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🥼Organic Chemistry

Unit 1 - Structure and Bonding

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1.1

Atomic Structure: The Nucleus

3 min read

1.2

Atomic Structure: Orbitals

3 min read

1.3

Atomic Structure: Electron Configurations

3 min read

1.4

Development of Chemical Bonding Theory

4 min read

1.5

Describing Chemical Bonds: Valence Bond Theory

3 min read

1.6

sp3 Hybrid Orbitals and the Structure of Methane

2 min read

1.7

sp3 Hybrid Orbitals and the Structure of Ethane

3 min read

1.8

sp2 Hybrid Orbitals and the Structure of Ethylene

3 min read

1.9

sp Hybrid Orbitals and the Structure of Acetylene

2 min read

1.10

Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur

3 min read

1.11

Describing Chemical Bonds: Molecular Orbital Theory

3 min read

1.12

Drawing Chemical Structures

2 min read

Unit 2 - Polar Covalent Bonds; Acids and Bases

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2.1

Polar Covalent Bonds and Electronegativity

3 min read

2.2

Polar Covalent Bonds and Dipole Moments

3 min read

2.3

Formal Charges

2 min read

2.4

Resonance

3 min read

2.5

Rules for Resonance Forms

2 min read

2.6

Drawing Resonance Forms

4 min read

2.7

Acids and Bases: The Brønsted–Lowry Definition

2 min read

2.8

Acid and Base Strength

2 min read

2.9

Predicting Acid–Base Reactions from pKa Values

3 min read

2.10

Organic Acids and Organic Bases

2 min read

2.11

Acids and Bases: The Lewis Definition

2 min read

2.12

Noncovalent Interactions between Molecules

2 min read

Unit 3 - Organic Compounds: Alkanes and Their Stereochemistry

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3.1

Functional Groups

4 min read

3.2

Alkanes and Alkane Isomers

2 min read

3.3

Alkyl Groups

2 min read

3.4

Naming Alkanes

3 min read

3.5

Properties of Alkanes

2 min read

3.6

Conformations of Ethane

2 min read

3.7

Conformations of Other Alkanes

3 min read

Unit 4 - Organic Compounds: Cycloalkanes and Their Stereochemistry

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4.1

Naming Cycloalkanes

2 min read

4.2

Cis–Trans Isomerism in Cycloalkanes

2 min read

4.3

Stability of Cycloalkanes: Ring Strain

3 min read

4.4

Conformations of Cycloalkanes

3 min read

4.5

Conformations of Cyclohexane

3 min read

4.6

Axial and Equatorial Bonds in Cyclohexane

2 min read

4.7

Conformations of Monosubstituted Cyclohexanes

3 min read

4.8

Conformations of Disubstituted Cyclohexanes

2 min read

4.9

Conformations of Polycyclic Molecules

3 min read

Unit 5 - Stereochemistry at Tetrahedral Centers

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5.1

Enantiomers and the Tetrahedral Carbon

2 min read

5.2

The Reason for Handedness in Molecules: Chirality

3 min read

5.3

Optical Activity

3 min read

5.4

Pasteur’s Discovery of Enantiomers

2 min read

5.5

Sequence Rules for Specifying Configuration

3 min read

5.6

Diastereomers

2 min read

5.7

Meso Compounds

3 min read

5.8

Racemic Mixtures and the Resolution of Enantiomers

2 min read

5.9

A Review of Isomerism

2 min read

5.10

Chirality at Nitrogen, Phosphorus, and Sulfur

2 min read

5.11

Prochirality

2 min read

5.12

Chirality in Nature and Chiral Environments

3 min read

Unit 6 - An Overview of Organic Reactions

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6.1

Kinds of Organic Reactions

3 min read

6.2

How Organic Reactions Occur: Mechanisms

3 min read

6.3

Polar Reactions

3 min read

6.4

An Example of a Polar Reaction: Addition of HBr to Ethylene

2 min read

6.5

Using Curved Arrows in Polar Reaction Mechanisms

3 min read

6.6

Radical Reactions

3 min read

6.7

Describing a Reaction: Equilibria, Rates, and Energy Changes

4 min read

6.8

Describing a Reaction: Bond Dissociation Energies

2 min read

6.9

Describing a Reaction: Energy Diagrams and Transition States

4 min read

6.10

Describing a Reaction: Intermediates

3 min read

6.11

A Comparison Between Biological Reactions and Laboratory Reactions

3 min read

Unit 7 - Alkenes: Structure and Reactivity

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7.1

Industrial Preparation and Use of Alkenes

3 min read

7.2

Calculating the Degree of Unsaturation

3 min read

7.3

Naming Alkenes

2 min read

7.4

Cis–Trans Isomerism in Alkenes

3 min read

7.5

Alkene Stereochemistry and the E,Z Designation

3 min read

7.6

Stability of Alkenes

3 min read

7.7

Electrophilic Addition Reactions of Alkenes

2 min read

7.8

Orientation of Electrophilic Additions: Markovnikov’s Rule

2 min read

7.9

Carbocation Structure and Stability

3 min read

7.10

The Hammond Postulate

3 min read

7.11

Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements

3 min read

Unit 8 - Alkenes: Reactions and Synthesis

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8.1

Preparing Alkenes: A Preview of Elimination Reactions

2 min read

8.2

Halogenation of Alkenes: Addition of X2

3 min read

8.3

Halohydrins from Alkenes: Addition of HO-X

2 min read

8.4

Hydration of Alkenes: Addition of H2O by Oxymercuration

2 min read

8.5

Hydration of Alkenes: Addition of H2O by Hydroboration

2 min read

8.6

Reduction of Alkenes: Hydrogenation

3 min read

8.7

Oxidation of Alkenes: Epoxidation and Hydroxylation

3 min read

8.8

Oxidation of Alkenes: Cleavage to Carbonyl Compounds

3 min read

8.9

Addition of Carbenes to Alkenes: Cyclopropane Synthesis

2 min read

8.10

Radical Additions to Alkenes: Chain-Growth Polymers

2 min read

8.11

Biological Additions of Radicals to Alkenes

3 min read

8.12

Reaction Stereochemistry: Addition of H2O to an Achiral Alkene

3 min read

8.13

Reaction Stereochemistry: Addition of H2O to a Chiral Alkene

2 min read

Unit 9 - Alkynes: An Introduction to Organic Synthesis

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9.1

Naming Alkynes

3 min read

9.2

Preparation of Alkynes: Elimination Reactions of Dihalides

3 min read

9.3

Reactions of Alkynes: Addition of HX and X2

2 min read

9.4

Hydration of Alkynes

2 min read

9.5

Reduction of Alkynes

2 min read

9.6

Oxidative Cleavage of Alkynes

2 min read

9.7

Alkyne Acidity: Formation of Acetylide Anions

2 min read

9.8

Alkylation of Acetylide Anions

2 min read

9.9

An Introduction to Organic Synthesis

3 min read

Unit 10 - Organohalides

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10.1

Names and Structures of Alkyl Halides

2 min read

10.2

Preparing Alkyl Halides from Alkanes: Radical Halogenation

3 min read

10.3

Preparing Alkyl Halides from Alkenes: Allylic Bromination

3 min read

10.4

Stability of the Allyl Radical: Resonance Revisited

3 min read

10.5

Preparing Alkyl Halides from Alcohols

2 min read

10.6

Reactions of Alkyl Halides: Grignard Reagents

3 min read

10.7

Organometallic Coupling Reactions

3 min read

10.8

Oxidation and Reduction in Organic Chemistry

4 min read

Unit 11 - Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations

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11.1

The Discovery of Nucleophilic Substitution Reactions

3 min read

11.2

The SN2 Reaction

3 min read

11.3

Characteristics of the SN2 Reaction

4 min read

11.4

The SN1 Reaction

2 min read

11.5

Characteristics of the SN1 Reaction

2 min read

11.6

Biological Substitution Reactions

3 min read

11.7

Elimination Reactions: Zaitsev’s Rule

3 min read

11.8

The E2 Reaction and the Deuterium Isotope Effect

3 min read

11.9

The E2 Reaction and Cyclohexane Conformation

2 min read

11.10

The E1 and E1cB Reactions

2 min read

11.11

Biological Elimination Reactions

3 min read

11.12

A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2

3 min read

Unit 12 - Structure Determination: Mass Spectrometry and Infrared Spectroscopy

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12.1

Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

2 min read

12.2

Interpreting Mass Spectra

4 min read

12.3

Mass Spectrometry of Some Common Functional Groups

3 min read

12.4

Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments

3 min read

12.5

Spectroscopy and the Electromagnetic Spectrum

3 min read

12.6

Infrared Spectroscopy

3 min read

12.7

Interpreting Infrared Spectra

4 min read

12.8

Infrared Spectra of Some Common Functional Groups

2 min read

Unit 13 - Structure Determination: Nuclear Magnetic Resonance Spectroscopy

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13.1

Nuclear Magnetic Resonance Spectroscopy

2 min read

13.2

The Nature of NMR Absorptions

3 min read

13.3

Chemical Shifts

3 min read

13.4

Chemical Shifts in 1H NMR Spectroscopy

2 min read

13.5

Integration of 1H NMR Absorptions: Proton Counting

3 min read

13.6

Spin–Spin Splitting in 1H NMR Spectra

3 min read

13.7

1H NMR Spectroscopy and Proton Equivalence

4 min read

13.8

More Complex Spin–Spin Splitting Patterns

3 min read

13.9

Uses of 1H NMR Spectroscopy

3 min read

13.10

13C NMR Spectroscopy: Signal Averaging and FT–NMR

2 min read

13.11

Characteristics of 13C NMR Spectroscopy

3 min read

13.12

DEPT 13C NMR Spectroscopy

3 min read

13.13

Uses of 13C NMR Spectroscopy

3 min read

Unit 14 - Conjugated Compounds and Ultraviolet Spectroscopy

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14.1

Stability of Conjugated Dienes: Molecular Orbital Theory

3 min read

14.2

Electrophilic Additions to Conjugated Dienes: Allylic Carbocations

3 min read

14.3

Kinetic versus Thermodynamic Control of Reactions

3 min read

14.4

The Diels–Alder Cycloaddition Reaction

2 min read

14.5

Characteristics of the Diels–Alder Reaction

2 min read

14.6

Diene Polymers: Natural and Synthetic Rubbers

2 min read

14.7

Ultraviolet Spectroscopy

3 min read

14.8

Interpreting Ultraviolet Spectra: The Effect of Conjugation

3 min read

14.9

Conjugation, Color, and the Chemistry of Vision

3 min read

Unit 15 - Benzene and Aromaticity

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15.1

Naming Aromatic Compounds

2 min read

15.2

Structure and Stability of Benzene

3 min read

15.3

Aromaticity and the Hückel 4n + 2 Rule

3 min read

15.4

Aromatic Ions

3 min read

15.5

Aromatic Heterocycles: Pyridine and Pyrrole

2 min read

15.6

Polycyclic Aromatic Compounds

3 min read

15.7

Spectroscopy of Aromatic Compounds

2 min read

Unit 16 - Chemistry of Benzene: Electrophilic Aromatic Substitution

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16.1

Electrophilic Aromatic Substitution Reactions: Bromination

2 min read

16.2

Other Aromatic Substitutions

3 min read

16.3

Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

3 min read

16.4

Substituent Effects in Electrophilic Substitutions

2 min read

16.5

Trisubstituted Benzenes: Additivity of Effects

3 min read

16.6

Nucleophilic Aromatic Substitution

3 min read

16.7

Benzyne

3 min read

16.8

Oxidation of Aromatic Compounds

3 min read

16.9

Reduction of Aromatic Compounds

2 min read

16.10

Synthesis of Polysubstituted Benzenes

3 min read

Unit 17 - Alcohols and Phenols

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17.1

Naming Alcohols and Phenols

3 min read

17.2

Properties of Alcohols and Phenols

3 min read

17.3

Preparation of Alcohols: A Review

3 min read

17.4

Alcohols from Carbonyl Compounds: Reduction

2 min read

17.5

Alcohols from Carbonyl Compounds: Grignard Reaction

3 min read

17.6

Reactions of Alcohols

2 min read

17.7

Oxidation of Alcohols

3 min read

17.8

Protection of Alcohols

2 min read

17.9

Phenols and Their Uses

2 min read

17.10

Reactions of Phenols

3 min read

17.11

Spectroscopy of Alcohols and Phenols

3 min read

Unit 18 - Ethers and Epoxides; Thiols and Sulfides

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18.1

Names and Properties of Ethers

3 min read

18.2

Preparing Ethers

3 min read

18.3

Reactions of Ethers: Acidic Cleavage

3 min read

18.4

Cyclic Ethers: Epoxides

2 min read

18.5

Reactions of Epoxides: Ring-Opening

3 min read

18.6

Crown Ethers

3 min read

18.7

Thiols and Sulfides

3 min read

18.8

Spectroscopy of Ethers

2 min read

Unit 19 - Aldehydes and Ketones: Nucleophilic Addition Reactions

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19.1

Naming Aldehydes and Ketones

3 min read

19.2

Preparing Aldehydes and Ketones

2 min read

19.3

Oxidation of Aldehydes and Ketones

2 min read

19.4

Nucleophilic Addition Reactions of Aldehydes and Ketones

3 min read

19.5

Nucleophilic Addition of H2O: Hydration

3 min read

19.6

Nucleophilic Addition of HCN: Cyanohydrin Formation

3 min read

19.7

Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation

2 min read

19.8

Nucleophilic Addition of Amines: Imine and Enamine Formation

2 min read

19.9

Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction

3 min read

19.10

Nucleophilic Addition of Alcohols: Acetal Formation

3 min read

19.11

Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction

2 min read

19.12

Biological Reductions

2 min read

19.13

Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones

4 min read

19.14

Spectroscopy of Aldehydes and Ketones

3 min read

Unit 20 - Carboxylic Acids and Nitriles

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20.1

Naming Carboxylic Acids and Nitriles

3 min read

20.2

Structure and Properties of Carboxylic Acids

2 min read

20.3

Biological Acids and the Henderson–Hasselbalch Equation

3 min read

20.4

Substituent Effects on Acidity

3 min read

20.5

Preparing Carboxylic Acids

2 min read

20.6

Reactions of Carboxylic Acids: An Overview

2 min read

20.7

Chemistry of Nitriles

3 min read

20.8

Spectroscopy of Carboxylic Acids and Nitriles

2 min read

Unit 21 - Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions

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21.1

Naming Carboxylic Acid Derivatives

3 min read

21.2

Nucleophilic Acyl Substitution Reactions

2 min read

21.3

Reactions of Carboxylic Acids

2 min read

21.4

Chemistry of Acid Halides

2 min read

21.5

Chemistry of Acid Anhydrides

2 min read

21.6

Chemistry of Esters

3 min read

21.7

Chemistry of Amides

3 min read

21.8

Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives

3 min read

21.9

Polyamides and Polyesters: Step-Growth Polymers

3 min read

21.10

Spectroscopy of Carboxylic Acid Derivatives

3 min read

Unit 22 - Carbonyl Alpha-Substitution Reactions

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22.1

Keto–Enol Tautomerism

2 min read

22.2

Reactivity of Enols: α-Substitution Reactions

3 min read

22.3

Alpha Halogenation of Aldehydes and Ketones

2 min read

22.4

Alpha Bromination of Carboxylic Acids

2 min read

22.5

Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation

3 min read

22.6

Reactivity of Enolate Ions

2 min read

22.7

Alkylation of Enolate Ions

2 min read

Unit 23 - Carbonyl Condensation Reactions

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23.1

Carbonyl Condensations: The Aldol Reaction

2 min read

23.2

Carbonyl Condensations versus Alpha Substitutions

2 min read

23.3

Dehydration of Aldol Products: Synthesis of Enones

2 min read

23.4

Using Aldol Reactions in Synthesis

3 min read

23.5

Mixed Aldol Reactions

3 min read

23.6

Intramolecular Aldol Reactions

3 min read

23.7

The Claisen Condensation Reaction

3 min read

23.8

Mixed Claisen Condensations

2 min read

23.9

Intramolecular Claisen Condensations: The Dieckmann Cyclization

2 min read

23.10

Conjugate Carbonyl Additions: The Michael Reaction

3 min read

23.11

Carbonyl Condensations with Enamines: The Stork Enamine Reaction

2 min read

23.12

The Robinson Annulation Reaction

2 min read

23.13

Some Biological Carbonyl Condensation Reactions

3 min read

Unit 24 - Amines and Heterocycles

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24.1

Naming Amines

2 min read

24.2

Structure and Properties of Amines

3 min read

24.3

Basicity of Amines

3 min read

24.4

Basicity of Arylamines

2 min read

24.5

Biological Amines and the Henderson–Hasselbalch Equation

3 min read

24.6

Synthesis of Amines

3 min read

24.7

Reactions of Amines

3 min read

24.8

Reactions of Arylamines

2 min read

24.9

Heterocyclic Amines

2 min read

24.10

Spectroscopy of Amines

3 min read

Unit 25 - Biomolecules: Carbohydrates

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25.1

Classification of Carbohydrates

2 min read

25.2

Representing Carbohydrate Stereochemistry: Fischer Projections

3 min read

25.3

D,L Sugars

3 min read

25.4

Configurations of the Aldoses

2 min read

25.5

Cyclic Structures of Monosaccharides: Anomers

3 min read

25.6

Reactions of Monosaccharides

3 min read

25.7

The Eight Essential Monosaccharides

3 min read

25.8

Disaccharides

3 min read

25.9

Polysaccharides and Their Synthesis

2 min read

25.10

Some Other Important Carbohydrates

2 min read

Unit 26 - Biomolecules: Amino Acids, Peptides, and Proteins

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26.1

Structures of Amino Acids

3 min read

26.2

Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points

3 min read

26.3

Synthesis of Amino Acids

2 min read

26.4

Peptides and Proteins

3 min read

26.5

Amino Acid Analysis of Peptides

2 min read

26.6

Peptide Sequencing: The Edman Degradation

3 min read

26.7

Peptide Synthesis

3 min read

26.8

Automated Peptide Synthesis: The Merrifield Solid-Phase Method

3 min read

26.9

Protein Structure

3 min read

26.10

Enzymes and Coenzymes

3 min read

26.11

How Do Enzymes Work? Citrate Synthase

2 min read

Unit 27 - Biomolecules: Lipids

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27.1

Waxes, Fats, and Oils

3 min read

27.2

Soap

4 min read

27.3

Phospholipids

2 min read

27.4

Prostaglandins and Other Eicosanoids

3 min read

27.5

Terpenoids

3 min read

27.6

Steroids

3 min read

27.7

Biosynthesis of Steroids

2 min read

Unit 28 - Biomolecules: Nucleic Acids

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28.1

Nucleotides and Nucleic Acids

3 min read

28.2

Base Pairing in DNA

3 min read

28.3

Replication of DNA

3 min read

28.4

Transcription of DNA

2 min read

28.5

Translation of RNA: Protein Biosynthesis

3 min read

28.6

DNA Sequencing

3 min read

28.7

DNA Synthesis

3 min read

28.8

The Polymerase Chain Reaction

3 min read

Unit 29 - The Organic Chemistry of Metabolic Pathways

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29.1

An Overview of Metabolism and Biochemical Energy

2 min read

29.2

Catabolism of Triacylglycerols: The Fate of Glycerol

3 min read

29.3

Catabolism of Triacylglycerols: β-Oxidation

2 min read

29.4

Biosynthesis of Fatty Acids

3 min read

29.5

Catabolism of Carbohydrates: Glycolysis

2 min read

29.6

Conversion of Pyruvate to Acetyl CoA

3 min read

29.7

The Citric Acid Cycle

3 min read

29.8

Carbohydrate Biosynthesis: Gluconeogenesis

2 min read

29.9

Catabolism of Proteins: Deamination

2 min read

29.10

Some Conclusions about Biological Chemistry

3 min read

Unit 30 - Orbitals and Organic Chemistry: Pericyclic Reactions

View all

30.1

Molecular Orbitals of Conjugated Pi Systems

3 min read

30.2

Electrocyclic Reactions

2 min read

30.3

Stereochemistry of Thermal Electrocyclic Reactions

2 min read

30.4

Photochemical Electrocyclic Reactions

2 min read

30.5

Cycloaddition Reactions

2 min read

30.6

Stereochemistry of Cycloadditions

3 min read

30.7

Sigmatropic Rearrangements

2 min read

30.8

Some Examples of Sigmatropic Rearrangements

3 min read

30.9

A Summary of Rules for Pericyclic Reactions

3 min read

Unit 31 - Synthetic Polymers

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31.1

Chain-Growth Polymers

3 min read

31.2

Stereochemistry of Polymerization: Ziegler–Natta Catalysts

2 min read

31.3

Copolymers

3 min read

31.4

Step-Growth Polymers

2 min read

31.5

Olefin Metathesis Polymerization

2 min read

31.6

Intramolecular Olefin Metathesis

4 min read

31.7

Polymer Structure and Physical

2 min read
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About Us
About FiveableBlogCareersCode of ConductTerms of UsePrivacy PolicyCCPA Privacy Policy
Resources
Cram ModeAP Score CalculatorsStudy GuidesPractice QuizzesGlossaryMerch ShopCrisis Text LineHelp Center

© 2024 Fiveable Inc. All rights reserved.

AP® and SAT® are trademarks registered by the College Board, which is not affiliated with, and does not endorse this website.

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