Table Of Content3000 Solved Problems in
Organic Chemistry
About the Authors
Estelle K Meislich earned a B.S. degree in Chemistry from Brooklyn College, and M.A. and PhD degrees in Organic
Chemistry from Columbia University. She held a Research Assistantship in the Dept. of Neurology at Columbia Medical
School, where she designed and synthesized the first antidote for a nerve gas. After teaching at City College of CUNY for
many years, she moved to Bergen Community College, where she is now Professor Emeritus. She is the author of a labora-
tory manual for nursing and other allied health students as well as several papers in the Journal of Chemical Education.
Herbert Meislich holds a B.A. degree from Brooklyn College and an M.A. and PhD from Columbia University. He is
Professor Emeritus from the City College of CUNY, where he taught Organic and General Chemistry for forty years at
both the undergraduate and doctoral levels. He received the Outstanding Teacher award in 1985 and has coauthored eight
textbooks, three laboratory manuals in General and Organic Chemistry and 15 papers on his research interests.
Jacob Sharefkin is Professor Emeritus of Chemistry at Brooklyn College. After receiving a B.S. from City College of
New York, he was awarded an M.A. from Columbia University and a PhD from New York University. His publications and
research interest in Qualitative Organic Analysis and organic boron and iodine compounds have been supported by grants
from the American Chemical Society, for whom he has also designed national examinations in Organic Chemistry.
3000 Solved Problems in
Organic Chemistry
Estelle K Meislich, PhD
Professor Emeritus of Chemistry
Bergen Community College
Herbert Meislich, PhD
Professor Emeritus of Chemistry
City College of CUNY
Jacob Sharefkin, PhD
Professor Emeritus of Chemistry
Brooklyn College of CUNY
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3000 Solved Problems in Organic Chemistry
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Contents
Preface xiii
1. STruCTurE aND PrOPErTIES 1.1 – 1.16
Definitions 1.1
Chemical Bonds 1.2
Structural Formulas and Isomers 1.6
Formal Charge 1.10
Functional Groups and Homologous Series 1.11
Calculations 1.13
Supplementary Problems 1.15
2. BONDING aND MOLECuLar STruCTurE 2.1 – 2.20
Quantum Theory; Atomic Orbitals 2.1
Molecular Orbitals 2.5
Hybridization and Shape 2.9
Electronegativity and Polarity 2.11
Oxidation Number 2.13
Intermolecular Forces 2.14
Resonance and Delocalized p Electrons 2.17
3. CHEMICaL rEaCTIvITy aND OrGaNIC rEaCTIONS 3.1 – 3.27
Reaction Mechanism 3.1
Reactive Carbon Intermediates 3.2
Types of Chemical Reactions 3.6
Electrophiles and Nucleophiles 3.7
Acids and Bases 3.8
Thermodynamics and Bond Energies 3.15
Chemical Kinetics 3.20
Transition States and Enthalpy Diagrams 3.22
Supplementary Problems 3.25
4. aLKaNES 4.1 – 4.21
Nomenclature and Structure 4.1
Physical Properties 4.4
Conformation 4.5
Thermochemistry 4.9
Preparation 4.10
viii Contents
Reactions 4.12
Syntheses 4.17
Supplementary Problems 4.19
5. CyCLOaLKaNES 5.1 – 5.22
General and Nomenclature 5.1
Geometric (cis-trans) Isomerism 5.4
Ring Strain and Stability 5.6
Substituted Cyclohexanes; Conformational Analysis 5.11
Preparation 5.16
Chemical Properties 5.18
Supplementary Problems 5.19
6. STErEOCHEMISTry 6.1 – 6.24
Definitions 6.1
Symmetry Elements 6.2
Chirality 6.3
Optical Activity 6.4
Absolute and Relative Configuration 6.5
Molecules with More Than One Chiral Center 6.9
Cyclic Compounds 6.12
Dynamic Stereochemistry 6.15
Supplementary Problems 6.17
7. aLKENES 7.1 – 7.48
Definitions and Structure 7.1
Nomenclature 7.3
Geometric (cis-trans) Isomerism 7.5
Preparation 7.8
Chemical Reactions 7.14
Syntheses 7.36
Analysis and Structure Proof 7.39
Supplementary Problems 7.43
8. aLKyL HaLIDES 8.1 – 8.38
Structure and Nomenclature 8.1
Physical Properties 8.3
Preparation 8.5
Reactions 8.7
Syntheses and Analysis 8.34
Supplementary Problems 8.36
9. aLKyNES, DIENES, aND OrBITaL SyMMETry 9.1 – 9.39
Structure of Alkynes 9.1
Nomenclature of Alkynes 9.3
Acidity of Terminal Alkynes 9.4
Preparation 9.6
Chemical Properties of Alkynes 9.9
Syntheses with Alkynes 9.16
Contents ix
Structure and Nomenclature of Dienes 9.19
Syntheses of Dienes 9.22
Reactions of Dienes 9.24
Analysis and Structure Proof 9.28
Orbital Symmetry 9.30
Supplementary Problems 9.35
10. arOMaTICITy aND BENzENE 10.1 – 10.28
Structure of Benzene 10.1
Nomenclature and Physical Properties 10.7
Aromaticity 10.10
Syntheses and Reactions 10.14
Polynuclear Aromatic Hydrocarbons 10.17
Supplementary Problems 10.23
11. arOMaTIC SuBSTITuTION, arENES 11.1 – 11.35
Electrophilic Aromatic Substitution 11.1
Substituent Effects in Electrophilic Aromatic Substitution 11.8
Electrophilic Substitution in Naphthalene 11.16
Nucleophilic Aromatic Substitution 11.19
Syntheses 11.24
Arenes 11.25
Miscellaneous Reactions 11.29
Analysis 11.30
Supplementary Problems 11.32
12. SPECTrOSCOPy aND STruCTurE PrOOf 12.1 – 12.55
Introduction 12.1
Ultraviolet and Visible Spectroscopy (Electron Excitation) 12.3
Infrared Spectroscopy 12.13
Nuclear Magnetic Resonance (Nmr) Spectroscopy 12.23
Mass Spectroscopy 12.43
Supplementary Problems 12.49
13. aLCOHOLS aND THIOLS 13.1 – 13.29
Nomenclature and Structure 13.1
Preparation 13.3
Reactions 13.8
Spectroscopy and Analysis 13.18
Thiols 13.22
Supplementary Problems 13.25
14. ETHErS, EPOxIDES, GLyCOLS, aND THIOETHErS 14.1 – 14.27
Ethers 14.1
Epoxides (Oxiranes) 14.13
Glycols 14.18
Thioethers (Sulfides) and Their Derivatives 14.20
Supplementary Problems 14.23
x Contents
15. aLDEHyDES aND KETONES 15.1 – 15.29
Structure and Nomenclature 15.1
Spectra 15.4
Preparation 15.5
Reactions 15.11
Analysis 15.23
Supplementary Problems 15.25
16. CarBOxyLIC aCIDS 16.1 – 16.30
Introduction and Nomenclature 16.1
Preparation 16.4
Acidity and Carboxylate Salts 16.8
Chemical Reactions 16.15
Substituted Carboxylic Acids 16.18
Syntheses 16.21
Analysis and Spectroscopy 16.24
Supplementary Problems 16.27
17. aCID DErIvaTIvES 17.1 – 17.29
General and Nomenclature 17.1
Structure and Physical Properties 17.3
Preparation 17.5
Reactions 17.10
Derivatives of Carbonic, S, and P Acids 17.19
Analysis and Spectroscopy 17.21
Supplementary Problems 17.25
18. CarBaNION-ENOLaTES aND ENOLS 18.1 – 18.45
Tautomerism; Acidity of a H’s 18.1
Alkylation 18.8
Malonic and Acetoacetic Ester Syntheses 18.11
a, b- Unsaturated Carbonyl Compounds; Michael Addition 18.17
Aldol-Type Additions 18.20
Claisen Condensations 18.30
Syntheses 18.33
Supplementary Problems 18.37
19. aMINES 19.1 – 19.33
Nomenclature, Structure, and Physical Properties 19.1
Basicity and Nucleophilicity 19.4
Preparation 19.10
Reactions 19.14
Synthesis 19.21
Analysis 19.27
Supplementary Problems 19.31
20. PHENOLS aND THEIr DErIvaTIvES 20.1 – 20.31
General, Nomenclature, and Physical Properties 20.1
Preparation 20.5
