Organic Chemistry: Mechanistic Patterns, 2nd Edition
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Organic Chemistry: Mechanistic Patterns is the very first introductory organic chemistry title that holistically focuses on a mechanistic approach; an approach that has proven to achieve a deeper understanding of chemical reactivity. This mechanistic approach to the dynamic world of organic chemistry visualizes reactivity as a collection of patterns in electron movement, making it possible for students to describe why a reaction occurred. Recognizing patterns of electron flow between seemingly different reactions can allow students to predict how a chemical will react, even if they have never seen a particular reaction before. The text takes great care to establish a progression of reactivity, from simple to complex, introducing functional groups as necessary, while focusing on the reaction at hand rather than the various things that each functional group does. Including Ghislain Deslongchamps’ acclaimed Organic ChemWare Learning Objects that bring static textbook molecular representations to life (including orbital depictions and energy graphs in many of the interactives) combined with Top Hat's active learning framework, the author's goal is to help students learn to think like chemists and be more successful in the course.
Lone pairs have been added to reaction sites in ch. 8-20, increasing the mechanistic focus of the text.
Chapter 2 includes nomenclature of different functional groups and multiple functional groups in a molecule. Solutions have been updated to be more consistent.
Chapter 3 includes new representations of Newman projections to better illustrate conformational relationships. All of the Newman projections throughout the text have been updated accordingly.
Chapter 5 adds more complete descriptions of different arrow styles for p and s electron movements. The descriptions of delocalization and resonance have also been improved to address common student issues and misconceptions.
Chapter 6 has improved end-of-chapter questions.
Chapter 8 has been expanded to better accommodate alkyne reactions and descriptions of stereoselectivity and stereospecificity.
Chapter 11 sections of the prediction of reaction pathways have been expanded and clarified. Additional explicit descriptions of reaction pathways are shown to better highlight the sequence of events with different types of catalysis.
Chapter 15 sees an increased section clarifying the patterns of carbonyl displacements.
Chapter 16 includes modifications to the description of anomers and of imine reactivity.
Chapters 17 and 18 feature a reorganization of the patterns section to better group reactions by nucleophile type.
Chapter 19 has an improved section of dissolving metal reactions, modified to reflect current research. The section describing reaction patterns has been completely re-written and re-organized.
Auto-gradable mechanism drawing functionality.
A reaction index sorted by functional group. This index also serves as a handy reference for both students and instructors.
An abbreviation index that includes selected descriptions and structures.
Table of Contents
About the Authors ix
CHAPTER 1 Carbon and Its Compounds 1
CHAPTER 2 Anatomy of an Organic Molecule 47
CHAPTER 3 Molecules in Motion: Conformations by Rotations 86
CHAPTER 4 Stereochemistry: Three-Dimensional Structure in Molecules 125
CHAPTER 5 Organic Reaction Mechanism: Using Curved Arrows to Analyze Reaction Mechanisms 186 CHAPTER 6 Acids and Bases 235
CHAPTER 7 π Bonds as Electrophiles: Reactions of Carbonyls and Related Functional Groups 272 CHAPTER 8 π Bonds as Nucleophiles: Reactions of Alkenes, Alkynes, Dienes, and Enols 328
CHAPTER 9 Conjugation and Aromaticity 398
CHAPTER 10 Synthesis Using Aromatic Materials: Electrophilic Aromatic Substitution and Directed Ortho Metalation 431
CHAPTER 11 Displacement Reactions on Saturated Carbons: SN1 and SN2 Substitution Reactions 494 CHAPTER 12 Formation of π Bonds by Elimination Processes: Elimination and Oxidation Reactions 540 CHAPTER 13 Structure Determination I: Nuclear Magnetic Resonance Spectroscopy 577
CHAPTER 14 Structure Determination II: Mass Spectrometry and Infrared Spectroscopy 648
CHAPTER 15 π Bond Electrophiles Connected to Leaving Groups: Carboxylic Acid Derivatives
and Their Reactions 696
CHAPTER 16 π Bonds with Hidden Leaving Groups: Reactions of Acetals and Related Compounds 764 CHAPTER 17 Carbonyl-Based Nucleophiles: Aldol, Claisen, Wittig, and Related Enolate Reactions 810 CHAPTER 18 Selectivity and Reactivity in Enolate Reactions: Control of Stereoselectivity and
CHAPTER 19 Radicals: Halogenation, Polymerization, and Reduction Reactions 971
CHAPTER 20 Reactions Controlled by Orbital Interactions: Ring Closures, Cycloadditions, and
Appendix A Answers to Checkpoint Problems A-1
Appendix B Common Errors in Organic Structures and Mechanisms A-137
Appendix C pKa Values of Selected Organic Compounds A-141
Appendix D NMR and IR Spectroscopic Data A-143
Appendix E Periodic Table of the Elements A-145