2 Memorizing Functional Groups
  
  
  • 129.3 Mnemonics for Functional Groups
  
  
  
  


• 130 Other appendices


• 131 Glossary Contents
  
  
  • 131.1 A
  
  
  • 131.2 B.
  
  
  • 131.3 C
  
  
  • 131.4 D
  
  
  • 131.5 E.
  
  
  • 131.6 F.
  
  
  • 131.7 G
  
  
  • 131.8 H
  
  
  • 131.9 I
  
  
  • 131.10 K
  
  
  • 131.11 L.
  
  
  • 131.12 M
  
  
  • 131.13 N
  
  
  • 131.14 O
  
  
  • 131.15 P.
  
  
  • 131.16 Q
  
  
  • 131.17 R
  
  
  • 131.18 S.
  
  
  • 131.19 T
  
  
  • 131.20 U
  
  
  • 131.21 V
  
  
  • 131.22 W, X, Y, Z
  
  
  
  


• 132 Short periodic table


• 133 External links


• 134 Resources


• 135 Other online textbooks


• 136 Contributors


• List of Figures


• 137 Licenses
  
  
  • 137.1 GNU GENERAL PUBLIC LICENSE
  
  
  • 137.2 GNU Free Documentation License
  
  
  • 137.3 GNU Lesser General Public License