The Survival Guide to Organic Chemistry: Bridging the Gap from General Chemistry enables organic chemistry students to bridge the gap between general chemistry and organic chemistry. It makes sense of the myriad of in-depth concepts of organic chemistry, without overwhelming them in the necessary detail often given in a complete organic chemistry text.

Table of Contents

• Preface
• Authors
• Chapter 1 General Concepts for Covalent Bonding and Constructing Lewis Structures for Organic Molecules
• 1.1 General Concepts
• 1.1.1 Covalent Bonding
• 1.1.2 Lewis Structures
• 1.2 Bonding Rules for Nonmetals in Covalent Molecules
• 1.2.1 General Concept of Normal Neutral Bond Numbers
• 1.2.2 Summary Table for Normal Neutral Bond Numbers in Covalent Molecules
• 1.2.2.1 For H, B, C, N, O, F (H Plus Row 2)
• 1.2.2.2 Common Bond Numbers for Certain Elements in Rows 3–6 (Si, P, S, Cl, Br, l)
• 1.3 Constructing Lewis Structures for Covalent Molecules: Molecules Which Do Not Require Exceptions to Normal Neutral Bonding Rules
• 1.3.1 Lewis Structure Concepts
• 1.3.2 Molecules Containing H, Be, B, C, N, O, F That Follow Normal Neutral Bonding Rules
• 1.3.3 Lewis Structures of Molecules Containing Atoms from Rows 3 to 6 (Si, P, S, Cl, Br, l)
• 1.4 Constructing Lewis Structures for Covalent Molecules: Molecules Which Require Exceptions to Normal Neutral Bonding Rules
• 1.4.1 Exceptions for Row-2 Elements: B, C, N, O
• 1.4.2 Lewis Structures for Polyatomic lons: Use of Exception Rule #1
• 1.4.3 Use of Exception Rule #3
• 1.5 Additional Concepts and Techniques for Constructing Lewis Structures
• 1.5.1 Other Uses of Exception Rule #3
• 1.5.2 Resonance Structures
• 1.6 Guidelines for Constructing Lewis Structures of Larger Molecules
• 1.6.1 General Concept
• 1.6.2 Bonding Pattern Template Method; Process Listed in Step Sequence
• Chapter 2 Guideline for Writing Organic Molecule Isomers and Determining Number of Rings Plus Pi-Bonds
• 2.1 General Concept
• 2.2 Use of the “Bonding-Pattern Template” Method to Find Sum of Rings Plus Pi-Bonds (Degree of Unsaturation)
• 2.3 Calculation of Sum of Rings Plus Pi-Bonds from the Molecular Formula
• 2.3.1 Process for Use of Formulas to Calculate Number of Rings Plus Pi-Bonds: Molecules Containing Only C, H, and 0
• 2.3.2 Expanding the Calculation Method to Molecules Which Include F, Cl, Br, l
• 2.3.3 Expanding the Calculation Method to Molecules Which Include Nitrogen
• Chapter 3 Guideline for Complete Analysis for Central Atoms and Molecules: Bonding/Hybridization/Geometry/Polarity
• 3.1 Process for Complete Hybridization/Geometry Analysis
• 3.2 General Summaries
• 3.2.1 Summary of Geometry/Hybridization for 2–4 Electron Regions
• 3.2.2 Summary for the Geometry/Hybridization for C, N, and O
• 3.3 Practice Exercises
• 3.4 Answers to Practice Exercises
• Chapter 4 Notation in Organic Chemistry: Guide to Writing and Using Condensed Formulas and Line Drawings
• 4.1 Condensed Structural Formulas
• 4.1.1 Guidelines for Converting a Lewis Structure into a Condensed Structural Formula
• 4.1.2 Notes and Other Simplifications
• 4.1.3 Expanding Condensed Formulas: Reconstructing the Complete Molecule
• 4.2 Line Drawings
• 4.2.1 Rules for Producing Line Drawings
• 4.2.2 Converting Line Drawings into Structural Formulas
• Chapter 5 Summary Guidelines for Organic Nomenclature
• 5.1 General Concepts
• Part 1: Description of General Process: Alkanes/Cycloalkanes/Alkyl Halides
• 5.2 Example for an Alkane/Alkyl Halide
• Part 2: Description of Complete General Process: Molecules with Higher-Priority Functional Groups
• 5.3 Examples for a Molecule with Higher-Priority Functional Groups
• Part 3: General Process for Esters and Amides
• 5.4 Adapted Process for Nomenclature of Esters
• 5.5 Adapted Process for Nomenclature of Amides
• Chapter 6 Guidelines for Analysis of Intermolecular Forces for Organic Molecules
• 6.1 Interparticle and Intermolecular Forces for Individual Pure Compounds: Forces between Molecules of the Same Compound
• 6.1.1 Interparticle Forces for Nonmolecular Compounds
• 6.1.2 Intermolecular Forces for Molecular Compounds
• 6.1.3 Guideline for Comparing Total Strength of Intermolecular Forces in Individual Compounds
• 6.2 Interparticle and Intermolecular Forces for Combinations of Compounds: Solutions and Solubility
• 6.2.1 Solubility and Solution Terms
• 6.2.2 Solubility Requirements
• 6.2.3 Interparticle (Intermolecular) Forces between Solute and Solvent
• 6.2.4 Analysis of Solubility for Possible Solute/Solvent Combinations
• Chapter 7 Alkane and Cycloalkane Conformations
• 7.1 Conformers
• 7.2 Process for Recognition and Identification of Alkane Conformers through the Use of Torsion Angle
• 7.3 Drawing and Using Newman Projections
• 7.4 Potential Energies/Stabilities of Alkane Conformations
• 7.4.1 Potential Energy and Torsional Strain
• 7.4.2 Potential Energy and Van der Waal's Repulsion (Steric Repulsion)
• 7.4.3 General Conclusions for Conformer Stability
• 7.4.4 Example
• 7.5 Cyclohexane Conformations
• 7.5.1 Description of the Chair Conformation of Cyclohexane
• 7.5.2 Drawing the Chair Conformation
• 7.5.3 Working with the Chair Conformation
• 7.5.4 Process for Solving Chair Conformation Problems
• 7.5.5 Additional Examples
• Chapter 8 Summary Guide to Thermodynamic Concepts for Organic Chemistry
• Part 1: Bond Energy, Enthalpy, and Potential Energy Diagrams
• 8.1 Concept of Energy
• 8.2 Conservation of Energy: First Law of Thermodynamics
• 8.3 Chemical Bond Energetics
• 8.3.1 PE and Chemical Bonds
• 8.3.2 Bond Energies and Changes
• 8.4 Energy and Chemical Reactions
• 8.4.1 Reactions and Bond Changes
• 8.4.2 Calculating Reaction Enthalpy Values Using Bond Energies
• 8.4.3 Reaction Energy-Level Diagrams
• 8.4.4 PE, Enthalpy, and Reversible Reactions
• 8.4.5 Example Problem: Reading an Energy Diagram
• Part 2: Entropy, Free Energy, Spontaneity, and Equilibrium
• 8.5 Entropy
• 8.5.1 General Concepts
• 8.5.2 Predicting Entropy Changes for a Chemical Process
• 8.5.3 Entropy and the Second and Third Laws of Thermodynamics
• 8.6 Reaction Spontaneity
• 8.6.1 General Concepts
• 8.6.2 Enthalpy and Spontaneity
• 8.6.3 Entropy and Spontaneity
• 8.6.4 Reaction Spontaneity: Combining Enthalpy and Entropy
• 8.7 Free Energy (∆G)
• 8.7.1 General Concepts
• 8.7.2 Standard Free Energy: ∆G°298 and ∆G° at Variable Temperatures
• 8.7.3 Nonstandard Free Energy (∆G) and Concentrations
• 8.8 Equilibrium
• 8.8.1 Concentrations and Equilibrium
• 8.8.2 Equilibrium Shifts
• 8.8.3 Comprehensive Example of All Concepts
• Chapter 9 Guide to Kinetics and Reaction Mechanisms
• 9.1 General Concepts
• 9.1.1 Reaction Mechanisms
• 9.1.2 General Concept of Kinetics
• 9.1.3 Additional Variables Affecting Reaction Rates
• 9.1.4 Information Relationships for Kinetics and Mechanisms
• 9.2 Description of Reactions by Mechanisms
• 9.2.1 Reaction Steps and Complete Reactions
• 9.2.2 Variability of Mechanisms
• 9.3 Reactant Concentrations and Experimental Kinetics: Determining Reactant Orders and Rate Constants
• 9.3.1 Experimental Concepts
• 9.3.2 Zero-Order Reactants
• 9.3.3 First-Order Reactants
• 9.3.4 Second-Order Reactants
• 9.3.5 Experimental Determination of Reactant Orders in Multiple-Concentration Rate Expressions
• 9.4 Predicting Rate Expressions from Reaction Mechanisms
• 9.4.1 General Concepts for Rate Expression Comparison; Identification of the Rate-Determining Step
• 9.4.2 Predicting Rate Expressions from Mechanisms: Reaction Step Rate Rule and One-Step Reactions
• 9.4.3 Predicting Rate Expressions from Mechanisms: Multiple-Step Reaction Mechanisms
• 9.4.4 General Reaction Examples for Multistep Reactions
• 9.5 Energy and Chemical Reactions
• 9.5.1 Bonding Changes and Activation Energy
• 9.5.2 Energetics of Bond Making and Bond Breaking
• 9.5.3 Reaction Rates, Temperature, and Ea
• 9.5.4 Rates and Catalysis
• 9.6 Interpretation of Energy Level Diagrams
• 9.6.1 General Construction of Energy Diagrams
• 9.6.2 Energy Diagram Examples
• 9.6.3 Example Problem: Reading an Energy Diagram
• 9.6.4 Problem 1 Answer
• 9.7 Practice Problems
• 9.8 Answers to Practice Problems
• Chapter 10 Review of Acid/Base Concepts for Organic Chemistry
• 10.1 Review of General Acid/Base Concepts
• 10.1.1 General Definitions
• 10.1.2 Review Process for Writing Acid/Base Reaction Equations
• 10.1.3 Concept of Conjugate Acid and Conjugate Base
• 10.1.4 Properties of Acids
• 10.1.5 Properties of Bases
• 10.2 Acid and Base Strength
• 10.2.1 Reference Reactions of Acids with Water
• 10.2.2 Reference Reactions of Bases with Water
• 10.2.3 Acid Strength
• 10.2.4 Base Strength
• 10.3 Relationship between Acid Strength (pKa) and Conjugate Base Strength
• 10.4 Determining the Equilibrium Position for Acid/Base Reactions
• 10.5 Additional Examples
• Chapter 11 Electrophiles and Nucleophiles in Organic Reaction Mechanisms
• 11.1 Overview of General Concepts
• 11.1.1 Electrophiles and Nucleophiles
• 11.1.2 Reaction Concepts
• 11.2 Species Identification and Characteristics
• 11.2.1 Electrophiles
• 11.2.2 Nucleophiles
• 11.3 Reaction Characteristics
• 11.3.1 Electrophiles and Nucleophiles in Mechanisms
• 11.3.2 Bond Formation with Electrophiles Having an Available Empty Orbital: Addition of the Electrophile to the Nucleophile
• 11.3.3 Bond Breaking between the Electrophile and Nucleophile by Elimination
• 11.3.4 Bond Formation with Electrophiles Having a Full Octet
• 11.4 Additional Concepts
• 11.4.1 Nucleophiles Using a Sigma-Bonding Electron Pair
• 11.4.2 Single Electron Transfer: Free Radical Reactions
• 11.5 Additional Problems
• 11.5.1 Practice Exercises
• 11.5.2 Answers to Practice Exercises
• Chapter 12 Conceptual Guide to Mechanisms in Organic Chemistry
• 12.1 Overview for Understanding Reaction Mechanisms
• 12.1.1 Reaction Electron Changes
• 12.1.2 Substitution Patterns on Carbon: Mechanistic Effects
• 12.2 Free Radical Halogenation of Alkanes/Alkyl Groups
• 12.2.1 Reaction Concepts
• 12.2.2 Summary of General Mechanism
• 12.2.3 Conceptual Description of Mechanistic Steps
• 12.2.4 Summary: Determining the Correct Products for Free Radical Halogenation
• 12.3 Nucleophilic Substitution
• 12.3.1 Description of the General Reaction
• 12.3.2 Factors Influencing Rate and Mechanisms
• 12.3.3 Nucleophilic Substitution: General Mechanistic Concepts
• 12.3.4 General Summaries (Selected Formats): Notation R = Alkyl Group
• 12.3.5 Summary: Determination of the Correct Product for Nucleophilic Substitution
• 12.4 Elimination Reactions of Alcohols and Alkyl Halides
• 12.4.1 General Reaction Concepts
• 12.4.2 Identification of Major Isomer Alkene Product in Eliminations (Non-Rearrangement)
• 12.4.3 Summary: Determination of Major Alkene Product for Elimination (Non-Rearrangement)
• 12.4.4 Mechanism Summary: E2 for Primary, Secondary, and Tertiary Alkyl Halides
• 12.4.5 Mechanism Summary: E1 for Tertiary Alkyl Halides
• 12.4.6 Mechanism Summary: E2 for Primary Alcohols
• 12.4.7 Mechanism Summary: E1 for Secondary and Tertiary Alcohols
• 12.5 Identification of Elimination versus Substitution Reactions
• 12.5.1 Reaction Analysis for Alcohols
• 12.5.2 Reaction Analysis for Alkyl Halides
• 12.6 Electrophilic Addition to Pi-Bonds of Alkenes and Alkynes
• 12.6.1 General Reaction Concepts
• 12.6.2 Mechanism Summary
• 12.6.3 Regiochemistry in Electrophilic Addition
• 12.6.4 Stereochemistry in Electrophilic Addition
• 12.6.5 Summary: Determination of the Correct Major Product for Electrophilic Addition to Alkenes (Excluding Rearrangements)
• 12.6.6 Specific Examples
• 12.6.7 General Summary
• Chapter 13 Guide to Stereochemistry Concepts and Analysis of Reaction Stereochemistry as Applied to Electrophilic Addition
• Part 1: Conceptual Guide to Stereochemistry
• 13.1 Concepts of Stereochemistry and Chirality
• 13.2 Absolute Configuration of Chiral Carbons
• 13.2.1 Priority System for Attached Atom Groups
• 13.2.2 Process to Apply the Priority System to the Four Different Groups Attached to Chiral Carbons
• 13.2.3 Process to Determine Absolute Configuration of Chiral Carbons
• 13.3 Molecular Relationships: Summary Example with Molecular Formula: C8H16
• Part 2: Analysis of Reaction Stereochemistry Applied to Electrophilic Addition
• 13.4 Stereochemistry Concepts for Electrophilic Addition
• 13.4.1 General Analysis for Reactions
• 13.4.2 Stereochemistry Concepts Applied to Alkene Electrophilic Addition
• 13.4.3 Analysis Requirements for Electrophilic Addition Possibilities
• 13.4.4 Stereospecificity
• 13.4.5 Stereospecific Reaction Summary
• 13.5 Stereospecificity and Reaction Analysis for Electrophilic Addition
• 13.5.1 Stereospecificity Options for Electrophilic Addition Mechanisms
• 13.5.2 Reaction Conditions That Require Analysis for Diastereomers
• 13.5.3 Example: All Requirements 1, 2, and 3 Are Met
• 13.6 Concepts of Ring Stereochemistry
• 13.6.1 Cycloalkene Diasteromers
• 13.6.2 Viewing Ring Diastereomers
• 13.6.3 Stereospecificity Options Viewed in Cycloalkenes
• 13.6.4 Notation for Product Identification
• Chapter 14 A Process for Calculation of Product Distribution through Relative Rate Analysis: Examples for Free Radical Halogenation
• 14.1 Methods for Product Percent and Ratio Calculations
• 14.2 Additional Practice Problem
• 14.3 Practice Problem Answer (Following Steps Similar to Example 1)
• Chapter 15 Process to Identify and Solve the Reactions for Organic 1
• 15.1 Reaction Flow Diagram
• 15.2 Summaries from Chapter 12
• 15.3 Reaction Examples
• 15.4 Additional Practice Problems
• 15.5 Additional Practice Problems: Answers
• Chapter 16 Electrophilic Addition and Addition/Elimination to Conjugated Double Bond and Aromatic Systems
• 16.1 General Concepts of Pi-Bonding Systems
• 16.1.1 Properties of Nonaromatic Conjugated Systems
• 16.1.2 Properties of Aromatic Conjugated Systems
• 16.2 Electrophilic Addition to Conjugated Double Bonds in Polyenes
• 16.2.1 General Reaction
• 16.2.2 Regiochemistry for Electrophilic Addition to Conjugated Systems: Concept of Allylic Carbon Cations and Radicals
• 16.2.3 Techniques for Drawing Correct Resonance Structures for Conjugated Systems
• 16.2.4 Regiochemistry for Electrophilic Addition to Conjugated Systems: Constitutional Isomers Based on Resonance Structures
• 16.2.5 Regiochemistry for Electrophilic Addition to Conjugated Systems: Determination of Major and Minor Isomer Products
• 16.2.6 Summary: Determination of Products for Electrophilic Addition to Conjugated Systems
• 16.2.7 Reproduction of Summary Table: E–Z Reagents for Electrophilic Addition
• 16.2.8 Example: Electrophilic Addition to a Conjugated Diene
• 16.3 Electrophilic Aromatic Substitution by an Addition/Elimination Mechanism
• 16.3.1 General Reaction
• 16.3.2 Electrophilic Aromatic Substitution: General Mechanism
• 16.3.3 Determination of the Major Product for Reactions at Substituted Aromatic Rings: Analysis of Resonance Forms
• 16.3.4 Determination of the Major Product for Reactions at Substituted Aromatic Rings: General Results for Stabilizing and Destabilizing Substituents
• 16.3.5 General Summary: Determination of Correct Major Products for Electrophilic Aromatic Substitution
• 16.3.6 Summary Table: Electrophiles for Electrophilic Aromatic Substitution
• 16.4 Examples: Electrophilic Aromatic Substitution
• 16.5 Additional Practice Problems
• Chapter 17 Oxidation/Reduction Relationships for Carbonyl Carbon
• 17.1 General Concept of Redox Reactions
• 17.2 Oxidation Numbers
• 17.3 Oxidation/Reduction for Carbon in Organic Molecules
• 17.4 Oxidation/Reduction Sequence for Alcohols, Aldehydes/Ketones, Carboxylic Acids, and Derivatives
• 17.5 Reagents and Results for Oxidation Reactions of Alcohols, Aldehydes/ Ketones, Carboxylic Acids, and Derivatives
• 17.5.1 Complete Oxidation
• 17.5.2 Selective Oxidation of Primary Alcohols to Aldehydes
• 17.6 Reagents and Results for Reduction Reactions of Alcohols; Aldehydes/ Ketones; Carboxylic Acids; and Derivatives
• 17.6.1 Hydrogenation: Reduction with Hydrogen
• 17.6.2 Metal Hydride Reduction of Aldehydes and Ketones Li + R3Al—H; Na+ R3B—H
• 17.6.3 Lithium Aluminum Hydride Reduction of Carboxylic Acids and Esters Li + R3Al—H
• Chapter 18 A Complete System for Organizing, Identifying, and Solving Carbonyl Reactions: Nucleophilic Addition and Addition/Elimination
• 18.1 Mechanisms and Classification of Carbonyl Reactions
• 18.1.1 General Concepts
• 18.1.2 Nucleophilic Addition to the Carbonyl Carbon: c=o
• 18.1.3 General Mechanisms for Nucleophilic Addition to Carbonyl c=o
• 18.2 Classification of Nucleophilic Addition/Elimination Reactions through the Structure of the Tetrahedral Intermediate: Determining the Final Product for Carbonyl Reactions
• 18.3 Descriptions of Group Reaction Results and Mechanisms
• 18.3.1 Group [1]
• 18.3.1.1 General Reactant Requirements
• 18.3.2 Group [2]
• 18.3.2.1 General Group Reactant Requirements
• 18.3.3 Subgroup [2A] Reaction Results and Mechanism
• 18.3.4 Group [2A] Examples
• 18.3.5 Subgroup [2B]: Reaction Results and Mechanism
• 18.3.6 Group [2B] Examples
• 18.3.7 Group [3]
• 18.3.7.1 General Reactant Requirements
• 18.3.8 Group [3] Examples
• 18.3.9 Group [4]
• 18.3.9.1 General Reactant Requirements
• 18.3.10 General Addition Mechanisms for Group [5]
• 18.3.11 Group [5] Examples
• 18.3.12 Group [6]
• 18.3.12.1 General Reactant Requirements
• 18.3.13 Group [6] Example
• 18.4 Process to Solve Nucleophilic Addition/Elimination Reactions at Carbonyl Additional Practice Examples for Groups [1] through [6]
• 18.5 Additional Practice Problems
• Chapter 19 A Brief Guideline for Applying Fundamental Concepts in NMR Spectroscopy
• 19.1 General Concepts for 1H NMR Interpretation: Number of Signals and Peak Ratios
• 19.1.1 Examples Demonstrating Principles #1 and #2
• 19.1.1.1 Example: Analysis for Molecules 1, 2, and 3
• 19.2 General Concepts for 1H NMR Interpretation: Signal Position and Proton Coupling
• 19.3 Table of Approximate Positions for 1H NMR Hydrogens
• 19.4 Examples: Predicting the 1H NMR for Molecules Using Principles #1 through 4
• 19.4.1 Chemical Shift Estimation Method for Common C−H Protons
• 19.5 Examples: Predicting the 1H NMR from Molecular Structure
• 19.6 Additional Practice Problems
• 19.7 Additional Practice Problems: Answers
• SECTION I—Organic Practice Exams
• Organic I: Practice exam 1
• organic I: Practice exam 2
• organic I: Practice exam 3
• organic I: Practice exam 4
• organic I: Practice exam 5
• organic I: Practice exam 6
• organic I: Practice exam 7
• organic I: Practice exam 8
• organic I: Practice exam 9
• organic I: Practice exam 10
• organic I: Practice exam 11
• organic I: Practice exam 12
• organic I: Practice exam 13
• organic I: Practice exam 14
• organic I: Practice exam 15
• organic I: Practice exam 16
• Organic I: Practice Exam 17
• Organic II: Practice exam 18
• organic II: Practice exam 19
• organic II: Practice exam 20
• Organic II: Practice exam 21
• organic II: Practice exam 22
• organic II: Practice exam 23
• organic II: Practice exam 24
• organic II: Practice exam 25
• organic II: Practice exam 26
• organic II: Practice exam 27
• SECTION II—Multiple-Choice Practice exams
• organic I: Multiple-Choice Practice exam 1
• organic I: Multiple-Choice Practice exam 2
• organic II: Multiple-Choice Practice exam 1
• organic II: Multiple-Choice Practice exam 2