Organic Chemistry 10th edition

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John McMurry
Publisher: OpenStax

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  • McMurry Organic Chemistry (Chs 1-12) 10e

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

  • Chapter T: Getting Started Help Tutorials
    • T: Getting Started Help Tutorials (4)

  • 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
    • 16: Additional Questions

  • 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
    • 17: Additional Questions

  • 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
    • 18: Additional Questions

  • 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
    • 19: Additional Questions

  • 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
    • 20: Additional Questions

  • 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
    • 21: Additional Questions


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Group Quantity Questions
Chapter T: Getting Started Help Tutorials
T.1 4 001 002 003 004
Chapter 1: Structure and Bonding
1.E 24 018a 018b 019a 019b 020 022 023 024 025 027 028 029 030 033 035 037 038 039 040 041 042 048 052-055 056
1.Q 11 001 002 003 004 005 006 007 008 009 010 011
Chapter 2: Polar Covalent Bonds; Acids and Bases
2.E 26 021 023 024a 024b 025 026 027 028 029a 029b 030 035-036 037 038 040 042 043a 043b 044a 044b 045 048b 049 050 051 055
2.Q 11 001 002 003 004 005 006 007 008 009 010 011
Chapter 3: Organic Compounds: Alkanes and Their Stereochemistry
3.E 29 019 020a 020b 021 022 023 026 027 028a 028b 029 030 031 032 033 034 035 036 037 038 039 040 041 043 050 051 052a 052b 053
3.Q 9 001 002 003 004 005 006 007 008 009
Chapter 4: Organic Compounds: Cycloalkanes and Their Stereochemistry
4.E 20 022 023 024 027 029 030 032 033 034 038 040 041 042 043 044a 044b 045 046 050 058
4.Q 8 001 002 003 004 005 006 007 008
Chapter 5: Stereochemistry at Tetrahedral Centers
5.E 35 026 027 028 029 030 032 035 036 037 038 039 040 041 042 043 044 045 046 047 049 050 051 052 054 055 056 057 058 059-061 062 063 065 066 076 077
5.Q 14 001 002 003 004 005 006 007 008 009 010 011 012 013 014
Chapter 6: An Overview of Organic Reactions
6.E 24 014 015 017 024 025 027 028 029 030 031 032 034 036 039 041 042 043a 044 045 046 047a 047b 048a 048b
6.Q 5 001 002 003 004 005
Chapter 7: Alkenes: Structure and Reactivity
7.E 34 022a 022b 023a 023b 024a 024b 025 026 027 028 030 031 032 033 035 036 037 039 040 041 042 043-044a 043-044b 045 046 047 053 057 058 059 060 063 064 067
7.Q 12 001 002 003 004 005 006 007 008 009 010 011 012
Chapter 8: Alkenes: Reactions and Synthesis
8.E 42 022 023 024 025 026 027 028 029 030 031a 031b 031c 033 034 036a 036b 037 038 040 041a 041b 042a 042b 045 046 047 048 049 050 051 052 053-054 055 056 057 059 060 063 067 068 069 070
8.Q 21 001 002 003 004 005 006 007 008 009 010 011 012 013 014 016 017 018 019 020 021 022
Chapter 9: Alkynes: An Introduction to Organic Synthesis
9.E 38 014a 014b 014c 015 016 018 019a 019b 020 021 022 023 024 026 027 028 029 031-032b 031a 032a 033 034 035 036 037 038a 038b-040 042 043 044 046 047 049 050 051 052 053 054
9.Q 13 001 002 003 004 005 006 007 008 009 010 011 012 013
Chapter 10: Organohalides
10.E 19 014 015 016 018 019 020 021 022a 022b 022c 023 024 025 027 028 029 033 036 040
10.Q 13 001 002 003 004 005 006 007 008 009 010 011 012 013
Chapter 11: Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations
11.E 35 021 022 023 024 025 026a 026b 027a 027b 028 029a 029b 029c 030 031 039 041 042 043-044 045 047 050 052 054 056 057 058 060 061 062 064 068 071 074 075
11.Q 8 001 002 003 004 005 006 007 008
Chapter 12: Structure Determination: Mass Spectrometry and Infrared Spectroscopy
12.E 25 012 013 014 015 018 020 021 022 023 024 026 027 030 031 032 034 035 039 043 044 045 047 048 049 050
12.Q 5 001 002 003 004 005
Chapter 13: Structure Determination: Nuclear Magnetic Resonance Spectroscopy
13.E 27 024 025 027 028 029 030 033 034 035 036 037 038 039 040-041 043 046 048 049 054 055 057 058 060-064 067-068 069 070 071
13.Q 10 001 002 003 004 005 006 007 008 009 010
Chapter 14: Conjugated Compounds and Ultraviolet Spectroscopy
14.E 19 017 019a 019b 020 025 026 027a 027b 027c 030 031 036 037 040 046 049 051 060 061
14.Q 7 001 002 003 004 005 006 007
Chapter 15: Benzene and Aromaticity
15.E 16 013 014-015 016 018 019 020 022a 022b 023 029 039 042 043 048 049 050
15.Q 4 001 002 003 004
Chapter 16: Chemistry of Benzene: Electrophilic Aromatic Substitution
16 0  
Chapter 17: Alcohols and Phenols
17 0  
Chapter 18: Ethers and Epoxides; Thiols and Sulfides
18 0  
Chapter 19: Aldehydes and Ketones: Nucleophilic Addition Reactions
19 0  
Chapter 20: Carboxylic Acids and Nitriles
20 0  
Chapter 21: Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions
21 0  
Total 568