Organic Chemistry I as a Second Language: Translating the Basic Concepts

by David R. Klein (Johns Hopkins Univ.)

ISBN13:

9780471272359

ISBN10:

0471272353

Format:

Paperback

Pub. Date:

10/1/2003

Publisher(s):

Wiley

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Summary

Organic chemistry may be challenging, but that doesn't mean you can't get the grade you want. This book points out the major principles in organic chemistry and explains why they are relevant to the rest of the course. It provides time-saving study tips and a clear roadmap for your studies that will help you focus your efforts. And it helps you develop the skills you need to solve a variety of problems types_even unfamiliar ones!

Introduction

iii

CHAPTER 1 BOND-LINE DRAWINGS

(19)

1.1 How to Read Bond-Line Drawings

(4)

1.2 How to Draw Bond-Line Drawings

(2)

1.3 Mistakes to Avoid

(1)

1.4 More Exercises

(2)

1.5 Identifying Formal Charges

(4)

1.6 Finding Lone Pairs That Are Not Drawn

(6)

CHAPTER 2 RESONANCE

(33)

2.1 What Is Resonance?

(1)

2.2 Curved Arrows: The Tools for Drawing Resonance Structures

(3)

2.3 The Two Commandments

(2)

2.4 Drawing Good Arrows

(3)

2.5 Formal Charges in Resonance Structures

(3)

2.6 Drawing Resonance Structures-Step by Step

(5)

2.7 Drawing Resonance Structures-By Recognizing Patterns

(10)

A Lone Pair Next to a Pi Bond

(3)

A Lone Pair Next to a Positive Charge

(2)

A Pi Bond Next to a Positive Charge

(1)

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

(1)

Pi Bonds Going All the Way Around a Ring

(2)

2.8 Assessing the Relative Importance of Resonance Structures

(6)

CHAPTER 3 ACID-BASE REACTIONS

(23)

3.1 Factor 1-What Atom Is the Charge on?

(3)

3.2 Factor 2-Resonance

(5)

3.3 Factor 3-Induction

(4)

3.4 Factor 4-Orbitals

(1)

3.5 Ranking the Four Factors

(4)

3.6 Quantitative Measurement (pKa values)

(1)

3.7 Predicting the Position of Equilibrium

(2)

3.8 Showing a Mechanism

(3)

CHAPTER 4 GEOMETRY

(8)

4.1 Orbitals and Hybridization States

(4)

4.2 Geometry

(4)

CHAPTER 5 NOMENCLATURE

(22)

5.1 Functional Group

(2)

5.2 Unsaturation

(2)

5.3 Naming the Parent Chain

(2)

5.4 Naming Substituents

(4)

5.5 Stereoisomerism

(3)

5.6 Numbering

(5)

5.7 Common Names

103

(1)

5.8 Going from a Name to a Structure

104

(2)

CHAPTER 6 CONFORMATIONS

106

(28)

6.1 How to Draw a Newman Projection

107

(4)

6.2 Ranking the Stability of Newman Projections

111

(4)

6.3 Drawing Chair Conformations

115

(3)

6.4 Placing Groups on the Chair

118

(5)

6.5 Ring Flipping

123

(6)

6.6 Comparing the Stability of Chairs

129

(4)

6.7 Don't Be Confused by the Nomenclature

133

(1)

CHAPTER 7 CONFIGURATIONS

134

(33)

7.1 Locating Stereocenters

135

(3)

7.2 Determining the Configuration of a Stereocenter

138

(8)

7.3 Nomenclature

146

(5)

7.4 Drawing Enantiomers

151

(5)

7.5 Diastereomers

156

(1)

7.6 Meso Compounds

157

(3)

7.7 Drawing Fischer Projections

160

(5)

7.8 Optical Activity

165

(2)

CHAPTER 8 MECHANISMS

167

(44)

8.1 Curved Arrows

168

(5)

8.2 Arrow Pushing

173

(2)

8.3 Drawing Intermediates

175

(3)

8.4 Nucleophiles and Electrophiles

178

(1)

8.5 Bases Versus Nucleophiles

179

(3)

8.6 The Regiochemistry Is Contained Within the Mechanism

182

(3)

8.7 The Stereochemistry Is Contained Within the Mechanism

185

(5)

8.8 A List of Mechanisms

190

(21)

CHAPTER 9 SUBSTITUTION REACTIONS

211

(18)

9.1 The Mechanisms

211

(3)

9.2 Factor 1-The Electrophile (Substrate)

214

(3)

9.3 Factor 2-The Nucleophile

217

(3)

9.4 Factor 3-The Leaving Group

220

(3)

9.5 Factor 4-The Solvent

223

(3)

9.6 Using All Four Factors

226

(1)

9.7 Substitution Reactions Teach Us Some Important Lessons

227

(2)

CHAPTER 10 ELIMINATION REACTIONS

229

(13)

10.1 Mechanisms (E1 and E2)

230

(1)

10.2 Factor 1-The Substrate

231

(1)

10.3 Factor 2-The Base

232

(3)

10.4 Factor 3-The Leaving Group

235

(1)

10.5 Factor 4-Solvent Effects

236

(1)

10.6 Using All of the Factors

236

(2)

10.7 Elimination Reactions-Regiochemistry and Stereochemistry

238

(4)

CHAPTER 11 ADDITION REACTIONS

242

(4)

CHAPTER 12 PREDICTING PRODUCTS

246

(17)

12.1 General Tips for Predicting Products

246

(1)

12.2 Getting Practice

247

(11)

12.3 Substitution Versus Elimination Reactions

258

(4)

12.4 Looking Forward

262

(1)

CHAPTER 13 SYNTHESIS

263

(17)

13.1 One-step Syntheses

265

(11)

13.2 Multistep Syntheses

276

(1)

13.3 Retrosynthetic Analysis

277

(1)

13.4 Creating Your Own Problems

278

(2)

Answer Key

280

(17)

Index

297

Organic Chemistry I as a Second Language: Translating the Basic Concepts

9780471272359

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