Organic Chemistry

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Subjects
Chemistry, Organic Chemistry
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Contents

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  1. Front Matter
  2. TitlePage
  3. InfoPage
  4. Table of Contents
  5. Licensing
  6. 1: Introduction and Review
  7. 1.1: The Origins of Organic Chemistry
  8. 1.2: Principles of Atomic Structure (Review)
  9. 1.3: Electronic Structure (Review)
  10. 1.4: Electron Configurations and Electronic Orbital Diagrams (Review)
  11. 1.5: Octet Rule - Ionic and Covalent Bonding (Review)
  12. 1.6: Lewis Structures and Formal Charges (Review)
  13. 1.7: Common Bonding Patterns for Organic Chemistry
  14. 1.8: Structural Formulas - Lewis, Kekule, Bond-line, Condensed, and Perspective
  15. 1.9: Electronegativity and Bond Polarity (Review)
  16. 1.10: Resonance
  17. 1.11: Arrhenius Acids and Bases (Review)
  18. 1.12: Lewis Acids and Bases
  19. 1.13: Distinguishing between pH and pKa
  20. 1.14: Predicting Relative Acidity
  21. 1.15: Molecular Formulas and Empirical Formulas (Review)
  22. 1.16: Additional Exercises
  23. 1.17: Solutions to Additional Exercises
  24. 1.18: Brønsted-Lowry Acids and Bases (Review)
  25. 2: Structure and Properties of Organic Molecules
  26. 2.1: Pearls of Wisdom
  27. 2.2: Molecular Orbital (MO) Theory (Review)
  28. 2.3: Hybridization and Molecular Shapes (Review)
  29. 2.4: 2.4 Conjugated Pi Bond Systems
  30. 2.5: Lone Pair Electrons and Bonding Theories
  31. 2.6: Bond Rotation
  32. 2.7: Isomerism Introduction
  33. 2.8: Hydrocarbons and the Homologous Series
  34. 2.9: Organic Functional Groups
  35. 2.10: Intermolecular Forces (IMFs) - Review
  36. 2.11: Intermolecular Forces and Relative Boiling Points (bp)
  37. 2.12: Intermolecular Forces and Solubilities
  38. 2.13: Additional Practice Problems
  39. 2.14: Organic Functional Groups- H-bond donors and H-bond acceptors
  40. 2.15: Solutions to Additional Exercises
  41. 2.16: Additional Exercises
  42. 3: Functional Groups and Nomenclature
  43. 3.1: Generic (Abbreviated) Structures (aka R Groups)
  44. 3.2: Overview of the IUPAC Naming Strategy
  45. 3.3: Alkanes
  46. 3.4: Cycloalkanes
  47. 3.5: Haloalkane - Classification and Nomenclature
  48. 3.6: Alkenes
  49. 3.7: Alkynes
  50. 3.8: 3.8 Alcohols - Classification and Nomenclature
  51. 3.9: Ethers, Epoxides and Sulfides
  52. 3.10: Benzene and its Derivatives
  53. 3.11: Aldehydes and Ketones
  54. 3.12: Amines - Classification and Nomenclature
  55. 3.13: Carboxylic Acids
  56. 3.14: The Carboxylic Acid Derivatives
  57. 3.15: Additional Exercises
  58. 3.16: Solutions to Additional Exercises
  59. 3.17: Appendix - IUPAC Nomenclature Rules
  60. 4: Structure and Stereochemistry of Alkanes
  61. 4.1: Hydrocarbon Functional Groups
  62. 4.2: Physical Properties of Alkanes
  63. 4.3: Structure and Conformations of Alkanes
  64. 4.4: Conformations of Butane
  65. 4.5: Conformations of Higher Alkanes
  66. 4.6: Cycloalkanes and Ring Strain
  67. 4.7: Cyclohexane Conformations
  68. 4.8: Conformations of Monosubstituted Cyclohexanes
  69. 4.9: Cis-trans Isomerism in Cycloalkanes
  70. 4.10: Conformations of Disubstituted Cyclohexanes
  71. 4.11: Joined Rings
  72. 4.12: Uses and Sources of Alkanes
  73. 4.13: Reactions of Alkanes - a Brief Overview
  74. 4.14: Additional Exercises
  75. 4.15: Solutions to Additional Exercises
  76. 5: An Introduction to Organic Reactions using Free Radical Halogenation of Alkanes
  77. 5.1: Types of Organic Reactions
  78. 5.2: Reaction Mechanism Notation and Symbols
  79. 5.3: Polar Reactions- the Dance of the Nucleophile and Electrophile
  80. 5.4: Describing a Reaction - Equilibrium and Free Energy Changes
  81. 5.5: Homolytic Cleavage and Bond Dissociation Energies
  82. 5.6: Reaction Energy Diagrams and Transition States
  83. 5.7: Reactive Intermediates - Carbocations
  84. 5.8: Reactive Intermediates - Radicals
  85. 5.9: Reactive Intermediates- Carbanions and Carbon Acids
  86. 5.10: The Free-Radical Halogenation of Alkanes
  87. 5.11: Reactivity and Selectivity
  88. 5.12: A Comparison between Biological Reactions and Laboratory Reactions
  89. 5.13: Additional Exercises
  90. 5.14: Solutions to Additional Exercises
  91. 6: Stereochemistry at Tetrahedral Centers
  92. 6.1: Chirality
  93. 6.2: Fischer Projections to communicate Chirality
  94. 6.3: Absolute Configuration and the (R) and (S) System
  95. 6.4: Diastereomers - more than one chiral center
  96. 6.5: Meso Compounds
  97. 6.6: Isomerism Summary Diagram
  98. 6.7: Optical Activity and Racemic Mixtures
  99. 6.8: Resolution (Separation) of Enantiomers
  100. 6.9: Stereochemistry of Molecules with Three or More Asymmetric Carbons
  101. 6.10: Absolute and Relative Configuration - the distinction
  102. 6.11: Chirality at Nitrogen, Phosphorus, and Sulfur
  103. 6.12: Biochemistry of Enantiomers
  104. 6.13: The Discovery of Enantiomers
  105. 6.14: Additional Exercises
  106. 6.15: Solutions to Additional Exercises
  107. 7: Alkyl Halides- Nucleophilic Substitution and Elimination
  108. 7.1: Alkyl Halides - Structure and Physical Properties
  109. 7.2: Common Uses of Alkyl Halides
  110. 7.3: Preparation of Alkyl Halides
  111. 7.4: Reactions of Alkyl Halides- Substitution and Elimination
  112. 7.5: The Sₙ2 Reaction
  113. 7.6: Characteristics of the Sₙ2 Reaction
  114. 7.7: Stereochemistry of the SN2 Reaction
  115. 7.8: The Sₙ1 Reaction
  116. 7.9: Characteristics of the Sₙ1 Reaction
  117. 7.10: Rearrangements of the Carbocation and Sₙ1 Reactions
  118. 7.11: The Hammond Postulate and Transition States
  119. 7.12: Comparison of SN1 and SN2 Reactions
  120. 7.13: Characteristics of the E2 Reaction
  121. 7.14: Zaitsev's Rule
  122. 7.15: Characteristics of the E1 Reaction
  123. 7.16: E2 Regiochemistry and Cyclohexane Conformations
  124. 7.17: The E2 Reaction and the Deuterium Isotope Effect
  125. 7.18: Comparison of E1 and E2 Reactions
  126. 7.19: Comparing Substitution and Elimination Reactions
  127. 7.20: Biological Substitution Reactions
  128. 7.21: Biological Elimination Reactions
  129. 7.22: Additional Exercises
  130. 7.23: Solutions to Additional Exercises
  131. 8: Structure and Synthesis of Alkenes
  132. 8.1: Alkene Structure
  133. 8.2: Physical Properties and Important Common Names
  134. 8.3: The Alkene Double Bond and Stereoisomerism
  135. 8.4: Degrees of Unsaturation
  136. 8.5: The E/Z System (when cis/trans does not work)
  137. 8.6: Stability of Alkenes
  138. 8.7: Alkene Synthesis by Elimination of Alkyl Halides
  139. 8.8: Alkene Synthesis by Dehydration of Alcohols
  140. 8.9: Uses and Sources of Alkenes
  141. 8.10: Additional Exercises
  142. 8.11: Solutions to Additional Exercises
  143. 9: Reactions of Alkenes
  144. 9.1: Electrophilic Addition Reactions (EARs)
  145. 9.2: Addition of Hydrogen Halides to Symmetrical Alkenes
  146. 9.3: Alkene Asymmetry and Markovnikov's Rule
  147. 9.4: Hydration- Acid Catalyzed Addition of Water
  148. 9.5: Hydration- Oxymercuration-Demercuration
  149. 9.6: Hydration - Hydroboration-Oxidation
  150. 9.7: Stereochemistry of Reactions - Hydration of Achiral Alkenes
  151. 9.8: Stereochemistry of Reactions - Hydration of Chiral Alkenes
  152. 9.9: Addition of Halogens
  153. 9.10: Formation of Halohydrins
  154. 9.11: Reduction of Alkenes - Catalytic Hydrogenation
  155. 9.12: Oxidation of Alkenes - Epoxidation
  156. 9.13: Dihydroxylation of Alkenes
  157. 9.14: Opening of Epoxides - Acidic versus Basic Conditions
  158. 9.15: Oxidative Cleavage of Alkenes
  159. 9.16: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  160. 9.17: Radical Chain-Growth Polymerization
  161. 9.18: Biological Additions of Radicals to Alkenes
  162. 9.19: Additional Exercises
  163. 9.20: Solutions to Additional Exercises
  164. 10: Alkynes
  165. 10.1: Structure and Physical Properties
  166. 10.2: 10.2 Synthesis of Alkynes - Elimination Reactions of Dihalides
  167. 10.3: Reactions of Alkynes - Addition of HX and X₂
  168. 10.4: Hydration of Alkynes for Markovnikov Products
  169. 10.5: Hydration of Alkynes for Anti-Markovnikov Products
  170. 10.6: 10.6 Reduction of Alkynes
  171. 10.7: Oxidation of Alkynes
  172. 10.8: Acidity of Terminal Alkynes and Acetylide Ions
  173. 10.9: Synthesis of Larger Alkynes from Acetylides
  174. 10.10: An Introduction to Multiple Step Synthesis
  175. 10.11: Additional Exercises
  176. 10.12: Solutions to Additional Exercises
  177. 11: Infrared Spectroscopy and Mass Spectrometry
  178. 11.1: The Electromagnetic Spectrum and Spectroscopy
  179. 11.2: Infrared (IR) Spectroscopy
  180. 11.3: IR-Active and IR-Inactive Vibrations
  181. 11.4: Interpretting IR Spectra
  182. 11.5: Infrared Spectra of Some Common Functional Groups
  183. 11.6: Summary and Tips to Distinguish between Carbonyl Functional Groups
  184. 11.7: Mass Spectrometry - an introduction
  185. 11.8: Fragmentation Patterns in Mass Spectrometry
  186. 11.9: Useful Patterns for Structure Elucidation
  187. 11.10: Determination of the Molecular Formula by High Resolution Mass Spectrometry
  188. 12: Nuclear Magnetic Resonance Spectroscopy
  189. 12.1: Theory of Nuclear Magnetic Resonance (NMR)
  190. 12.2: NMR Spectra - an introduction and overview
  191. 12.3: Chemical Shifts and Shielding
  192. 12.4: ¹H NMR Spectroscopy and Proton Equivalence
  193. 12.5: Functional Groups and Chemical Shifts in ¹H NMR Spectroscopy
  194. 12.6: Integration of ¹H NMR Absorptions- Proton Counting
  195. 12.7: Spin-Spin Splitting in ¹H NMR Spectra
  196. 12.8: More Complex Spin-Spin Splitting Patterns
  197. 12.9: Uses of ¹H NMR Spectroscopy
  198. 12.10: ¹³C NMR Spectroscopy
  199. 12.11: Chemical Shifts and Interpreting ¹³C NMR Spectra
  200. 12.12: ¹³C NMR Spectroscopy and DEPT
  201. 12.13: Uses of ¹³C NMR Spectroscopy
  202. 12.14: More NMR Examples
  203. 12.15: Sample NMR Spectra
  204. 13: Structure and Synthesis of Alcohols
  205. 13.1: Introduction to Structure and Synthesis of Alcohols
  206. 13.2: Classification of Alcohols
  207. 13.3: Physical Properties of Alcohols
  208. 13.4: Spectroscopy of Alcohols
  209. 13.5: Acidity of Alcohols and Phenols
  210. 13.6: Synthesis of Alcohols - Review
  211. 13.7: Reduction of the Carbonyl Group - Synthesis of 1º and 2º Alcohols
  212. 13.8: Organometallic Reagents
  213. 13.9: Organometallic Reagents in Alcohol Synthesis
  214. 13.10: Thiols (Mercaptans)
  215. 13.11: Commercially Important Alcohols
  216. 13.12: 13.12 Additional Exercises
  217. 13.13: Solutions to Additional Exercises
  218. 14: Reactions of Alcohols
  219. 14.1: Reactions of Alcohols with Hydrohalic Acids
  220. 14.2: Reactions with Phosphorus Halides and Thionyl Chloride
  221. 14.3: Alcohol conversion to Esters - Tosylate and Carboxylate
  222. 14.4: Dehydration Reactions of Alcohols
  223. 14.5: Oxidation States of Alcohols and Related Functional Groups
  224. 14.6: Oxidation Reactions of Alcohols
  225. 14.7: Determining Alcohol Classifications in the Lab - alternate reactions
  226. 14.8: Protection of Alcohols
  227. 14.9: Cleavage of Diols
  228. 14.10: Reactions of Alkoxides
  229. 14.11: Biological Oxidation - An Introduction
  230. 14.12: Additional Exercises
  231. 14.13: Solutions to Additional Exercises
  232. Back Matter
  233. Index
  234. 15: Ethers, Epoxides and Thioethers
  235. 15.1: Physical Properties of Ethers
  236. 15.2: Spectroscopy of Ethers
  237. 15.3: The Williamson Ether Synthesis
  238. 15.4: Alkoxymercuration-Demercuration Synthesis of Ethers
  239. 15.5: Acidic Cleavage of Ethers
  240. 15.6: Autoxidation of Ethers
  241. 15.7: Synthesis of Epoxides
  242. 15.8: Opening of Epoxides
  243. 15.9: Reactions of Epoxides with Grignard and Organolithium Reagents
  244. 15.10: Crown Ethers
  245. 15.11: Epoxy Resins - The Advent of Modern Glues
  246. 15.12: Thioethers (Sulfides) and Silyl Ethers
  247. 15.13: Additional Exercises
  248. 15.14: Solutions to Additional Exercises
  249. 16: Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
  250. 16.1: Stability of Conjugated Dienes - Molecular Orbital Theory
  251. 16.2: Allylic Cations
  252. 16.3: Electrophilic Additions to Conjugated Dienes
  253. 16.4: Kinetic versus Thermodynamic Control
  254. 16.5: SN2 Reactions of Allylic Halides and Tosylates
  255. 16.6: The Diels-Alder (4 + 2) Cycloaddition Reaction
  256. 16.7: Diels-Alder Stereochemistry
  257. 16.8: Diene Polymers - Natural and Synthetic Rubbers
  258. 16.9: Structure Determination in Conjugated Systems - Ultraviolet Spectroscopy
  259. 16.10: Interpreting Ultraviolet Spectra - The Effect of Conjugation
  260. 16.11: Conjugation, Color, and the Chemistry of Vision
  261. 16.12: Additional Exercises
  262. 16.13: Solutions to Additional Exercises
  263. 17: Aromatic Compounds
  264. 17.1: Introduction- The Discovery of Benzene
  265. 17.2: The Structure and Properties of Benzene and its Derivatives
  266. 17.3: Resonance and the Molecular Orbitals of Benzene
  267. 17.4: The Molecular Orbital Picture of Cyclobutadiene
  268. 17.5: Aromaticity and Huckel's Rule
  269. 17.6: Aromatic Ions - a closer look
  270. 17.7: Heterocyclic Aromatic Compounds - a closer look
  271. 17.8: Polycyclic Aromatic Hydrocarbons
  272. 17.9: Spectroscopy of Aromatic Compounds
  273. 17.10: Additional Exercises
  274. 17.11: Solutions to Additional Exercises
  275. 18: Reactions of Aromatic Compounds
  276. 18.1: Electrophilic Aromatic Substitution (EAS)
  277. 18.2: Halogenation of Benzene (an EAS Reaction)
  278. 18.3: Nitration of Benzene (an EAS Reaction)
  279. 18.4: Sulfonation of Benzene (an EAS Reaction)
  280. 18.5: Alkylation and Acylation of Benzene - The Friedel-Crafts EAS Reactions
  281. 18.6: Substituent Effects on the EAS Reaction
  282. 18.7: Side-Chain Reactions of Benzene Derivatives
  283. 18.8: Synthetic Strategies for Di-substituted Benzenes
  284. 18.9: Trisubstituted Benzenes - Effects of Multiple Substituents
  285. 18.10: Nucleophilic Aromatic Substitution - The Addition-Elimantion Mechanism
  286. 18.11: NAS Reactions - the Elimination-Addition (Benzyne) Mechanism
  287. 18.12: Reduction of Aromatic Compounds
  288. 18.13: Additional Exercises
  289. 18.14: Solutions to Additional Exercises
  290. 19: Ketones and Aldehydes
  291. 19.1: Carbonyl Compound Structure and Properties
  292. 19.2: Spectroscopy of Ketones and Aldehydes
  293. 19.3: Review of Ketone and Aldehyde Synthesis
  294. 19.4: 19.4 New Synthesis of Aldehydes and Ketones
  295. 19.5: Nucleophilic Addition Reactions of Ketones and Aldehydes
  296. 19.6: Nucleophilic Addition of Water (Hydration)
  297. 19.7: Nucleophilic Addition of Cyanide and Acetylide
  298. 19.8: Nucleophilic Addition of Grignards
  299. 19.9: Nucelophilic Addition of Amines (Imine and Enamine Formation)
  300. 19.10: Nucleophilic Addition of Hydrazine (Wolff-Kishner Reaction)
  301. 19.11: Nucelophilic Addition of Alcohols (Acetal Formation)
  302. 19.12: Acetals as Protecting Groups
  303. 19.13: Nucelophilic Addition of Phosphorus Ylides (The Wittig Reaction)
  304. 19.14: Oxidation of Aldehydes
  305. 19.15: Reductions of Ketones and Aldehydes
  306. 19.16: Additional Exercises
  307. 19.17: Solutions to Additional Exercises
  308. 20: Amines
  309. 20.1: Structure and Physical Properties of Amines
  310. 20.2: Basicity of Amines and Ammonium Salt Formation
  311. 20.3: Spectroscopy of Amines
  312. 20.4: Synthesis of Amines
  313. 20.5: Synthesis of Primary Amines
  314. 20.6: Reactions of Amines
  315. 20.7: Reactions of Arylamines
  316. 20.8: The Hofmann Elimination- Amines as Leaving Groups
  317. 20.9: Oxidation of Amines - The Cope Elimination
  318. 20.10: Sulfa Drugs - a closer look
  319. 20.11: Additional Exercises
  320. 20.12: Solutions to Additional Exercises
  321. 21: Carboxylic Acids
  322. 21.1: Structure and Properties of Carboxylic Acids and their Salts
  323. 21.2: Acidity of Carboxylic Acids
  324. 21.3: Spectroscopy of Carboxylic Acids
  325. 21.4: Synthesis of Carboxylic Acids
  326. 21.5: Reactions of Carboxylic Acids Overview
  327. 21.6: Condensation of Acids with Alcohols- The Fischer Esterification
  328. 21.7: Methyl Ester Synthesis Using Diazomethane
  329. 21.8: Condensation of Acids with Amines
  330. 21.9: Reduction of Carboxylic Acids
  331. 21.10: Biochemically Interesting Carboxylic Acids
  332. 21.11: Additional Exercises
  333. 21.12: Solutions to Additional Exercises
  334. 22: Carboxylic Acid Derivatives and Nitriles
  335. 22.1: Structure and Physical Properties of Acid Derivatives
  336. 22.2: Spectroscopy of Carboxylic Acid Derivatives
  337. 22.3: Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
  338. 22.4: Acid Halide Chemistry
  339. 22.5: Acid Anhydride Chemistry
  340. 22.6: Ester Chemistry
  341. 22.7: Amide Chemistry
  342. 22.8: Nitrile Chemistry
  343. 22.9: Thioesters- Biological Carboxylic Acid Derivatives
  344. 22.10: Polyamides and Polyesters- Step-Growth Polymers
  345. 22.11: Beta-Lactams- An Application
  346. 22.12: Biological Acylation Reactions
  347. 22.13: Additional Exercises
  348. 22.14: Solutions to Additional Exercises
  349. 23: Alpha Substitutions and Condensations of Carbonyl Compounds
  350. 23.1: Relative Acidity of alpha-Hydrogens
  351. 23.2: Enols, Enolate Ions and Tautomerization
  352. 23.3: Reaction Overview
  353. 23.4: Alpha Halogenation of Carbonyls
  354. 23.5: Bromination of Acids- The HVZ Reaction
  355. 23.6: Alkylation of the alpha-Carbon via the LDA pathway
  356. 23.7: Alkylation of the Alpha-Carbon via the Enamine Pathway
  357. 23.8: The Aldol Reaction and Condensation of Ketones and Aldehydes
  358. 23.9: The Claisen Condensation Reactions of Esters
  359. 23.10: Conjugate Additions- The Michael Reaction
  360. 23.11: Decarboxylation Reactions
  361. 23.12: Additional Exercises
  362. 23.13: Solutions to Additional Exercises
  363. 24: Carbohydrates
  364. 24.1: Introduction
  365. 24.2: Classification of Carbohydrates
  366. 24.3: Fischer Projections
  367. 24.4: D and L Sugars
  368. 24.5: Configuration of Aldoses
  369. 24.6: Cyclic Structures of Monosaccharides
  370. 24.7: Reactions of Monosaccharides
  371. 24.8: Disaccharides and Glycosidic Bonds
  372. 24.9: Polysaccharides
  373. 24.10: Other Important Carbohydrates
  374. 24.11: Cell Surface Carbohydrates and Influenza Viruses
  375. 25: Amino Acids, Peptides, and Proteins
  376. 25.1: Introduction
  377. 25.2: Structure and Stereochemistry of the Amino Acids
  378. 25.3: Isoelectric Points and Electrophoresis
  379. 25.4: Synthesis of Amino Acids
  380. 25.5: Peptides and Proteins
  381. 25.6: Amino Acid Analysis of Peptides
  382. 25.7: Peptide Sequencing- The Edman Degradation
  383. 25.8: Peptide Synthesis
  384. 25.9: Automated Peptide Synthesis- The Merrifield Solid-Phase Technique
  385. 25.10: Levels of Protein Structure
  386. 25.11: Enzymes and Coenzymes
  387. 25.12: How do enzymes work?
  388. 26: Lipids
  389. 26.1: Introduction
  390. 26.2: Waxes, Fats, and Oils
  391. 26.3: Saponification of Fats and Oils; Soaps and Detergents
  392. 26.4: Phospholipids
  393. 26.5: Prostaglandins and other Eicosanoids
  394. 26.6: Terpenes and Terpenoids
  395. 26.7: Steroids
  396. 26.8: Biosynthesis of Steroids
  397. 27: Nucleic Acids
  398. 27.1: Nucleotides and Nucleic Acids
  399. 27.2: DNA Base Pairs
  400. 27.3: DNA Replication
  401. 27.4: Transcription of DNA
  402. 27.5: Translation of RNA- Protein Biosynthesis
  403. 27.6: DNA Sequencing
  404. 27.7: Polymerase Chain Reactions
  405. Back Matter
  406. Index
  407. Glossary
  408. Detailed Licensing