Organic Chemistry I as a Second LanguageTM: Translating the Basic Concepts, 2nd Edition

by David R. Klein (Johns Hopkins Univ. )

• ISBN13: 9780470129296
• ISBN10: 0470129298
• Edition: 2nd
• Format: Paperback
• Copyright: 2007-06-01
• Publisher: WILEY

Summary

Get a Better Grade in Organic Chemistry Organic Chemistry may be challenging, but that doesn't mean you can't get the grade you want. With David Klein's Organic Chemistry as a Second Language: Translating the Basic Concepts, you'll be able to better understand fundamental principles, solve problems, and focus on what you need to know to succeed. Here's how you can get a better grade in Organic Chemistry: Understand the Big Picture. Organic Chemistry as a Second Language points out the major principles in Organic Chemistry and explains why they are relevant to the rest of the course. By putting these principles together, you'll have a coherent framework that will help you better understand your textbook. Study More Efficiently and Effectively Organic Chemistry as a Second Language provides time-saving study tips and a clear roadmap for your studies that will help you to focus your efforts. Improve Your Problem-Solving Skills Organic Chemistry as a Second Language will help you develop the skills you need to solve a variety of problem types-even unfamiliar ones! Need Help in Your Second Semester? Get Klein's Organic Chemistry II as a Second Language! 978-0-471-73808-5

Table of Contents

Introduction

Bond-Line Drawings

How to Read Bond-Line Drawings

How to Draw Bond-Line Drawings

Mistakes to Avoid

More Exercises

Identifying Formal Charges

Finding Lone Pairs That Are Not Drawn

Resonance

What Is Resonance?

Curved Arrows: The Tools for Drawing Resonance Structures

The Two Commandments

Drawing Good Arrows

Formal Charges in Resonance Structures

Drawing Resonance Structures--Step by Step

Drawing Resonance Structures--By Recognizing Patterns

A Lone Pair Next to a Pi Bond

A Lone Pair Next to a Positive Charge

A Pi Bond Next to a Positive Charge

A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.)

Pi Bonds Going All the Way Around a Ring

Assessing the Relative Importance of Resonance Structures

Acid-Base Reactions

Factor 1--What Atom Is the Charge on?

Factor 2--Resonance

Factor 3--Induction

Factor 4--Orbitals

Ranking the Four Factors

Quantitative Measurement (pKa values)

Predicting the Position of Equilibrium

Showing a Mechanism

Geometry

Orbitals and Hybridization States

Geometry

Nomenclature

Functional Group

Unsaturation

Naming the Parent Chain

Naming Substituents

Stereoisomerism

Numbering

Common Names

Going from a Name to a Structure

Conformations

How to Draw a Newman Projection

Ranking the Stability of Newman Projections

Drawing Chair Conformations

Placing Groups on the Chair

Ring Flipping

Comparing the Stability of Chairs

Don't Be Confused by the Nomenclature

Configurations

Locating Stereocenters

Determining the Configuration of a Stereocenter

Nomenclature

Drawing Enantiomers

Diastereomers

Meso Compounds

Drawing Fischer Projections

Optical Activity

Mechanisms

Curved Arrows

Arro w Pushing

Drawing Intermediates

Nucleophiles and Electrophiles

Bases Versus Nucleophiles

The Regiochemistry Is Contained Within the Mechanism

The Stereochemistry Is Contained Within the Mechanism

A List of Mechanisms

Substitution Reactions

The Mechanisms

Factor 1--The Electrophile (Substrate)

Factor 2--The Nucleophile

Factor 3--The Leaving Group

Factor 4--The Solvent

Using All Four Factors

Substitution Reactions Teach Us Some Important Lessons

Elimination Reactions

Mechanisms (E1 and E2)

Factor 1--The Substrate

Factor 2--The Base

Factor 3--The Leaving Group

Factor 4--Solvent Effects

Using All of the Factors

Elimination Reactions--Regiochemistry and Stereochemistry

Addition Reactions

Terminology Describing Regiochemistry

Terminology Describing Stereochemistry

Adding H and H

Adding H and X, Markovnikov

Adding H and Br, Anti-Markovnikov

Adding H and OH, Markovnikov

Adding H and OH, Anti-Markovnikov

Synthesis Techniques

Adding Br and Br; Adding Br and OH

Adding OH and OH, Anti

Adding OH and OH, Syn

Oxidati ve Cleavage of an Alkene

Predicting Products

General Tips for Predicting Products

Getting Practice

Substitution Versus Elimination Reactions

Looking Forward

Synthesis

One-step Syntheses

Multistep Syntheses

Retrosynthetic Analysis

Creating Your Own Problems

Answer Key

Index

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