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Organic Chemistry I as a Second Language: Translating the Basic Concepts,9780471272359

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

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ISBN13:

9780471272359

ISBN10:
0471272353
Format:
Paperback
Pub. Date:
10/1/2003
Publisher(s):
Wiley
List Price: $37.33
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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!

Table of Contents

Introduction iii
CHAPTER 1 BOND-LINE DRAWINGS 1(19)
1.1 How to Read Bond-Line Drawings
1(4)
1.2 How to Draw Bond-Line Drawings
5(2)
1.3 Mistakes to Avoid
7(1)
1.4 More Exercises
8(2)
1.5 Identifying Formal Charges
10(4)
1.6 Finding Lone Pairs That Are Not Drawn
14(6)
CHAPTER 2 RESONANCE 20(33)
2.1 What Is Resonance?
20(1)
2.2 Curved Arrows: The Tools for Drawing Resonance Structures
21(3)
2.3 The Two Commandments
24(2)
2.4 Drawing Good Arrows
26(3)
2.5 Formal Charges in Resonance Structures
29(3)
2.6 Drawing Resonance Structures-Step by Step
32(5)
2.7 Drawing Resonance Structures-By Recognizing Patterns
37(10)
A Lone Pair Next to a Pi Bond
38(3)
A Lone Pair Next to a Positive Charge
41(2)
A Pi Bond Next to a Positive Charge
43(1)
A Pi Bond Between Two Atoms, Where One of Those Atoms Is Electronegative (N, O, etc.)
44(1)
Pi Bonds Going All the Way Around a Ring
45(2)
2.8 Assessing the Relative Importance of Resonance Structures
47(6)
CHAPTER 3 ACID-BASE REACTIONS 53(23)
3.1 Factor 1-What Atom Is the Charge on?
54(3)
3.2 Factor 2-Resonance
57(5)
3.3 Factor 3-Induction
62(4)
3.4 Factor 4-Orbitals
66(1)
3.5 Ranking the Four Factors
67(4)
3.6 Quantitative Measurement (pKa values)
71(1)
3.7 Predicting the Position of Equilibrium
71(2)
3.8 Showing a Mechanism
73(3)
CHAPTER 4 GEOMETRY 76(8)
4.1 Orbitals and Hybridization States
76(4)
4.2 Geometry
80(4)
CHAPTER 5 NOMENCLATURE 84(22)
5.1 Functional Group
85(2)
5.2 Unsaturation
87(2)
5.3 Naming the Parent Chain
89(2)
5.4 Naming Substituents
91(4)
5.5 Stereoisomerism
95(3)
5.6 Numbering
98(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


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