Organic Chemistry

by OpenStax

Read here Read at LibreTextsPDF

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.

Description from LibreTexts.

Subjects
Chemistry, Organic Chemistry
Licence
CC BY-NC-SA 4.0, as LibreTexts states it. Non-commercial use only.
Who can read
Teens 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: Structure and Bonding
  7. 1.0: Why This Chapter?
  8. 1.1: Atomic Structure - The Nucleus
  9. 1.2: Atomic Structure - Orbitals
  10. 1.3: Atomic Structure - Electron Configurations
  11. 1.4: Development of Chemical Bonding Theory
  12. 1.5: Describing Chemical Bonds - Valence Bond Theory
  13. 1.6: sp³ Hybrid Orbitals and the Structure of Methane
  14. 1.7: sp³ Hybrid Orbitals and the Structure of Ethane
  15. 1.8: sp² Hybrid Orbitals and the Structure of Ethylene
  16. 1.9: sp Hybrid Orbitals and the Structure of Acetylene
  17. 1.10: Hybridization of Nitrogen, Oxygen, Phosphorus and Sulfur
  18. 1.11: Describing Chemical Bonds - Molecular Orbital Theory
  19. 1.12: Drawing Chemical Structures
  20. 1.13: Chemistry Matters—Organic Foods- Risk versus Benefit
  21. 1.14: Key Terms
  22. 1.15: Summary
  23. 1.16: Additional Problems
  24. 2: Polar Covalent Bonds; Acids and Bases
  25. 2.0: Why This Chapter?
  26. 2.1: Polar Covalent Bonds - Electronegativity
  27. 2.2: Polar Covalent Bonds - Dipole Moments
  28. 2.3: Formal Charges
  29. 2.4: Resonance
  30. 2.5: Rules for Resonance Forms
  31. 2.6: Drawing Resonance Forms
  32. 2.7: Acids and Bases - The Brønsted-Lowry Definition
  33. 2.8: Acid and Base Strength
  34. 2.9: Predicting Acid-Base Reactions from pKa Values
  35. 2.10: Organic Acids and Organic Bases
  36. 2.11: Acids and Bases - The Lewis Definition
  37. 2.12: Noncovalent Interactions Between Molecules
  38. 2.13: Chemistry Matters—Alkaloids- From Cocaine to Dental Anesthetics
  39. 2.14: Key Terms
  40. 2.15: Summary
  41. 2.16: Additional Problems
  42. 3: Organic Compounds- Alkanes and Their Stereochemistry
  43. 3.0: Why This Chapter?
  44. 3.1: Functional Groups
  45. 3.2: Alkanes and Alkane Isomers
  46. 3.3: Alkyl Groups
  47. 3.4: Naming Alkanes
  48. 3.5: Properties of Alkanes
  49. 3.6: Conformations of Ethane
  50. 3.7: Conformations of Other Alkanes
  51. 3.8: Chemistry Matters—Gasoline
  52. 3.9: Key Terms
  53. 3.10: Summary
  54. 3.11: Additional Problems
  55. 4: Organic Compounds - Cycloalkanes and their Stereochemistry
  56. 4.0: Why This Chapter?
  57. 4.1: Naming Cycloalkanes
  58. 4.2: Cis-Trans Isomerism in Cycloalkanes
  59. 4.3: Stability of Cycloalkanes - Ring Strain
  60. 4.4: Conformations of Cycloalkanes
  61. 4.5: Conformations of Cyclohexane
  62. 4.6: Axial and Equatorial Bonds in Cyclohexane
  63. 4.7: Conformations of Monosubstituted Cyclohexanes
  64. 4.8: Conformations of Disubstituted Cyclohexanes
  65. 4.9: Conformations of Polycyclic Molecules
  66. 4.10: Chemistry Matters—Molecular Mechanics
  67. 4.11: Key Terms
  68. 4.12: Summary
  69. 4.13: Additional Problems
  70. 5: Stereochemistry at Tetrahedral Centers
  71. 5.0: Why This Chapter?
  72. 5.1: Enantiomers and the Tetrahedral Carbon
  73. 5.2: The Reason for Handedness in Molecules - Chirality
  74. 5.3: Optical Activity
  75. 5.4: Pasteur's Discovery of Enantiomers
  76. 5.5: Sequence Rules for Specifying Configuration
  77. 5.6: Diastereomers
  78. 5.7: Meso Compounds
  79. 5.8: Racemic Mixtures and the Resolution of Enantiomers
  80. 5.9: A Review of Isomerism
  81. 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
  82. 5.11: Prochirality
  83. 5.12: Chirality in Nature and Chiral Environments
  84. 5.13: Chemistry Matters—Chiral Drugs
  85. 5.14: Key Terms
  86. 5.15: Summary
  87. 5.16: Additional Problems
  88. 6: An Overview of Organic Reactions
  89. 6.0: Why This Chapter?
  90. 6.1: Kinds of Organic Reactions
  91. 6.2: How Organic Reactions Occur - Mechanisms
  92. 6.3: Polar Reactions
  93. 6.4: An Example of a Polar Reaction - Addition of HBr to Ethylene
  94. 6.5: Using Curved Arrows in Polar Reaction Mechanisms
  95. 6.6: Radical Reactions
  96. 6.7: Describing a Reaction - Equilibria, Rates, and Energy Changes
  97. 6.8: Describing a Reaction - Bond Dissociation Energies
  98. 6.9: Describing a Reaction - Energy Diagrams and Transition States
  99. 6.10: Describing a Reaction- Intermediates
  100. 6.11: A Comparison between Biological Reactions and Laboratory Reactions
  101. 6.12: Chemistry Matters—Where Do Drugs Come From?
  102. 6.13: Key Terms
  103. 6.14: Summary
  104. 6.15: Additional Problems
  105. 7: Alkenes - Structure and Reactivity
  106. 7.0: Why This Chapter?
  107. 7.1: Industrial Preparation and Use of Alkenes
  108. 7.2: Calculating Degree of Unsaturation
  109. 7.3: Naming Alkenes
  110. 7.4: Cis-Trans Isomerism in Alkenes
  111. 7.5: Alkene Stereochemistry and the E,Z Designation
  112. 7.6: Stability of Alkenes
  113. 7.7: Electrophilic Addition Reactions of Alkenes
  114. 7.8: Orientation of Electrophilic Additions - Markovnikov's Rule
  115. 7.9: Carbocation Structure and Stability
  116. 7.10: The Hammond Postulate
  117. 7.11: Evidence for the Mechanism of Electrophilic Additions - Carbocation Rearrangements
  118. 7.12: Chemistry Matters - Bioprospecting - Hunting for Natural Products
  119. 7.13: Key Terms
  120. 7.14: Summary
  121. 7.15: Additional Problems
  122. 8: Alkenes - Reactions and Synthesis
  123. 8.0: Why This Chapter?
  124. 8.1: Preparation of Alkenes - A Preview of Elimination Reactions
  125. 8.2: Halogenation of Alkenes - Addition of X₂
  126. 8.3: Halohydrins from Alkenes - Addition of HO-X
  127. 8.4: Hydration of Alkenes - Addition of H₂O by Oxymercuration
  128. 8.5: Hydration of Alkenes - Addition of H₂O by Hydroboration
  129. 8.6: Reduction of Alkenes - Hydrogenation
  130. 8.7: Oxidation of Alkenes - Epoxidation and Hydroxylation
  131. 8.8: Oxidation of Alkenes - Cleavage to Carbonyl Compounds
  132. 8.9: Addition of Carbenes to Alkenes - Cyclopropane Synthesis
  133. 8.10: Radical Additions to Alkenes - Chain-Growth Polymers
  134. 8.11: Biological Additions of Radicals to Alkenes
  135. 8.12: Stereochemistry of Reactions - Addition of H₂O to an Achiral Alkene
  136. 8.13: Stereochemistry of Reactions - Addition of H₂O to a Chiral Alkene
  137. 8.14: Chemistry Matters—Terpenes- Naturally Occurring Alkenes
  138. 8.15: Key Terms
  139. 8.16: Summary
  140. 8.17: Summary of Reactions
  141. 8.18: Additional Problems
  142. 9: Alkynes - An Introduction to Organic Synthesis
  143. 9.0: Why This Chapter?
  144. 9.1: Naming Alkynes
  145. 9.2: Preparation of Alkynes - Elimination Reactions of Dihalides
  146. 9.3: Reactions of Alkynes - Addition of HX and X₂
  147. 9.4: Hydration of Alkynes
  148. 9.5: Reduction of Alkynes
  149. 9.6: Oxidative Cleavage of Alkynes
  150. 9.7: Alkyne Acidity - Formation of Acetylide Anions
  151. 9.8: Alkylation of Acetylide Anions
  152. 9.9: An Introduction to Organic Synthesis
  153. 9.10: Chemistry Matters - The Art of Organic Synthesis
  154. 9.11: Key Terms
  155. 9.12: Summary
  156. 9.13: Summary of Reactions
  157. 9.14: Additional Problems
  158. 10: Organohalides
  159. 10.0: Why This Chapter?
  160. 10.1: Names and Properties of Alkyl Halides
  161. 10.2: Preparing Alkyl Halides from Alkanes - Radical Halogenation
  162. 10.3: Preparing Alkyl Halides from Alkenes - Allylic Bromination
  163. 10.4: Stability of the Allyl Radical - Resonance Revisited
  164. 10.5: Preparing Alkyl Halides from Alcohols
  165. 10.6: Reactions of Alkyl Halides - Grignard Reagents
  166. 10.7: Organometallic Coupling Reactions
  167. 10.8: Oxidation and Reduction in Organic Chemistry
  168. 10.9: Chemistry Matters - Naturally Occurring Organohalides
  169. 10.10: Key Terms
  170. 10.11: Summary
  171. 10.12: Summary of Reactions
  172. 10.13: Additional Problems
  173. 11: Reactions of Alkyl Halides- Nucleophilic Substitutions and Eliminations
  174. 11.0: Why This Chapter?
  175. 11.1: The Discovery of Nucleophilic Substitution Reactions
  176. 11.2: The Sₙ2 Reaction
  177. 11.3: Characteristics of the SN2 Reaction
  178. 11.5: Characteristics of the SN1 Reaction
  179. 11.6: Biological Substitution Reactions
  180. 11.7: Elimination Reactions- Zaitsev's Rule
  181. 11.8: The E2 Reaction and the Deuterium Isotope Effect
  182. 11.9: The E2 Reaction and Cyclohexane Conformation
  183. 11.10: The E1 and E1cB Reactions
  184. 11.11: Biological Elimination Reactions
  185. 11.12: A Summary of Reactivity - SN1, SN2, E1, E1cB, and E2
  186. 11.13: Chemistry Matters—Green Chemistry
  187. 11.14: Key Terms
  188. 11.15: Summary
  189. 11.16: Summary of Reactions
  190. 11.17: Additional Problems
  191. 11.4: The SN1 Reaction
  192. 12: Structure Determination - Mass Spectrometry and Infrared Spectroscopy
  193. 12.0: Why This Chapter?
  194. 12.1: Mass Spectrometry of Small Molecules - Magnetic-Sector Instruments
  195. 12.2: Interpreting Mass Spectra
  196. 12.3: Mass Spectrometry of Some Common Functional Groups
  197. 12.4: Mass Spectrometry in Biological - Time-of-flight (TOF) Instruments
  198. 12.5: Spectroscopy and the Electromagnetic Spectrum
  199. 12.6: Infrared Spectroscopy
  200. 12.7: Interpreting Infrared Spectra
  201. 12.8: Infrared Spectra of Some Common Functional Groups
  202. 12.9: Chemistry Matters—X-Ray Crystallography
  203. 12.10: Key Terms
  204. 12.11: Summary
  205. 12.12: Additional Problems
  206. 13: Structure Determination - Nuclear Magnetic Resonance Spectroscopy
  207. 13.0: Why This Chapter?
  208. 13.1: Nuclear Magnetic Resonance Spectroscopy
  209. 13.2: The Nature of NMR Absorptions
  210. 13.3: Chemical Shifts
  211. 13.4: Chemical Shifts in ¹H NMR Spectroscopy
  212. 13.5: Integration of ¹H NMR Absorptions- Proton Counting
  213. 13.6: Spin-Spin Splitting in ¹H NMR Spectra
  214. 13.7: ¹H NMR Spectroscopy and Proton Equivalence
  215. 13.8: More Complex Spin-Spin Splitting Patterns
  216. 13.9: Uses of ¹H NMR Spectroscopy
  217. 13.10: ¹³C NMR Spectroscopy - Signal Averaging and FT-NMR
  218. 13.11: Characteristics of ¹³C NMR Spectroscopy
  219. 13.12: DEPT ¹³C NMR Spectroscopy
  220. 13.13: Uses of ¹³C NMR Spectroscopy
  221. 13.14: Chemistry Matters—Magnetic Resonance Imaging (MRI)
  222. 13.15: Key Terms
  223. 13.16: Summary
  224. 13.17: Additional Problems
  225. 14: Conjugated Compounds and Ultraviolet Spectroscopy
  226. 14.0: Why This Chapter?
  227. 14.1: Stability of Conjugated Dienes- Molecular Orbital Theory
  228. 14.2: Electrophilic Additions to Conjugated Dienes- Allylic Carbocations
  229. 14.3: Kinetic vs. Thermodynamic Control of Reactions
  230. 14.4: The Diels-Alder Cycloaddition Reaction
  231. 14.5: Characteristics of the Diels-Alder Reaction
  232. 14.6: Diene Polymers - Natural and Synthetic Rubbers
  233. 14.7: Ultraviolet Spectroscopy
  234. 14.8: Interpreting Ultraviolet Spectra- The Effect of Conjugation
  235. 14.9: Conjugation, Color, and the Chemistry of Vision
  236. 14.10: Chemistry Matters—Photolithography
  237. 14.11: Key Terms
  238. 14.12: Summary
  239. 14.13: Summary of Reactions
  240. 14.14: Additional Problems
  241. 15: Benzene and Aromaticity
  242. 15.0: Why This Chapter?
  243. 15.1: Naming Aromatic Compounds
  244. 15.2: Structure and Stability of Benzene
  245. 15.3: Aromaticity and the Hückel 4n + 2 Rule
  246. 15.4: Aromatic Ions
  247. 15.5: Aromatic Heterocycles - Pyridine and Pyrrole
  248. 15.6: Polycyclic Aromatic Compounds
  249. 15.7: Spectroscopy of Aromatic Compounds
  250. 15.8: Chemistry Matters—Aspirin, NSAIDs, and COX-2 Inhibitors
  251. 15.9: Key Terms
  252. 15.10: Summary
  253. 15.11: Additional Problems
  254. 16: Chemistry of Benzene - Electrophilic Aromatic Substitution
  255. 16.0: Why This Chapter?
  256. 16.1: Electrophilic Aromatic Substitution Reactions - Bromination
  257. 16.2: Other Aromatic Substitutions
  258. 16.3: Alkylation and Acylation of Aromatic Rings - The Friedel-Crafts Reaction
  259. 16.4: Substituent Effects in Electrophilic Substitutions
  260. 16.5: Trisubstituted Benzenes- Additivity of Effects
  261. 16.6: Nucleophilic Aromatic Substitution
  262. 16.7: Benzyne
  263. 16.8: Oxidation of Aromatic Compounds
  264. 16.9: Reduction of Aromatic Compounds
  265. 16.10: Synthesis of Polysubstituted Benzenes
  266. 16.11: Chemistry Matters—Combinatorial Chemistry
  267. 16.12: Key Terms
  268. 16.13: Summary
  269. 16.14: Summary of Reactions
  270. 16.15: Additional Problems
  271. 17: Alcohols and Phenols
  272. 17.0: Why This Chapter?
  273. 17.1: Naming Alcohols and Phenols
  274. 17.2: Properties of Alcohols and Phenols
  275. 17.3: Preparation of Alcohols- A Review
  276. 17.4: Alcohols from Carbonyl Compounds - Reduction
  277. 17.5: Alcohols from Carbonyl Compounds - Grignard Reagents
  278. 17.6: Reactions of Alcohols
  279. 17.7: Oxidation of Alcohols
  280. 17.8: Protection of Alcohols
  281. 17.9: Phenols and Their Uses
  282. 17.10: Reactions of Phenols
  283. 17.11: Spectroscopy of Alcohols and Phenols
  284. 17.12: Chemistry Matters—Ethanol- Chemical, Drug, and Poison
  285. 17.13: Key Terms
  286. 17.14: Summary
  287. 17.15: Summary of Reactions
  288. 17.16: Additional Problems
  289. 18: Ethers and Epoxides; Thiols and Sulfides
  290. 18.0: Why This Chapter?
  291. 18.1: Names and Properties of Ethers
  292. 18.2: Preparing Ethers
  293. 18.3: Reactions of Ethers - Acidic Cleavage
  294. 18.4: Cyclic Ethers - Epoxides
  295. 18.5: Reactions of Epoxides - Ring-opening
  296. 18.6: Crown Ethers
  297. 18.7: Thiols and Sulfides
  298. 18.8: Spectroscopy of Ethers
  299. 18.9: Chemistry Matters—Epoxy Resins and Adhesives
  300. 18.10: Key Terms
  301. 18.11: Summary
  302. 18.12: Summary of Reactions
  303. 18.13: Additional Problems
  304. 18.14: Preview of Carbonyl Chemistry
  305. 19: Aldehydes and Ketones- Nucleophilic Addition Reactions
  306. 19.0: Why This Chapter?
  307. 19.1: Naming Aldehydes and Ketones
  308. 19.2: Preparing Aldehydes and Ketones
  309. 19.3: Oxidation of Aldehydes and Ketones
  310. 19.4: Nucleophilic Addition Reactions of Aldehydes and Ketones
  311. 19.5: Nucleophilic Addition of Water- Hydration
  312. 19.6: Nucleophilic Addition of HCN - Cyanohydrin Formation
  313. 19.7: Nucleophilic Addition of Hydride and Grignard Reagents- Alcohol Formation
  314. 19.8: Nucleophilic Addition of Amines- Imine and Enamine Formation
  315. 19.9: Nucleophilic Addition of Hydrazine - The Wolff-Kishner Reaction
  316. 19.10: Nucleophilic Addition of Alcohols - Acetal Formation
  317. 19.11: Nucleophilic Addition of Phosphorus Ylides- The Wittig Reaction
  318. 19.12: Biological Reductions
  319. 19.13: Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones
  320. 19.14: Spectroscopy of Aldehydes and Ketones
  321. 19.15: Chemistry Matters—Enantioselective Synthesis
  322. 19.16: Key Terms
  323. 19.17: Summary
  324. 19.18: Summary of Reactions
  325. 19.19: Additional Problems
  326. 20: Carboxylic Acids and Nitriles
  327. 20.0: Why This Chapter?
  328. 20.1: Naming Carboxylic Acids and Nitriles
  329. 20.2: Structure and Properties of Carboxylic Acids
  330. 20.3: Biological Acids and the Henderson-Hasselbalch Equation
  331. 20.4: Substituent Effects on Acidity
  332. 20.5: Preparing Carboxylic Acids
  333. 20.6: Reactions of Carboxylic Acids - An Overview
  334. 20.7: Chemistry of Nitriles
  335. 20.8: Spectroscopy of Carboxylic Acids and Nitriles
  336. 20.9: Chemistry Matters—Vitamin C
  337. 20.10: Key Terms
  338. 20.11: Summary
  339. 20.12: Summary of Reactions
  340. 20.13: Additional Problems
  341. 21: Carboxylic Acid Derivatives- Nucleophilic Acyl Substitution Reactions
  342. 21.0: Why This Chapter?
  343. 21.1: Naming Carboxylic Acid Derivatives
  344. 21.2: Nucleophilic Acyl Substitution Reactions
  345. 21.3: Reactions of Carboxylic Acids
  346. 21.4: Chemistry of Acid Halides
  347. 21.5: Chemistry of Acid Anhydrides
  348. 21.6: Chemistry of Esters
  349. 21.7: Chemistry of Amides
  350. 21.8: Chemistry of Thioesters and Acyl Phosphates - Biological Carboxylic Acid Derivatives
  351. 21.9: Polyamides and Polyesters - Step-Growth Polymers
  352. 21.10: Spectroscopy of Carboxylic Acid Derivatives
  353. 21.11: Chemistry Matters—β-Lactam Antibiotics
  354. 21.12: Key Terms
  355. 21.13: Summary
  356. 21.14: Summary of Reactions
  357. 21.15: Additional Problems
  358. 22: Carbonyl Alpha-Substitution Reactions
  359. 22.0: Why This Chapter?
  360. 22.1: Keto-Enol Tautomerism
  361. 22.2: Reactivity of Enols- α-Substitution Reactions
  362. 22.3: Alpha Halogenation of Aldehydes and Ketones
  363. 22.4: Alpha Bromination of Carboxylic Acids
  364. 22.5: Acidity of Alpha Hydrogen Atoms- Enolate Ion Formation
  365. 22.6: Reactivity of Enolate Ions
  366. 22.7: Alkylation of Enolate Ions
  367. 22.8: Chemistry Matters—Barbiturates
  368. 22.9: Key Terms
  369. 22.10: Summary
  370. 22.11: Summary of Reactions
  371. 22.12: Additional Problems
  372. 23: Carbonyl Condensation Reactions
  373. 23.0: Why This Chapter?
  374. 23.1: Carbonyl Condensations - The Aldol Reaction
  375. 23.2: Carbonyl Condensations versus Alpha Substitutions
  376. 23.3: Dehydration of Aldol Products - Synthesis of Enones
  377. 23.4: Using Aldol Reactions in Synthesis
  378. 23.5: Mixed Aldol Reactions
  379. 23.6: Intramolecular Aldol Reactions
  380. 23.7: The Claisen Condensation Reaction
  381. 23.8: Mixed Claisen Condensations
  382. 23.9: Intramolecular Claisen Condensations - The Dieckmann Cyclization
  383. 23.10: Conjugate Carbonyl Additions - The Michael Reaction
  384. 23.11: Carbonyl Condensations with Enamines - The Stork Enamine Reaction
  385. 23.12: The Robinson Annulation Reaction
  386. 23.13: Some Biological Carbonyl Condensation Reactions
  387. 23.14: Chemistry Matters - A Prologue to Metabolism
  388. 23.15: Key Terms
  389. 23.16: Summary
  390. 23.17: Summary of Reactions
  391. 23.18: Additional Problems
  392. 24: Amines and Heterocycles
  393. 24.0: Why This Chapter?
  394. 24.1: Naming Amines
  395. 24.2: Structure and Properties of Amines
  396. 24.3: Basicity of Amines
  397. 24.4: Basicity of Arylamines
  398. 24.5: Biological Amines and the Henderson-Hasselbalch Equation
  399. 24.6: Synthesis of Amines
  400. 24.7: Reactions of Amines
  401. 24.8: Reactions of Arylamines
  402. 24.9: Heterocyclic Amines
  403. 24.10: Spectroscopy of Amines
  404. 24.11: Chemistry Matters - Green Chemistry II- Ionic Liquids
  405. 24.12: Key Terms
  406. 24.13: Summary
  407. 24.14: Summary of Reactions
  408. 24.15: Additional Problems
  409. 25: Biomolecules - Carbohydrates
  410. 25.0: Why This Chapter?
  411. 25.1: Classification of Carbohydrates
  412. 25.2: Representing Carbohydrate Stereochemistry- Fischer Projections
  413. 25.3: D, L Sugars
  414. 25.4: Configurations of Aldoses
  415. 25.5: Cyclic Structures of Monosaccharides - Anomers
  416. 25.6: Reactions of Monosaccharides
  417. 25.7: The Eight Essential Monosaccharides
  418. 25.8: Disaccharides
  419. 25.9: Polysaccharides and Their Synthesis
  420. 25.10: Some Other Important Carbohydrates
  421. 25.11: Chemistry Matters—Sweetness
  422. 25.12: Key Terms
  423. 25.13: Summary
  424. 25.14: Summary of Reactions
  425. 25.15: Additional Problems
  426. 26: Biomolecules- Amino Acids, Peptides, and Proteins
  427. 26.0: Why This Chapter?
  428. 26.1: Structures of Amino Acids
  429. 26.2: Amino Acids, the Henderson-Hasselbalch Equation, and Isoelectric Points
  430. 26.3: Synthesis of Amino Acids
  431. 26.4: Peptides and Proteins
  432. 26.5: Amino Acid Analysis of Peptides
  433. 26.6: Peptide Sequencing- The Edman Degradation
  434. 26.7: Peptide Synthesis
  435. 26.8: Automated Peptide Synthesis- The Merrifield Solid-Phase Method
  436. 26.9: Protein Structure
  437. 26.10: Enzymes and Coenzymes
  438. 26.11: How do Enzymes Work? Citrate Synthase
  439. 26.12: Chemistry Matters - The Protein Data Bank
  440. 26.13: Key Terms
  441. 26.14: Summary
  442. 26.15: Summary of Reactions
  443. 26.16: Additional Problems
  444. 27: Biomolecules - Lipids
  445. 27.0: Why This Chapter?
  446. 27.1: Waxes, Fats, and Oils
  447. 27.2: Soap
  448. 27.3: Phospholipids
  449. 27.4: Prostaglandins and Other Eicosanoids
  450. 27.5: Terpenoids
  451. 27.6: Steroids
  452. 27.7: Biosynthesis of Steroids
  453. 27.8: Chemistry Matters—Saturated Fats, Cholesterol, and Heart Disease
  454. 27.9: Key Terms
  455. 27.10: Summary
  456. 27.11: Additional Problems
  457. 28: Biomolecules - Nucleic Acids
  458. 28.0: Why This Chapter?
  459. 28.1: Nucleotides and Nucleic Acids
  460. 28.2: Base Pairing in DNA
  461. 28.3: Replication of DNA
  462. 28.4: Transcription of DNA
  463. 28.5: Translation of RNA - Protein Biosynthesis
  464. 28.6: DNA Sequencing
  465. 28.7: DNA Synthesis
  466. 28.8: The Polymerase Chain Reaction
  467. 28.9: Chemistry Matters—DNA Fingerprinting
  468. 28.10: Key Terms
  469. 28.11: Summary
  470. 28.12: Additional Problems
  471. 29: The Organic Chemistry of Metabolic Pathways
  472. 29.0: Why This Chapter?
  473. 29.1: An Overview of Metabolism and Biochemical Energy
  474. 29.2: Catabolism of Triacylglycerols - The Fate of Glycerol
  475. 29.3: Catabolism of Triacylglycerols - β-Oxidation
  476. 29.4: Biosynthesis of Fatty Acids
  477. 29.5: Catabolism of Carbohydrates- Glycolysis
  478. 29.6: Conversion of Pyruvate to Acetyl CoA
  479. 29.7: The Citric Acid Cycle
  480. 29.8: Carbohydrate Biosynthesis- Gluconeogenesis
  481. 29.9: Catabolism of Proteins- Deamination
  482. 29.10: Some Conclusions about Biological Chemistry
  483. 29.11: Chemistry Matters—Statin Drugs
  484. 29.12: Key Terms
  485. 29.13: Summary
  486. 29.14: Additional Problems
  487. 30: Orbitals and Organic Chemistry - Pericyclic Reactions
  488. 30.0: Why This Chapter?
  489. 30.1: Molecular Orbitals of Conjugated Pi Systems
  490. 30.2: Electrocyclic Reactions
  491. 30.3: Stereochemistry of Thermal Electrocyclic Reactions
  492. 30.4: Photochemical Electrocyclic Reactions
  493. 30.5: Cycloaddition Reactions
  494. 30.6: Stereochemistry of Cycloadditions
  495. 30.7: Sigmatropic Rearrangements
  496. 30.8: Some Examples of Sigmatropic Rearrangements
  497. 30.9: A Summary of Rules for Pericyclic Reactions
  498. 30.10: Chemistry Matters—Vitamin D, the Sunshine Vitamin
  499. 30.11: Key Terms
  500. 30.12: Summary
  501. 30.13: Additional Problems
  502. 31: Synthetic Polymers
  503. 31.0: Why This Chapter?
  504. 31.1: Chain-Growth Polymers
  505. 31.2: Stereochemistry of Polymerization- Ziegler-Natta Catalysts
  506. 31.3: Copolymers
  507. 31.4: Step-Growth Polymers
  508. 31.5: Olefin Metathesis Polymerization
  509. 31.6: Intramolecular Olefin Metathesis
  510. 31.7: Polymer Structure and Physical Properties
  511. 31.8: Chemistry Matters—Degradable Polymers
  512. 31.9: Key Terms
  513. 31.10: Summary
  514. 31.11: Additional Problems
  515. 32: Appendix
  516. 32.0: Appendix A - Nomenclature of Polyfunctional Organic Compounds
  517. 32.1: Appendix B - Acidity Constants for Some Organic Compounds
  518. 32.2: Appendix C - Glossary
  519. 32.3: Appendix C - Periodic Table
  520. 32.4: Answer Key
  521. 32.4.0: Chapter 1
  522. 32.4.1: Chapter 2
  523. 32.4.2: Chapter 3
  524. 32.4.3: Chapter 4
  525. 32.4.4: Chapter 5
  526. 32.4.5: Chapter 6
  527. 32.4.6: Chapter 7
  528. 32.4.7: Chapter 8
  529. 32.4.8: Chapter 9
  530. 32.4.9: Chapter 10
  531. 32.4.10: Chapter 11
  532. 32.4.11: Chapter 12
  533. 32.4.12: Chapter 13
  534. 32.4.13: Chapter 14
  535. 32.4.14: Chapter 15
  536. 32.4.15: Chapter 16
  537. 32.4.16: Chapter 17
  538. 32.4.17: Chapter 18
  539. 32.4.18: Chapter 19
  540. 32.4.19: Chapter 20
  541. 32.4.20: Chapter 21
  542. 32.4.21: Chapter 22
  543. 32.4.22: Chapter 23
  544. 32.4.23: Chapter 24
  545. 32.4.24: Chapter 25
  546. 32.4.25: Chapter 26
  547. 32.4.26: Chapter 27
  548. 32.4.27: Chapter 28
  549. 32.4.28: Chapter 29
  550. 32.4.29: Chapter 30
  551. 32.4.30: Chapter 31
  552. Back Matter
  553. Index
  554. Glossary
  555. Detailed Licensing