, Study Guide and Student Solutions Manual
Organic Chemistry
EIGHTH EDITION
John McMurry
Prepared by
Susan McMurry
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
,Contents
Solutions to Problems
Chapter 1 Structure and Bonding 1
Chapter 2 Polar Covalent Bonds; Acids and Bases 20
Review Unit 1 38
Chapter 3 Organic Compounds: Alkanes and Their Stereochemistry 41
Chapter 4 Organic Compounds Cycloalkanes and Their Stereochemistry 64
Chapter 5 Stereochemistry 88
Review Unit 2 112
Chapter 6 An Overview of Organic Reactions 116
Chapter 7 Alkenes: Structure and Reactivity 132
Chapter 8 Alkenes: Reactions and Synthesis 158
Review Unit 3 186
Chapter 9 Alkynes: An Introduction to Organic Synthesis 190
Chapter 10 Organohalides 213
Chapter 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 233
Review Unit 4 264
Chapter 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy 268
Chapter 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 289
Review Unit 5 316
Chapter 14 Conjugated Dienes and Ultraviolet Spectroscopy 319
Chapter 15 Benzene and Aromaticity 342
Chapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution 361
Review Unit 6 400
Chapter 17 Alcohols and Phenols 404
Chapter 18 Ethers and Epoxides; Thiols and Sulfides 440
Review Unit 7 469
Carbonyl Preview 472
Chapter 19 Aldehydes and Ketones: Nucleophilic Addition Reactions 474
Chapter 20 Carboxylic Acids and Nitriles 518
Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 544
Review Unit 8 584
Chapter 22 Carbonyl Alpha-Substitution Reactions 588
Chapter 23 Carbonyl Condensation Reactions 616
Chapter 24 Amines and Heterocycles 654
Review Unit 9 698
Chapter 25 Biomolecules: Carbohydrates 701
Chapter 26 Biomolecules: Amino Acids, Peptides, and Proteins 733
Review Unit 10 762
Chapter 27 Biomolecules: Lipids 765
Chapter 28 Biomolecules: Nucleic Acids 790
Chapter 29 The Organic Chemistry of Metabolic Pathways 807
Review Unit 11 832
Chapter 30 Orbitals and Organic Chemistry: Pericyclic Reactions 836
Chapter 31 Synthetic Polymers 857
Review Unit 12 874
Appendices
Functional-Group Synthesis 877
Functional-Group Reactions 882
Reagents in Organic Chemistry 886
Name Reactions in Organic Chemistry 893
Abbreviations 901
Infrared Absorption Frequencies 904
Proton NMR Chemical Shifts 907
Nobel Prize Winners in Chemistry 908
Answers to Review-Unit Questions 917
iii
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
, Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
Organic Chemistry
EIGHTH EDITION
John McMurry
Prepared by
Susan McMurry
Australia • Brazil • Japan • Korea • Mexico • Singapore • Spain • United Kingdom • United States
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
,Contents
Solutions to Problems
Chapter 1 Structure and Bonding 1
Chapter 2 Polar Covalent Bonds; Acids and Bases 20
Review Unit 1 38
Chapter 3 Organic Compounds: Alkanes and Their Stereochemistry 41
Chapter 4 Organic Compounds Cycloalkanes and Their Stereochemistry 64
Chapter 5 Stereochemistry 88
Review Unit 2 112
Chapter 6 An Overview of Organic Reactions 116
Chapter 7 Alkenes: Structure and Reactivity 132
Chapter 8 Alkenes: Reactions and Synthesis 158
Review Unit 3 186
Chapter 9 Alkynes: An Introduction to Organic Synthesis 190
Chapter 10 Organohalides 213
Chapter 11 Reactions of Alkyl Halides: Nucleophilic Substitutions and Eliminations 233
Review Unit 4 264
Chapter 12 Structure Determination: Mass Spectrometry and Infrared Spectroscopy 268
Chapter 13 Structure Determination: Nuclear Magnetic Resonance Spectroscopy 289
Review Unit 5 316
Chapter 14 Conjugated Dienes and Ultraviolet Spectroscopy 319
Chapter 15 Benzene and Aromaticity 342
Chapter 16 Chemistry of Benzene: Electrophilic Aromatic Substitution 361
Review Unit 6 400
Chapter 17 Alcohols and Phenols 404
Chapter 18 Ethers and Epoxides; Thiols and Sulfides 440
Review Unit 7 469
Carbonyl Preview 472
Chapter 19 Aldehydes and Ketones: Nucleophilic Addition Reactions 474
Chapter 20 Carboxylic Acids and Nitriles 518
Chapter 21 Carboxylic Acid Derivatives: Nucleophilic Acyl Substitution Reactions 544
Review Unit 8 584
Chapter 22 Carbonyl Alpha-Substitution Reactions 588
Chapter 23 Carbonyl Condensation Reactions 616
Chapter 24 Amines and Heterocycles 654
Review Unit 9 698
Chapter 25 Biomolecules: Carbohydrates 701
Chapter 26 Biomolecules: Amino Acids, Peptides, and Proteins 733
Review Unit 10 762
Chapter 27 Biomolecules: Lipids 765
Chapter 28 Biomolecules: Nucleic Acids 790
Chapter 29 The Organic Chemistry of Metabolic Pathways 807
Review Unit 11 832
Chapter 30 Orbitals and Organic Chemistry: Pericyclic Reactions 836
Chapter 31 Synthetic Polymers 857
Review Unit 12 874
Appendices
Functional-Group Synthesis 877
Functional-Group Reactions 882
Reagents in Organic Chemistry 886
Name Reactions in Organic Chemistry 893
Abbreviations 901
Infrared Absorption Frequencies 904
Proton NMR Chemical Shifts 907
Nobel Prize Winners in Chemistry 908
Answers to Review-Unit Questions 917
iii
Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
, Copyright 2013 Cengage Learning. All Rights Reserved. May not be copied, scanned, or duplicated, in whole or in part. Due to electronic rights, some third party content may be suppressed from the eBook and/or eChapter(s).
Editorial review has deemed that any suppressed content does not materially affect the overall learning experience. Cengage Learning reserves the right to remove additional content at any time if subsequent rights restrictions require it.
