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Organic Chemistry

Chapter 0 Students Guide to Succcess in Organic Chemistry
0.1 What is Organic Chemistry?
0.2 Organic Chemistry in the Everyday World
0.3 Organic Chemists are People, Too
0.4 Learning to Think Like a Chemist
0.5 Developing Study Methods for Success

Chapter 1 Atoms, Orbitals, and Bonds
1.1 The Periodic Table
1.2 Atomic Structure
1.3 Energy Levels and Atomic Orbitals
1.4 How Electrons Fill Orbitals
1.5 Bond Formation
1.6 Molecular Orbitals
1.7 Orbital Hybridization
1.8 Multiple Bonding
1.9 Drawing Lewis Structures
1.10 Polar Covalent Bonds
1.11 Inductive Effects on Bond Polarity
1.12 Formal Charges
1.13 Resonance

Chapter 2 Introduction to Organic Nomenclature and Functional Groups
2.1 Drawing Organic Structures
2.2 Alkanes
2.3 Structural Isomerism
2.4 IUPAC Nomenclature
2.5 Naming Alkanes
2.6 Naming Cycloalkanes
2.7 Naming Complex Alkyl Groups
2.8 Functional Groups
2.9 Naming Alkenes and Alkynes
2.10 Naming Alkenes, Part II
2.11 Arenes
2.12 Organohalogens
2.13 Using Molecular Formulas

Chapter 3 Molecular Conformations
3.1 Representing Three-Dimensional Molecules in Two Dimensions
3.2 Dihedral Angles
3.3 The Conformations of Ethane
3.4 Conformational Analysis of Butane
3.5 Angle Strain in Cycloalkanes
3.6 Conformations of Cyclohexane
3.7 Conformational Inversion of Cyclohexane
3.8 Conformational Analysis of Monosubstituted Cyclohexanes
3.9 Naming Stereoisomers
3.10 Conformational Analysis of Disubstituted Cyclohexanes Special Topic – Computer Modeling
3.11 Conformations of Other Cycloalkanes
3.12 Naming Polycyclic Ring Systems
3.13 Polycyclic Ring Systems
Sidebar – Higher Polycyclic Structures

Chapter 4 Physical Properties of Organic Compounds
4.1 Phases of Matter
Sidebar – Liquid Crystals
4.2 Melting Points
4.3 Boiling Points
4.4 Solubility
Sidebar – Surfactants
4.5 Density

Chapter 5 Acid-Base Theory
5.1 Acids and Bases
5.2 Acid and Base Strength
5.3 Hard and Soft Acids and Bases
5.4 Organic Acids and Bases
5.5 Relative Acidity and Basicity
5.6 Substituent Effects on Acidity and Basicity

Chapter 6 Reaction Mechanisms
An Overview of Organic Chemistry
6.1 Chemical Equilibria and Rates
6.2 Equilibrium Thermodynamics
6.3 Reaction Kinetics
6.4 Reaction Profiles and Mechanisms
6.5 Why Reactions Occur
6.6 Organic Reaction Terminology
6.7 Classification of Reagents in Organic Reactions
6.8 Writing Reaction Mechanisms
6.9 Substitution Reactions
6.10 Addition Reactions
6.11 Elimination Reactions

Chapter 7 Nucleophilic Additions to the Carbonyl Group
7.1 Naming Carbon—Oxygen Double Bonds
7.2 Reactivity of the Carbonyl Group
7.3 Guide for Learning Organic Reactions
7.4 The Cyanohydrin Reaction
7.5 Addition of Water and Alcohols
7.6 Reaction with Nitrogen Nucleophiles
Sidebar – Biochemical Transamination
7.7 Reaction with Hydride Nucleophiles
7.8 Carbon Nucleophiles
Synthesis of Triphenylmethanol
7.9 Organic Synthesis
7.10 The Wittig Reaction
Synthesis of Methylene-4-tert-butylcyclohexane

Chapter 8-A Reaction Summary I
A summary of the reactions learned in Chapters 7-8

Chapter 8 Nucleophilic Substitution on the Carbonyl Group
8.1 The Acyl Transfer Mechanism
8.2 Water and Alcohol Nucleophiles
Synthesis of Isoamyl Acetate (Banana Oil)
8.3 Halide and Carboxylic Acid Nucleophiles
Sidebar – Aspirin and Acetaminophen
8.4 Reaction with Nitrogen Nucleophiles
8.5 Reaction with the Hydride Nucleophile
8.6 Carbon Nucleophiles
8.7 Nitriles
8.8 The Baeyer-Villiger Oxidation
Synthesis of Caprolactone
8.9 Solving Mechanistic Problems

Chapter 9 Infrared Spectroscopy and Mass Spectrometry
9.1 Electromagnetic Radiation and Spectroscopy
9.2 Molecular Vibrations in Infrared Spectroscopy
9.3 Introduction to Interpreting Infrared Spectra
9.4 Hydrogen Bonded to sp3 Hybrid Atoms
9.5 Hydrogen Bonded to sp2 and sp Hybrid Atoms
9.6 Carbon—Heteroatom Bonds
9.7 Other Bonds
9.8 Interpreting Infrared Spectra, Part 2
9.9 Mass Spectrometry
9.10 The Molecular Ion

Chapter 10 Nuclear Magnetic Resonance
10.1 Theory of Nuclear Magnetic Resonance
10.2 Shielding
10.3 Chemical Shift and Molecular Structure
10.4 Interpreting Proton NMR Spectra
10.5 Spin-Spin Splitting
10.6 Integration Signals in an NMR Spectrum
10.7 Analyzing an NMR Spectrum
Sidebar – Magnetic Resonance Imaging
10.8 Strategy for Solving Spectral Problems

Chirality
11.1 Symmetry and Asymmetry
11.2 Nomenclature of Stereocenters
11.3 Properties of Asymmetric Molecules
Sidebar – Chiral Recognition
11.4 Optical Isomerism
11.5 Fisher Projections
11.6 Molecules with Two Stereocenters
11.7 Resolution of Enantiomers
11.8 Stereocenters Other than Carbon
Key Ideas from Chapter 11

Chapter 12 Aliphatic Nucleophilic Substitution
12.1 Naming Single Bonded Heteroatom Functional Groups
12.2 Comparing Nucleophilic Substitution Reaction Mechanisms
12.3 The SN1 and SN2 Reaction Mechanisms
12.4 Stereochemistry of Nucleophilic Substitutions
12.5 The Substrate
12.6 Nucleophiles and Leaving Groups
12.7 Common Nucleophiles
12.8 The Reaction Medium
12.9 SN1 versus SN2
12.10 Halide Nucleophiles
Synthesis of 1-Bromobutane
12.11 Oxygen Nucleophiles
12.12 Nitrogen Nucleophiles
Synthesis of 2,5-Diaminoadipic Acid
12.13 Carbon Nucleophiles
12.14 Neighboring Group Participation
Special Topic – SN1 vs. SN2

Chapter 13 Elimination Reactions
13.1 The Elimination Mechanisms
13.2 Stereochemistry of Eliminations
13.3 Direction of Elimination
13.4 E1 vs. E2
13.5 Elimination vs. Substitution
13.6 Summary of Elimination and Substitution
13.7 E & Z Nomenclature
13.8 Elimination of Organohalogens
13.9 Dehydration of Alcohols
Synthesis of Cyclohexene
13.10 Pinacol Rearrangement
13.11 Hofmann Elimination
13.12 Oxidation of Alcohols
Synthesis of Citronellal

Chapter 14 Electrophilic Addition to Unsaturated Carbons
14.1 Addition Reaction Mechanisms
14.2 Direction and Stereochemistry of Addition Reactions
14.3 Addition of Hydrogen Halides
14.4 Addition of Water and Alcohols
14.5 Hydroboration-Oxidation
Synthesis of (-)-Isopinocampheol
14.6 Electrophilic Addition of Halogens
14.7 Addition of Hydrogen
14.8 Dihydroxylation Reactions
14.9 Addition of Carbenes
Synthesis of 7,7-Dichlorobicyclo[4.1.0]heptane
14.10 Oxidation of Alkenes

Chapter 15 Organic Synthesis
15.1 Synthesis Design and Strategy
15.2 Principles of Retrosynthetic Analysis
15.3 Protecting Groups
Synthesis of the Ethylene Glycol Acetal of Cyclohexanone
15.4 Lithium Dialkylcuprate Reagents
Synthesis of trans-Stilbene
15.5 A Synthetic Example
15.6 Synthesis of Difunctional Compounds

Chapter 16 Conjugation and Resonance
16.1 Naming Compounds with Multiple Functionaln Groups
16.2 Conjugated Dienes
16.3 The Allyl Group and Resonance
16.4 Conjugate Addition Reactions
Special Topic – Ultraviolet Spectroscopy
16.5 Double Bonds Conjugated With Carbonyl Groups
Sidebar – The Chemistry of Vision
16.6 The Diels-Alder Reaction
Synthesis of cis-Norbornene-5,6-endo-dicarboxylic Anhydride
16.7 Orbital Symmetry and the Diels-Alder Reaction
16.8 Synthesis with the Diels-Alder Reaction

Chapter 17 Aromaticity
17.1 Benzene
Sidebar – Diamond, Graphite, and Buckyballs
17.2 The Stability of Benzene
17.3 Molecular Orbitals in Benzene
17.4 The Molecular Orbitals of Cyclobutadiene
17.5 Aromaticity
17.6 Hückel’s Rule
17.7 Aromatic Ions
17.8 Naming Benzene Derivatives
17.9 Aromatic Heterocyclic Compounds
17.10 Polynuclear Aromatic Hydrocarbons
17.11 The Benzyl Group

Chapter 18 Aromatic Substitution Reactions
18.1 Mechanism of Aromatic Electrophilic Substitution
18.2 The Nitration of Benzene
18.3 Halogenation and Sulfonation of Benzene
18.4 Friedel-Crafts Alkylation and Acylation
18.5 Effects of Monosubstituted Arenes on Substitution
18.6 Rate Effects with Monosubstituted Arenes
18.7 Classification of Substituents
18.8 Friedel-Crafts Acylation
Synthesis of o-Benzoylbenzoic Acid
18.9 Multiple Substituent Effects
18.10 Substitution on Polycyclic Arenes
18.11 Diazotization
Synthesis of Methyl Orange
Sidebar – Sulfa Drugs
18.12 Other Diazonium Salt Reactions
18.13 Nucleophilic Aromatic Substitution
18.14 Benzyne
Synthesis of Trypticene
18.15 Synthesis Examples

Chapter 19 a Substitution on Carbonyl Compounds
19.1 Keto-Enol Tautomerism
19.2 Enols and Enolate Ions
19.3 The Mechanism of a Substitution
19.4 a Halogenations
Synthesis of 2-Bromocholestanone
19.5 Alkylation of Enolate Ions
19.6 Stabilized Enolate Ions
Sidebar – Barbiturates 1
19.7 Enamine Reaction
Synthesis of 2-Acetylcyclohexanone
19.8 Silyl Enol Ethers
19.9 1,3-Dithianes

Chapter 20  Carbonyl Condensation Reactions
20.1 The Carbonyl Condensation Mechanism
20.2 Carbonyl Condensation Vs a Substitution
Sidebar – Borodin and Aldehydes
20.3 Mixed Aldol Condensations
20.4 Intramolecular Aldol Condensations
Synthesis of 1,5-Diphenyl-1,4-pentadien-3-one
20.5 The Claisen Condensation
Sidebar – Biochemical Carbonyl Condensation Reactions
20.6 The Dieckmann Cyclization
20.7 The Michael Addition Reaction
20.8 The Robinson Annulation Reaction
Synthesis of 4,4-Dimethyl-2-cyclohexen-2-one
20.9 Carbonyl Condensations in Synthesis

Chapter 21 Radical Reactions
21.1 Radical Structure and Stability
21.2 Halogenation of Alkanes
Sidebar – Atmospheric Ozone Depletion
21.3 Allylic Bromination
21.4 Benzylic Bromination
Synthesis of 1-Bromo-1-phenylethane
21.5 Radical Addition to Alkenes
21.6 Radical Oxidations
21.7 Radical Reductions
Synthesis of 1-Methoxy-1,4-cyclohexadiene
Special Topic – Electron Spin Resonance Spectroscopy

Chapter 22 Polymer Chemistry
22.1 Structural Characteristics of Polymers
22.2 Polymer Nomenclature
22.3 Types of Polymerization Reactions
22.4 Chain-Growth Polymerization
Synthesis of Poly(vinyl acetate)
Sidebar – Natural Rubber
22.5 Controlling Stereochemistry in Vinyl Polymers
22.6 Nonvinyl Chain-Growth Polymerization
22.7 Step-Growth Polymerization
Synthesis of Poly(ethylene terephthalate)
Sidebar – Plastic Recycling
22.8 Copolymers
Sidebar – Plasticizers
22.9 Cross-Linked Polymers

Chapter 24 Carbohydrates
24.1 Classification of Carbohydrates
24.2 Monosaccharides
24.3 Cyclic Forms of Monosaccharides
Sidebar – The Sweet Taste
24.4 Reactions of Monosaccharides
24.5 Oxidation and Reduction Reactions
24.6 Changing the Chain Length
24.7 Fischer Proof of Glucose Structure
24.8 Glycolysis – I
24.9 Glycolysis – II
Sidebar – Arsenic Poisoning
24.10 Glycoside Formation
24.11 Disaccharides
24.12 Polysaccharides
Key Ideas from Chapter 24

Chapter 25 Nucleic Acids
25.1 Nucleosides and Nucleotides
25.2 Laboratory Synthesis of Nucleotides and Nucleosides
25.3 Nucleic Acids
25.4 Replication of DNA
Sidebar – The Polymerase Chain Reaction
25.5 Structure and Biosynthesis of RNA
25.6 RNA and Peptide Biosynthesis
25.7 Sequencing of DNA
25.8 Laboratory Nucleic Acid Synthesis
Sidebar – Self Replicating Organic Compounds

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