Organic Chemistry as a Second Language: First Semester Topics

Cover
Title Page
Copyright
Introduction
	Is Organic Chemistry Really all about Memorization?
	The Plot
	How to use this Book
	How to Study
Contents
Chapter 1 Bond‐Line Drawings
	1.1 How to Read Bond‐Line Drawings
	1.2 How to Draw Bond‐Line Drawings
	1.3 Mistakes to Avoid
	1.4 More Exercises
	1.5 Identifying Formal Charges
	1.6 Finding Lone Pairs that are Not Drawn
Chapter 2 Resonance
	2.1 What is Resonance?
	2.2 Curved Arrows: The Tools for Drawing Resonance Structures
	2.3 The Two Commandments
	2.4 Drawing Good Arrows
	2.5 Formal Charges in Resonance Structures
	2.6 Drawing Resonance Structures—Step by Step
	2.7 Drawing Resonance Structures—by Recognizing Patterns
		A Lone Pair Next to a Pi Bond
		A Lone Pair Next to C+
		A Pi Bond Next to C+
		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
	2.8 Assessing the Relative Importance of Resonance Structures
Chapter 3 Acid–Base Reactions
	3.1 Factor 1—What Atom is the Charge On?
	3.2 Factor 2—Resonance
	3.3 Factor 3—Induction
	3.4 Factor 4—Orbitals
	3.5 Ranking the Four Factors
	3.6 Other Factors
	3.7 Quantitative Measurement (pKa Values)
	3.8 Predicting the Position of Equilibrium
	3.9 Showing a Mechanism
Chapter 4 Geometry
	4.1 Orbitals and Hybridization States
	4.2 Geometry
	4.3 Lone Pairs
Chapter 5 Nomenclature
	5.1 Functional Group
	5.2 Unsaturation
	5.3 Naming the Parent Chain
	5.4 Naming Substituents
	5.5 Stereoisomerism
	5.6 Numbering
	5.7 Common Names
	5.8 Going from a Name to a Structure
Chapter 6 Conformations
	6.1 How to Draw a Newman Projection
	6.2 Ranking the Stability of Newman Projections
	6.3 Drawing Chair Conformations
	6.4 Placing Groups on the Chair
	6.5 Ring Flipping
	6.6 Comparing the Stability of Chairs
	6.7 Don\'t be Confused by the Nomenclature
Chapter 7 Configurations
	7.1 Locating Chiral Centers
	7.2 Determining the Configuration of a Chiral Center
	7.3 Nomenclature
	7.4 Drawing Enantiomers
	7.5 Diastereomers
	7.6 MESO Compounds
	7.7 Drawing Fischer Projections
	7.8 Optical Activity
Chapter 8 Mechanisms
	8.1 Introduction to Mechanisms
	8.2 Nucleophiles and Electrophiles
	8.3 Basicity vs. Nucleophilicity
	8.4 Arrow‐Pushing Patterns for Ionic Mechanisms
	8.5 Carbocation Rearrangements
	8.6 Information Contained in a Mechanism
Chapter 9 Substitution Reactions
	9.1 The Mechanisms
	9.2 Factor 1—The Electrophile (Substrate)
	9.3 Factor 2—The Nucleophile
	9.4 Factor 3—The Leaving Group
	9.5 Factor 4—The Solvent
	9.6 Using All Four Factors
	9.7 Substitution Reactions Teach Us Some Important Lessons
Chapter 10 Elimination Reactions
	10.1 The E2 Mechanism
	10.2 The Regiochemical Outcome of an E2 Reaction
	10.3 The Stereochemical Outcome of an E2 Reaction
	10.4 The E1 Mechanism
	10.5 The Regiochemical Outcome of an E1 Reaction
	10.6 The Stereochemical Outcome of an E1 Reaction
	10.7 Substitution vs. Elimination
	10.8 Determining the Function of the Reagent
	10.9 Identifying the Mechanism(s)
	10.10 Predicting the Products
Chapter 11 Addition Reactions
	11.1 Terminology Describing Regiochemistry
	11.2 Terminology Describing Stereochemistry
	11.3 Adding H and H
	11.4 Adding H and X, Markovnikov
	11.5 Adding H and Br, Anti‐Markovnikov
	11.6 Adding H and OH, Markovnikov
	11.7 Adding H and OH, Anti‐Markovnikov
	11.8 Synthesis Techniques
		11.8A One‐Step Syntheses
		11.8B Changing the Position of a Bromine Atom
		11.8C Changing the Position of a π Bond
		11.8D Introducing Functionality
	11.9 Adding Br and Br; Adding Br and OH
	11.10 Adding OH and OH, Anti
	11.11 Adding OH and OH, syn
	11.12 Oxidative Cleavage of an Alkene
	Summary of Reactions
Chapter 12 Alkynes
	12.1 Structure and Properties of Alkynes
	12.2 Preparation of Alkynes
	12.3 Alkylation of Terminal Alkynes
	12.4 Reduction of Alkynes
	12.5 Hydration of Alkynes
	12.6 Keto‐Enol Tautomerization
	12.7 Ozonolysis of Alkynes
Chapter 13 Alcohols
	13.1 Naming and Designating Alcohols
	13.2 Predicting Solubility of Alcohols
	13.3 Predicting Relative Acidity of Alcohols
	13.4 Preparing Alcohols: A Review
	13.5 Preparing Alcohols via Reduction
	13.6 Preparing Alcohols via Grignard Reactions
	13.7 Summary of Methods for Preparing Alcohols
	13.8 Reactions of Alcohols: Substitution and Elimination
	13.9 Reactions of Alcohols: Oxidation
	13.10 Converting an Alcohol into an Ether
Chapter 14 Ethers and Epoxides
	14.1 Introduction to Ethers
	14.2 Preparation of Ethers
	14.3 Reactions of Ethers
	14.4 Preparation of Epoxides
	14.5 Ring‐Opening Reactions of Epoxides
Chapter 15 Synthesis
	15.1 One‐Step Syntheses
	15.2 Multistep Syntheses
	15.3 Retrosynthetic Analysis
	15.4 Creating Your Own Problems
Detailed Solutions
Index
EULA