Organic Chemistry

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Organic chemistry studies the structure, properties and reactions of organic compounds, which contain carbon in covalent bonding. Study of structure determines their structural formula. Study of properties includes physical and chemical properties, and evaluation of chemical reactivity to understand their behavior. The study of organic reactions includes the chemical synthesis of natural products, drugs, and polymers, and study of individual organic molecules in the laboratory and theoretically.

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Chemistry
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Teens profiles and older, judged from its title and subjects

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  1. Front Matter
  2. TitlePage
  3. InfoPage
  4. Table of Contents
  5. About the Authors
  6. Licensing
  7. 1: Structure and Bonding
  8. 1.1: Introduction to Organic Chemistry
  9. 1.2: Atomic Structure - The Nucleus
  10. 1.3: Atomic Structure - Orbitals
  11. 1.4: Atomic Structure - Electron Configurations
  12. 1.5: Development of Chemical Bonding Theory
  13. 1.6: Describing Chemical Bonds - Valence Bond Theory
  14. 1.7: sp³ Hybrid Orbitals and the Structure of Methane
  15. 1.8: sp³ Hybrid Orbitals and the Structure of Ethane
  16. 1.9: sp² Hybrid Orbitals and the Structure of Ethylene
  17. 1.10: sp Hybrid Orbitals and the Structure of Acetylene
  18. 1.11: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
  19. 1.12: Describing Chemical Bonds - Molecular Orbital Theory
  20. 1.13: Drawing Chemical Structures
  21. 1.S: Structure and Bonding (Summary)
  22. 2: Polar Covalent Bonds; Acids and Bases
  23. 2.1: Polar Covalent Bonds - Electronegativity
  24. 2.2: Polar Covalent Bonds - Dipole Moments
  25. 2.3: Formal Charges
  26. 2.4: Resonance
  27. 2.5: Rules for Resonance Forms
  28. 2.6: Drawing Resonance Forms
  29. 2.7: Acids and Bases - The Brønsted-Lowry Definition
  30. 2.8: Acid and Base Strength
  31. 2.9: Predicting Acid-Base Reactions from pKa Values
  32. 2.10: Organic Acids and Organic Bases
  33. 2.11: Acids and Bases - The Lewis Definition
  34. 2.12: Noncovalent Interactions Between Molecules
  35. 2.MM: Molecular Models
  36. 2.S: Polar Covalent Bonds; Acids and Bases (Summary)
  37. 3: Organic Compounds- Alkanes and Their Stereochemistry
  38. 3.1: Chapter Objectives
  39. 3.2: Functional Groups
  40. 3.3: Alkanes and Alkane Isomers
  41. 3.4: Alkyl Groups
  42. 3.5: Naming Alkanes
  43. 3.6: Properties of Alkanes
  44. 3.7: Conformations of Ethane
  45. 3.8: Conformations of Other Alkanes
  46. 3.9: Gasoline - A Deeper Look
  47. 3.S: Organic Compounds- Alkanes and Their Stereochemistry (Summary)
  48. 4: Organic Compounds - Cycloalkanes and their Stereochemistry
  49. 4.1: Chapter Objectives
  50. 4.2: Naming Cycloalkanes
  51. 4.3: Cis-Trans Isomerism in Cycloalkanes
  52. 4.4: Stability of Cycloalkanes - Ring Strain
  53. 4.5: Conformations of Cycloalkanes
  54. 4.6: Conformations of Cyclohexane
  55. 4.7: Axial and Equatorial Bonds in Cyclohexane
  56. 4.8: Conformations of Monosubstituted Cyclohexanes
  57. 4.9: Conformations of Disubstituted Cyclohexanes
  58. 4.10: Conformations of Polycyclic Molecules
  59. 4.S: Organic Compounds- Cycloalkanes and their Stereochemistry (Summary)
  60. 5: Stereochemistry at Tetrahedral Centers
  61. 5.1: Chapter Objectives and Introduction
  62. 5.2: Enantiomers and the Tetrahedral Carbon
  63. 5.3: The Reason for Handedness in Molecules - Chirality
  64. 5.4: Optical Activity
  65. 5.5: Pasteur's Discovery of Enantiomers
  66. 5.6: Sequence Rules for Specifying Configuration
  67. 5.7: Diastereomers
  68. 5.8: Meso Compounds
  69. 5.9: Racemic Mixtures and the Resolution of Enantiomers
  70. 5.10: A Review of Isomerism
  71. 5.11: Chirality at Nitrogen, Phosphorus, and Sulfur
  72. 5.12: Prochirality
  73. 5.13: Chirality in Nature and Chiral Environments
  74. 5.S: Stereochemistry at Tetrahedral Centers (Summary)
  75. 5.xx: Enantiomers and Diastereomers
  76. 6: An Overview of Organic Reactions
  77. 6.1: Chapter Objectives
  78. 6.2: Kinds of Organic Reactions
  79. 6.3: How Organic Reactions Occur - Mechanisms
  80. 6.4: Radical Reactions
  81. 6.5: Polar Reactions
  82. 6.6: An Example of a Polar Reaction - Addition of HBr to Ethylene
  83. 6.7: Using Curved Arrows in Polar Reaction Mechanisms
  84. 6.8: Describing a Reaction - Equilibria, Rates, and Energy Changes
  85. 6.9: Describing a Reaction - Bond Dissociation Energies
  86. 6.10: Describing a Reaction - Energy Diagrams and Transition States
  87. 6.11: Describing a Reaction- Intermediates
  88. 6.12: A Comparison between Biological Reactions and Laboratory Reactions
  89. 6.S: An Overview of Organic Reactions (Summary)
  90. 7: Alkenes- Structure and Reactivity
  91. 7.1: Chapter Objectives
  92. 7.2: Introduction to Alkenes
  93. 7.3: Industrial Preparation and Use of Alkenes
  94. 7.4: Calculating Degree of Unsaturation
  95. 7.5: Naming Alkenes
  96. 7.6: Cis-Trans Isomerism in Alkenes
  97. 7.7: Sequence Rules - The E,Z Designation
  98. 7.8: Stability of Alkenes
  99. 7.9: Electrophilic Addition Reactions of Alkenes
  100. 7.10: Orientation of Electrophilic Additions - Markovnikov's Rule
  101. 7.11: Carbocation Structure and Stability
  102. 7.12: The Hammond Postulate
  103. 7.13: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
  104. 7.S: Alkenes- Structure and Reactivity (Summary)
  105. 8: Alkenes- Reactions and Synthesis
  106. 8.1: Chapter Objectives
  107. 8.2: Preparation of Alkenes - A Preview of Elimination Reactions
  108. 8.3: Halogenation of Alkenes - Addition of X₂
  109. 8.4: Halohydrins from Alkenes - Addition of HOX
  110. 8.5: Hydration of Alkenes - Addition of H₂O by Oxymercuration
  111. 8.6: Hydration of Alkenes - Addition of H₂O by Hydroboration
  112. 8.7: Reduction of Alkenes - Hydrogenation
  113. 8.8: Oxidation of Alkenes - Epoxidation and Hydroxylation
  114. 8.9: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
  115. 8.10: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  116. 8.11: Radical Additions to Alkenes - Chain-Growth Polymers
  117. 8.12: Biological Additions of Radicals to Alkenes
  118. 8.13: Stereochemistry of Reactions - Addition of H₂O to an Achiral Alkene
  119. 8.14: Stereochemistry of Reactions - Addition of H₂O to a Chiral Alkene
  120. 8.S: Alkenes - Reactions and Synthesis (Summary)
  121. 9: Alkynes - An Introduction to Organic Synthesis
  122. 9.1: Chapter Objectives
  123. 9.2: Naming Alkynes
  124. 9.3: Preparation of Alkynes - Elimination Reactions of Dihalides
  125. 9.4: Reactions of Alkynes - Addition of HX and X₂
  126. 9.5: Hydration of Alkynes
  127. 9.6: Reduction of Alkynes
  128. 9.7: Oxidative Cleavage of Alkynes
  129. 9.8: Alkyne Acidity - Formation of Acetylide Anions
  130. 9.9: Alkylation of Acetylide Anions
  131. 9.10: An Introduction to Organic Synthesis
  132. 9.S: Alkynes - An Introduction to Organic Synthesis (Summary)
  133. 10: Organohalides
  134. 10.1: Introduction to Organohalides
  135. 10.2: Names and Properties of Alkyl Halides
  136. 10.3: Preparing Alkyl Halides from Alkanes - Radical Halogenation
  137. 10.4: Preparing Alkyl Halides from Alkenes - Allylic Bromination
  138. 10.5: Stability of the Allyl Radical - Resonance Revisited
  139. 10.6: Preparing Alkyl Halides from Alcohols
  140. 10.7: Reactions of Alkyl Halides - Grignard Reagents
  141. 10.8: Organometallic Coupling Reactions
  142. 10.9: Oxidation and Reduction in Organic Chemistry
  143. 10.S: Organohalides (Summary)
  144. 11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  145. 11.1: Introduction
  146. 11.2: The Discovery of Nucleophilic Substitution Reactions
  147. 11.3: The SN2 Reaction
  148. 11.4: Characteristics of the SN2 Reaction
  149. 11.5: The SN1 Reaction
  150. 11.6: Characteristics of the SN1 Reaction
  151. 11.7: Biological Substitution Reactions
  152. 11.8: Elimination Reactions- Zaitsev's Rule
  153. 11.9: The E2 Reaction and the Deuterium Isotope Effect
  154. 11.10: The E2 Reaction and Cyclohexane Conformation
  155. 11.11: The E1 and E1cB Reactions
  156. 11.12: Biological Elimination Reactions
  157. 11.13: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2
  158. 11.S: Reactions of Alkyl Halides - Nucleophilic Substitutions and Eliminations (Summary)
  159. 12: Structure Determination - Mass Spectrometry and Infrared Spectroscopy
  160. 12.1: Introduction
  161. 12.2: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
  162. 12.3: Interpreting Mass Spectra
  163. 12.4: Mass Spectrometry of Some Common Functional Groups
  164. 12.5: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments
  165. 12.6: Spectroscopy and the Electromagnetic Spectrum
  166. 12.7: Infrared Spectroscopy
  167. 12.8: Interpreting Infrared Spectra
  168. 12.9: Infrared Spectra of Some Common Functional Groups
  169. 12.S: Structure Determination - Mass Spectrometry and Infrared Spectroscopy (Summary)
  170. 13: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
  171. 13.1: Nuclear Magnetic Resonance Spectroscopy
  172. 13.2: The Nature of NMR Absorptions
  173. 13.3: The Chemical Shift
  174. 13.4: Chemical Shifts in ¹H NMR Spectroscopy
  175. 13.5: Integration of ¹H NMR Absorptions- Proton Counting
  176. 13.6: Spin-Spin Splitting in ¹H NMR Spectra
  177. 13.7: ¹H NMR Spectroscopy and Proton Equivalence
  178. 13.8: More Complex Spin-Spin Splitting Patterns
  179. 13.9: Uses of ¹H NMR Spectroscopy
  180. 13.10: ¹³C NMR Spectroscopy - Signal Averaging and FT-NMR
  181. 13.11: Characteristics of ¹³C NMR Spectroscopy
  182. 13.12: DEPT ¹³C NMR Spectroscopy
  183. 13.13: Uses of ¹³C NMR Spectroscopy
  184. 13.S: Structure Determination - Nuclear Magnetic Resonance Spectroscopy (Summary)
  185. 14: Conjugated Compounds and Ultraviolet Spectroscopy
  186. 14.1: Introduction
  187. 14.2: Stability of Conjugated Dienes- Molecular Orbital Theory
  188. 14.3: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
  189. 14.4: Kinetic vs. Thermodynamic Control of Reactions
  190. 14.5: The Diels-Alder Cycloaddition Reaction
  191. 14.6: Characteristics of the Diels-Alder Reaction
  192. 14.7: Diene Polymers- Natural and Synthetic Rubbers
  193. 14.8: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
  194. 14.9: Interpreting Ultraviolet Spectra- The Effect of Conjugation
  195. 14.10: Conjugation, Color, and the Chemistry of Vision
  196. 14.S: Conjugated Compounds and Ultraviolet Spectroscopy (Summary)
  197. 15: Benzene and Aromaticity
  198. 15.1: Introduction
  199. 15.2: Naming Aromatic Compounds
  200. 15.3: Structure and Stability of Benzene
  201. 15.4: Aromaticity and the Hückel 4n + 2 Rule
  202. 15.5: Aromatic Ions
  203. 15.6: Aromatic Heterocycles - Pyridine and Pyrrole
  204. 15.7: Polycyclic Aromatic Compounds
  205. 15.8: Spectroscopy of Aromatic Compounds
  206. 15.S: Benzene and Aromaticity (Summary)
  207. 16: Chemistry of Benzene - Electrophilic Aromatic Substitution
  208. 16.1: Introduction
  209. 16.2: Electrophilic Aromatic Substitution Reactions - Bromination
  210. 16.3: Other Aromatic Substitutions
  211. 16.4: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
  212. 16.5: Substituent Effects in Substituted Aromatic Rings
  213. 16.6: An Explanation of Substituent Effects
  214. 16.7: Trisubstituted Benzenes - Additivity of Effects
  215. 16.8: Nucleophilic Aromatic Substitution
  216. 16.9: Benzyne
  217. 16.10: Oxidation of Aromatic Compounds
  218. 16.11: Reduction of Aromatic Compounds
  219. 16.12: Synthesis of Polysubstituted Benzenes
  220. 16.S: Chemistry of Benzene - Electrophilic Aromatic Substitution (Summary)
  221. 17: Alcohols and Phenols
  222. 17.1: Introduction
  223. 17.2: Naming Alcohols and Phenols
  224. 17.3: Properties of Alcohols and Phenols
  225. 17.4: Preparation of Alcohols- A Review
  226. 17.5: Alcohols from Carbonyl Compounds- Reduction
  227. 17.6: Alcohols from Carbonyl Compounds- Grignard Reagents
  228. 17.7: Reactions of Alcohols
  229. 17.8: Oxidation of Alcohols
  230. 17.9: Protection of Alcohols
  231. 17.10: Phenols and Their Uses
  232. 17.11: Reactions of Phenols
  233. 17.12: Spectroscopy of Alcohols and Phenols
  234. 17.S: Alcohols and Phenols (Summary)
  235. 18: Ethers and Epoxides; Thiols and Sulfides
  236. 18.1: Introduction
  237. 18.2: Names and Properties of Ethers
  238. 18.3: Preparing Ethers
  239. 18.4: Reactions of Ethers- Acidic Cleavage
  240. 18.5: Reactions of Ethers- Claisen Rearrangement
  241. 18.6: Cyclic Ethers - Epoxides
  242. 18.7: Reactions of Epoxides- Ring-opening
  243. 18.8: Crown Ethers
  244. 18.9: Thiols and Sulfides
  245. 18.10: Spectroscopy of Ethers
  246. 18.11: Interchapter- A Preview of Carbonyl Chemistry
  247. 18.S: Ethers and Epoxides; Thiols and Sulfides (Summary)
  248. 19: Aldehydes and Ketones- Nucleophilic Addition Reactions
  249. 19.1: Chapter Objectives and Preview of Carbonyl Chemistry
  250. 19.2: Naming Aldehydes and Ketones
  251. 19.3: Preparing Aldehydes and Ketones
  252. 19.4: Oxidation of Aldehydes and Ketones
  253. 19.5: Nucleophilic Addition Reactions of Aldehydes and Ketones
  254. 19.6: Nucleophilic Addition of Water- Hydration
  255. 19.7: Nucleophilic Addition of HCN- Cyanohydrin Formation
  256. 19.8: Nucleophilic Addition of Hydride and Grignard Reagents- Alcohol Formation
  257. 19.9: Nucleophilic Addition of Amines- Imine and Enamine Formation
  258. 19.10: Nucleophilic Addition of Hydrazine - The Wolff-Kishner Reaction
  259. 19.11: Nucleophilic Addition of Alcohols- Acetal Formation
  260. 19.12: Nucleophilic Addition of Phosphorus Ylides- The Wittig Reaction
  261. 19.13: Biological Reductions
  262. 19.14: Conjugate Nucleophilic Addition to alpha, beta-unsaturated Aldehydes and Ketones
  263. 19.15: Spectroscopy of Aldehydes and Ketones
  264. 19.S: Aldehydes and Ketones (Summary)
  265. 20: Carboxylic Acids and Nitriles
  266. 20.1: Chapter Objectives and Introduction to Carboxylic Acids
  267. 20.2: Naming Carboxylic Acids and Nitriles
  268. 20.3: Structure and Properties of Carboxylic Acids
  269. 20.4: Biological Acids and the Henderson-Hasselbalch Equation
  270. 20.5: Substituent Effects on Acidity
  271. 20.6: Preparing Carboxylic Acids
  272. 20.7: Reactions of Carboxylic Acids - An Overview
  273. 20.8: Chemistry of Nitriles
  274. 20.9: Spectroscopy of Carboxylic Acids and Nitriles
  275. 20.S: Carboxylic Acids and Nitriles (Summary)
  276. 21: Carboxylic Acid Derivatives- Nucleophilic Acyl Substitution Reactions
  277. 21.1: Chapter Objectives and Introduction to Carboxylic Acid Derivatives
  278. 21.2: Naming Carboxylic Acid Derivatives
  279. 21.3: Nucleophilic Acyl Substitution Reactions
  280. 21.4: Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
  281. 21.5: Chemistry of Acid Halides
  282. 21.6: Chemistry of Acid Anhydrides
  283. 21.7: Chemistry of Esters
  284. 21.8: Chemistry of Amides
  285. 21.9: Chemistry of Thioesters and Acyl Phosphates - Biological Carboxylic Acid Derivatives
  286. 21.10: Polyamides and Polyesters- Step-Growth Polymers
  287. 21.11: Spectroscopy of Carboxylic Acid Derivatives
  288. 21.S: Carboxylic Acid Derivatives (Summary)
  289. 22: Carbonyl Alpha-Substitution Reactions
  290. 22.1: Chapter Objectives and Introduction to Carbonyl Alpha-Substitution Reactions
  291. 22.2: Keto-Enol Tautomerism
  292. 22.3: Reactivity of Enols- The Mechanism of Alpha-Substitution Reactions
  293. 22.4: Alpha Halogenation of Aldehydes and Ketones
  294. 22.5: Alpha Bromination of Carboxylic Acids
  295. 22.6: Acidity of Alpha Hydrogen Atoms- Enolate Ion Formation
  296. 22.7: Reactivity of Enolate Ions
  297. 22.8: Alkylation of Enolate Ions
  298. 22.S: Carbonyl Alpha-Substitution Reactions (Summary)
  299. 23: Carbonyl Condensation Reactions
  300. 23.1: Chapter Objectives
  301. 23.2: Carbonyl Condensations - The Aldol Reaction
  302. 23.3: Carbonyl Condensations versus Alpha Substitutions
  303. 23.4: Dehydration of Aldol Products - Synthesis of Enones
  304. 23.5: Using Aldol Reactions in Synthesis
  305. 23.6: Mixed Aldol Reactions
  306. 23.7: Intramolecular Aldol Reactions
  307. 23.8: The Claisen Condensation Reaction
  308. 23.9: Mixed Claisen Condensations
  309. 23.10: Intramolecular Claisen Condensations - The Dieckmann Cyclization
  310. 23.11: Conjugate Carbonyl Additions - The Michael Reaction
  311. 23.12: Carbonyl Condensations with Enamines - The Stork Reaction
  312. 23.13: The Robinson Annulation Reaction
  313. 23.14: Some Biological Carbonyl Condensation Reactions
  314. 23.S: Carbonyl Condensation Reactions (Summary)
  315. 24: Amines and Heterocycles
  316. 24.1: Chapter Objectives
  317. 24.2: Naming Amines
  318. 24.3: Structure and Properties of Amines
  319. 24.4: Basicity of Amines
  320. 24.5: Basicity of Arylamines
  321. 24.6: Biological Amines and the Henderson-Hasselbalch Equation
  322. 24.7: Synthesis of Amines
  323. 24.8: Reactions of Amines
  324. 24.9: Reactions of Arylamines
  325. 24.10: Heterocyclic Amines
  326. 24.11: Spectroscopy of Amines
  327. 24.S: Amines and Heterocycles (Summary)
  328. 25: Biomolecules- Carbohydrates
  329. 25.1: Introduction
  330. 25.2: Classification of Carbohydrates
  331. 25.3: Depicting Carbohydrate Stereochemistry - Fischer Projections
  332. 25.4: D, L Sugars
  333. 25.5: Configurations of Aldoses
  334. 25.6: Cyclic Structures of Monosaccharides - Anomers
  335. 25.7: Reactions of Monosaccharides
  336. 25.8: The Eight Essential Monosaccharides
  337. 25.9: Disaccharides
  338. 25.10: Polysaccharides and Their Synthesis
  339. 25.11: Other Important Carbohydrates
  340. 25.12: Cell-Surface Carbohydrates and Influenza Viruses
  341. 25.S: Biomolecules- Carbohydrates (Summary)
  342. 26: Biomolecules- Amino Acids, Peptides, and Proteins
  343. 26.1: Chapter Objectives
  344. 26.2: Introduction
  345. 26.3: Structures of Amino Acids
  346. 26.4: Amino Acids, the Henderson-Hasselbalch Equation, and Isoelectric Points
  347. 26.5: Synthesis of Amino Acids
  348. 26.6: Peptides and Proteins
  349. 26.7: Amino Acid Analysis of Peptides
  350. 26.8: The Edman Degradation
  351. 26.9: Peptide Synthesis
  352. 26.10: The Merrifield Solid-Phase Technique
  353. 26.11: Protein Structure
  354. 26.12: Enzymes and Coenzymes
  355. 26.13: How do Enzymes Work? Citrate Synthase
  356. 27: Biomolecules - Lipids
  357. 27.1: Introduction to Lipids
  358. 27.2: Waxes, Fats, and Oils
  359. 27.3: Soap
  360. 27.4: Phospholipids
  361. 27.5: Prostaglandins and Other Eicosanoids
  362. 27.6: Terpenoids
  363. 27.7: Steroids
  364. 27.8: Biosynthesis of Steroids
  365. 27.S: Biomolecules - Lipids (Summary)
  366. 28: Biomolecules - Nucleic Acids
  367. 28.1: Nucleotides and Nucleic Acids
  368. 28.2: Base Pairing in DNA - The Watson-Crick Model
  369. 28.3: Replication of DNA
  370. 28.4: Transcription of DNA
  371. 28.5: Translation of RNA - Protein Biosynthesis
  372. 28.6: DNA Sequencing
  373. 28.7: DNA Synthesis
  374. 28.8: The Polymerase Chain Reaction
  375. 29: Orbitals and Organic Chemistry - Pericyclic Reactions
  376. 29.1: Molecular Orbitals of Conjugated Pi Systems
  377. 29.2: Electrocyclic Reactions
  378. 29.3: Stereochemistry of Thermal Electrocyclic Reactions
  379. 29.4: Photochemical Electrocyclic Reactions
  380. 29.5: Cycloaddition Reactions
  381. 29.6: Stereochemistry of Cycloadditions
  382. 29.7: Sigmatropic Rearrangements
  383. 29.8: Some Examples of Sigmatropic Rearrangements
  384. 29.9: A Summary of Rules for Pericyclic Reactions
  385. 30: Synthetic Polymers
  386. 30.1: Chain-Growth Polymers
  387. 30.2: Stereochemistry of Polymerization- Ziegler-Natta Catalysts
  388. 30.3: Copolymers
  389. 30.4: Step-Growth Polymers
  390. 30.5: Olefin Metathesis Polymerization
  391. 30.6: Polymer Structure and Physical Properties
  392. Back Matter
  393. Index
  394. Glossary
  395. Detailed Licensing