Organic Chemistry A Short Course

by Hart, Harold; Craine, Leslie E.; Hart, David J.; Hadad, Christopher M.

• ISBN13: 9780618590735
• ISBN10: 0618590730
• Edition: 12th
• Format: Hardcover
• Copyright: 2006-03-01
• Publisher: Brooks Cole

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.

Table of Contents

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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