Skip to ContentGo to accessibility pageKeyboard shortcuts menu
OpenStax Logo
Organic Chemistry

Additional Problems

Organic ChemistryAdditional Problems

Table of contents
  1. Dedication and Preface
  2. 1 Structure and Bonding
    1. Why This Chapter?
    2. 1.1 Atomic Structure: The Nucleus
    3. 1.2 Atomic Structure: Orbitals
    4. 1.3 Atomic Structure: Electron Configurations
    5. 1.4 Development of Chemical Bonding Theory
    6. 1.5 Describing Chemical Bonds: Valence Bond Theory
    7. 1.6 sp3 Hybrid Orbitals and the Structure of Methane
    8. 1.7 sp3 Hybrid Orbitals and the Structure of Ethane
    9. 1.8 sp2 Hybrid Orbitals and the Structure of Ethylene
    10. 1.9 sp Hybrid Orbitals and the Structure of Acetylene
    11. 1.10 Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
    12. 1.11 Describing Chemical Bonds: Molecular Orbital Theory
    13. 1.12 Drawing Chemical Structures
    14. Chemistry Matters—Organic Foods: Risk versus Benefit
    15. Key Terms
    16. Summary
    17. Additional Problems
  3. 2 Polar Covalent Bonds; Acids and Bases
    1. Why This Chapter?
    2. 2.1 Polar Covalent Bonds and Electronegativity
    3. 2.2 Polar Covalent Bonds and Dipole Moments
    4. 2.3 Formal Charges
    5. 2.4 Resonance
    6. 2.5 Rules for Resonance Forms
    7. 2.6 Drawing Resonance Forms
    8. 2.7 Acids and Bases: The Brønsted–Lowry Definition
    9. 2.8 Acid and Base Strength
    10. 2.9 Predicting Acid–Base Reactions from pKa Values
    11. 2.10 Organic Acids and Organic Bases
    12. 2.11 Acids and Bases: The Lewis Definition
    13. 2.12 Noncovalent Interactions between Molecules
    14. Chemistry Matters—Alkaloids: From Cocaine to Dental Anesthetics
    15. Key Terms
    16. Summary
    17. Additional Problems
  4. 3 Organic Compounds: Alkanes and Their Stereochemistry
    1. Why This Chapter?
    2. 3.1 Functional Groups
    3. 3.2 Alkanes and Alkane Isomers
    4. 3.3 Alkyl Groups
    5. 3.4 Naming Alkanes
    6. 3.5 Properties of Alkanes
    7. 3.6 Conformations of Ethane
    8. 3.7 Conformations of Other Alkanes
    9. Chemistry Matters—Gasoline
    10. Key Terms
    11. Summary
    12. Additional Problems
  5. 4 Organic Compounds: Cycloalkanes and Their Stereochemistry
    1. Why This Chapter?
    2. 4.1 Naming Cycloalkanes
    3. 4.2 Cis–Trans Isomerism in Cycloalkanes
    4. 4.3 Stability of Cycloalkanes: Ring Strain
    5. 4.4 Conformations of Cycloalkanes
    6. 4.5 Conformations of Cyclohexane
    7. 4.6 Axial and Equatorial Bonds in Cyclohexane
    8. 4.7 Conformations of Monosubstituted Cyclohexanes
    9. 4.8 Conformations of Disubstituted Cyclohexanes
    10. 4.9 Conformations of Polycyclic Molecules
    11. Chemistry Matters—Molecular Mechanics
    12. Key Terms
    13. Summary
    14. Additional Problems
  6. 5 Stereochemistry at Tetrahedral Centers
    1. Why This Chapter?
    2. 5.1 Enantiomers and the Tetrahedral Carbon
    3. 5.2 The Reason for Handedness in Molecules: Chirality
    4. 5.3 Optical Activity
    5. 5.4 Pasteur’s Discovery of Enantiomers
    6. 5.5 Sequence Rules for Specifying Configuration
    7. 5.6 Diastereomers
    8. 5.7 Meso Compounds
    9. 5.8 Racemic Mixtures and the Resolution of Enantiomers
    10. 5.9 A Review of Isomerism
    11. 5.10 Chirality at Nitrogen, Phosphorus, and Sulfur
    12. 5.11 Prochirality
    13. 5.12 Chirality in Nature and Chiral Environments
    14. Chemistry Matters—Chiral Drugs
    15. Key Terms
    16. Summary
    17. Additional Problems
  7. 6 An Overview of Organic Reactions
    1. Why This Chapter?
    2. 6.1 Kinds of Organic Reactions
    3. 6.2 How Organic Reactions Occur: Mechanisms
    4. 6.3 Polar Reactions
    5. 6.4 An Example of a Polar Reaction: Addition of HBr to Ethylene
    6. 6.5 Using Curved Arrows in Polar Reaction Mechanisms
    7. 6.6 Radical Reactions
    8. 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes
    9. 6.8 Describing a Reaction: Bond Dissociation Energies
    10. 6.9 Describing a Reaction: Energy Diagrams and Transition States
    11. 6.10 Describing a Reaction: Intermediates
    12. 6.11 A Comparison Between Biological Reactions and Laboratory Reactions
    13. Chemistry Matters—Where Do Drugs Come From?
    14. Key Terms
    15. Summary
    16. Additional Problems
  8. 7 Alkenes: Structure and Reactivity
    1. Why This Chapter?
    2. 7.1 Industrial Preparation and Use of Alkenes
    3. 7.2 Calculating the Degree of Unsaturation
    4. 7.3 Naming Alkenes
    5. 7.4 Cis–Trans Isomerism in Alkenes
    6. 7.5 Alkene Stereochemistry and the E,Z Designation
    7. 7.6 Stability of Alkenes
    8. 7.7 Electrophilic Addition Reactions of Alkenes
    9. 7.8 Orientation of Electrophilic Additions: Markovnikov’s Rule
    10. 7.9 Carbocation Structure and Stability
    11. 7.10 The Hammond Postulate
    12. 7.11 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements
    13. Chemistry Matters—Bioprospecting: Hunting for Natural Products
    14. Key Terms
    15. Summary
    16. Additional Problems
  9. 8 Alkenes: Reactions and Synthesis
    1. Why This Chapter?
    2. 8.1 Preparing Alkenes: A Preview of Elimination Reactions
    3. 8.2 Halogenation of Alkenes: Addition of X2
    4. 8.3 Halohydrins from Alkenes: Addition of HO-X
    5. 8.4 Hydration of Alkenes: Addition of H2O by Oxymercuration
    6. 8.5 Hydration of Alkenes: Addition of H2O by Hydroboration
    7. 8.6 Reduction of Alkenes: Hydrogenation
    8. 8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation
    9. 8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds
    10. 8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis
    11. 8.10 Radical Additions to Alkenes: Chain-Growth Polymers
    12. 8.11 Biological Additions of Radicals to Alkenes
    13. 8.12 Reaction Stereochemistry: Addition of H2O to an Achiral Alkene
    14. 8.13 Reaction Stereochemistry: Addition of H2O to a Chiral Alkene
    15. Chemistry Matters—Terpenes: Naturally Occurring Alkenes
    16. Key Terms
    17. Summary
    18. Summary of Reactions
    19. Additional Problems
  10. 9 Alkynes: An Introduction to Organic Synthesis
    1. Why This Chapter?
    2. 9.1 Naming Alkynes
    3. 9.2 Preparation of Alkynes: Elimination Reactions of Dihalides
    4. 9.3 Reactions of Alkynes: Addition of HX and X2
    5. 9.4 Hydration of Alkynes
    6. 9.5 Reduction of Alkynes
    7. 9.6 Oxidative Cleavage of Alkynes
    8. 9.7 Alkyne Acidity: Formation of Acetylide Anions
    9. 9.8 Alkylation of Acetylide Anions
    10. 9.9 An Introduction to Organic Synthesis
    11. Chemistry Matters—The Art of Organic Synthesis
    12. Key Terms
    13. Summary
    14. Summary of Reactions
    15. Additional Problems
  11. 10 Organohalides
    1. Why This Chapter?
    2. 10.1 Names and Structures of Alkyl Halides
    3. 10.2 Preparing Alkyl Halides from Alkanes: Radical Halogenation
    4. 10.3 Preparing Alkyl Halides from Alkenes: Allylic Bromination
    5. 10.4 Stability of the Allyl Radical: Resonance Revisited
    6. 10.5 Preparing Alkyl Halides from Alcohols
    7. 10.6 Reactions of Alkyl Halides: Grignard Reagents
    8. 10.7 Organometallic Coupling Reactions
    9. 10.8 Oxidation and Reduction in Organic Chemistry
    10. Chemistry Matters—Naturally Occurring Organohalides
    11. Key Terms
    12. Summary
    13. Summary of Reactions
    14. Additional Problems
  12. 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
    1. Why This Chapter?
    2. 11.1 The Discovery of Nucleophilic Substitution Reactions
    3. 11.2 The SN2 Reaction
    4. 11.3 Characteristics of the SN2 Reaction
    5. 11.4 The SN1 Reaction
    6. 11.5 Characteristics of the SN1 Reaction
    7. 11.6 Biological Substitution Reactions
    8. 11.7 Elimination Reactions: Zaitsev’s Rule
    9. 11.8 The E2 Reaction and the Deuterium Isotope Effect
    10. 11.9 The E2 Reaction and Cyclohexane Conformation
    11. 11.10 The E1 and E1cB Reactions
    12. 11.11 Biological Elimination Reactions
    13. 11.12 A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
    14. Chemistry Matters—Green Chemistry
    15. Key Terms
    16. Summary
    17. Summary of Reactions
    18. Additional Problems
  13. 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy
    1. Why This Chapter?
    2. 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
    3. 12.2 Interpreting Mass Spectra
    4. 12.3 Mass Spectrometry of Some Common Functional Groups
    5. 12.4 Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
    6. 12.5 Spectroscopy and the Electromagnetic Spectrum
    7. 12.6 Infrared Spectroscopy
    8. 12.7 Interpreting Infrared Spectra
    9. 12.8 Infrared Spectra of Some Common Functional Groups
    10. Chemistry Matters—X-Ray Crystallography
    11. Key Terms
    12. Summary
    13. Additional Problems
  14. 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy
    1. Why This Chapter?
    2. 13.1 Nuclear Magnetic Resonance Spectroscopy
    3. 13.2 The Nature of NMR Absorptions
    4. 13.3 Chemical Shifts
    5. 13.4 Chemical Shifts in 1H NMR Spectroscopy
    6. 13.5 Integration of 1H NMR Absorptions: Proton Counting
    7. 13.6 Spin–Spin Splitting in 1H NMR Spectra
    8. 13.7 1H NMR Spectroscopy and Proton Equivalence
    9. 13.8 More Complex Spin–Spin Splitting Patterns
    10. 13.9 Uses of 1H NMR Spectroscopy
    11. 13.10 13C NMR Spectroscopy: Signal Averaging and FT–NMR
    12. 13.11 Characteristics of 13C NMR Spectroscopy
    13. 13.12 DEPT 13C NMR Spectroscopy
    14. 13.13 Uses of 13C NMR Spectroscopy
    15. Chemistry Matters—Magnetic Resonance Imaging (MRI)
    16. Key Terms
    17. Summary
    18. Additional Problems
  15. 14 Conjugated Compounds and Ultraviolet Spectroscopy
    1. Why This Chapter?
    2. 14.1 Stability of Conjugated Dienes: Molecular Orbital Theory
    3. 14.2 Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
    4. 14.3 Kinetic versus Thermodynamic Control of Reactions
    5. 14.4 The Diels–Alder Cycloaddition Reaction
    6. 14.5 Characteristics of the Diels–Alder Reaction
    7. 14.6 Diene Polymers: Natural and Synthetic Rubbers
    8. 14.7 Ultraviolet Spectroscopy
    9. 14.8 Interpreting Ultraviolet Spectra: The Effect of Conjugation
    10. 14.9 Conjugation, Color, and the Chemistry of Vision
    11. Chemistry Matters—Photolithography
    12. Key Terms
    13. Summary
    14. Summary of Reactions
    15. Additional Problems
  16. 15 Benzene and Aromaticity
    1. Why This Chapter?
    2. 15.1 Naming Aromatic Compounds
    3. 15.2 Structure and Stability of Benzene
    4. 15.3 Aromaticity and the Hückel 4n + 2 Rule
    5. 15.4 Aromatic Ions
    6. 15.5 Aromatic Heterocycles: Pyridine and Pyrrole
    7. 15.6 Polycyclic Aromatic Compounds
    8. 15.7 Spectroscopy of Aromatic Compounds
    9. Chemistry Matters—Aspirin, NSAIDs, and COX-2 Inhibitors
    10. Key Terms
    11. Summary
    12. Additional Problems
  17. 16 Chemistry of Benzene: Electrophilic Aromatic Substitution
    1. Why This Chapter?
    2. 16.1 Electrophilic Aromatic Substitution Reactions: Bromination
    3. 16.2 Other Aromatic Substitutions
    4. 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction
    5. 16.4 Substituent Effects in Electrophilic Substitutions
    6. 16.5 Trisubstituted Benzenes: Additivity of Effects
    7. 16.6 Nucleophilic Aromatic Substitution
    8. 16.7 Benzyne
    9. 16.8 Oxidation of Aromatic Compounds
    10. 16.9 Reduction of Aromatic Compounds
    11. 16.10 Synthesis of Polysubstituted Benzenes
    12. Chemistry Matters—Combinatorial Chemistry
    13. Key Terms
    14. Summary
    15. Summary of Reactions
    16. Additional Problems
  18. 17 Alcohols and Phenols
    1. Why This Chapter?
    2. 17.1 Naming Alcohols and Phenols
    3. 17.2 Properties of Alcohols and Phenols
    4. 17.3 Preparation of Alcohols: A Review
    5. 17.4 Alcohols from Carbonyl Compounds: Reduction
    6. 17.5 Alcohols from Carbonyl Compounds: Grignard Reaction
    7. 17.6 Reactions of Alcohols
    8. 17.7 Oxidation of Alcohols
    9. 17.8 Protection of Alcohols
    10. 17.9 Phenols and Their Uses
    11. 17.10 Reactions of Phenols
    12. 17.11 Spectroscopy of Alcohols and Phenols
    13. Chemistry Matters—Ethanol: Chemical, Drug, and Poison
    14. Key Terms
    15. Summary
    16. Summary of Reactions
    17. Additional Problems
  19. 18 Ethers and Epoxides; Thiols and Sulfides
    1. Why This Chapter?
    2. 18.1 Names and Properties of Ethers
    3. 18.2 Preparing Ethers
    4. 18.3 Reactions of Ethers: Acidic Cleavage
    5. 18.4 Cyclic Ethers: Epoxides
    6. 18.5 Reactions of Epoxides: Ring-Opening
    7. 18.6 Crown Ethers
    8. 18.7 Thiols and Sulfides
    9. 18.8 Spectroscopy of Ethers
    10. Chemistry Matters—Epoxy Resins and Adhesives
    11. Key Terms
    12. Summary
    13. Summary of Reactions
    14. Additional Problems
    15. Preview of Carbonyl Chemistry
  20. 19 Aldehydes and Ketones: Nucleophilic Addition Reactions
    1. Why This Chapter?
    2. 19.1 Naming Aldehydes and Ketones
    3. 19.2 Preparing Aldehydes and Ketones
    4. 19.3 Oxidation of Aldehydes and Ketones
    5. 19.4 Nucleophilic Addition Reactions of Aldehydes and Ketones
    6. 19.5 Nucleophilic Addition of H2O: Hydration
    7. 19.6 Nucleophilic Addition of HCN: Cyanohydrin Formation
    8. 19.7 Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
    9. 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation
    10. 19.9 Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction
    11. 19.10 Nucleophilic Addition of Alcohols: Acetal Formation
    12. 19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
    13. 19.12 Biological Reductions
    14. 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones
    15. 19.14 Spectroscopy of Aldehydes and Ketones
    16. Chemistry Matters—Enantioselective Synthesis
    17. Key Terms
    18. Summary
    19. Summary of Reactions
    20. Additional Problems
  21. 20 Carboxylic Acids and Nitriles
    1. Why This Chapter?
    2. 20.1 Naming Carboxylic Acids and Nitriles
    3. 20.2 Structure and Properties of Carboxylic Acids
    4. 20.3 Biological Acids and the Henderson–Hasselbalch Equation
    5. 20.4 Substituent Effects on Acidity
    6. 20.5 Preparing Carboxylic Acids
    7. 20.6 Reactions of Carboxylic Acids: An Overview
    8. 20.7 Chemistry of Nitriles
    9. 20.8 Spectroscopy of Carboxylic Acids and Nitriles
    10. Chemistry Matters—Vitamin C
    11. Key Terms
    12. Summary
    13. Summary of Reactions
    14. Additional Problems
  22. 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
    1. Why This Chapter?
    2. 21.1 Naming Carboxylic Acid Derivatives
    3. 21.2 Nucleophilic Acyl Substitution Reactions
    4. 21.3 Reactions of Carboxylic Acids
    5. 21.4 Chemistry of Acid Halides
    6. 21.5 Chemistry of Acid Anhydrides
    7. 21.6 Chemistry of Esters
    8. 21.7 Chemistry of Amides
    9. 21.8 Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
    10. 21.9 Polyamides and Polyesters: Step-Growth Polymers
    11. 21.10 Spectroscopy of Carboxylic Acid Derivatives
    12. Chemistry Matters—β-Lactam Antibiotics
    13. Key Terms
    14. Summary
    15. Summary of Reactions
    16. Additional Problems
  23. 22 Carbonyl Alpha-Substitution Reactions
    1. Why This Chapter?
    2. 22.1 Keto–Enol Tautomerism
    3. 22.2 Reactivity of Enols: α-Substitution Reactions
    4. 22.3 Alpha Halogenation of Aldehydes and Ketones
    5. 22.4 Alpha Bromination of Carboxylic Acids
    6. 22.5 Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
    7. 22.6 Reactivity of Enolate Ions
    8. 22.7 Alkylation of Enolate Ions
    9. Chemistry Matters—Barbiturates
    10. Key Terms
    11. Summary
    12. Summary of Reactions
    13. Additional Problems
  24. 23 Carbonyl Condensation Reactions
    1. Why This Chapter?
    2. 23.1 Carbonyl Condensations: The Aldol Reaction
    3. 23.2 Carbonyl Condensations versus Alpha Substitutions
    4. 23.3 Dehydration of Aldol Products: Synthesis of Enones
    5. 23.4 Using Aldol Reactions in Synthesis
    6. 23.5 Mixed Aldol Reactions
    7. 23.6 Intramolecular Aldol Reactions
    8. 23.7 The Claisen Condensation Reaction
    9. 23.8 Mixed Claisen Condensations
    10. 23.9 Intramolecular Claisen Condensations: The Dieckmann Cyclization
    11. 23.10 Conjugate Carbonyl Additions: The Michael Reaction
    12. 23.11 Carbonyl Condensations with Enamines: The Stork Enamine Reaction
    13. 23.12 The Robinson Annulation Reaction
    14. 23.13 Some Biological Carbonyl Condensation Reactions
    15. Chemistry Matters—A Prologue to Metabolism
    16. Key Terms
    17. Summary
    18. Summary of Reactions
    19. Additional Problems
  25. 24 Amines and Heterocycles
    1. Why This Chapter?
    2. 24.1 Naming Amines
    3. 24.2 Structure and Properties of Amines
    4. 24.3 Basicity of Amines
    5. 24.4 Basicity of Arylamines
    6. 24.5 Biological Amines and the Henderson–Hasselbalch Equation
    7. 24.6 Synthesis of Amines
    8. 24.7 Reactions of Amines
    9. 24.8 Reactions of Arylamines
    10. 24.9 Heterocyclic Amines
    11. 24.10 Spectroscopy of Amines
    12. Chemistry Matters—Green Chemistry II: Ionic Liquids
    13. Key Terms
    14. Summary
    15. Summary of Reactions
    16. Additional Problems
  26. 25 Biomolecules: Carbohydrates
    1. Why This Chapter?
    2. 25.1 Classification of Carbohydrates
    3. 25.2 Representing Carbohydrate Stereochemistry: Fischer Projections
    4. 25.3 D,L Sugars
    5. 25.4 Configurations of the Aldoses
    6. 25.5 Cyclic Structures of Monosaccharides: Anomers
    7. 25.6 Reactions of Monosaccharides
    8. 25.7 The Eight Essential Monosaccharides
    9. 25.8 Disaccharides
    10. 25.9 Polysaccharides and Their Synthesis
    11. 25.10 Some Other Important Carbohydrates
    12. Chemistry Matters—Sweetness
    13. Key Terms
    14. Summary
    15. Summary of Reactions
    16. Additional Problems
  27. 26 Biomolecules: Amino Acids, Peptides, and Proteins
    1. Why This Chapter?
    2. 26.1 Structures of Amino Acids
    3. 26.2 Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points
    4. 26.3 Synthesis of Amino Acids
    5. 26.4 Peptides and Proteins
    6. 26.5 Amino Acid Analysis of Peptides
    7. 26.6 Peptide Sequencing: The Edman Degradation
    8. 26.7 Peptide Synthesis
    9. 26.8 Automated Peptide Synthesis: The Merrifield Solid-Phase Method
    10. 26.9 Protein Structure
    11. 26.10 Enzymes and Coenzymes
    12. 26.11 How Do Enzymes Work? Citrate Synthase
    13. Chemistry Matters—The Protein Data Bank
    14. Key Terms
    15. Summary
    16. Summary of Reactions
    17. Additional Problems
  28. 27 Biomolecules: Lipids
    1. Why This Chapter?
    2. 27.1 Waxes, Fats, and Oils
    3. 27.2 Soap
    4. 27.3 Phospholipids
    5. 27.4 Prostaglandins and Other Eicosanoids
    6. 27.5 Terpenoids
    7. 27.6 Steroids
    8. 27.7 Biosynthesis of Steroids
    9. Chemistry Matters—Saturated Fats, Cholesterol, and Heart Disease
    10. Key Terms
    11. Summary
    12. Additional Problems
  29. 28 Biomolecules: Nucleic Acids
    1. Why This Chapter?
    2. 28.1 Nucleotides and Nucleic Acids
    3. 28.2 Base Pairing in DNA
    4. 28.3 Replication of DNA
    5. 28.4 Transcription of DNA
    6. 28.5 Translation of RNA: Protein Biosynthesis
    7. 28.6 DNA Sequencing
    8. 28.7 DNA Synthesis
    9. 28.8 The Polymerase Chain Reaction
    10. Chemistry Matters—DNA Fingerprinting
    11. Key Terms
    12. Summary
    13. Additional Problems
  30. 29 The Organic Chemistry of Metabolic Pathways
    1. Why This Chapter?
    2. 29.1 An Overview of Metabolism and Biochemical Energy
    3. 29.2 Catabolism of Triacylglycerols: The Fate of Glycerol
    4. 29.3 Catabolism of Triacylglycerols: β-Oxidation
    5. 29.4 Biosynthesis of Fatty Acids
    6. 29.5 Catabolism of Carbohydrates: Glycolysis
    7. 29.6 Conversion of Pyruvate to Acetyl CoA
    8. 29.7 The Citric Acid Cycle
    9. 29.8 Carbohydrate Biosynthesis: Gluconeogenesis
    10. 29.9 Catabolism of Proteins: Deamination
    11. 29.10 Some Conclusions about Biological Chemistry
    12. Chemistry Matters—Statin Drugs
    13. Key Terms
    14. Summary
    15. Additional Problems
  31. 30 Orbitals and Organic Chemistry: Pericyclic Reactions
    1. Why This Chapter?
    2. 30.1 Molecular Orbitals of Conjugated Pi Systems
    3. 30.2 Electrocyclic Reactions
    4. 30.3 Stereochemistry of Thermal Electrocyclic Reactions
    5. 30.4 Photochemical Electrocyclic Reactions
    6. 30.5 Cycloaddition Reactions
    7. 30.6 Stereochemistry of Cycloadditions
    8. 30.7 Sigmatropic Rearrangements
    9. 30.8 Some Examples of Sigmatropic Rearrangements
    10. 30.9 A Summary of Rules for Pericyclic Reactions
    11. Chemistry Matters—Vitamin D, the Sunshine Vitamin
    12. Key Terms
    13. Summary
    14. Additional Problems
  32. 31 Synthetic Polymers
    1. Why This Chapter?
    2. 31.1 Chain-Growth Polymers
    3. 31.2 Stereochemistry of Polymerization: Ziegler–Natta Catalysts
    4. 31.3 Copolymers
    5. 31.4 Step-Growth Polymers
    6. 31.5 Olefin Metathesis Polymerization
    7. 31.6 Intramolecular Olefin Metathesis
    8. 31.7 Polymer Structure and Physical Properties
    9. Chemistry Matters—Degradable Polymers
    10. Key Terms
    11. Summary
    12. Additional Problems
  33. A | Nomenclature of Polyfunctional Organic Compounds
  34. B | Acidity Constants for Some Organic Compounds
  35. C | Glossary
  36. D | Periodic Table
  37. Answer Key
    1. Chapter 1
    2. Chapter 2
    3. Chapter 3
    4. Chapter 4
    5. Chapter 5
    6. Chapter 6
    7. Chapter 7
    8. Chapter 8
    9. Chapter 9
    10. Chapter 10
    11. Chapter 11
    12. Chapter 12
    13. Chapter 13
    14. Chapter 14
    15. Chapter 15
    16. Chapter 16
    17. Chapter 17
    18. Chapter 18
    19. Chapter 19
    20. Chapter 20
    21. Chapter 21
    22. Chapter 22
    23. Chapter 23
    24. Chapter 24
    25. Chapter 25
    26. Chapter 26
    27. Chapter 27
    28. Chapter 28
    29. Chapter 29
    30. Chapter 30
    31. Chapter 31
  38. Index

17 • Additional Problems

17 • Additional Problems

Visualizing Chemistry

Problem 17-20
Give IUPAC names for the following compounds:
(a)
A ball-and-stick model of six-carbon chain with hydroxyl on C 3 and methyl on C 5 position.
(b)
A ball-and-stick model of cyclohexane with hydroxyl group on C 1 and methyl on C 3 position.
(c)
A ball-and-stick model of cyclopentane linked to a carbon atom that has H, methyl, and O H substituents.
(d)
A ball-and-stick model of a benzene with O H on C 1, a nitro group on C 3 and a methyl group on C 4 position.
Problem 17-21
Draw the structure of the carbonyl compound(s) from which each of the following alcohols might have been prepared, and show the products you would obtain by treatment of each alcohol with (1) Na metal, (2) SOCl2, and (3) Dess–Martin periodinane.
(a)
A ball-and-stick model of a six-carbon chain with hydroxyl on C 2, and methyl group on C 5 position.
(b)
A ball-and-stick model of five carbon chain with hydroxyl on C 1, and methyl group on C 3 position.
Problem 17-22

Predict the product from reaction of the following substance (reddish brown = Br) with:

A ball-and-stick model of benzene with bromine on C 1, C 3 of benzene has the substituent 2-butanol attached by C 3 of 2-butanol.
(a)
PBr3
(b)
Aqueous H2SO4
(c)
SOCl2
(d)
Dess–Martin periodinane
(e)
Br2, FeBr3
Problem 17-23

Predict the product from reaction of the following substance with:

A ball-and-stick model of a five-carbon chain with C O O C H 3 on C 1, and a methyl group on C 4 position.
(a)
NaBH4; then H3O+
(b)
LiAlH4; then H3O+
(c)
2 CH3CH2MgBr; then H3O+
Problem 17-24

Name and assign R or S stereochemistry to the product(s) you would obtain by reaction of the following substance with ethylmagnesium bromide. Is the product chiral? Is it optically active? Explain.

A ball-and-stick model of a five-carbon chain with keto group on C 2, and C 3 has a methyl group.

Mechanism Problems

Problem 17-25

Evidence for the intermediate carbocations in the acid-catalyzed dehydration of alcohols comes from the observation that rearrangements sometimes occur. Propose a mechanism to account for the formation of 2,3-dimethyl-2-butene from 3,3-dimethyl-2-butanol.

3,3-dimethyl-2-butanol reacts with sulfuric acid to form 2,3-dimethyl-2-butene and water.
Problem 17-26

Acid-catalyzed dehydration of 2,2-dimethylcyclohexanol yields a mixture of 1,2-dimethylcyclohexene and isopropylidenecyclopentane. Propose a mechanism to account for the formation of both products.

The structure of isopropylidenecyclopentane. It is an isocyclopentane with a double bond between C 1 of cyclopentane and C 2 of the propyl group.
Problem 17-27

Epoxides react with Grignard reagents to yield alcohols. Propose a mechanism.

cyclopentane with dashed hydrogen and wedged hydroxyl on C 1 and wedged hydrogen and dashed methyl on C 2.
Problem 17-28

Treatment of the following epoxide with aqueous acid produces a carbocation intermediate that reacts with water to give a diol product. Show the structure of the carbocation, and propose a mechanism for the second step.

An epoxide reacts with hydronium ion to form a carbocation. This reacts with water to form a diol.
Problem 17-29
Reduction of 2-butanone with NaBH4 yields 2-butanol. Is the product chiral? Is it optically active? Explain.
Problem 17-30
The conversion of 3° alcohols into 3° alkyl halides under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.
(a)
1-methylcyclohexanol reacts with H Cl to form 1-chloro-1-methylcyclohexane.
(b)
2-methylbutan-2-ol reacts with H Br to form 2-bromo-2-methylbutane.
(c)
Two fused cyclohexane rings with a hydroxyl at a bridgehead carbon reacts with H Cl to substitute chlorine for the hydroxyl group.
Problem 17-31
Identify the type of substitution mechanism (SN1, SN2) involved in the conversion of the following alcohols into the corresponding alkyl halide.
(a)
2-methylbutan-2-ol reacts with H Cl to form 2-chloro-2-methylbutane.
(b)
2-butanol reacts with P Br 3 to form 2-bromobutane.
(c)
1-propanol reacts first with tosyl chloride and pyridine, then sodium bromide, to form 1-bromopropane.
Problem 17-32
The conversion of 3° alcohols into alkenes under acidic conditions involves two cationic intermediates. For each reaction, draw the complete mechanism using curved arrows.
(a)
1-methylcyclohexanol reacts with hydronium to form 1-methylcyclohexene.
(b)
2-methylbutan-2-ol reacts with hydronium to form 2-methylbut-2-ene.
(c)
Methanol with two methyl and one phenyl substituents reacts with hydronium to form 1-methyl-1-phenylethene
Problem 17-33
For each reaction, write the mechanism using curved arrows for the conversion of the alcohol into the corresponding alkene with POCl3. In each case, explain the regiochemistry of the elimination.
(a)
Cyclohexane with dashed bond to isopropyl, wedged bond to hydroxyl on adjacent (clockwise) carbon reacts with phosphoryl chloride to form R-3-isopropylcyclohexene.
(b)
3-methyl-2-pentanol reacts with P O Cl 3 in pyridine to produce E-3-methyl-2-pentene.
(c)
1-phenyl-propan-1-ol reacts with phosphoryl chloride and pyridine to form prop-1-en-1-ylbenzene.
Problem 17-34
The trimethylsilyl (TMS) protecting group is one of several silicon protecting groups for alcohols. For each reaction, draw the mechanism for the protection of (R)-3-bromo-1-butanol with the following silyl chlorides, using triethylamine as the base:
(a)
tert-butyldimethylsilyl chloride (TBS-Cl)
(b)
triisopropylsilyl chloride (TIPS-Cl)
(c)
triethylsilyl chloride (TES-Cl)
Problem 17-35

When the following alcohol is treated with POCl3 and pyridine, the expected elimination product is formed. However, when the same alcohol is treated with H2SO4, the elimination product is 1,2-dimethylcyclopentene. Propose a mechanism for each pathway to account for these differences.

Propan-2-ylidenecyclobutane reacts with 2-cyclobutylpropan-2-ol. This reacts with sulfuric acid to form 1,2-dimethylcyclopent-1-ene.
Problem 17-36
Phenols generally have lower pKa’s than alcohols because of resonance stabilization with the aromatic ring. Draw all of the resonance contributors for the following phenolate ions.
(a)
Chemical structure of 4-methylphenoxide.
(b)
Chemical structure of 4-cyanophenoxide.
(c)
Chemical structure of 3-methoxyphenoxide.

Naming Alcohols

Problem 17-37
Give IUPAC names for the following compounds:
(a)
Condensed structural formula of a four carbon chain with (counting from left) hydroxyl groups on first and fourth carbons, methyl on third carbon.
(b)
Condensed structural formula of a five carbon chain with (counting from left) hydroxyl group on second carbon, n-propyl group on third carbon.
(c)
Four-carbon ring with wedged hydroxyl and dashed hydrogen on C 1, and dashed hydrogen and wedged hydroxyl on C 3 position.
(d)
Seven-membered ring with hydroxyl (wedge) and hydrogen (dash) on a carbon, methyl (wedge) and hydrogen (dash) on clockwise adjacent carbon, and double bond starting two carbons further clockwise.
(e)
Five-carbon ring with phenyl (wedge) and hydrogen (dash) on a carbon, and hydroxyl (wedge) and hydrogen (dash) two carbons away, clockwise.
(f)
Benzene with hydroxyl on C 1, bromine group on C 2, and cyano group on C 4 position.
Problem 17-38
Draw and name the eight isomeric alcohols with formula C5H12O.
Problem 17-39
Draw structures corresponding to the following IUPAC names:
(a)
Trans-3-Chlorocycloheptanol
(b)
2-Ethyl-2-buten-1-ol
(c)
o-(2-Hydroxyethyl)phenol
(d)
3-Methyl-1-phenyl-1-butanol
Problem 17-40
Bombykol, the sex pheromone secreted by the female silkworm moth has the formula C16H28O and the systematic name (10E,12Z)-10,12-hexadecadien-1-ol. Draw bombykol, showing the correct geometry for the two double bonds.
Problem 17-41

Carvacrol is a naturally occurring substance isolated from oregano, thyme, and marjoram. What is its IUPAC name?

The structure of carvacrol. It is a benzene with hydroxyl on C 1, methyl on C 2, and isopropyl on C 5.

Synthesizing Alcohols

Problem 17-42
What Grignard reagent and what carbonyl compound might you start with to prepare the following alcohols:
(a)
A four-carbon chain with hydroxyl on C 2 position.
(b)
A five-carbon chain with hydroxyl on C 3 position.
(c)
Chemical structure of 2-methylprop-2-en-1-ol.
(d)
Chemical structure of triphenylmethanol.
(e)
Methanol with two methyl and one phenyl substituents.
(f)
Cyclohexene with C H 2 O H group on C 1 position.
Problem 17-43
What carbonyl compounds would you reduce to prepare the following alcohols: List all possibilities.
(a)
A six-carbon chain with hydroxyl on C 1, and two methyl on C 2 position.
(b)
A three-carbon chain with hydroxyl on C 2 and two methyl groups on C 3 position.
(c)
Chemical structure of 1-cyclohexylpropan-1-ol.
Problem 17-44
What carbonyl compounds might you start with to prepare the following compounds by Grignard reaction? List all possibilities.
(a)
2-Methyl-2-propanol
(b)
1-Ethylcyclohexanol
(c)
3-Phenyl-3-pentanol
(d)
2-Phenyl-2-pentanol
(e)
Benzene with C H 2 C H 2 O H on C 1 and methyl on C 4 position.
(f)
Chemical structure of 1-cyclopentyl-2-methylpropan-2-ol.
Problem 17-45
How would you synthesize the following alcohols, starting with benzene and other alcohols of six or fewer carbons as your only organic reagents?
(a)
The structure having cyclohexanol with ethyl group on C 1.
(b)
A six-carbon chain with hydroxy on C 1 and methyl group on C 3 position.
(c)
Benzyl alcohol with methyl and n-propyl substituents on benzyl carbon.
(d)
A six-carbon chain with hydroxy on C 3 and methyl on C 5 position.

Reactions of Alcohols

Problem 17-46
What products would you obtain from reaction of 1-pentanol with the following reagents:
(a)
PBr3
(b)
SOCl2
(c)
Dess–Martin periodinane
Problem 17-47
How would you prepare the following compounds from 2-phenylethanol: More than one step may be required.
(a)
Styrene (PhCH = CH2)
(b)
Phenylacetaldehyde (PhCH2CHO)
(c)
Phenylacetic acid (PhCH2CO2H)
(d)
Benzoic acid
(e)
Ethylbenzene
(f)
Benzaldehyde
(g)
1-Phenylethanol
(h)
1-Bromo-2-phenylethane
Problem 17-48
How would you prepare the following compounds from 1-phenylethanol: More than one step may be required.
(a)
Acetophenone (PhCOCH3)
(b)
Benzyl alcohol
(c)
m-Bromobenzoic acid
(d)
2-Phenyl-2-propanol
Problem 17-49
How would you prepare the following substances from cyclopentanol: More than one step may be required.
(a)
Cyclopentanone
(b)
Cyclopentene
(c)
1-Methylcyclopentanol
(d)
trans-2-Methylcyclopentanol
Problem 17-50
What products would you expect to obtain from reaction of 1-methylcyclohexanol with the following reagents?
(a)
HBr
(b)
NaH
(c)
H2SO4

Spectroscopy

Problem 17-51

The following 1H NMR spectrum is that of an alcohol, C8H10O. Propose a structure.

H N M R spectrum with shifts at 2.32 (singlet), 2.43 (singlet), 4.50, 7.10 and 7.17 (two doublets). Relative areas are 3, 1, 2, 2, and 2 respectively.
Problem 17-52
Propose structures for alcohols that have the following 1H NMR spectra:
(a)

C5H12O

H N M R spectrum with shifts at 0.93 (triplet), 1.42 (quartet), 1.83 (singlet), and 3.41 (singlet). Relative areas are 6, 4, 1, and 1 respectively.
(b)

C8H10O

H N M R spectrum with shifts at 1.42 (doublet), 2.43 (singlet), 4.80 (quartet), and 7.32 (multiplet). Relative areas are 3, 1, 1, and 5 respectively.
Problem 17-53

Propose a structure consistent with the following spectral data for a compound C8H18O2:

  • IR: 3350 cm–1
  • 1H NMR: 1.24 δ (12 H, singlet); 1.56 δ (4 H, singlet); 1.95 δ (2 H, singlet)
Problem 17-54

The 1H NMR spectrum shown is that of 3-methyl-3-buten-1-ol. Assign all the observed resonance peaks to specific protons, and account for the splitting patterns.

H N M R spectrum with shifts at 1.76 (singlet), 2.13 (singlet), 2.30 (triplet), 3.72 (triplet), 4.79 (singlet), 4.85 (singlet). Relative areas are 3, 1, 2, 2, 1, 1, respectively.
Problem 17-55

A compound of unknown structure gave the following spectroscopic data:

  • Mass spectrum: M+ = 88.1
  • IR: 3600 cm–1
  • 1H NMR: 1.4 δ (2 H, quartet, J = 7 Hz); 1.2 δ (6 H, singlet); 1.0 δ (1 H, singlet); 0.9 δ (3 H, triplet, J = 7 Hz)
  • 13C NMR: 74, 35, 27, 25 δ
(a)
Assuming that the compound contains C and H but may or may not contain O, give three possible molecular formulas.
(b)
How many hydrogens does the compound contain?
(c)
What functional group(s) does the compound contain?
(d)
How many carbons does the compound contain?
(e)
What is the molecular formula of the compound?
(f)
What is the structure of the compound?
(g)
Assign peaks in the molecule’s 1H NMR spectrum corresponding to specific protons.
Problem 17-56

Propose a structure for a compound C15H24O that has the following 1H NMR spectrum. The peak marked by an asterisk disappears when D2O is added to the sample.

H N M R spectrum with shifts at 1.41, 2.24, 5.00, and 6.97 (all singlets). Relative areas of 18, 3, 1, and 2 respectively.

General Problems

Problem 17-57
How would you carry out the following transformations?
(a)
Cinnamic acid ((E)-3-phenyl prop-2-enoic acid) reacts with an unknown reagent represented as question mark to form 3-phenylpropanoic acid.
(b)
Cinnamic acid ((E)-3-phenyl prop-2-enoic acid) reacts with an unknown reagent represented as question mark to form trans-3-phenylprop-2-en-1-ol
(c)
Cinnamic acid ((E)-3-phenyl prop-2-enoic acid) reacts with an unknown reagent represented as question mark to form trans-3-phenylprop-2-en-1-thiol
Problem 17-58
Benzoquinone is an excellent dienophile in the Diels–Alder reaction. What product would you expect from reaction of benzoquinone with 1 equivalent of 1,3-butadiene? From reaction with 2 equivalents of 1,3-butadiene?
Problem 17-59

Rank the following substituted phenols in order of increasing acidity, and explain your answer:

The structure of four compounds named phenol, 4-fluorophenol, 4-methoxyphenol and 4-hydroxybenzonitrile.
Problem 17-60

Benzyl chloride can be converted into benzaldehyde by treatment with nitromethane and base. The reaction involves initial conversion of nitromethane into its anion, followed by SN2 reaction of the anion with benzyl chloride and subsequent E2 reaction. Write the mechanism in detail, using curved arrows to indicate the electron flow in each step.

Benzyl chloride reacts with nitromethane anion to form benzaldehyde.
Problem 17-61

Reaction of (S)-3-methyl-2-pentanone with methylmagnesium bromide followed by acidification yields 2,3-dimethyl-2-pentanol. What is the stereochemistry of the product? Is the product optically active?

The structure of 3-methyl-2-pentanone. It is a five-carbon chain with keto group on C 2 and methyl group on C 3.
Problem 17-62

Testosterone is one of the most important male steroid hormones. When testosterone is dehydrated by treatment with acid, rearrangement occurs to yield the product shown. Propose a mechanism to account for this reaction.

Testosterone reacts with hydronium ion to form a compound with alkene group.
Problem 17-63
Starting from testosterone (Problem 17-62), how would you prepare the following substances?
(a)
Cyclopentanone fused to cyclohexane with wedged methyl, dashed hydrogen. This is connected to cyclohexane with wedged hydrogen and methyl, dashed hydrogen. This is bonded to cyclohexanone with alkene.
(b)
Cyclopentane with wedged hydroxyl, dashed hydrogen fused to cyclohexane with wedged methyl, dashed hydrogen. This is connected to cyclohexane with wedged hydrogen and methyl, dashed hydrogen, bonded to cyclohexene.
(c)
Cyclopentanone fused to cyclohexane with wedged methyl, dashed hydrogen. This is connected to cyclohexane with wedged hydrogen and methyl, dashed hydrogen. This is bonded to cyclohexanone.
(d)
Cyclopentane with wedged hydroxyl, dashed hydrogen fused to cyclohexane with wedged methyl, dashed hydrogen. This is connected to cyclohexane with wedged hydrogen and methyl, dashed hydrogen, bonded to cyclohexane.
Problem 17-64

p-Nitrophenol and 2,6-dimethyl-4-nitrophenol both have pKa = 7.15, but 3,5-dimethyl-4-nitrophenol has pKa = 8.25. Why is 3,5-dimethyl-4-nitrophenol so much less acidic?

The structure of 4-nitrophenol, 2,6-dimethyl-4-nitrophenol, and 3,5-dimethyl-4-nitrophenol with p K a values 7.15, 7.15, and 8.25, respectively.
Problem 17-65
Compound A, C10H18O, undergoes reaction with dilute H2SO4 at 25 °C to yield a mixture of two alkenes, C10H16. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Write the reactions involved, and identify A and B.
Problem 17-66

Compound A, C5H10O, is one of the basic building blocks of nature. All steroids and many other naturally occurring compounds are built from compound A. Spectroscopic analysis of A yields the following information:

  • IR: 3400 cm–1; 1640 cm–1
  • 1H NMR: 1.63 δ (3 H, singlet); 1.70 δ (3 H, singlet); 3.83 δ (1 H, broad singlet); 4.15 δ (2 H, doublet, J = 7 Hz); 5.70 δ (1 H, triplet, J = 7 Hz)
(a)
How many double bonds and/or rings does A have?
(b)
From the IR spectrum, what is the identity of the oxygen-containing functional group?
(c)
What kinds of hydrogens are responsible for the NMR absorptions listed?
(d)
Propose a structure for A.
Problem 17-67
Dehydration of trans-2-methylcyclopentanol with POCl3 in pyridine yields predominantly 3-methylcyclopentene. Is the stereochemistry of this dehydration syn or anti?
Problem 17-68

2,3-Dimethyl-2,3-butanediol has the common name pinacol. On heating with aqueous acid, pinacol rearranges to pinacolone, 3,3-dimethyl-2-butanone. Suggest a mechanism for this reaction.

Pinacol (2,3-dihydroxy-2,3-dimethylbutane) reacts with hydronium ion to form pinacolone (t-butyl methyl ketone) and water.
Problem 17-69
As a rule, axial alcohols oxidize somewhat faster than equatorial alcohols. Which would you expect to oxidize faster, cis-4-tert-butylcyclohexanol or trans-4-tert-butylcyclohexanol? Draw the more stable chair conformation of each molecule.
Problem 17-70

Propose a synthesis of bicyclohexylidene, starting from cyclohexanone as the only source of carbon.

The structure of bicyclohexylidene. It is two cyclohexane rings linked via a double bond between their C 1 positions.
Problem 17-71

A problem often encountered in the oxidation of primary alcohols to carboxylic acids is that esters are sometimes produced as by-products. For example, oxidation of ethanol yields acetic acid and ethyl acetate:

Ethanol reacts with chromium trioxide to form acetic acid and ethylacetate.

Propose a mechanism to account for the formation of ethyl acetate. Take into account the reversible reaction between aldehydes and alcohols:

An aldehyde, R C H O reacts with R dash O H to form carbon linked to H , R, O H and O R dash group.
Problem 17-72

Identify the reagents af in the following scheme:

Cyclohexanol reacts with reagent a to form cyclohexanol. b to form cyclohexylbromide. c to form cyclohexylmethanol. d to form cyclohexanecarbaldehyde, e to form 1-cyclohexyl-2-phenylethanol, f to form (E)-(2-cyclohexylvinyl)benzene.
Problem 17-73

Galactose, a constituent of the disaccharide lactose found in dairy products, is metabolized by a pathway that includes the isomerization of UDP-galactose to UDP-glucose, where UDP = uridylyl diphosphate. The enzyme responsible for the transformation uses NAD+ as cofactor. Propose a mechanism.

The compound, U D P-galactose isomerizes to form U D P-glucose.
Problem 17-74
Propose structures for alcohols that have the following 1H NMR spectra:
(a)

C9H12O

H N M R spectrum with shifts at 0.88 (triplet), 1.80 (quartet), 2.32 (singlet), 4.54 (triplet), and 7.24 (multiplet). Relative areas are 3, 2, 1, 1, and 5 respectively.
(b)

C8H10O2

H N M R spectrum with shifts at 2.60 (singlet), 3.76 (singlet), 4.53 (singlet), 6.85 (doublet), and 7.23 (doublet). Relative areas are 1, 3, 2, 2, and 2 respectively.
Problem 17-75

Compound A, C8H10O, has the IR and 1H NMR spectra shown. Propose a structure consistent with the observed spectra, and label each peak in the NMR spectrum. Note that the absorption at 5.5 δ disappears when D2O is added.

An I R spectrum with broad peak around 3400, peaks just below 3000, and peaks at 1500 and 1600 wavenumbers. H N M R spectrum with shifts at 1.16 triplet), 2.55 (quartet), 5.50 (singlet), 6.74 (doublet), and 7.03 (doublet). Relative areas are 3, 2, 1, 2, and 2 respectively.
Citation/Attribution

Want to cite, share, or modify this book? This book uses the Creative Commons Attribution-NonCommercial-ShareAlike License and you must attribute OpenStax.

Attribution information
  • If you are redistributing all or part of this book in a print format, then you must include on every physical page the following attribution:
    Access for free at https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
  • If you are redistributing all or part of this book in a digital format, then you must include on every digital page view the following attribution:
    Access for free at https://openstax.org/books/organic-chemistry/pages/1-why-this-chapter
Citation information

© Sep 25, 2023 OpenStax. Textbook content produced by OpenStax is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike License . The OpenStax name, OpenStax logo, OpenStax book covers, OpenStax CNX name, and OpenStax CNX logo are not subject to the Creative Commons license and may not be reproduced without the prior and express written consent of Rice University.