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Organic Chemistry 10th edition

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John McMurry
Publisher: OpenStax

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  • McMurry Organic Chemistry 10e

Access is contingent on use of this textbook in the instructor's classroom.

  • Chapter I: Introduction
    • I: Getting Set Up (2)
    • I: Question Types (7)
    • I: Submitting Answers (1)
    • I: Chemical Drawings (13)

  • Chapter 1: Structure and Bonding
    • 1.1: Atomic Structure: The Nucleus
    • 1.2: Atomic Structure: Orbitals
    • 1.3: Atomic Structure: Electron Configurations
    • 1.4: Development of Chemical Bonding Theory
    • 1.5: Describing Chemical Bonds: Valence Bond Theory
    • 1.6: sp3 Hybrid Orbitals and the Structure of Methane
    • 1.7: sp3 Hybrid Orbitals and the Structure of Ethane
    • 1.8: sp2 Hybrid Orbitals and the Structure of Ethylene
    • 1.9: sp Hybrid Orbitals and the Structure of Acetylene
    • 1.10: Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur
    • 1.11: Describing Chemical Bonds: Molecular Orbital Theory
    • 1.12: Drawing Chemical Structures
    • 1: End-of-Chapter Problems (24)
    • 1: Additional Questions (11)

  • Chapter 2: Polar Covalent Bonds; Acids and Bases
    • 2.1: Polar Covalent Bonds and Electronegativity
    • 2.2: Polar Covalent Bonds and Dipole Moments
    • 2.3: Formal Charges
    • 2.4: Resonance
    • 2.5: Rules for Resonance Forms
    • 2.6: Drawing Resonance Forms
    • 2.7: Acids and Bases: The Brønsted–Lowry Definition
    • 2.8: Acid and Base Strength
    • 2.9: Predicting Acid–Base Reactions from pKa Values
    • 2.10: Organic Acids and Organic Bases
    • 2.11: Acids and Bases: The Lewis Definition
    • 2.12: Noncovalent Interactions between Molecules
    • 2: End-of-Chapter Problems (26)
    • 2: Additional Questions (11)

  • Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
    • 3.1: Functional Groups
    • 3.2: Alkanes and Alkane Isomers
    • 3.3: Alkyl Groups
    • 3.4: Naming Alkanes
    • 3.5: Properties of Alkanes
    • 3.6: Conformations of Ethane
    • 3.7: Conformations of Other Alkanes
    • 3: End-of-Chapter Problems (29)
    • 3: Additional Questions (9)

  • Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry
    • 4.1: Naming Cycloalkanes
    • 4.2: Cis–Trans Isomerism in Cycloalkanes
    • 4.3: Stability of Cycloalkanes: Ring Strain
    • 4.4: Conformations of Cycloalkanes
    • 4.5: Conformations of Cyclohexane
    • 4.6: Axial and Equatorial Bonds in Cyclohexane
    • 4.7: Conformations of Monosubstituted Cyclohexanes
    • 4.8: Conformations of Disubstituted Cyclohexanes
    • 4.9: Conformations of Polycyclic Molecules
    • 4: End-of-Chapter Problems (20)
    • 4: Additional Questions (8)

  • Chapter 5: Stereochemistry at Tetrahedral Centers
    • 5.1: Enantiomers and the Tetrahedral Carbon
    • 5.2: The Reason for Handedness in Molecules: Chirality
    • 5.3: Optical Activity
    • 5.4: Pasteur's Discovery of Enantiomers
    • 5.5: Sequence Rules for Specifying Configuration
    • 5.6: Diastereomers
    • 5.7: Meso Compounds
    • 5.8: Racemic Mixtures and the Resolution of Enantiomers
    • 5.9: A Review of Isomerism
    • 5.10: Chirality at Nitrogen, Phosphorus, and Sulfur
    • 5.11: Prochirality
    • 5.12: Chirality in Nature and Chiral Environments
    • 5: End-of-Chapter Problems (35)
    • 5: Additional Questions (14)

  • Chapter 6: An Overview of Organic Reactions
    • 6.1: Kinds of Organic Reactions
    • 6.2: How Organic Reactions Occur: Mechanisms
    • 6.3: Polar Reactions
    • 6.4: An Example of a Polar Reaction: Addition of HBr to Ethylene
    • 6.5: Using Curved Arrows in Polar Reaction Mechanisms
    • 6.6: Radical Reactions
    • 6.7: Describing a Reaction: Equilibria, Rates, and Energy Changes
    • 6.8: Describing a Reaction: Bond Dissociation Energies
    • 6.9: Describing a Reaction: Energy Diagrams and Transition States
    • 6.10: Describing a Reaction: Intermediates
    • 6.11: A Comparison Between Biological Reactions and Laboratory Reactions
    • 6: End-of-Chapter Problems (24)
    • 6: Additional Questions (5)

  • Chapter 7: Alkenes: Structure and Reactivity
    • 7.1: Industrial Preparation and Use of Alkenes
    • 7.2: Calculating the Degree of Unsaturation
    • 7.3: Naming Alkenes
    • 7.4: Cis–Trans Isomerism in Alkenes
    • 7.5: Alkene Stereochemistry and the E,Z Designation
    • 7.6: Stability of Alkenes
    • 7.7: Electrophilic Addition Reactions of Alkenes
    • 7.8: Orientation of Electrophilic Additions: Markovnikov's Rule
    • 7.9: Carbocation Structure and Stability
    • 7.10: The Hammond Postulate
    • 7.11: Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements
    • 7: End-of-Chapter Problems (34)
    • 7: Additional Questions (12)

  • Chapter 8: Alkenes: Reactions and Synthesis
    • 8.1: Preparing Alkenes: A Preview of Elimination Reactions
    • 8.2: Halogenation of Alkenes: Addition of X2
    • 8.3: Halohydrins from Alkenes: Addition of HO-X
    • 8.4: Hydration of Alkenes: Addition of H2O by Oxymercuration
    • 8.5: Hydration of Alkenes: Addition of H2O by Hydroboration
    • 8.6: Reduction of Alkenes: Hydrogenation
    • 8.7: Oxidation of Alkenes: Epoxidation and Hydroxylation
    • 8.8: Oxidation of Alkenes: Cleavage to Carbonyl Compounds
    • 8.9: Addition of Carbenes to Alkenes: Cyclopropane Synthesis
    • 8.10: Radical Additions to Alkenes: Chain-Growth Polymers
    • 8.11: Biological Additions of Radicals to Alkenes
    • 8.12: Reaction Stereochemistry: Addition of H2O to an Achiral Alkene
    • 8.13: Reaction Stereochemistry: Addition of H2O to a Chiral Alkene
    • 8: End-of-Chapter Problems (42)
    • 8: Additional Questions (21)

  • Chapter 9: Alkynes: An Introduction to Organic Synthesis
    • 9.1: Naming Alkynes
    • 9.2: Preparation of Alkynes: Elimination Reactions of Dihalides
    • 9.3: Reactions of Alkynes: Addition of HX and X2
    • 9.4: Hydration of Alkynes
    • 9.5: Reduction of Alkynes
    • 9.6: Oxidative Cleavage of Alkynes
    • 9.7: Alkyne Acidity: Formation of Acetylide Anions
    • 9.8: Alkylation of Acetylide Anions
    • 9.9: An Introduction to Organic Synthesis
    • 9: End-of-Chapter Problems (38)
    • 9: Additional Questions (13)

  • Chapter 10: Organohalides
    • 10.1: Names and Structures of Alkyl Halides
    • 10.2: Preparing Alkyl Halides from Alkanes: Radical Halogenation
    • 10.3: Preparing Alkyl Halides from Alkenes: Allylic Bromination
    • 10.4: Stability of the Allyl Radical: Resonance Revisited
    • 10.5: Preparing Alkyl Halides from Alcohols
    • 10.6: Reactions of Alkyl Halides: Grignard Reagents
    • 10.7: Organometallic Coupling Reactions
    • 10.8: Oxidation and Reduction in Organic Chemistry
    • 10: End-of-Chapter Problems (19)
    • 10: Additional Questions (13)

  • Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
    • 11.1: The Discovery of Nucleophilic Substitution Reactions
    • 11.2: The SN2 Reaction
    • 11.3: Characteristics of the SN2 Reaction
    • 11.4: The SN1 Reaction
    • 11.5: Characteristics of the SN1 Reaction
    • 11.6: Biological Substitution Reactions
    • 11.7: Elimination Reactions: Zaitsev's Rule
    • 11.8: The E2 Reaction and the Deuterium Isotope Effect
    • 11.9: The E2 Reaction and Cyclohexane Conformation
    • 11.10: The E1 and E1cB Reactions
    • 11.11: Biological Elimination Reactions
    • 11.12: A Summary of Reactivity: SN1, SN2, E1, E1cB, and E2
    • 11: End-of-Chapter Problems (35)
    • 11: Additional Questions (8)

  • Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
    • 12.1: Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments
    • 12.2: Interpreting Mass Spectra
    • 12.3: Mass Spectrometry of Some Common Functional Groups
    • 12.4: Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments
    • 12.5: Spectroscopy and the Electromagnetic Spectrum
    • 12.6: Infrared Spectroscopy
    • 12.7: Interpreting Infrared Spectra
    • 12.8: Infrared Spectra of Some Common Functional Groups
    • 12: End-of-Chapter Problems (25)
    • 12: Additional Questions (5)

  • Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
    • 13.1: Nuclear Magnetic Resonance Spectroscopy
    • 13.2: The Nature of NMR Absorptions
    • 13.3: Chemical Shifts
    • 13.4: Chemical Shifts in 1H NMR Spectroscopy
    • 13.5: Integration of 1H NMR Absorptions: Proton Counting
    • 13.6: Spin–Spin Splitting in 1H NMR Spectra
    • 13.7: 1H NMR Spectroscopy and Proton Equivalence
    • 13.8: More Complex Spin–Spin Splitting Patterns
    • 13.9: Uses of 1H NMR Spectroscopy
    • 13.10: 13C NMR Spectroscopy: Signal Averaging and FT–NMR
    • 13.11: Characteristics of 13C NMR Spectroscopy
    • 13.12: DEPT 13C NMR Spectroscopy
    • 13.13: Uses of 13C NMR Spectroscopy
    • 13: End-of-Chapter Problems (27)
    • 13: Additional Questions (10)

  • Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
    • 14.1: Stability of Conjugated Dienes: Molecular Orbital Theory
    • 14.2: Electrophilic Additions to Conjugated Dienes: Allylic Carbocations
    • 14.3: Kinetic versus Thermodynamic Control of Reactions
    • 14.4: The Diels–Alder Cycloaddition Reaction
    • 14.5: Characteristics of the Diels–Alder Reaction
    • 14.6: Diene Polymers: Natural and Synthetic Rubbers
    • 14.7: Ultraviolet Spectroscopy
    • 14.8: Interpreting Ultraviolet Spectra: The Effect of Conjugation
    • 14.9: Conjugation, Color, and the Chemistry of Vision
    • 14: End-of-Chapter Problems (19)
    • 14: Additional Questions (7)

  • Chapter 15: Benzene and Aromaticity
    • 15.1: Naming Aromatic Compounds
    • 15.2: Structure and Stability of Benzene
    • 15.3: Aromaticity and the Hückel 4n + 2 Rule
    • 15.4: Aromatic Ions
    • 15.5: Aromatic Heterocycles: Pyridine and Pyrrole
    • 15.6: Polycyclic Aromatic Compounds
    • 15.7: Spectroscopy of Aromatic Compounds
    • 15: End-of-Chapter Problems (16)
    • 15: Additional Questions (4)

  • Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution
    • 16.1: Electrophilic Aromatic Substitution Reactions: Bromination
    • 16.2: Other Aromatic Substitutions
    • 16.3: Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction
    • 16.4: Substituent Effects in Electrophilic Substitutions
    • 16.5: Trisubstituted Benzenes: Additivity of Effects
    • 16.6: Nucleophilic Aromatic Substitution
    • 16.7: Benzyne
    • 16.8: Oxidation of Aromatic Compounds
    • 16.9: Reduction of Aromatic Compounds
    • 16.10: Synthesis of Polysubstituted Benzenes
    • 16: End-of-Chapter Problems (32)
    • 16: Additional Questions (13)

  • Chapter 17: Alcohols and Phenols
    • 17.1: Naming Alcohols and Phenols
    • 17.2: Properties of Alcohols and Phenols
    • 17.3: Preparation of Alcohols: A Review
    • 17.4: Alcohols from Carbonyl Compounds: Reduction
    • 17.5: Alcohols from Carbonyl Compounds: Grignard Reaction
    • 17.6: Reactions of Alcohols
    • 17.7: Oxidation of Alcohols
    • 17.8: Protection of Alcohols
    • 17.9: Phenols and Their Uses
    • 17.10: Reactions of Phenols
    • 17.11: Spectroscopy of Alcohols and Phenols
    • 17: End-of-Chapter Problems (39)
    • 17: Additional Questions (17)

  • Chapter 18: Ethers and Epoxides; Thiols and Sulfides
    • 18.1: Names and Properties of Ethers
    • 18.2: Preparing Ethers
    • 18.3: Reactions of Ethers: Acidic Cleavage
    • 18.4: Cyclic Ethers: Epoxides
    • 18.5: Reactions of Epoxides: Ring-Opening
    • 18.6: Crown Ethers
    • 18.7: Thiols and Sulfides
    • 18.8: Spectroscopy of Ethers
    • 18: End-of-Chapter Problems (32)
    • 18: Additional Questions (6)

  • Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
    • 19.1: Naming Aldehydes and Ketones
    • 19.2: Preparing Aldehydes and Ketones
    • 19.3: Oxidation of Aldehydes and Ketones
    • 19.4: Nucleophilic Addition Reactions of Aldehydes and Ketones
    • 19.5: Nucleophilic Addition of H2O: Hydration
    • 19.6: Nucleophilic Addition of HCN: Cyanohydrin Formation
    • 19.7: Nucleophilic Addition of Hydride and Grignard Reagents: Alcohol Formation
    • 19.8: Nucleophilic Addition of Amines: Imine and Enamine Formation
    • 19.9: Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction
    • 19.10: Nucleophilic Addition of Alcohols: Acetal Formation
    • 19.11: Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction
    • 19.12: Biological Reductions
    • 19.13: Conjugate Nucleophilic Addition to α,β-Unsaturated Aldehydes and Ketones
    • 19.14: Spectroscopy of Aldehydes and Ketones
    • 19: End-of-Chapter Problems (35)
    • 19: Additional Questions (20)

  • Chapter 20: Carboxylic Acids and Nitriles
    • 20.1: Naming Carboxylic Acids and Nitriles
    • 20.2: Structure and Properties of Carboxylic Acids
    • 20.3: Biological Acids and the Henderson–Hasselbalch Equation
    • 20.4: Substituent Effects on Acidity
    • 20.5: Preparing Carboxylic Acids
    • 20.6: Reactions of Carboxylic Acids: An Overview
    • 20.7: Chemistry of Nitriles
    • 20.8: Spectroscopy of Carboxylic Acids and Nitriles
    • 20: End-of-Chapter Problems (39)
    • 20: Additional Questions (6)

  • Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
    • 21.1: Naming Carboxylic Acid Derivatives
    • 21.2: Nucleophilic Acyl Substitution Reactions
    • 21.3: Reactions of Carboxylic Acids
    • 21.4: Chemistry of Acid Halides
    • 21.5: Chemistry of Acid Anhydrides
    • 21.6: Chemistry of Esters
    • 21.7: Chemistry of Amides
    • 21.8: Chemistry of Thioesters and Acyl Phosphates: Biological Carboxylic Acid Derivatives
    • 21.9: Polyamides and Polyesters: Step-Growth Polymers
    • 21.10: Spectroscopy of Carboxylic Acid Derivatives
    • 21: End-of-Chapter Problems (41)
    • 21: Additional Questions (24)

  • Chapter 22: Carbonyl Alpha-Substitution Reactions
    • 22.1: Keto–Enol Tautomerism
    • 22.2: Reactivity of Enols: α-Substitution Reactions
    • 22.3: Alpha Halogenation of Aldehydes and Ketones
    • 22.4: Alpha Bromination of Carboxylic Acids
    • 22.5: Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation
    • 22.6: Reactivity of Enolate Ions
    • 22.7: Alkylation of Enolate Ions
    • 22: End-of-Chapter Problems (33)
    • 22: Additional Questions

  • Chapter 23: Carbonyl Condensation Reactions
    • 23.1: Carbonyl Condensations: The Aldol Reaction
    • 23.2: Carbonyl Condensations versus Alpha Substitutions
    • 23.3: Dehydration of Aldol Products: Synthesis of Enones
    • 23.4: Using Aldol Reactions in Synthesis
    • 23.5: Mixed Aldol Reactions
    • 23.6: Intramolecular Aldol Reactions
    • 23.7: The Claisen Condensation Reaction
    • 23.8: Mixed Claisen Condensations
    • 23.9: Intramolecular Claisen Condensations: The Dieckmann Cyclization
    • 23.10: Conjugate Carbonyl Additions: The Michael Reaction
    • 23.11: Carbonyl Condensations with Enamines: The Stork Enamine Reaction
    • 23.12: The Robinson Annulation Reaction
    • 23.13: Some Biological Carbonyl Condensation Reactions
    • 23: End-of-Chapter Problems (34)
    • 23: Additional Questions

  • Chapter 24: Amines and Heterocycles
    • 24.1: Naming Amines
    • 24.2: Structure and Properties of Amines
    • 24.3: Basicity of Amines
    • 24.4: Basicity of Arylamines
    • 24.5: Biological Amines and the Henderson–Hasselbalch Equation
    • 24.6: Synthesis of Amines
    • 24.7: Reactions of Amines
    • 24.8: Reactions of Arylamines
    • 24.9: Heterocyclic Amines
    • 24.10: Spectroscopy of Amines
    • 24: End-of-Chapter Problems (42)
    • 24: Additional Questions

  • Chapter 25: Biomolecules: Carbohydrates
    • 25.1: Classification of Carbohydrates
    • 25.2: Representing Carbohydrate Stereochemistry: Fischer Projections
    • 25.3: D,L Sugars
    • 25.4: Configurations of the Aldoses
    • 25.5: Cyclic Structures of Monosaccharides: Anomers
    • 25.6: Reactions of Monosaccharides
    • 25.7: The Eight Essential Monosaccharides
    • 25.8: Disaccharides
    • 25.9: Polysaccharides and Their Synthesis
    • 25.10: Some Other Important Carbohydrates
    • 25: End-of-Chapter Problems (25)
    • 25: Additional Questions

  • Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins
    • 26.1: Structures of Amino Acids
    • 26.2: Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points
    • 26.3: Synthesis of Amino Acids
    • 26.4: Peptides and Proteins
    • 26.5: Amino Acid Analysis of Peptides
    • 26.6: Peptide Sequencing: The Edman Degradation
    • 26.7: Peptide Synthesis
    • 26.8: Automated Peptide Synthesis: The Merrifield Solid-Phase Method
    • 26.9: Protein Structure
    • 26.10: Enzymes and Coenzymes
    • 26.11: How Do Enzymes Work? Citrate Synthase
    • 26: End-of-Chapter Problems (28)
    • 26: Additional Questions

  • Chapter 27: Biomolecules: Lipids
    • 27.1: Waxes, Fats, and Oils
    • 27.2: Soap
    • 27.3: Phospholipids
    • 27.4: Prostaglandins and Other Eicosanoids
    • 27.5: Terpenoids
    • 27.6: Steroids
    • 27.7: Biosynthesis of Steroids
    • 27: End-of-Chapter Problems (19)
    • 27: Additional Questions

  • Chapter 28: Biomolecules: Nucleic Acids
    • 28.1: Nucleotides and Nucleic Acids
    • 28.2: Base Pairing in DNA
    • 28.3: Replication of DNA
    • 28.4: Transcription of DNA
    • 28.5: Translation of RNA: Protein Biosynthesis
    • 28.6: DNA Sequencing
    • 28.7: DNA Synthesis
    • 28.8: The Polymerase Chain Reaction
    • 28: End-of-Chapter Problems (16)
    • 28: Additional Questions

  • Chapter 29: The Organic Chemistry of Metabolic Pathways
    • 29.1: An Overview of Metabolism and Biochemical Energy
    • 29.2: Catabolism of Triacylglycerols: The Fate of Glycerol
    • 29.3: Catabolism of Triacylglycerols: β-Oxidation
    • 29.4: Biosynthesis of Fatty Acids
    • 29.5: Catabolism of Carbohydrates: Glycolysis
    • 29.6: Conversion of Pyruvate to Acetyl CoA
    • 29.7: The Citric Acid Cycle
    • 29.8: Carbohydrate Biosynthesis: Gluconeogenesis
    • 29.9: Catabolism of Proteins: Deamination
    • 29.10: Some Conclusions about Biological Chemistry
    • 29: End-of-Chapter Problems (21)
    • 29: Additional Questions

  • Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions
    • 30.1: Molecular Orbitals of Conjugated Pi Systems
    • 30.2: Electrocyclic Reactions
    • 30.3: Stereochemistry of Thermal Electrocyclic Reactions
    • 30.4: Photochemical Electrocyclic Reactions
    • 30.5: Cycloaddition Reactions
    • 30.6: Stereochemistry of Cycloadditions
    • 30.7: Sigmatropic Rearrangements
    • 30.8: Some Examples of Sigmatropic Rearrangements
    • 30.9: A Summary of Rules for Pericyclic Reactions
    • 30: End-of-Chapter Problems (6)
    • 30: Additional Questions

  • Chapter 31: Synthetic Polymers
    • 31.1: Chain-Growth Polymers
    • 31.2: Stereochemistry of Polymerization: Ziegler–Natta Catalysts
    • 31.3: Copolymers
    • 31.4: Step-Growth Polymers
    • 31.5: Olefin Metathesis Polymerization
    • 31.6: Intramolecular Olefin Metathesis
    • 31.7: Polymer Structure and Physical Properties
    • 31: End-of-Chapter Problems (8)
    • 31: Additional Questions


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Group Quantity Questions
Chapter I: Introduction
I.A 1 001
I.D 13 001 002 003 004 005 006 007 008 009 010 011 012 013
I.Q 7 001 002 003 004 005 006 007
I.T 2 001 002
Chapter 1: Structure and Bonding
1.D 7 001 002 003 004 005 006 007
1.E 24 018a 018b 018b.alt 019a 019a.alt 019b 019b.alt 020 020.alt 022 023 024 025 027 027.alt 028 029 030 030.alt 033 033.alt 035 037 038 038.alt 039 040 041 041.alt 042 048 048.alt 052-055 052-055.alt 056
1.Q 11 001 002 003 004 004.alt 005 005.alt 006 006.alt 007 008 009 010 011
Chapter 2: Polar Covalent Bonds; Acids and Bases
2.D 8 001 002 003 004 005 006 007 008
2.E 26 021 021.alt 023 023.alt 024a 024a.alt 024b 024b.alt 025 025.alt 026 026.alt 027 027.alt 028 029a 029b 030 035-036 037 038 038.alt 040 040.alt 042 042.alt 043a 043a.alt 043b 043b.alt 044a 044b 045 048b 048b.alt 049 050 051 055
2.Q 11 001 002 003 004 004.alt 005 005.alt 006 007 007.alt 008 009 010 011
Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
3.D 2 001 002
3.E 29 019 020a 020b 020b.alt 021 022 023 023.alt 026 026.alt 027 027.alt 028a 028a.alt 028b 029 030 030.alt 031 031.alt 032 032.alt 033 033.alt 034 034.alt 035 035.alt 036 036.alt 037 037.alt 038 039 040 041 043 050 050.alt 051 052a 052b 053
3.Q 9 001 002 002.alt 003 004 004.alt 005 006 007 007.alt 008 009
Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry
4.D 5 001 002 003 004 005
4.E 20 022 023 024 027 027.alt 029 029.alt 030 032 033 034 038 040 041 042 043 044a 044b 044b.alt 045 046 046.alt 050 058
4.Q 8 001 002 002.alt 003 003.alt 004 005 006 007 008
Chapter 5: Stereochemistry at Tetrahedral Centers
5.D 10 001 002 003 004 004.alt 005 006 007 008 009
5.E 35 026 027 028 029 030 032 035 035.alt 036 037 038 039 040 041 042 043 044 045 046 046.alt 047 049 050 051 051.alt 052 052.alt 054 054.alt 055 056 057 058 058.alt 059-061 062 062.alt 063 063.alt 065 065.alt 066 076 077 077.alt
5.Q 14 001 002 003 004 005 006 007 008 009 009.alt 010 010.alt 011 012 013 014
Chapter 6: An Overview of Organic Reactions
6.D 7 001 001.v2 002 003 004 005 006
6.E 24 014 014.alt 015 015.alt 017 024 025 025.alt 027 027.alt 028 028.alt 029 030 031 032 034 034.alt 036 039 039.alt 041 041.alt 042 043a 043a.alt 044 044.alt 045 045.alt 046 046.alt 047a 047b 047b.alt 048a 048a.alt 048b
6.Q 5 001 001.alt 002 002.alt 003 003.alt 004 005
Chapter 7: Alkenes: Structure and Reactivity
7.D 6 001 002 003 004 005 006
7.E 34 022a 022b 022b.alt 023a 023b 023b.alt 024a 024a.alt 024b 024b.alt 025 025.alt 026 026.alt 027 027.alt 028 028.alt 030 030.alt 031 031.alt 032 032.alt 033 033.alt 035 036 037 039 040 041 042 042.alt 043-044a 043-044a.alt 043-044b 045 046 047 053 057 057.alt 058 058.alt 059 059.alt 060 060.alt 063 064 067
7.Q 12 001 002 002.alt 003 004 005 006 007 007.alt 008 008.alt 009 010 010.alt 011 011.alt 012 012.alt
Chapter 8: Alkenes: Reactions and Synthesis
8.D 14 001 002 003 004 005 006 007 008 009 010 011 012 013 014
8.E 42 022 022.alt 023 023.alt 024 025 026 026.alt 027 027.alt 028 028.alt 029 029.alt 030 031a 031a.alt 031b 031b.alt 031c 031c.alt 033 033.alt 034 034.alt 036a 036a.alt 036b 036b.alt 037 037.alt 038 038.alt 040 040.alt 041a 041a.alt 041b 041b.alt 042a 042a.alt 042b 042b.alt 045 045.alt 046 046.alt 047 047.alt 048 049 049.alt 050 050.alt 051 051.alt 052 052.alt 053-054 055 055.alt 056 056.alt 057 057.alt 059 059.alt 060 060.alt 063 063.alt 067 067.alt 068 068.alt 069 069.alt 070 070.alt
8.Q 21 001 001.alt 002 002.alt 003 003.alt 004 004.alt 005 005.alt 006 006.alt 007 007.alt 008 008.alt 009 009.alt 010 010.alt 011 011.alt 012 013 013.alt 014 014.alt 016 016.alt 017 018 018.alt 019 019.alt 020 021 021.alt 022 022.alt
Chapter 9: Alkynes: An Introduction to Organic Synthesis
9.D 4 001 002 003 004
9.E 38 014a 014b 014b.alt 014c 014c.alt 015 015.alt 016 018 018.alt 019a 019a.alt 019b 019b.alt 020 020.alt 021 021.alt 022 022.alt 023 024 024.alt 026 027 027.alt 028 029 029.alt 031-032b 031-032b.alt 031a 031a.alt 032a 032a.alt 033 033.alt 034 034.alt 035 036 036.alt 037 038a 038b-040 042 043 043.alt 044 046 047 047.alt 049 049.alt 050 050.alt 051 051.alt 052 052.alt 053 053.alt 054 054.alt
9.Q 13 001 002 002.alt 003 003.alt 004 004.alt 005 005.alt 006 006.alt 007 007.alt 008 008.alt 009 009.alt 010 010.alt 011 011.alt 012 012.alt 013
Chapter 10: Organohalides
10.D 32 001 002 003 004 005 006 007 007.alt.v2 008 008.alt.v2 009 009.alt.v2 010 011 012 013 013.v2 014 015 016 017 018 019 020 021 022 023 024 025 026 027 028
10.E 19 014 015 015.alt 016 018 019 019.alt 020 020.alt 021 022a 022a.alt 022b 022b.alt 022c 022c.alt 023 023.alt 024 024.alt 025 025.alt 027 028 029 033 033.alt 036 040
10.Q 13 001 001.alt 002 003 003.alt 004 005 006 007 007.alt 008 008.alt 009 009.alt 010 010.alt 011 011.alt 012 012.alt 013
Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
11.D 37 001 002 003 004 005 006 007 008 009 010 011 011.v2 012 013 014 015 016 017 018 019 020 021 022 023 024 025 026 027 028 029 030 031 032 033 034 035 036
11.E 35 021 021.alt 022 022.alt 023 023.alt 024 024.alt 025 025.alt 026a 026a.alt 026b 026b.alt 027a 027a.alt 027b 027b.alt 028 028.alt 029a 029a.alt 029b 029b.alt 029c 029c.alt 030 030.alt 031 031.alt 039 039.alt 041 042 043-044 045 045.alt 047 047.alt 050 050.alt 052 052.alt 054 054.alt 056 057 058 058.alt 060 061 061.alt 062 062.alt 064 064.alt 068 068.alt 071 071.alt 074 074.alt 075 075.alt
11.Q 8 001 001.alt 002 002.alt 003 004 005 006 006.alt 007 007.alt 008
Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
12.D 3 001 002 003
12.E 25 012 013 013.alt 014 015 018 020 021 022 023 023.alt 024 024.alt 026 026.alt 027 030 030.alt 031 032 034 035 039 043 043.alt 044 045 045.alt 047 047.alt 048 049 050
12.Q 5 001 002 002.alt 003 004 005
Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
13.D 9 001 002 003 004 004.v2 005 006 007 008
13.E 27 024 025 027 028 029 030 033 034 035 036 037 037.alt 038 039 040-041 043 046 048 049 054 054.alt 055 055.alt 057 057.alt 058 058.alt 060-064 060-064.alt 067-068 067-068.alt 069 069.alt 070 070.alt 071 071.alt
13.Q 10 001 002 003 004 005 005.alt 006 007 008 009 009.alt 010 010.alt
Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
14.D 11 001 002 003 004 005 006 007 008 009 010 010.v2
14.E 19 017 017.alt 019a 019a.alt 019b 019b.alt 020 020.alt 025 026 027a 027a.alt 027b 027b.alt 027c 027c.alt 030 030.alt 031 031.alt 036 036.alt 037 040 040.alt 046 049 049.alt 051 060 061 061.alt
14.Q 7 001 001.alt 002 002.alt 003 003.alt 004 004.alt 005 005.alt 006 006.alt 007 007.alt
Chapter 15: Benzene and Aromaticity
15.D 5 001 002 003 004 005
15.E 16 013 014-015 016 016.alt 018 019 019.alt 020 022a 022a.alt 022b 023 023.alt 029 029.alt 039 039.alt 042 042.alt 043 048 048.alt 049 049.alt 050 050.alt
15.Q 4 001 001.alt 002 003 004 004.alt
Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution
16.D 30 001 002 002.alt 003 004 005 006 007 007.v2 008 008.v2 009 010 011 012 013 014 015 016 017 018 019 020 021 022 023 024 025 026 027
16.E 32 024 024.alt 026 028 028.alt 029 029.alt 030 030.alt 033 033.alt 035 035.alt 037 037.alt 038 038.alt 039 039.alt 040 040.alt 041 041.alt 044 044.alt 045 045.alt 046 047 047.alt 048 049 049.alt 050 050.alt 051 051.alt 052 053 053.alt 054 056 058 058.alt 060 060.alt 062 062.alt 064 069 069.alt 070 070.alt 074 077 077.alt
16.Q 13 001 001.alt 002 003 004 005 006 006.alt 007 007.alt 008 008.alt 009 009.alt 010a 010a.alt 010b 010b.alt 011 011.alt 012
Chapter 17: Alcohols and Phenols
17.D 12 001 002 003 004 005 006 007 007.v2 008 009 010 011
17.E 39 020 021 021.alt 022 022.alt 023 023.alt 024 024.alt 027 027.alt 028 028.alt 030 030.alt 031 032 032.alt 033 033.alt 034 034.alt 035 035.alt 036 036.alt 037 038a 038a.alt 038b 040 040.alt 041 042 042.alt 043 043.alt 044 044.alt 045 045.alt 046 046.alt 047 048 049 050 050.alt 053 053.alt 055 057 058 058.alt 059 060 060.alt 061 061.alt 063 065 065.alt 071 071.alt 072
17.Q 17 001 001.alt 002 002.alt 003 004 004.alt 005 005.alt 006a 006a.alt 006b 006b.alt 006c 006c.alt 007a 007a.alt 007b 007b.alt 007c 007c.alt 008 008.alt 009 009.alt 010 010.alt 011 011.alt 012 013
Chapter 18: Ethers and Epoxides; Thiols and Sulfides
18.D 13 001 002 003 003.v2 004 005 006 007 008 009 010 011 012
18.E 32 019 020 020.alt 023 023.alt 024 024.alt 025 025.alt 026 026.alt 027 027.alt 028 028.alt 032 032.alt 034 034.alt 035 035.alt 036a 036a.alt 036b 036b.alt 037 037.alt 038 038.alt 039 040 041 043 043.alt 044 044.alt 045 046 046.alt 047-048 047-048.alt 049 049.alt 055 055.alt 056 056.alt 058 060 062 063 063.alt 066 066.alt 068 068.alt
18.Q 6 001 001.alt 002 002.alt 003 003.alt 004a 004a.alt 004b 004b.alt 005
Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
19.D 14 001 002 003 004 005 006 007 008 009 010 011 012 013 014
19.E 35 027 027.alt 028a 028a.alt 028b 028b.alt 030a 030a.alt 030b 030b.alt 031 031.alt 032 032.alt 033 033.alt 034 034.alt 035 035.alt 037 037.alt 046a 046a.alt 046b 046b.alt 051a 051a.alt 051b 051b.alt 052 052.alt 053 053.alt 055a 055b 057a 057a.alt 057b 057b.alt 058 058.alt 059 059.alt 060 061 062 063 063.alt 064 065 069 069.alt 070 070.alt 073 073.alt 075 079 079.alt 080-083 080-083.alt
19.Q 20 001 002 002.alt 003 003.alt 004 004.alt 005 005.alt 006 006.alt 007 007.alt 008 008.alt 009a 009a.alt 009b 009b.alt 010 010.alt 011 011.alt 012 012.alt 013 013.alt 014 014.alt 015 015.alt 016 016.alt 017a 017a.alt 017b 017b.alt 018 018.alt
Chapter 20: Carboxylic Acids and Nitriles
20.D 7 001 002 003 004 005 006 007
20.E 39 017 021 021.alt 022 022.alt 023 023.alt 024 024.alt 025 025.alt 026 026.alt 027 027.alt 028 028.alt 030 030.alt 031 032 032.alt 033a 033a.alt 033b 034 034.alt 036 037 038 039 041 043 044 045 046 047 047.alt 048 049 050 051 054 055 056 056.alt 059 060 061 063 065 069 069.alt 070 070.alt
20.Q 6 001 001.alt 002 002.alt 003 004 005 006 006.alt
Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
21.D 17 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017
21.E 41 027 029 029.alt 031a 031a.alt 031b 031b.alt 032a 032a.alt 032b 032b.alt 033a 033a.alt 033b 033b.alt 034a 034a.alt 034b 034b.alt 036 036.alt 039 039.alt 041 041.alt 044 044.alt 045 046 046.alt 047a1 047a2 047a2.alt 047b1 047b2 047b2.alt 047c1 047c2 047c2.alt 048 048.alt 049 049.alt 050 050.alt 051 051.alt 052 053 053.alt 054 056 057 057.alt 060 060.alt 061 061.alt 062 062.alt 063 063.alt 064 071 071.alt 072 072.alt 073 073.alt 074 074.alt 078 078.alt
21.Q 24 001 002 003 003.alt 004 004.alt 005 005.alt 006 006.alt 007 007.alt 008 008.alt 009 009.alt 010 010.alt 011a 011a.alt 011b 011b.alt 012 012.alt 013 013.alt 014 014.alt 015 015.alt 016 016.alt 017a 017a.alt 017b 017b.alt 017c 017c.alt 018 018.alt 019 019.alt 020 020.alt 021 021.alt
Chapter 22: Carbonyl Alpha-Substitution Reactions
22.D 12 001 002 003 004 005 006 007 008 009 010 011 012
22.E 33 017 019 019.alt 020 020.alt 021 021.alt 022 022.alt 023 023.alt 024 024.alt 026 026.alt 027 027.alt 028 028.alt 029 029.alt 031 031.alt 032 032.alt 033 033.alt 034 034.alt 035 035.alt 037 038 039 039.alt 042 042.alt 043 043.alt 044 045 046 047 048 049 049.alt 050 051-052 054 054.alt 056 058 063 063.alt
Chapter 23: Carbonyl Condensation Reactions
23.D 10 001 002 003 004 005 006 007 008 009 010
23.E 34 023 023.alt 024a 024a.alt 024b 024b.alt 024c 024c.alt 025 025.alt 026 026.alt 027 027.alt 029 029.alt 030 030.alt 031 031.alt 032 032.alt 033 033.alt 034 034.alt 037 037.alt 038 038.alt 045 045.alt 046 046.alt 047 047.alt 048 048.alt 049 049.alt 050 050.alt 051 051.alt 052 052.alt 056 056.alt 058 058.alt 060 060.alt 062 062.alt 064 064.alt 065 065.alt 067 067.alt 068 069 070 071 071.alt
Chapter 24: Amines and Heterocycles
24.D 28 001 002 003 004 005 006 007 008 009 010 011 012 013 014 015 016 017 017.v2 018 019 020 021 022 023 024 025 026 027
24.E 42 026 027 028a 028b 028b.alt 029 029.alt 030 030.alt 031 031.alt 032 032.alt 033 033.alt 034 034.alt 035 035.alt 037 037.alt 038 038.alt 040 040.alt 041 041.alt 042 042.alt 043 043.alt 044 044.alt 045 045.alt 046 046.alt 047 048 048.alt 049 051 053 054 055 056 057 058 058.alt 059 060 060.alt 061 061.alt 062 062.alt 063 064 064.alt 071.NMR 071.NMR.alt 074 074.alt 077 077.alt 078 078.alt 079 079.alt 080
Chapter 25: Biomolecules: Carbohydrates
25.D 6 001 002 003 004 005 006
25.E 25 026 028 029c 029c.alt 031 031.alt 032 032.alt 033 033.alt 034 034.alt 036 041 043 043.alt 044 045 046 046.alt 047 047.alt 048a 048a.alt 048b 051-052 051-052.alt 053 053.alt 054 054.alt 055a 056 057 058 068 068.alt 069 069.alt
Chapter 26: Biomolecules: Amino Acids, Peptides, and Proteins
26.D 7 001 002 003 004 005 006 007
26.E 28 019 020 021 022 024 024.alt 025 025.alt 026 026.alt 027 027.alt 028 028.alt 032 032.alt 033 034 036a 036b 036b.alt 037 037.alt 040 040.alt 042 042.alt 043 043.alt 045 045.alt 046 048 049 056 057 057.alt 058 058.alt 059 059.alt 060 060.alt 062 062.alt
Chapter 27: Biomolecules: Lipids
27.D 10 001 002 003 004 005 006 007 008 009 010
27.E 19 013 014 014.alt 015 015.alt 016 016.alt 017 017.alt 020 020.alt 021 025 025.alt 026 028a 028b 029 036b 037 037.alt 039 041 041.alt 042 042.alt 047 047.alt 050 050.alt
Chapter 28: Biomolecules: Nucleic Acids
28.D 2 001 002
28.E 16 013 014a 017 017.alt 018 018.alt 019 019.alt 020 020.alt 023 025 026 027 028 031-032 033 034 036 037 037.alt
Chapter 29: The Organic Chemistry of Metabolic Pathways
29.E 21 017 018 021 021.alt 023 023.alt 024 024.alt 025 025.alt 027 027.alt 029 029.alt 030 030.alt 031 031.alt 037-039 040 041 043 043.alt 045 046 047 047.alt 050 052 053 053.alt 054-056
Chapter 30: Orbitals and Organic Chemistry: Pericyclic Reactions
30.D 8 001 002 003 004 005 006 007 008
30.E 6 013 013.alt 020 022 027 030a 030a.alt 035
Chapter 31: Synthetic Polymers
31.D 7 001 002 003 004 005 005.v2 006
31.E 8 014 014.alt 015 015.alt 020a 020a.alt 020b 023b 023b.alt 023c 023c.alt 025b 025b.alt 028 028.alt
Total 1466 (670)  

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