Klein and Straumanis Guided

Read here Read at LibreTextsPDF
Subjects
Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
Who can read
Tweens profiles and older, judged from its title and subjects

Contents

LibreTexts writes equations in TeX, and here they show as TeX; the PDF has them typeset.

  1. Front Matter
  2. TitlePage
  3. InfoPage
  4. Table of Contents
  5. Licensing
  6. 1: A Review of General Chemistry - Electrons, Bonds, and Molecular Properties
  7. 1.1: Introduction to Organic Chemistry
  8. 1.2: 1-3 Atomic Orbitals and Hybridization
  9. 1.2.1: \(sp\) Hybrid Orbitals and the Structure of Acetylene
  10. 1.2.2: (sp^2\) Hybrid Orbitals and the Structure of Ethylene
  11. 1.2.3: (sp^3\) Hybrid Orbitals and the Structure of Ethane
  12. 1.2.4: (sp^3\) Hybrid Orbitals and the Structure of Methane
  13. 1.3: Valence Bond Theory
  14. 1.4: Molecular Orbital Theory
  15. 1.5: Intermolecular Forces and Physical Properties
  16. 1.6: Solubility
  17. 1.7: 1-2 Electron-Dot Model of Bonding- Lewis Structures and Formal Charges
  18. 1.8: 1-4 Determining Molecular Shape
  19. 1.9: 1-5 Dipole Moments and Molecular Polarity
  20. 1.9.1: Polar Covalent Bonds- Electronegativity
  21. 1.9.2: Polar Covalent Bonds- Dipole Moments
  22. 1.10: 1-6 Induction and Polar Covalent Bonds
  23. 1.10.1: Noncovalent Interactions Between Molecules
  24. 1.E: A Review of General Chemistry (Exercises)
  25. 2: Molecular Representations
  26. 2.1: Molecular Representations
  27. 2.2: Bond-Line Structures
  28. 2.3: 2.2 Polar Covalent Bonds- Dipole Moments
  29. 2.4: Identifying Functional Groups
  30. 2.5: Carbon Atoms with Formal Charges
  31. 2.6: Identifying Lone Pairs
  32. 2.7: Three-Dimensional Bond-Line Structures
  33. 2.8: 2-2 Introduction to Resonance
  34. 2.8.1: Building Resonance Structures
  35. 2.8.2: Rules for Resonance Forms
  36. 2.9: Curved Arrows
  37. 2.10: Formal Charges in Resonance Structures
  38. 2.11: Assessing Relative Importance of Resonance Structures
  39. 2.12: Delocalized and Localized Lone Pairs
  40. 2.13: 2-1 Drawing Chemical Structures
  41. 2.14: 2-3 Drawing Resonance Structures
  42. 2.14.1: Drawing Resonance Forms Using Pattern Recognition
  43. 2.E: Molecular Representations (Exercises)
  44. 3: Acids and Bases
  45. 3.1: 1.21 How the Structure of an Acid Affects its pka Value
  46. 3.2: An Introduction to Brønsted-Lowry Acids and Bases
  47. 3.3: Flow of Electron Density - Curved Arrow Notation
  48. 3.4: Brønsted-Lowry Acidity - A Quantitative Perspective
  49. 3.5: Brønsted-Lowry Acidity - Qualitative Perspective
  50. 3.6: Position of Equilibrium and Choice of Reagents
  51. 3.7: Choice of Solvent
  52. 3.8: Solvating Effects
  53. 3.9: Counterions
  54. 3.10: Lewis Acids and Bases
  55. 3.11: Hydrogen Bonds
  56. 3.12: 3-1 Physical properties of organic compounds
  57. 3.13: 3-3 Acids and Bases; Electrophiles and Nucleophiles
  58. 3.14: 3-4 Organic Acids and Bases
  59. 3.15: 3-5 How to Predict the Outcome of an Acid-Base Reaction
  60. 3.16: 3-6 How Substituents Affect the Strength of an Acid
  61. 3.17: 3-7 Factors That Determine Acid Strength
  62. 3.E: Acids and Bases (Exercises)
  63. 4: Alkanes and Cycloalkanes
  64. 4.1: 3.5 Properties of Alkanes
  65. 4.2: 3-1 Conformations of open-chain organic molecules
  66. 4.2.1: Alkanes and Their Stereochemistry
  67. 4.3: 3-2 Conformations of cyclic organic molecules
  68. 4.3.1: Conformations of Cyclohexane
  69. 4.4: Introduction to Alkanes
  70. 4.5: Nomenclature of Alkanes
  71. 4.6: Constitutional Isomers of Alkanes
  72. 4.7: Relative Stability of Isomeric Alkanes
  73. 4.8: Sources and Uses of Alkanes
  74. 4.9: Drawing Newman Projections
  75. 4.10: Cycloalkanes
  76. 4.11: Conformations of Cyclohexane
  77. 4.12: Drawing Chair Conformations
  78. 4.13: Monosubstituted Cyclohexane
  79. 4.14: Disubstituted Cyclohexane
  80. 4.15: cis-trans Stereoisomerism
  81. 4.16: Polycyclic Systems
  82. 4.17: 4-1 Naming Alkanes
  83. 4.18: 4-2 Naming Cycloalkanes
  84. 4.19: 4-3 Cis-Trans Isomerism in Cycloalkanes
  85. 4.20: 4-4 Alkanes and Alkane Isomers
  86. 4.21: 4-5 Combustion. Heats of Reaction. Bond Energies
  87. 4.E: Alkanes and Cycloalkanes (Exercises)
  88. 5: Stereoisomerism
  89. 5.1: Prelude to Stereoisomerism
  90. 5.2: Overview of Isomerism
  91. 5.3: Introduction to Stereoisomerism
  92. 5.4: Designating Configuration Using the Cahn-Ingold-Prelog System
  93. 5.5: Optical Activity
  94. 5.6: 5-4 Stereoisomeric Relationships - Enantiomers and Diastereomers
  95. 5.6.1: 001 Pasteur's Discovery of Enantiomers
  96. 5.6.2: Diastereomers
  97. 5.6.3: Meso Compounds
  98. 5.7: Symmetry and Chirality
  99. 5.8: Fischer Projections
  100. 5.9: Conformationally Mobile Systems
  101. 5.10: Resolution of Enantiomers
  102. 5.11: Chiral Molecules
  103. 5.12: 5-1 Looking Glass Chemistry—Chiral and Achiral Molecules
  104. 5.13: 5-2 The Reason for Handedness in Molecules- Chirality
  105. 5.14: 5-3 Optical Activity
  106. 5.15: 5-5 Sequence Rules for Specifying Configuration
  107. 5.15.1: Diastereomers and Fischer Projections
  108. 5.E: Stereoisomerism (Exercises)
  109. 6: Chemical Reactivity and Mechanisms
  110. 6.1: Enthalpy
  111. 6.2: Entropy
  112. 6.3: Gibbs Free Energy
  113. 6.4: Equilibria
  114. 6.5: Kinetics
  115. 6.6: Reading Energy Diagrams
  116. 6.7: Mechanisms and Arrow Pushing
  117. 6.8: Combining the Patterns of Arrow Pushing
  118. 6.9: Catalysts
  119. 6.10: Drawing Curved Arrows
  120. 6.11: Carbocation Rearrangements
  121. 6.12: Nucleophiles and Electrophiles
  122. 6.13: 6-10 Describing a Reaction- Intermediates
  123. 6.14: 6-11 Reaction Mechanisms Involving Polar Functional Groups- Using "Electron-Pushing'" Arrows
  124. 6.15: 6-1 Writing Equations for Organic Reactions
  125. 6.16: 6-2 Kinds of Organic Reactions
  126. 6.17: 6-3 Bond Breaking and Bond Making
  127. 6.18: 6-4 Bond Dissociation Energy
  128. 6.19: 6-5 Thermodynamics
  129. 6.20: 6-6 Enthalpy and Entropy
  130. 6.21: 6-7 Energy Diagrams
  131. 6.22: 6-8 Energy Diagram for a Two-Step Reaction Mechanism
  132. 6.23: 6-9 Kinetics
  133. 6.E: Chemical Reactivity and Mechanisms (Exercises)
  134. 7: Substitution Reactions
  135. 7.1: 7-2 The \(S_{N}2\) Reaction
  136. 7.2: 7-3 Characteristics of the \(S_{N}2\) Reaction
  137. 7.3: 7-4 The \(S_{N}1\) Reaction
  138. 7.4: 7-5 Characteristics of the \(S_{N}1\) Reaction
  139. 7.5: Introduction to Substitution Reactions
  140. 7.6: Alkyl Halides
  141. 7.7: Possible Mechanisms for Substitution Reactions
  142. 7.8: The SN2 Mechanism
  143. 7.9: The SN1 Mechanism
  144. 7.10: Drawing the Complete Mechanism of an SN1 Reaction
  145. 7.11: Drawing the Complete Mechanism of an SN2 Reaction
  146. 7.12: Determining Which Mechanism Predominates
  147. 7.13: Selecting Reagents to Accomplish Functional Group Transformation
  148. 7.14: 7-7 When Is the Mechanism \(S_{N}1\) or \(S_{N}2\)?
  149. 7.15: 7-1 Introduction to Nucleophilic Substitution Reactions
  150. 7.16: 7-8 Carbocation Structure and Stability
  151. 7.17: 7-9 Carbocation Stability
  152. 7.18: 7-6 Structural and Solvent Effects in \(S_N\) Reactions
  153. 7.E: Substitution Reactions (Exercises)
  154. 8: Alkenes- Structure and Preparation via Elimination Reactions
  155. 8.1: Introduction to Elimination Reactions
  156. 8.2: Alkenes in Nature and in Industry
  157. 8.3: Nomenclature of Alkenes
  158. 8.4: Stereoisomerism in Alkenes
  159. 8.5: Alkene Stability
  160. 8.6: Possible Mechanisms for Elimination
  161. 8.7: The E2 Mechanism
  162. 8.8: Drawing the Products of an E2 Reaction
  163. 8.9: The E1 Mechanism
  164. 8.10: Drawing the Complete Mechanism of an E1 Process
  165. 8.11: Drawing the Complete Mechanism of an E2 Process 372
  166. 8.12: Substitution vs. Elimination- Identifying the Reagent
  167. 8.13: Substitution vs. Elimination- Identifying the Mechanism(s)
  168. 8.14: Substitution vs. Elimination- Predicting the Products
  169. 8.15: 8-1 Elimination Reactions- Zaitsev's Rule
  170. 8.16: 8-1 Nucleophilic Character of the Pi Bond- Electrophilic Addition of Hydrogen Halides
  171. 8.17: 8-3 The E2 Reaction and the Deuterium Isotope Effect
  172. 8.18: 8-2 Unimolecular Elimination- E1
  173. 8.19: 8-4 The E2 Reaction and Cyclohexane Conformation
  174. 8.20: 8-5 Keys to Success- Substitutin Versus Elimination-Structure Determines Function
  175. 8.E: Alkenes (Exercises)
  176. 9: Addition Reactions of Alkenes
  177. 9.1: Vicinal SYn Dihydroxylation with Osmium Tetroxide
  178. 9.2: Oxidative Cleavage- Ozonolysis
  179. 9.3: 9-6 Halogenation of Alkenes- Addition of \(X_2\)
  180. 9.4: 9-10 Hydration of Alkenes- Addition of \(H_{2}O\) by Hydroboration
  181. 9.5: Introduction to Addition Reactions
  182. 9.6: Addition vs. Elimination - A Thermodynamic Perspective
  183. 9.7: Hydrohalogenation
  184. 9.8: Acid-Catalyzed Hydration
  185. 9.9: Oxymercuration-Demercuration
  186. 9.10: Hydroboration-Oxidation
  187. 9.11: Catalytic Hydrogenation
  188. 9.12: Halogenation and Halohydrin Formation
  189. 9.13: Anti Dihydroxylation
  190. 9.14: Syn Dihydroxylation
  191. 9.15: Oxidative Cleavage
  192. 9.16: Predicting Products of an Addition Reaction
  193. 9.17: Synthesis Strategies
  194. 9.18: 9-10 Reduction of Alkenes- Hydrogenation
  195. 9.19: 9-11 Catalytic Hydrogenation
  196. 9.20: 9-12 Reduction of Alkynes
  197. 9.21: 9-13 Oxidation of Alkenes- Cleavage to Carbonyl Compounds
  198. 9.22: 9-14 Naming Alkenes
  199. 9.23: 9-15 Cis-Trans Isomerism in Alkenes
  200. 9.24: 9-16 Sequence Rules- The E,Z Designation
  201. 9.25: 9-1 Nucleophilic Character of the Pi Bond- Electrophilic Addition of Hydrogen Halides
  202. 9.26: 9-2 Alcohol Synthesis by Electrophilic Hydration- Thermodynamic Control
  203. 9.27: 9-3 Oxymercuration-Demercuration- A Special Elcctrophilic Addition
  204. 9.28: 9-4 Hydroboration-Oxidation- A Stereospecific Anti-Markovnikov Hydration
  205. 9.29: 9-7 Halohydrins from Alkenes- Addition of HOX
  206. 9.30: 9-8 Radical Additions- Anti-Markovnikov Product Formation
  207. 9.31: 9-8 Oxacyclopropane ( Epoxide) Synthesis- Epoxidation by Peroxycarboxylic Acids
  208. 9.32: 9-9 Oxidation of Alkenes- Epoxidation and Hydroxylation
  209. 9.E: Addition Reactions of Alkenes (Exercises)
  210. 10: Alkynes
  211. 10.1: Alkylation of Terminal Alkynes
  212. 10.2: Synthesis Strategies
  213. 10.3: Introduction to Alkynes
  214. 10.4: Nomenclature of Alkynes
  215. 10.5: Acidity of Acetylene and Terminal Alkynes
  216. 10.6: Preparing Alkynes
  217. 10.7: Reduction of Alkynes
  218. 10.8: Hydrohalogenation of Alkynes
  219. 10.9: Hydration of Alkynes
  220. 10.10: Halogenation of Alkynes
  221. 10.11: Ozonolysis of Alkynes
  222. 10.12: 10-1 Naming Alkynes
  223. 10.13: 10-2 Alkyne Acidity- Formation of Acetylide Anions
  224. 10.14: 10-3 Alkylation of Acetylide Anions
  225. 10.15: 10-4 Preparation of Alkynes- Elimination Reactions of Dihalides
  226. 10.16: 10-6 Oxidative Cleavage of Alkynes
  227. 10.17: 10-7 Hydration of Triple Bonds
  228. 10.18: 10-8 Hydroboration–Oxidation
  229. 10.19: 10-5 Reactions of Alkynes- Addition of HX and \(X_2\)
  230. 10.E: Alkynes (Exercises)
  231. 11: Radical Reactions
  232. 11.1: Radicals
  233. 11.2: Common Patterns in Radical Mechanisms
  234. 11.3: Chlorination of Methane
  235. 11.4: Thermodynamic Considerations for Halogenation Reactions
  236. 11.5: Regioselectivity of Halogenation
  237. 11.6: Stereochemistry of Halogenation
  238. 11.7: Allylic Bromination
  239. 11.8: Atmospheric Chemistry and the Ozone Layer
  240. 11.9: Autooxidation and Antioxidants
  241. 11.10: Addition of HBr- Anti-Markovnikov Addition
  242. 11.11: Radical Polymerization
  243. 11.12: Radical Processes in the Petrochemical Industry
  244. 11.13: Halogenation as a Synthetic Technique
  245. 11.14: 11-1 Preparing Alkyl Halides from Alkanes- Radical Halogenation
  246. 11.15: 11-2 Chlorination of Methane- The Radical Chain Mechanism
  247. 11.16: 11-3 Selectivity in Radical Halogenation with Fluorine and Bromine
  248. 11.17: 11-4 Radical Halogenation at an Allylic Carbon
  249. 11.18: 11-5 Radical chain reactions
  250. 11.19: 11-6 Radical Additions- Anti-Markovnikov Product Formation
  251. 11.E: Radical Reactions (Exercises)
  252. 12: Synthesis
  253. 12.1: One-Step Syntheses
  254. 12.2: Retrosynthetic Analysis
  255. 12.3: Practical Tips for Increasing Proficiency
  256. 12.4: An Introduction to Organic Synthesis
  257. 12.5: Building the Carbon Skeleton
  258. 12.6: The Logic of Synthesis
  259. 12.E: Synthesis (Exercises)
  260. 13: Alcohols and Phenols
  261. 13.1: Physical Properties of Alcohols; Hydrogen Bonding
  262. 13.2: Preparation of Alcohols via Reduction
  263. 13.3: Preparation of Diols
  264. 13.4: Reactions of Alcohols - Substitution and Elimination
  265. 13.5: Reactions of Alcohols- Oxidation
  266. 13.6: Biological Redox Reactions
  267. 13.7: Oxidation of Phenol
  268. 13.8: Synthesis Strategies
  269. 13.9: Physical Properties of Alcohols; Hydrogen Bonding
  270. 13.10: Acidity of Alcohols and Phenols
  271. 13.11: Synthesis of Alcohols - Review
  272. 13.12: Dehydration Reactions of Alcohols
  273. 13.13: Oxidation Reactions of Alcohols
  274. 13.14: Alcohols from Reaction of Carbonyl Compounds- Grignard Reagents
  275. 13.15: 13.7 Reactions of Alcohols
  276. 13.16: Protection of Alcohols
  277. 13.17: 13.9 Alcohols from Carbonyl Compounds- Reduction
  278. 13.E: Alcohols and Phenols (Exercises)
  279. 14: Ethers and Epoxides; Thiols and Sulfides
  280. 14.1: Introduction to Ethers
  281. 14.2: Nomenclature of Ethers
  282. 14.3: Crown Ethers
  283. 14.4: Nomenclature of Epoxides
  284. 14.5: Enantioselective Epoxidation
  285. 14.6: Reactions of Epoxides - Ring-opening
  286. 14.7: Thiols and Sulfides
  287. 14.8: Synthesis Strategies Involving Epoxides
  288. 14.9: Names and Properties of Ethers
  289. 14.10: Synthesis of Ethers
  290. 14.11: Reactions of Ethers - Acidic Cleavage
  291. 14.E: Ethers and Epoxides; Thiols and Sulfides (Exercises)
  292. 15: Infrared Spectroscopy and Mass Spectrometry
  293. 15.1: 6-1 Spectroscopy and the Electromagnetic Spectrum
  294. 15.2: 6-2 Infrared Spectroscopy
  295. 15.3: 6-3 Interpreting Infrared Spectra
  296. 15.4: 6-4 Infrared Spectra of Some Common Functional Groups
  297. 15.5: 6-5 Mass Spectrometry of Small Molecules- Magnetic-Sector Instruments
  298. 15.5.1: Mass Spectroscopy in Further Detail
  299. 15.6: 6-6 Interpreting Mass Spectra
  300. 15.7: 6-7 Mass Spectrometry of Some Common Functional Groups
  301. 15.8: 6-8 Isotopes in Mass Spectrometry
  302. 15.9: 6-9 Fragmentation Patterns of Organic Molecules
  303. 15.9.1: More Fragmentation
  304. 16: Nuclear Magnetic Resonance Spectroscopy
  305. 16.1: Introduction to NMR Spectroscopy
  306. 16.2: Acquiring a ¹H NMR Spectrum
  307. 16.3: Characteristics of a ¹H NMR Spectrum
  308. 16.4: Number of Signals
  309. 16.5: Chemical Shift
  310. 16.6: Integration
  311. 16.7: Multiplicity
  312. 16.8: Using ¹H NMR Spectroscopy to Distinguish between Compounds
  313. 16.9: Analyzing a ¹H NMR Spectrum
  314. 16.10: Acquiring a ¹³C NMR Spectrum
  315. 16.11: Chemical Shifts in ¹³C NMR Spectroscopy
  316. 16.12: DEPT ¹³C NMR Spectroscopy
  317. 16.13: Drawing the Expected ¹H NMR Spectrum of a Compound
  318. 16.14: 16-10 Integration of ¹H NMR Absorptions- Proton Counting
  319. 16.15: 16-10 Spin-Spin Splitting in ¹H NMR Spectra
  320. 16.16: 16-11 More Complex Spin-Spin Splitting Patterns
  321. 16.17: 16-12 Nuclear Magnetic Resonance Spectroscopy - Extra Details
  322. 16.18: 16-1 Nuclear Magnetic Resonance Spectroscopy
  323. 16.19: 16-2 The Nature of NMR Absorptions
  324. 16.20: 16-3 Chemical Shifts
  325. 16.21: 16-4 ¹³C NMR Spectroscopy- Signal Averaging and FT-NMR
  326. 16.22: 16-5 Characteristics of ¹³C NMR Spectroscopy
  327. 16.23: 16-6 DEPT ¹³C NMR Spectroscopy
  328. 16.24: 16-7 Uses of ¹³C NMR Spectroscopy
  329. 16.25: 16-8 ¹H NMR Spectroscopy and Proton Equivalence
  330. 16.26: 16-9 Chemical Shifts in ¹H NMR Spectroscopy
  331. 16.27: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
  332. 16.E: Nuclear Magnetic Resonance Spectroscopy (Exercises)
  333. 17: Conjugated Pi Systems and Pericyclic Reactions
  334. 17.1: An Introduction to Pericyclic Reactions
  335. 17.2: MO Description of Cycloadditions
  336. 17.3: Electrocyclic Reactions
  337. 17.4: Sigmatropic Rearrangements
  338. 17.5: Electronic Spectra- Ultraviolet and Visible Spectroscopy
  339. 17.6: Color
  340. 17.7: The Chemistry of Vision
  341. 17.8: Introduction
  342. 17.9: Two Neighboring Double Bonds- Conjugated Dienes
  343. 17.10: Two Neighboring Double Bonds- Conjugated Dienes and MO Theory
  344. 17.11: 1,3- or Conjugated Dienes. Electrophilic and Radical Addition
  345. 17.12: Electrophilic Attack on Conjugated Dienes-Kinetic and Thermodynamic Control
  346. 17.13: Kinetic versus Thermodynamic Control
  347. 17.14: Polymerization Reactions of Conjugated Dienes
  348. 17.15: The Diels-Alder Cycloaddition
  349. 17.16: Diels-Alder - a closer look
  350. 17.17: Electrocyclic Reactions
  351. 17.E: Conjugated Pi Systems and Pericyclic Reactions (Exercises)
  352. 18: Aromatic Compounds
  353. 18.1: Aromaticity and the Hückel 4n + 2 Rule
  354. 18.2: Introduction to Aromatic Compounds
  355. 18.3: Nomenclature of Benzene Derivatives
  356. 18.4: Reactions at the Benzylic Position
  357. 18.5: Reduction of the Aromatic Moiety
  358. 18.6: Delocalized Electrons Explain Benzene’s Structure
  359. 18.7: Structure and Resonance Energy of Benzene- A First Look at Aromaticity
  360. 18.8: Spectral Characteristics of the Benzene Ring
  361. 18.E: Aromatic Compounds (Exercises)
  362. 19: Aromatic Substitution Reactions
  363. 19.1: Nitration
  364. 19.2: Friedel-Crafts Alkylation
  365. 19.3: Friedel-Crafts Acylation
  366. 19.4: Halogens - The Exception
  367. 19.5: Activation or Deactivation by Substituents on a Benzene Ring
  368. 19.6: Trisubstituted Benzenes - Additivity of Effects
  369. 19.7: An Explanation of Substituent Effects
  370. 19.8: Synthesis of Polysubstituted Benzenes
  371. 19.9: Nucleophilic Aromatic Substitution
  372. 19.10: Benzyne
  373. 19.11: Elimination-Addition
  374. 19.12: 19.15 Identifying the Mechanism of an Aromatic Substitution Reaction
  375. 19.13: Synthesis of Benzene Derivatives- Electrophilic Aromatic Substitution
  376. 19.14: Electrophilic Aromatic Substitution Reactions - Bromination
  377. 19.15: Other Aromatic Substitutions
  378. 19.16: Substituent Effects in Substituted Aromatic Rings
  379. 19.17: An Explanation of Substituent Effects
  380. 19.E: Aromatic Substitution Reactions (Exercises)
  381. 20: Aldehydes and Ketones
  382. 20.1: 19.5 Nucleophilic Addition of
  383. 20.1.1: (H 2O
  384. 20.1.1.1: 20.4 Nucleophilic Addition of \(H_2O\)- Hydration
  385. 20.2: Mechanism Strategies
  386. 20.3: Sulfur Nucleophiles
  387. 20.4: Hydrogen Nucleophiles
  388. 20.5: 20.10 Nucleophilic Addition of Phosphorus Ylides- The Wittig Reaction
  389. 20.6: Baeyer-Villiger Oxidation of Aldehydes and Ketones
  390. 20.7: Synthesis Strategies
  391. 20.8: Spectroscopic Analysis of Aldehydes and Ketones
  392. 20.9: 20.1 Oxidation of Aldehydes and Ketones
  393. 20.10: 20.2 Naming Aldehydes and Ketones
  394. 20.11: 20.3 Preparing Aldehydes and Ketones
  395. 20.12: Nucleophilic Addition of Alcohols- Acetal Formation
  396. 20.13: 20.5a Nucleophilic Addition Reactions of Aldehydes and Ketones
  397. 20.14: Nucleophilic Addition of Amines- Imine and Enamine Formation
  398. 20.15: 20.7a Nucleophilic Addition of Hydrazin - The Wolff-Kishner Reaction
  399. 20.E: Aldehydes and Ketones (Exercises)
  400. 21: Carboxylic Acids and Their Derivatives
  401. 21.1: 20.2 Naming Carboxylic Acids and Nitriles
  402. 21.2: 20.3 Structure and Properties of Carboxylic Acids
  403. 21.3: Introduction to Carboxylic Acids
  404. 21.4: Nomenclature of Carboxylic Acids
  405. 21.5: Preparation of Carboxylic Acids
  406. 21.6: Introduction to Carboxylic Acid Derivatives
  407. 21.7: 21.10 Chemistry of Esters
  408. 21.8: Reactions of Esters
  409. 21.9: 21.12 Chemistry of Amides
  410. 21.10: 21.13 Preparing Carboxylic Acids
  411. 21.11: Synthesis Strategies
  412. 21.12: Spectroscopy of Carboxylic Acids and Their Derivatives
  413. 21.13: 21.4 Preparing Carboxylic Acids
  414. 21.14: 21.5 Structure and Properties of Carboxylic Acids
  415. 21.15: 21.7 Nucleophilic Acyl Substitution Reactions
  416. 21.16: 21.8 Chemistry of Acid Halides
  417. 21.17: 21.8 Nucleophilic Acyl Substitution Reactions of Carboxylic Acids
  418. 21.18: 21.9 Chemistry of Acid Anhydrides
  419. 21.E: Carboxylic Acids and Their Derivatives (Exercises)
  420. 22: Alpha Carbon Chemistry- Enols and Enolates
  421. 22.1: 19.13 Conjugate Nucleophilic Addition to
  422. 22.1.1: (
  423. 22.1.1.1: alpha
  424. 22.2: 22.1 Intro to Enols and Enolates
  425. 22.3: Halogenation of Aldehydes and Ketones
  426. 22.4: 22.3a Carbonyl Condensations - The Aldol Reaction
  427. 22.5: 22.3b Dehydration of Aldol Products - Synthesis of Enones
  428. 22.6: 22.4 Claisen Condensation Reactions
  429. 22.7: Alkylation of the Alpha Position
  430. 22.8: 22.5 Alkylation of Enolate Ions
  431. 22.9: 22.6 Conjugate Nucleophilic Addition to \(\alpha\), \(\beta\)-unsaturated Aldehydes and Ketones
  432. 22.10: Synthesis Strategies
  433. 22.E: Alpha Carbon Chemistry- Enols and Enolates (Exercises)
  434. 23: Amines
  435. 23.1: Introduction to Amines
  436. 23.2: Preparation of Amines - A Review
  437. 23.3: Preparation of Amines via Substitution Reactions
  438. 23.4: Preparation of Amines via Reductive Amination
  439. 23.5: Synthesis Strategies
  440. 23.6: Acylation of Amines
  441. 23.7: The Hofmann Elimination
  442. 23.8: Reactions of Amines with Nitrous Acid
  443. 23.9: Reactions of Aryldiazonium Ions
  444. 23.10: Nitrogen Heterocycles
  445. 23.11: 23.12 Heterocyclic Amines
  446. 23.12: Spectroscopy of Amines
  447. 23.13: 23.2 Naming Amines
  448. 23.14: 23.3 Basicity of Amines
  449. 23.15: 23.3 Structure and Properties of Amines
  450. 23.16: Synthesis of Amines by Alkylation
  451. 23.17: 23.5 Synthesis of Amines
  452. 23.E: Amines (Exercises)
  453. 24: Carbohydrates
  454. 24.1: Introduction to Carbohydrates
  455. 24.2: Classification of Monosaccharides
  456. 24.3: Configuration of Aldoses
  457. 24.4: Configuration of Ketoses
  458. 24.5: Cyclic Structures of Monosaccharides
  459. 24.6: Reactions of Monosaccharides
  460. 24.7: Disaccharides
  461. 24.8: Polysaccharides
  462. 24.9: Amino Sugars
  463. 24.10: N-Glycosides
  464. 24.E: Carbohydrates (Exercises)
  465. 25: Amino Acids, Peptides, and Proteins
  466. 25.1: Introduction to Amino Acids, Peptides and Proteins
  467. 25.2: Structure and Properties of Amino Acids
  468. 25.3: Amino Acid Synthesis
  469. 25.4: Structure of Peptides
  470. 25.5: Sequencing a Peptide
  471. 25.6: Peptide Synthesis
  472. 25.7: Protein Structure
  473. 25.8: Protein Function
  474. 25.E: Amino Acids, Peptides, and Proteins (Exercises)
  475. 26: Lipids
  476. 26.1: Introduction to Lipids
  477. 26.2: Waxes
  478. 26.3: Triglycerides
  479. 26.4: Reactions of Triglycerides
  480. 26.5: Phospholipids
  481. 26.6: Steroids
  482. 26.7: Prostaglandins
  483. 26.8: Terpenes
  484. 26.E: Lipids (Exercises)
  485. 27: Synthetic Polymers
  486. 27.1: Introduction to Synthetic Polymers
  487. 27.2: Nomenclature of Synthetic Polymers
  488. 27.3: Copolymers
  489. 27.4: Polymer Classification by Reaction Type
  490. 27.5: Polymer Classification by Mode of Assembly
  491. 27.6: Polymer Classification by Structure
  492. 27.7: Polymer Classification by Properties
  493. 27.8: Polymer Recycling
  494. 27.E: Synthetic Polymers (Exercises)
  495. Back Matter
  496. Index
  497. Glossary
  498. Detailed Licensing