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Organic Chemistry I

Topics include bonding principles, intermolecular forces, nomenclature, isomerism, stereochemistry; synthesis and reactions of alkanes, alkenes, alkynes, alcohols, alkyl halides, and functional groups. Addition, elimination, rearrangement and substitution mechanisms. Also an introduction to aromatic compounds, polymers, lipids, carbohydrates, proteins, and nucleic acids.

Chemistry

Author: Sridhar Budhi
Publisher: Indiana Institute of Technology
Source: LibreTexts
Language: EN
Category: Basic Sciences

Read online Download PDF (open licence)

Contents· 228 sections

01: Electronic Structure and Covalent Bonding
1.01: The Structure of an Atom
1.02: How Electrons in an Atom are Distributed
1.03: Ionic and Covalent Bonds
1.04: How the Structure of a Compound is Represented
1.05: Atomic Orbitals
1.06: How atoms form Covalent Bonds
1.07: How Single Bonds Are Formed in Organic Compounds
1.08: How a Double Bond is Formed- The Bonds in Ethene
1.09: How a Triple Bond is Formed- The Bonds in Ethyne
1.10: Bonding in the Methyl Cation the Methyl Radical and the Methyl Anion
1.11: The Bonds in Water
1.12: The Bonds in Ammonia and in the Ammonium Ion
1.13: The Bond in a Hydrogen Halide
1.14: Summary- Hybridization Bond Lengths Bond Strengths and Bond Angles
1.15: The Dipole Moments of Molecules
1.16: An Introduction to Acids and Bases
1.17: pka and pH
1.18: 1.18 Organic Acids and Bases
1.19: How to Predict the Outcome of an Acid-Base Reaction
1.20: How to Determine the Position of Equilibrium
1.21: How the Structure of an Acid Affects its pka Value
1.22: How Substituents Affect the Strength of an Acid
1.23: An Introduction to Delocalized Electrons
1.24: A Summary of the Factors that Determine Acid Strength
1.25: How pH Affects the Structure of an Organic Compound
1.26: Buffer Solutions
1.27: Lewis Acids and Bases
02: Acids and Bases
2.01: An Introduction to Acids and Bases
2.02: pka and pH
2.03: Organic Acids and Bases
2.04: How to Predict the Outcome of an Acid-Base Reaction
2.05: How to Determine the Position of Equilibrium
2.06: How the Structure of an Acid Affects its pka Value
2.07: How pH Affects the Structure of an Organic Compound
2.08: Buffer Solutions
2.09: Lewis Acids and Bases
03: An Introduction to Organic Compounds- Nomenclature Physical Properties and Representation of Structure
3.01: How Alkyl Substituents Are Named
3.02: The Nomenclature of Alkanes
3.03: The Nomenclature of Cycloalkanes Skeletal Structures
3.04: The Nomenclature of Alkyl Halides
3.05: The Structures of Alkyl Halides Alcohols Ethers and Amines
3.06: The Physical Properties of Alkanes Alkyl Halides Alcohols Ethers and Amines
3.07: Rotation Occurs About Carbon-Carbon Single Bonds
3.08: Some Cycloalkanes Have Angle Strain
3.09: Conformers of Cyclohexane
3.10: Conformers of Monosubstituted Cyclohexanes
3.11: Conformers of Disubstituted Cyclohexanes
3.12: Fused Cyclohexane Rings
04: Alkenes- Structure Nomenclature and an Introduction to Reactivity
4.01: Molecular Formulas and the Degree of Unsaturation
4.02: The Nomenclature of Alkenes
4.03: The Structures of Alkenes
4.04: Alkenes Can Have Cis and Trans Isomers
4.05: Naming Alkenes Using the E Z System
4.06: How Alkenes React (Curved Arrows Show the Flow of Electrons)
4.07: A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction
05: The Reactions of Alkenes and Alkynes- An Introduction to Multistep Synthesis
5.01: The Addition of a Hydrogen Halide to an Alkene
5.02: Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon
5.03: Electrophilic Addition Reactions Are Regioselective
5.04: The Addition of Water to an Alkene
5.05: The Addition of an Alcohol to an Alkene
5.06: The Nomenclature of Alkynes
5.07: The Structure of Alkynes
5.08: The Physical Properties of Unsaturated Hydrocarbons
5.09: The Addition of Hydrogen Halides and Addition of Halogens to an Alkyne
5.10: The Addition of Hydrogen to Alkenes and Alkynes
5.11: A Hydrogen Bonded to an sp Carbon is Acidic
5.12: Synthesis Using Acetylide Ions
5.13: An Introduction to Multistep Synthesis
06: Isomers and Stereochemistry
6.01: Cis-Trans Isomers Result from Restricted Rotation
6.02: A Chiral Object Has a Nonsuperimposable Mirror Image
6.03: An Asymmetric Center Is a Cause of Chirality in a Molecule
6.04: Isomers with One Asymmetric Center
6.05: Asymmetric Centers and Stereocenters
6.06: How to Draw Enantiomers
6.07: Naming Enantiomers by the RS System
6.08: Chiral Compounds Are Optically Active
6.09: How Specific Rotation is Measured
6.10: Enantiomeric Excess
6.11: Isomers with More than One Asymmetric Center
6.12: Meso Compounds Have Asymmetric Centers but Are Optically Inactive
6.13: How to Name Isomers with More than One Asymmetric Center
6.14: Reactions of Compounds that Contain an Asymmetric Center
6.15: Using Reactions that Do Not Break Bonds to an Asymmetric Center to Determine Relative Configurations
6.16: How Enantiomers Can Be Separated
6.17: Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers
6.18: Stereochemistry of Reactions- Regioselective Stereoselective and Stereospecific Reactions
6.19: The Stereochemistry of Electrophilic addition Reactions of Alkenes
6.20: The Stereochemistry of Enzyme-Catalyzed Reactions
6.21: Enantiomers Can Be Distinguished by Biological Molecules
07: Delocalized Electrons and Their Effect on Stability Reactivity and pKa (Ultraviolet and Visible Spectroscopy)
7.01: Delocalized Electrons Explain Benzenes Structure
7.02: The Bonding in Benzene
7.03: Resonance Contributors and the Resonance Hybrid
7.04: How to Draw Resonance Contributors
7.05: The Predicted Stabilities of Resonance Contributors
7.06: Delocalized Energy Is the Additional Stability Delocalized Electrons Give to a Compound
7.07: Examples That Show How Delocalized Electrons Affect Stability
7.08: A Molecular Orbital Description of Stability
7.09: How Delocalized Electrons Affect pKa Values
7.10: Delocalized Electrons Can Affect the Product of a Reaction
7.11: Thermodynamic Versus Kinetic Control of Reactions
7.12: The Diels-Adler Reaction Is a 14-Addition Reaction
08: Aromaticity- Reactions of Benzene and Substituted Benzenes
8.01: The Two Criteria for Aromaticity
8.02: Applying the Criteria for Aromaticity
8.03: Aromatic Heterocyclic Compounds
8.04: The Nomenclature of Monosubstituted Benzenes
8.05: How Benzene Reacts
8.06: The General Mechanism for Electrophilic Aromatic Substitution Reactions
8.07: Halogenation of Benzene
8.08: Nitration of Benzene
8.09: Sulfonation of Benzene
8.10: The Friedel-Crafts Acylation of Benzene
8.11: The Friedel-Crafts Alkylation of Benzene
8.12: The Nomenclature of Disubstituted and Polysubstituted Benzenes
8.13: The Effect of Substituents on Reactivity
8.14: The Effect of Substituents on Orientation
8.15: The Effect of Substituents on pKa
09: Substitution and Elimination Reactions of Alkyl Halides
9.01: How Alkyl Halides React
9.02: The Mechanism For an (S N2) Reaction
9.03: Factors That Affect (S N2) Reactions
9.04: The Mechanism for an (S N1) Reaction
9.05: Factors That Affect (S N1) Reactions
9.06: Comparing the (S N2) and (S N1) Reactions of Alkyl Halides
9.07: Elimination Reaction of Alkyl Halides
9.08: Products of Elimination Reactions
9.09: Comparing the E2 and E1 Reactions of Alkyl Halides
9.10: Does an Alkyl Halide Undergo SN2 E2 Reactions or SN1 Reactions
9.11: Does an Alkyl Halide Undergo SN2 E2 Reactions or SN1 E1 Reactions
9.12: Solvent Effects
9.13: Using Substitution Reactions to Synthesize Organic Compounds
9.14: Biological Methylating Reagents
10: Reactions of Alcohols Amines Ethers and Epoxides
10.01: Nomenclature of Alcohols
10.02: Substitution Reactions of Alcohols
10.03: Elimination Reactions of Alcohols- Dehydration
10.04: Oxidation of Alcohols
10.05: Amines Do Not Undergo Substitution or Elimination Reactions
10.06: Nomenclature of Ethers
10.07: Nucleophilic Substitution Reactions of Ethers
10.08: Nucleophilic Substitution Reactions of Epoxides
10.09: Using Carbocation Stability to Determine the Carcinogenicity of an Arene Oxide
11: Carbonyl Compounds I- Reactions of Carboxylic Acids and Carboxylic Derivatives
11.01: The Nomenclature of Carboxylic Acids and Carboxylic Acid Derivatives
11.02: The Structures of Carboxylic Acids and Carboxylic Acid Derivatives
11.03: The Physical Properties of Carbonyl Compounds
11.04: Carboxylic Acids and Carboxylic Acid Derivatives found in Nature
11.05: How Carboxylic Acids and Carboxylic Acids Compounds React
11.06: Relative Reactivities of Carboxylic Acids and Carboxylic Acid Derivatives
11.07: Reactions of Acyl Halides
11.08: Reactions of Esters
11.09: Acid-Catalyzed Ester Hydrolysis
11.10: Soaps Detergents and Micelles
11.11: Reactions of Carboxylic Acids
11.12: Reactions of Amides
11.13: Acid-Catalyzed Amide Hydrolysis
11.14: The Synthesis of Carboxylic Acid Derivatives
11.15: Nitriles
12: Carbonyl Compounds II- Reactions of Aldehydes and Ketones More Reactions of Carboxylic Acid Derivatives
12.01: The Nomenclature of Aldehydes and Ketones
12.02: The Relative Reactivities of Carbonyl Compounds
12.03: How Aldehydes and Ketones React
12.04: Gringard Reagents
12.05: Reactions of Carbonyl Compounds with Hydride Ion
12.06: Reactions of Aldehydes and Ketones with Amines
12.07: Reactions of Aldehydes and Ketones with Water
12.08: Reactions of Aldehydes and Ketones with Alcohols
12.09: Nucleophilic Addition to - Unsaturated Carboxylic Acid Derivatives
12.10: Nucleophilic Addition to - Unsaturated Carbonyl Compounds
12.11: Protecting Groups
12.12: Addition of Sulfur Nucleophiles
12.13: The Wittig Reaction Forms an Alkene
12.14: Stereochemistry of Nucleophilic Addition Reactions- Re and Si Faces
12.15: Designing a Synthesis VI- Disconnections Synthons and Synthetic Equivalents
12.16: Enzyme-Catalyzed Additions to - Unsaturated Carbonyl Compounds
13: Carbonyl Compounds III- Reactions at the - Carbon
13.01: Alkylation and Acylation of the -Carbon Using an Enamine Intermediate
13.02: Alkylation of the -Carbon- The Michael Reaction
13.03: An Aldol Addition Forms -Hydroxaldehydes or -Hydroxyketones
13.04: Dehydration of Aldol Addition Products Form -Unsaturated Aldehydes and Ketones
13.05: The Crossed Aldol Addition
13.06: A Claisen Condensation Forms a -Keto Ester
13.07: Other Crossen Condensations
13.08: Intramolecular Condensation and Addition Reactions
13.09: The Robinson Annulation
13.10: Carboxylic Acids with a Carbonyl Group at the 3-Position can be Decarboxylated
13.11: The Acidity of an - Hydrogen
13.12: The Malonic Ester Synthesis- A Way to Synthesize a Carboxylic Acid
13.13: The Acetoacetic Ester Synthesis- A Way to Synthesize a Methyl Ketone
13.14: Designing a Synthesis VII- Making New Carbon-Carbon Bonds
13.15: Reactions at the -Carbon in Biological Systems
13.16: Keto-Enol Tautomers
13.17: Keto-Enol Interconversion
13.18: How Enolate Ions and Enols React
13.19: Halogenation of the - Carbon and Aldehydes and Ketones
13.20: Halogenation of the - Carbon of Carboxylic Acids- The Hell-Volhard-Zelinski Reaction
13.21: - Halogenated Carbonyl Compounds Are Useful in Synthesis
13.22: Using LDA to Form an Enolate Ion
13.23: Alkylating the -Carbon of Carbonyl Compounds
14: Determing the Structure of Organic Compounds
15: The Organic Chemistry of Carbohydrates
15.01: Classification of Carbohydrates
15.02: The D and L Notation
15.03: The Configurations of Aldoses
15.04: The Configurations of Ketoses
15.05: The Reactions of Monosaccharides in Basic Solutions
15.06: The Oxidation-Reduction Reactions of Monosaccharides
15.07: Monosaccharides form Crystalline Osazones
15.08: Lengthening the Chain- The Kiliani-Fischer Synthesis
15.09: Shortening the Chain- The Wohl Degradation
15.10: The Stereochemistry of Glucose- The Fischer Proof
15.11: Monosaccharides Form Cyclic Hemiacetals
15.12: Glucose is the Most Stable Aldohexose
15.13: Formation of Glycosides
15.14: The Anomeric Effect
15.15: Reducing and Nonreducing Sugars
15.16: Disaccharides
15.17: Polysaccharides
15.18: Some Naturally Occurring Products Derived from Carbohydrates
15.19: Carbohydrates on Cell Surfaces
15.20: Synthetic Sweeteners