Summary

Designed specifically for the one-semester short course in organic chemistry, this market leader appeals to a range of non-chemistry science majors through its emphasis on practical, real-life applications of chemistry, coverage of basic concepts, and engaging visual style. In contrast to competitors who offer mainly streamlined versions of full-year texts, this text has always been aimed at the short course and its writing style, approach, and selection of topics best suit the needs of this market. The Twelfth Edition further develops the strengths of the previous editions through an updated, dynamic art program--online, on CD, and in the text--new content to keep students current with developments in the organic chemistry field, and a revised lab manual. New! The updated art program offers newly designed electrostatic potential maps and new ball-and-stick structures. The former aid discussions of acid-base chemistry and the latter help students visualize molecules in three dimensions. New! Engaging animations on the Online Study Center further help students visualize chemistry concepts. New! Increased usage of arrow-pushing formalism assists professors teaching reaction mechanisms. New! Problems that emphasize the development of three-dimensional visualization skills have been added. New! A Closer Look At boxes now include coverage of mass spectrometry and carbon dating (Chapter 12), Nobel laureates and protein chemistry (Chapter 17), and the polymerase chain reaction (Chapter 18). These features guide students in using multimedia resources on the web to expand concepts in the text and apply them to real-life examples. Revised! The Laboratory Manual, with the assistance of new co-author T.K. Vinod at Western Illinois University, now includes a new experiment on green chemistry, new pre-laboratory exercises, and revised safety instructions to students. Worked out examples throughout the text along with numerous practice problems guide students through learning and mastering chapter concepts. Within each set of end-of-chapter material, the problems gradually increased in difficulty, reinforcing basic principles and problem-solving skills before moving on to more challenging ones. Engaging A Word About essays motivate students by demonstrating how chemistry relates to other branches of science and to their everyday lives. They include coverage of Quinones and the Bombadier Beetle, Alkaloids and the Dart Poison Frog, Prostaglandins, and Aspirin and Pain.

Note: Each chapter concludes with Additional Problems
Bonding and Isomerism
How Electrons are Arranged in Atoms
Ionic and Covalent Bonding
Carbon and the Covalent Bond
Carbon-Carbon Single Bonds
Polar Covalent Bonds
Multiple Covalent Bonds
Valence
Isomerism
Writing Structural Formulas
Abbreviated Structural Formulas
Formal Charge
Resonance
Arrow Formalism
The Orbital View of Bonding; the Sigma Bond
Carbon sp3 Hybrid Orbitals
Tetrahedral Carbon; the Bonding in Methane
Classification According to Molecular Framework
Classification According to Functional Group
Alkanes and Cycloalkanes; Conformational and Geometric Isomerism
The Structures of Alkanes
Nomenclature of Organic Compounds
IUPAC Rules for Naming Alkanes
Alkyl and Halogen Substituents
Use of the IUPAC Rules A Closer Look at...Natural Gas
Sources of Alkanes
Physical Properties of Alkanes and Nonbonding Intermolecular Interactions
A Closer Look at...Hydrogen Bonding
Conformations of Alkanes
Cycloalkane Nomenclature and Conformation
Cis-transIsomerism in Cycloalkanes
A Word About: Isomers- Possible and Impossible
Summary of Isomerism
Reactions of Alkanes
A Word About: Methane, Marsh Gas, and Miller's Experiment
The Free-Radical Chain Mechanism of Halogenation
Reaction Summary
Mechanism Summary
Alkenes and Alkynes
Definition and Classification
Nomenclature
Some Facts About Double Bonds
The Orbital Model of a Double Bond; the Pi Bond
Cis-transIsomerism in Alkenes
A Word About: The Chemistry of Vision
Addition and Substitution Reactions Compared
Polar Addition Reactions
Addition of Unsymmetric Reagents to Unsymmetric Alkenes; Markovnikov's Rule
Mechanism of Electrophilic Addition to Alkenes
Markovnikov's Rule Explained
Reaction Equilibrium: What Makes a Reaction Go?
Reaction Rates: How Fast Does a Reaction Go?
Hydroboration of Alkenes
Addition of Hydrogen
Additions to Conjugated Systems
Free-Radical Additions; Polyethylene
Oxidation of Alkenes
A Word About: Ethylene: Raw Material and Plant Hormone
Some Facts About Triple Bonds
The Orbital Model of a Triple Bonds
Additon Reactions of Alkynes
A Word About: Petroleum, Gasoline, and Octane Number
Acidity of Alkynes
Reaction Summary
Mechanism Summary
Aromatic Compounds
Some Facts About Benzene
The Kekuleacute; Structure of Benzene
The Resonance Model for Benzene
Orbital Model for Benzene
Symbols for Benzene
Nomenclature of Aromatic Compounds
The Resonance Energy of Benzene
Electrophilic Aromatic Substitution
The Mechanism of Electrophilic Aromatic Substitution
Ring-Activating and Ring-Deactivating Substituents
Ortho, Para-Directing, andMeta-Directing Groups
The Importance of Directing Effects in Synthesis
Polycyclic Aromatic Hydrocarbons
A Word About: Polycyclic Aromatic Hydrocarbons and Cancer
A Closer Look at...Polycyclic Aromatic Hydrocarbons
A Word About: C60, an Aromatic Sphere: The Fullerenes
Reaction Summary
Mechanism Summary
Stereoisomerism
Chirality and Enantiomers
Stereogenic Centers; the Stereogenic Carbon Atom
Configuration and theR-SConvention
TheE-ZConvention forCis-transIsomers
Polarized Light and Optical Activity
A Word About: Pasteur's Experiments and the van't Hoff-LeBel Explanation
Properties of Enantiomers
Fischer Projection Formulas
Compounds with
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