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Test Bank for Organic Chemistry, 9th Edition, Leroy G. Wade, ISBN-10: 032197137X, ISBN-13: 9780321971371

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This is completed downloadable of Test Bank for Organic Chemistry, 9th Edition, Leroy G. Wade, ISBN-10: 032197137X, ISBN-13: 9780321971371

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ISBN-10 ‏ : ‎ 013416038X
ISBN-13 ‏ : ‎ 978-0134160382
Author: Leroy G. Wade

Wade & Simek’s Ninth Edition of Organic Chemistry presents key principles of organic chemistry in the context of fundamental reasoning and problem solving. Authored to complement how students use a textbook today, new Problem Solving Strategies, Partially Solved Problems, Visual Reaction Guides and Reaction Starbursts encourage students to use the text before class as a primary introduction to organic chemistry as well as a comprehensive study tool for working problems and/or preparing for exams. With unparalleled and highly refined pedagogy, this Ninth edition gives students a contemporary overview of organic principles and the tools for organizing and understanding reaction mechanisms and synthetic organic chemistry.

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MasteringChemistry from Pearson is the leading online homework, tutorial, and assessment system, designed to improve results by engaging students before, during, and after class with powerful content. Instructors ensure students arrive ready to learn by assigning educationally effective content before class, and encourage critical thinking and retention with in-class resources such as Learning Catalytics^TM. Students can further master concepts after class through traditional and adaptive homework assignments that provide hints and answer-specific feedback. The Mastering gradebook records scores for all automatically graded assignments in one place, while diagnostic tools give instructors access to rich data to assess student understanding and misconceptions.

Table of Content:

1 Structure and Bonding
Goals for Chapter 1
1-1 The Origins of Organic Chemistry
1-2 Principles of Atomic Structure
1-2A Structure of the Atom
1-2B Electron Shells and Orbitals
1-2C Electronic Configurations of Atoms
Problem 1-1
1-3 Bond Formation: The Octet Rule
1-3A Ionic Bonding
1-3B Covalent Bonding
1-4 Lewis Structures
Problem 1-2
1-5 Multiple Bonding
Summary Common Bonding Patterns (Uncharged)
Problem 1-3
Problem 1-4
1-6 Electronegativity and Bond Polarity
Problem 1-5
1-7 Formal Charges
SOLUTION
SOLUTION
SOLUTION
SOLUTION
1-8 Ionic Structures
Problem 1-6
1-9 Resonance
1-9A Resonance Hybrids
1-9B Major and Minor Resonance Contributors
SOLUTION (a)
SOLUTION (b)
SOLUTION (c)
Problem 1-7
Problem 1-8 (PARTIALLY SOLVED)
SOLUTION
Problem-Solving Strategy Drawing and Evaluating Resonance Forms
Solved Problem 1-3
Solved Problem 1-4
SOLUTION
Solved Problem 1-5
Problem 1-9
Problem 1-10
1-10 Structural Formulas
1-10A Condensed Structural Formulas
Problem 1-11
1-10B Line–Angle Formulas
Problem 1-12
Problem 1-13
1-11 Molecular Formulas and Empirical Formulas
1-12 Wave Properties of Electrons in Orbitals
1-12A Waveforms and Nodes
1-12B Linear Combination of Atomic Orbitals
1-13 Molecular Orbitals
1-13A The Hydrogen Molecule; Sigma Bonding
1-13B Sigma Overlap Involving p Orbitals
SOLUTION
1-14 Pi Bonding
1-14A Single and Double Bonds
1-15 Hybridization and Molecular Shapes
1-15A sp Hybrid Orbitals
SOLUTION
1-15B sp2 Hybrid Orbitals
SOLUTION
1-15C sp3 Hybrid Orbitals
1-16 Drawing Three-Dimensional Molecules
Problem 1-15
1-17 General Rules of Hybridization and Geometry
Summary Hybridization and Geometry
SOLUTION
Problem 1-16
SOLUTION
Problem 1-17
SOLUTION
Problem 1-18
SOLUTION
Problem 1-19
Problem 1-20
SOLUTION
Problem 1-21 (PARTIALLY SOLVED)
SOLUTION
1-18 Bond Rotation
1-18A Rotation of Single Bonds
1-18B Rigidity of Double Bonds
Problem 1-22
Problem 1-23
1-19 Isomerism
1-19A Constitutional Isomerism
1-19B Stereoisomers
Problem 1-24
Problem 1-25
Essential Terms
Essential Problem-Solving Skills in Chapter 1
Study Problems
2 Acids and Bases; Functional Groups
Goals for Chapter 2
2-1 Polarity of Bonds and Molecules
2-1A Bond Dipole Moments
SOLUTION
Problem 2-1
2-1B Molecular Dipole Moments
Problem 2-2
Problem 2-3 (PARTIALLY SOLVED)
Problem 2-4
2-2 Intermolecular Forces
2-2A Dipole–Dipole Forces
2-2B The London Dispersion Force
2-2C Hydrogen Bonding
Problem 2-5
SOLUTION
Problem 2-6
2-3 Polarity Effects on Solubilities
Problem 2-7
2-4 Arrhenius Acids and Bases
Problem 2-8
2-5 Brønsted–Lowry Acids and Bases
2-6 Strengths of Acids and Bases
2-6A Acid Strength
SOLUTION
Problem 2-9
2-6B Base Strength
2-7 Equilibrium Positions of Acid–Base Reactions
Problem-Solving Strategy Predicting Acid–Base Equilibrium Positions
Problem 2-10 (PARTIALLY SOLVED)
SOLUTION
Problem 2-11
2-8 Solvent Effects on Acidity and Basicity
Summary Acidity and Basicity Limitations in Common Solvents
Problem 2-12
2-9 Effects of Size and Electronegativity on Acidity
2-10 Inductive Effects on Acidity
Problem 2-13
Problem 2-14
2-11 Hybridization Effects on Acidity
Problem 2-15
Problem 2-16
Problem 2-17
2-12 Resonance Effects on Acidity and Basicity
Problem 2-18
Problem 2-19
Problem 2-20
Problem 2-21 (PARTIALLY SOLVED)
SOLUTION
Problem 2-22 (PARTIALLY SOLVED)
SOLUTION
2-13 Lewis Acids and Bases
2-14 The Curved-Arrow Formalism
Problem 2-23 (PARTIALLY SOLVED)
2-15 Hydrocarbons
2-15A Alkanes
2-15B Alkenes
2-15C Alkynes
2-15D Aromatic Hydrocarbons
Problem 2-24
2-16 Functional Groups with Oxygen
2-16A Alcohols
2-16B Ethers
2-16C Aldehydes and Ketones
2-16D Carboxylic Acids
Problem 2-25
2-16E Carboxylic Acid Derivatives
2-17 Functional Groups with Nitrogen
2-17A Amines
2-17B Amides
2-17C Nitriles
Problem 2-26
Problem 2-27
Essential Terms
Essential Problem-Solving Skills in Chapter 2
Study Problems
3 Structure and Stereochemistry of Alkanes
Goals for Chapter 3
3-1 Classification of Hydrocarbons (Review)
3-2 Molecular Formulas of Alkanes
Problem 3-1
3-3 Nomenclature of Alkanes
3-3A Common Names
3-3B IUPAC or Systematic Names
SOLUTION
Problem 3-2
SOLUTION
Summary Rules for Naming Alkanes
Problem 3-3
Problem 3-4
Problem 3-5
Problem 3-6
Complex Substituents
Problem 3-7
Problem 3-8
Problem 3-9
3-4 Physical Properties of Alkanes
3-4A Solubilities and Densities of Alkanes
3-4B Boiling Points of Alkanes
3-4C Melting Points of Alkanes
Problem 3-10
3-5 Uses and Sources of Alkanes
3-5A Major Uses of Alkanes
3-5B Alkane Sources; Petroleum Refining
3-5C Natural Gas; Methane
3-6 Reactions of Alkanes
3-6A Combustion
3-6B Cracking and Hydrocracking
3-6C Halogenation
3-7 Structure and Conformations of Alkanes
3-7A Structure of Methane
3-7B Conformations of Ethane
Problem 3-11 (PARTIALLY SOLVED)
SOLUTION (a)
3-7C Conformations of Propane
Problem 3-12
3-8 Conformations of Butane
3-8A Torsional Energy of Butane
3-8B Steric Strain
Problem 3-13
3-9 Conformations of Higher Alkanes
Problem 3-14
3-10 Cycloalkanes
3-10A General Molecular Formulas of Cycloalkanes
3-10B Physical Properties of Cycloalkanes
3-10C Nomenclature of Cycloalkanes
Problem 3-15
Problem 3-16
3-11 Cis-trans Isomerism in Cycloalkanes
Problem 3-17
Problem 3-18
3-12 Stabilities of Cycloalkanes; Ring Strain
3-12A Heats of Combustion
3-12B Cyclopropane
Problem 3-19
3-12C Cyclobutane
Problem 3-20
3-12D Cyclopentane
3-13 Cyclohexane Conformations
3-13A Chair and Boat Conformations
3-13B Axial and Equatorial Positions
Problem-Solving Strategy Drawing Chair Conformations
Problem 3-21
Problem 3-22
3-14 Conformations of Monosubstituted Cyclohexanes
Problem 3-23
Problem 3-24
Problem 3-25
3-15 Conformations of Disubstituted Cyclohexanes
Problem-Solving Strategy Recognizing Cis and Trans Isomers
Problem 3-26
SOLUTION
Problem 3-27
Problem 3-28
3-15A Substituents of Different Sizes
SOLUTION
Problem 3-29
3-15B Extremely Bulky Groups
Problem 3-30
3-16 Bicyclic Molecules
3-16A Nomenclature of Bicyclic Alkanes
Problem 3-31
3-16B cis- and trans-Decalin
Problem 3-32
Essential Terms
Essential Problem-Solving Skills in Chapter 3
Study Problems
4 The Study of Chemical Reactions
Goals for Chapter 4
4-1 Introduction
4-2 Chlorination of Methane
4-3 The Free-Radical Chain Reaction
4-3A The Initiation Step: Generation of Radicals
Problem 4-1
4-3B Propagation Steps
Problem 4-2
4-3C Termination Reactions
Problem 4-3
Problem 4-4
4-4 Equilibrium Constants and Free Energy
SOLUTION
Problem 4-5
Problem 4-6
4-5 Enthalpy and Entropy
4-5A Enthalpy
4-5B Entropy
SOLUTION
Problem 4-7
Problem 4-8
4-6 Bond-Dissociation Enthalpies
4-7 Enthalpy Changes in Chlorination
Problem 4-9
4-8 Kinetics and the Rate Equation
SOLUTION
Problem 4-11
Problem 4-12
Problem 4-13
4-9 Activation Energy and the Temperature Dependence of Rates
4-10 Transition States
4-11 Rates of Multistep Reactions
4-12 Temperature Dependence of Halogenation
Problem 4-16
Problem 4-17
4-13 Selectivity in Halogenation
4-13A Chlorination of Propane: Product Ratios
Problem 4-18
Problem 4-19
4-13B Free-Radical Stabilities
SOLUTION
Problem 4-20
Problem 4-21
Problem 4-22
4-13C Bromination of Propane
4-14 Hammond’s Postulate
Problem 4-23
Problem-Solving Strategy Proposing Reaction Mechanisms
Free-Radical Reactions
Common Mistakes to Avoid
Problem 4-24
Problem 4-25
4-15 Radical Inhibitors
Problem 4-26
Problem 4-27
4-16 Reactive Intermediates
4-16A Carbocations
Problem 4-28
Problem 4-29
4-16B Free Radicals
Problem 4-30
4-16C Carbanions
Problem 4-31
Problem 4-32
4-16D Carbenes
Problem 4-33
Summary Reactive Intermediates
Essential Terms
Essential Problem-Solving Skills in Chapter 4
Study Problems
5 Stereochemistry
Goals for Chapter 5
5-1 Introduction
5-2 Chirality
Problem 5-1
5-2A Chirality and Enantiomers in Organic Molecules
Problem 5-2
5-2B Asymmetric Carbon Atoms, Chiral Centers, and Stereocenters
SOLUTION
Problem 5-3
Problem 5-4
5-2C Mirror Planes of Symmetry
Problem 5-5
5-3 (R) and (S) Nomenclature of Asymmetric Carbon Atoms
SOLUTION
SOLUTION
Problem 5-6
Problem 5-7
5-4 Optical Activity
5-4A Plane-Polarized Light
5-4B Rotation of Plane-Polarized Light
5-4C Polarimetry
5-4D Specific Rotation
SOLUTION
Problem 5-8
Problem 5-9
Problem 5-10
5-5 Biological Discrimination of Enantiomers
Problem 5-11
5-6 Racemic Mixtures
5-7 Enantiomeric Excess and Optical Purity
SOLUTION
Problem 5-12
Problem 5-13
5-8 Chirality of Conformationally Mobile Systems
SOLUTION
SOLUTION
Problem 5-14
5-9 Chiral Compounds Without Asymmetric Atoms
5-9A Conformational Enantiomerism
5-9B Allenes
Problem 5-15
5-10 Fischer Projections
5-10A Drawing Fischer Projections
Problem 5-16
Problem 5-17
5-10B Drawing Mirror Images of Fischer Projections
Problem 5-18
5-10C Assigning (R) and (S) Configurations from Fischer Projections
Problem 5-19
Summary Fischer Projections and Their Use
5-11 Diastereomers
5-11A Cis-trans Isomerism on Double Bonds
5-11B Cis-trans Isomerism on Rings
5-11C Diastereomers of Molecules with Two or More Chiral Centers
Summary Types of Isomers
Problem 5-20
5-12 Stereochemistry of Molecules with Two or More Asymmetric Carbons
5-13 Meso Compounds
SOLUTION
SOLUTION
Problem 5-21
Problem 5-22
5-14 Absolute and Relative Configuration
5-15 Physical Properties of Diastereomers
Problem 5-23
5-16 Resolution of Enantiomers
5-16A Chemical Resolution of Enantiomers
Problem 5-24
5-16B Chromatographic Resolution of Enantiomers
Essential Terms
Essential Problem-Solving Skills in Chapter 5
Study Problems
6 Alkyl Halides; Nucleophilic Substitution
Goals for Chapter 6
6-1 Introduction
Problem 6-1
6-2 Nomenclature of Alkyl Halides
Problem 6-2
Problem 6-3
6-3 Common Uses of Alkyl Halides
6-3A Solvents
6-3B Reagents
6-3C Anesthetics
6-3D Freons: Refrigerants and Foaming Agents
6-3E Pesticides
Problem 6-4
6-4 Structure of Alkyl Halides
Problem 6-5
6-5 Physical Properties of Alkyl Halides
6-5A Boiling Points
Problem 6-6
6-5B Densities
Problem 6-7
6-6 Preparation of Alkyl Halides
6-6A Free-Radical Halogenation
6-6B Allylic Bromination
Problem 6-8
Problem 6-9
Problem 6-10
Summary Methods for Preparing Alkyl Halides
6-7 Reactions of Alkyl Halides: Substitution and Elimination
Problem 6-11
Problem 6-12
6-8 Bimolecular Nucleophilic Substitution: The SN2 Reaction
6-9 Generality of the SN2 Reaction
Summary SN2 Reactions of Alkyl Halides
6-10 Factors Affecting SN2 Reactions: Strength of the Nucleophile
Summary Trends in Nucleophilicity
6-10A Steric Effects on Nucleophilicity
Problem 6-16
6-10B Solvent Effects on Nucleophilicity
6-11 Reactivity of the Substrate in SN2 Reactions
6-11A Leaving-Group Effects on the Substrate
Problem 6-17
6-11B Steric Effects on the Substrate
Problem 6-18
Problem 6-19
6-12 Stereochemistry of the SN2 Reaction
Problem 6-20
Problem 6-21
6-13 Unimolecular Nucleophilic Substitution: The SN1 Reaction
Problem 6-22
6-13A Substituent Effects
6-13B Leaving-Group Effects
Problem 6-23
Problem 6-24
6-13C Solvent Effects on SN1 Reactions
6-14 Stereochemistry of the SN1 Reaction
6-15 Rearrangements in SN1 Reactions
Problem 6-25
Problem 6-26
6-16 Comparison of SN1 and SN2 Reactions
Essential Terms
Essential Problem-Solving Skills in Chapter 6
Study Problems
7 Structure and Synthesis of Alkenes; Elimination
Goals for Chapter 7
7-1 Introduction
7-2 The Orbital Description of the Alkene Double Bond
7-2A The Sigma Bond Framework
7-2B The Pi Bond
7-3 Elements of Unsaturation
7-3A Elements of Unsaturation in Hydrocarbons
Problem 7-1
Problem 7-2
7-3B Elements of Unsaturation with Heteroatoms
Halogens
Oxygen
Nitrogen
SOLUTION
Problem 7-3
Problem 7-4
7-4 Nomenclature of Alkenes
7-5 Nomenclature of Cis-Trans Isomers
7-5A Cis-Trans Nomenclature
7-5B E-Z Nomenclature
Summary Rules for Naming Alkenes
Problem 7-6
Problem 7-7
Problem 7-8
Problem 7-9*
7-6 Commercial Importance of Alkenes
Problem 7-10
7-7 Physical Properties of Alkenes
7-7A Boiling Points and Densities
7-7B Polarity
Problem 7-11
7-8 Stability of Alkenes
7-8A Heats of Hydrogenation
7-8B Substitution Effects
Problem 7-12
7-8C Energy Differences in cis-trans Isomers
Problem 7-13
7-8D Stability of Cycloalkenes
Cyclobutene
Cyclopropene
Trans Cycloalkenes
7-8E Bredt’s Rule
SOLUTION
Problem 7-14
7-8F Enhanced Stability of Conjugated Double Bonds
Problem 7-15
7-9 Formation of Alkenes by Dehydrohalogenation of Alkyl Halides
7-10 Unimolecular Elimination: The E1 Reaction
Problem 7-16
7-10A Competition between the E1 and SN1 Reactions
Problem 7-17
7-10B Orbitals and Energetics of the E1 Reaction
7-10C Rearrangements in E1 Reactions
PARTIAL SOLUTION
Problem 7-18
Problem 7-19
Summary Carbocation Reactions
Problem 7-20
7-11 Positional Orientation of Elimination: Zaitsev’s Rule
SOLUTION
Problem 7-21
Problem 7-22
7-12 Bimolecular Elimination: The E2 Reaction
Problem 7-23
7-13 Bulky Bases in E2 Eliminations; Hofmann Orientation
7-14 Stereochemistry of the E2 Reaction
7-14A Anti-Coplanar and Syn-Coplanar E2 Eliminations
7-14B Stereospecific E2 Reactions
Problem 7-26
Problem 7-27
7-15 E2 Reactions in Cyclohexane Systems
SOLUTION
Problem 7-28
Problem 7-29
Problem 7-30
Problem 7-31
7-16 Comparison of E1 and E2 Elimination Mechanisms
7-17 Competition Between Substitutions and Eliminations
7-17A Bimolecular Substitution Versus Elimination (Strong Base or Nucleophile)
7-17B Unimolecular Substitution Versus Elimination (Weak Base or Nucleophile)
SOLUTION
SOLUTION
Problem-Solving Strategy Predicting Substitutions and Eliminations
Problem 7-33
7-18 Alkene Synthesis by Dehydration of Alcohols
SOLUTION
Partial Solution:
Problem 7-34
Problem 7-35
7-19 Alkene Synthesis by High-Temperature Industrial Methods
7-19A Catalytic Cracking of Alkanes
7-19B Dehydrogenation of Alkanes
Problem 7-36
Problem-Solving Strategy Proposing Reaction Mechanisms
First, Classify the Reaction
General Principles for Drawing Mechanisms
Reactions Involving Strong Nucleophiles
Reactions Involving Strong Electrophiles
Problem 7-37
Problem 7-38
Problem 7-39
Summary Methods for Synthesis of Alkenes
Essential Terms
Essential Problem-Solving Skills in Chapter 7
Study Problems
8 Reactions of Alkenes
Goals for Chapter 8
8-1 Reactivity of the Carbon–Carbon Double Bond
8-2 Electrophilic Addition to Alkenes
8-3 Addition of Hydrogen Halides to Alkenes
8-3A Orientation of Addition: Markovnikov’s Rule
Markovnikov’s Rule
Problem 8-1
Problem 8-2
8-3B Free-Radical Addition of HBr: Anti-Markovnikov Addition
Radical Addition of HBr to Unsymmetrical Alkenes
Problem 8-3
SOLUTION
SOLUTION
Problem 8-4
8-4 Addition of Water: Hydration of Alkenes
8-4A Mechanism of Hydration
8-4B Orientation of Hydration
Problem 8-5
Problem 8-6
8-5 Hydration by Oxymercuration–Demercuration
8-6 Alkoxymercuration–Demercuration
SOLUTION
Problem 8-7
Problem 8-8
Problem 8-9
8-7 Hydroboration of Alkenes
8-7A Mechanism of Hydroboration
SOLUTION
Problem 8-10
Problem 8-11
8-7B Stoichiometry of Hydroboration
8-7C Stereochemistry of Hydroboration
SOLUTION
Problem 8-12
Problem 8-13
Problem 8-14
Problem 8-15
Problem 8-16
8-8 Addition of Halogens to Alkenes
8-8A Mechanism of Halogen Addition
8-8B Stereochemistry of Halogen Addition
Problem 8-17
Problem 8-18
8-9 Formation of Halohydrins
8-10 Catalytic Hydrogenation of Alkenes
Problem 8-23
Problem 8-24
Problem 8-25
8-11 Addition of Carbenes to Alkenes
8-11A The Simmons–Smith Reaction
Problem 8-26
8-11B Formation of Carbenes by Alpha Elimination
Problem 8-27
Problem 8-28
8-12 Epoxidation of Alkenes
Problem 8-29
8-13 Acid-Catalyzed Opening of Epoxides
Problem 8-30
Problem 8-31
Problem 8-32
Problem 8-33
8-14 Syn Dihydroxylation of Alkenes
8-14A Osmium Tetroxide Dihydroxylation
8-14B Permanganate Dihydroxylation
8-14C Choosing a Reagent
Problem 8-34
Problem 8-35
8-15 Oxidative Cleavage of Alkenes
8-15A Cleavage by Permanganate
8-15B Ozonolysis
SOLUTION
Problem 8-36
8-15C Comparison of Permanganate Cleavage and Ozonolysis
Problem 8-37
8-16 Polymerization of Alkenes
8-16A Cationic Polymerization
Problem 8-38
Problem 8-39
8-16B Free-Radical Polymerization
Problem 8-40
Problem 8-41
8-16C Anionic Polymerization
Problem 8-42
8-17 Olefin Metathesis
8-17A Catalysts for Olefin Metathesis
8-17B Mechanism of Olefin Metathesis
Problem 8-43
Problem 8-44
Problem-Solving Strategy Organic Synthesis
Problem 8-45
Summary Reactions of Alkenes
Summary Electrophilic Additions to Alkenes
Summary Oxidation and Cyclopropanation Reactions of Alkenes
Guide to Organic Reactions in Chapter 8
Essential Terms
Essential Problem-Solving Skills in Chapter 8
Study Problems
9 Alkynes
Goals for Chapter 9
9-1 Introduction
Problem 9-1
9-2 Nomenclature of Alkynes
9-3 Physical Properties of Alkynes
9-4 Commercial Importance of Alkynes
9-4A Uses of Acetylene and Methylacetylene
9-4B Manufacture of Acetylene
Problem 9-3
9-5 Electronic Structure of Alkynes
9-6 Acidity of Alkynes; Formation of Acetylide Ions
Problem 9-4
Problem 9-5
9-7 Synthesis of Alkynes from Acetylides
9-7A Alkylation of Acetylide Ions
Solution
Problem 9-6
Problem 9-7
9-7B Addition of Acetylide Ions to Carbonyl Groups
Solution
Problem 9-8
Problem 9-9
9-8 Synthesis of Alkynes by Elimination Reactions
Problem 9-10
Problem 9-11
Summary Syntheses of Alkynes
9-9 Addition Reactions of Alkynes
9-9A Catalytic Hydrogenation to Alkanes
9-9B Partial Catalytic Hydrogenation to cis Alkenes
9-9C Metal–Ammonia Reduction to trans Alkenes
Mechanism 9-1 Metal–Ammonia Reduction of an Alkyne
Problem 9-12
Problem 9-13
9-9D Addition of Halogens
Problem 9-14
9-9E Addition of Hydrogen Halides
Problem 9-15
Problem 9-16
Problem 9-17
Problem 9-18
9-9F Hydration of Alkynes to Ketones and Aldehydes
Mercuric Ion-Catalyzed Hydration
Mechanism 9-2 Acid-Catalyzed Keto–Enol Tautomerism
Problem 9-19
Hydroboration–Oxidation
Mechanism 9-3 Base-Catalyzed Keto–Enol Tautomerism
Problem 9-20
Problem 9-21
Problem 9-22
9-10 Oxidation of Alkynes
9-10A Permanganate Oxidations
Problem 9-23
9-10B Ozonolysis
Problem 9-24
Problem-Solving Strategy
Multistep Synthesis
Problem 9-25
Summary Reactions of Alkynes
Summary Reactions of Terminal Alkynes
Essential Terms
Essential Problem-Solving Skills in Chapter 9
Study Problems
10 Structure and Synthesis of Alcohols
Goals for Chapter 10
10-1 Introduction
10-2 Structure and Classification of Alcohols
10-3 Nomenclature of Alcohols and Phenols
10-3A IUPAC Names (“Alkanol” Names)
SOLUTION
Problem 10-1
10-3B Common Names of Alcohols
Problem 10-2
Problem 10-3
10-3C Names of Diols
Problem 10-4
10-3D Names of Phenols
10-4 Physical Properties of Alcohols
10-4A Boiling Points of Alcohols
10-4B Solubility Properties of Alcohols
Problem 10-5
Problem 10-6
10-5 Commercially Important Alcohols
10-5A Methanol
10-5B Ethanol
10-5C Propan-2-ol
10-6 Acidity of Alcohols and Phenols
10-6A Effects on Acidity
Problem 10-7
Problem 10-8
10-6B Formation of Sodium and Potassium Alkoxides
10-6C Acidity of Phenols
Problem 10-9
Problem 10-10
10-7 Synthesis of Alcohols: Introduction and Review
Summary Previous Alcohol Syntheses
10-8 Organometallic Reagents for Alcohol Synthesis
10-8A Grignard Reagents
10-8B Organolithium Reagents
Problem 10-11
Problem 10-12
10-9 Reactions of Organometallic Compounds
10-9A Addition to Formaldehyde: Formation of Primary Alcohols
Problem 10-13
10-9B Addition to Aldehydes: Formation of Secondary Alcohols
Problem 10-14
10-9C Addition to Ketones: Formation of Tertiary Alcohols
SOLUTION
Problem 10-15
10-9D Addition to Acid Chlorides and Esters
Problem 10-16
Problem 10-17
Problem 10-18
10-9E Ring-Opening with Ethylene Oxide
Problem 10-19
Problem 10-20
Summary Grignard Reactions
10-9F Lithium Dialkylcuprates
Problem 10-21
10-10 Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides
10-10A Reactions with Acidic Compounds
Problem 10-22
10-10B Reactions with Electrophilic Multiple Bonds
Problem 10-23
10-11 Reduction of the Carbonyl Group: Synthesis of 1° and 2° Alcohols
10-11A Uses of Sodium Borohydride
10-11B Uses of Lithium Aluminum Hydride
Problem 10-24
Problem 10-25
Problem 10-26
10-11C Catalytic Hydrogenation of Ketones and Aldehydes
Summary Alcohol Syntheses by Nucleophilic Additions to Carbonyl Groups
10-12 Thiols (Mercaptans)
Problem 10-27
Problem 10-28
Problem 10-29
Summary Synthesis of Alcohols from Carbonyl Compounds
Essential Terms
Essential Problem-Solving Skills in Chapter 10
Study Problems
11 Reactions of Alcohols
Goals for Chapter 11
11-1 Oxidation States of Alcohols and Related Functional Groups
Problem 11-1
11-2 Oxidation of Alcohols
11-2A Oxidation of Secondary Alcohols
11-2B Oxidation of Primary Alcohols
11-2C Resistance of Tertiary Alcohols to Oxidation
Problem 11-2
11-3 Additional Methods for Oxidizing Alcohols
Problem 11-3
Problem 11-4
Problem 11-5
SOLUTION
SOLUTION
Problem 11-6
11-4 Biological Oxidation of Alcohols
Problem 11-7
Problem 11-8
11-5 Alcohols as Nucleophiles and Electrophiles; Formation of Tosylates
Summary SN2 Reactions of Tosylate Esters
Problem 11-9
Problem 11-10
11-6 Reduction of Alcohols
Problem 11-11
11-7 Reactions of Alcohols with Hydrohalic Acids
11-7A Reactions with Hydrobromic Acid
Problem 11-12
11-7B Reactions with Hydrochloric Acid
Problem 11-13
The Lucas Test
Problem 11-14
11-7C Limitations on the Use of Hydrohalic Acids with Alcohols
SOLUTION
Problem 11-15
Problem 11-16
Problem 11-17
11-8 Reactions of Alcohols with Phosphorus Halides
Problem 11-18
11-9 Reactions of Alcohols with Thionyl Chloride
Problem 11-19
Problem 11-20
Problem 11-21
11-10 Dehydration Reactions of Alcohols
11-10A Formation of Alkenes
SOLUTION
SOLUTION
Problem 11-22
Problem 11-23
11-10B Bimolecular Condensation to Form Ethers (Industrial)
Problem 11-24
Problem 11-25
Problem-Solving Strategy Proposing Reaction Mechanisms
Determining the Type of Mechanism
Reactions Involving Strong Electrophiles
Common Mistakes to Avoid in Drawing Mechanisms
Sample Problem
Problem 11-26
Problem 11-27
11-11 Unique Reactions of Diols
11-11A The Pinacol Rearrangement
Problem 11-28
Problem 11-29
11-11B Periodic Acid Cleavage of Glycols
Problem 11-30
11-12 Esterification of Alcohols
Problem 11-31
11-13 Esters of Inorganic Acids
11-13A Sulfate Esters
Problem 11-32
11-13B Nitrate Esters
11-13C Phosphate Esters
11-14 Reactions of Alkoxides
Problem 11-33
Problem 11-34
Problem 11-35
Problem 11-36
Problem-Solving Strategy Multistep Synthesis
Sample Problem
Problem 11-37
Problem 11-38
Summary Reactions of Alcohols
Summary Reactions of Alcohols: O―H Cleavage
Summary Reactions of Alcohols: C―O Cleavage
Essential Terms
Essential Problem-Solving Skills in Chapter 11
Study Problems
12 Infrared Spectroscopy and Mass Spectrometry
Goals for Chapter 12
12-1 Introduction
12-2 The Electromagnetic Spectrum
12-3 The Infrared Region
Problem 12-1
12-4 Molecular Vibrations
12-5 IR-Active and IR-Inactive Vibrations
Problem 12-2
12-6 Measurement of the IR Spectrum
12-7 Infrared Spectroscopy of Hydrocarbons
12-7A Carbon–Carbon Bond Stretching
12-7B Carbon–Hydrogen Bond Stretching
12-7C Interpreting the IR Spectra of Hydrocarbons
Problem 12-3
12-8 Characteristic Absorptions of Alcohols and Amines
12-9 Characteristic Absorptions of Carbonyl Compounds
12-9A Simple Ketones, Aldehydes, and Acids
SOLUTION
Problem 12-4
12-9B Resonance Lowering of Carbonyl Frequencies
12-9C Carbonyl Absorptions Above 1725 cm-1
12-10 Characteristic Absorptions of C―N Bonds
Problem 12-5
12-11 Simplified Summary of IR Stretching Frequencies
12-12 Reading and Interpreting IR Spectra (Solved Problems)
12-13 Introduction to Mass Spectrometry
12-13A The Mass Spectrometer
Electron Impact Ionization
Separation of Ions of Different Masses
12-13B The Mass Spectrum
12-13C Mass Spectrometry of Mixtures: The GC–MS
12-14 Determination of the Molecular Formula by Mass Spectrometry
12-14A High-Resolution Mass Spectrometry
12-14B Use of Heavier Isotope Peaks
Problem 12-7
12-15 Fragmentation Patterns in Mass Spectrometry
12-15A Mass Spectra of Alkanes
Problem 12-8
Problem 12-9
12-15B Fragmentation Giving Resonance-Stabilized Cations
Problem 12-10
12-15C Fragmentation Splitting Out a Small Molecule; Mass Spectra of Alcohols
Problem 12-11
Summary Common Fragmentation Patterns
Essential Terms
Essential Problem-Solving Skills in Chapter 12
Study Problems
13 Nuclear Magnetic Resonance Spectroscopy
Goals for Chapter 13
13-1 Introduction
13-2 Theory of Nuclear Magnetic Resonance
SOLUTION
13-3 Magnetic Shielding by Electrons
13-4 The NMR Spectrometer
13-5 The Chemical Shift
13-5A Measurement of Chemical Shifts
SOLUTION
Problem 13-1
13-5B Characteristic Values of Chemical Shifts
SOLUTION
13-6 The Number of Signals
Problem 13-3
Problem 13-4
13-7 Areas of the Peaks
Problem 13-5
Problem 13-6
13-8 Spin-Spin Splitting
13-8A Theory of Spin-Spin Splitting
13-8B The N + 1 Rule
13-8C The Range of Magnetic Coupling
Problem-Solving Strategy Drawing an NMR Spectrum
Problem 13-7
13-8D Coupling Constants
Problem 13-8
Problem 13-9
Problem 13-10
Problem 13-11
13-9 Complex Splitting
Problem 13-12
Problem 13-13
Problem 13-14
Problem 13-15
13-10 Stereochemical Nonequivalence of Protons
Problem 13-16
*Problem 13-17
*Problem 13-18
13-11 Time Dependence of NMR Spectroscopy
13-11A Conformational Changes
13-11B Fast Proton Transfers
Hydroxy Protons
Problem 13-19
N ― H Protons
Problem 13-20
Problem 13-21
Problem-Solving Strategy Interpreting Proton NMR Spectra
Problem 13-22
SOLUTION
Problem 13-23
Problem 13-24
13-12 Carbon-13 NMR Spectroscopy
13-12A Sensitivity of Carbon NMR
13-12B Fourier Transform NMR Spectroscopy
13-12C Carbon Chemical Shifts
13-12D Important Differences Between Proton and Carbon Techniques
Operating Frequency
Peak Areas
13-12E Spin-Spin Splitting
Proton Spin Decoupling
Problem 13-25
Off-Resonance Decoupling
Problem 13-26
Problem 13-27
13-12F DEPT 13C NMR
Problem 13-28
13-13 Interpreting Carbon NMR Spectra
Problem 13-29
Problem 13-30
Problem 13-31
13-14 Nuclear Magnetic Resonance Imaging
Problem-Solving Strategy Spectroscopy Problems
Problem 13-32 (PARTIALLY SOLVED)
Essential Terms
Essential Problem-Solving Skills in Chapter 13
Study Problems
14 Ethers, Epoxides, and Thioethers
Goals for Chapter 14
14-1 Introduction
14-2 Physical Properties of Ethers
14-2A Structure and Polarity of Ethers
14-2B Boiling Points of Ethers; Hydrogen Bonding
14-2C Ethers as Polar Solvents
Problem 14-1
14-2D Stable Complexes of Ethers with Reagents
Complexes with Electrophiles
Problem 14-2
Crown Ether Complexes
Problem 14-3
14-3 Nomenclature of Ethers
14-3A Common Names (Alkyl Alkyl Ether Names)
14-3B IUPAC Names (Alkoxy Alkane Names)
Problem 14-4
14-3C Nomenclature of Cyclic Ethers
Epoxides (Oxiranes)
Oxetanes
Furans (Oxolanes)
Pyrans (Oxanes)
Dioxanes
Problem 14-5
Problem 14-6
14-4 Spectroscopy of Ethers
14-5 The Williamson Ether Synthesis
SOLUTION
Problem 14-8
14-6 Synthesis of Ethers by Alkoxymercuration–Demercuration
Problem 14-10
14-7 Industrial Synthesis: Bimolecular Condensation of Alcohols
Problem 14-11
Problem 14-12
Problem 14-13
Summary Syntheses of Ethers (Review)
14-8 Cleavage of Ethers by HBr and HI
Problem 14-14
14-9 Autoxidation of Ethers
Summary Reactions of Ethers
14-10 Thioethers (Sulfides) and Silyl Ethers
14-10A Thioethers (Sulfides)
Problem 14-17
Problem 14-18
14-10B Silyl Ethers as Alcohol-Protecting Groups
Problem 14-19
14-11 Synthesis of Epoxides
14-11A Peroxyacid Epoxidation
14-11B Base-Promoted Cyclization of Halohydrins
Problem 14-20
Problem 14-21
Summary Epoxide Syntheses
14-12 Acid-Catalyzed Ring Opening of Epoxides
14-13 Base-Catalyzed Ring Opening of Epoxides
Problem 14-25
Problem 14-26
14-14 Orientation of Epoxide Ring Opening
Summary Orientation of Epoxide Ring Opening
SOLUTION
Problem 14-27
14-15 Reactions of Epoxides with Grignard and Organolithium Reagents
Problem 14-28
14-16 Epoxy Resins: The Advent of Modern Glues
Summary Reactions of Epoxides
Essential Terms
Essential Problem-Solving Skills in Chapter 14
Study Problems
15 Conjugated Systems, Orbital Symmetry, and Ultraviolet Spectroscopy
Goals for Chapter 15
15-1 Introduction
15-2 Stabilities of Dienes
Problem 15-1
Problem 15-2
Problem 15-3
15-3 Molecular Orbital Picture of a Conjugated System
15-3A Structure and Bonding of Buta-1,3-diene
15-3B Constructing the Molecular Orbitals of Buta-1,3-diene
15-4 Allylic Cations
Problem 15-4
Problem 15-5
15-5 1,2- and 1,4-Addition to Conjugated Dienes
Problem 15-6
Problem 15-7
15-6 Kinetic Versus Thermodynamic Control in the Addition of HBr to Buta-1,3-diene
15-7 Allylic Radicals
15-8 Molecular Orbitals of the Allylic System
15-9 Electronic Configurations of the Allyl Radical, Cation, and Anion
Problem 15-12
15-10 SN2 Displacement Reactions of Allylic Halides and Tosylates
Problem 15-13
15-11 The Diels–Alder Reaction
Problem 15-14
Problem 15-15
15-11A Stereochemical Requirements of the Diels–Alder Transition State
s-cis Conformation of the Diene
syn Stereochemistry
The Endo Rule
SOLUTION
Problem 15-16
15-11B Diels–Alder Reactions Using Unsymmetrical Reagents
SOLUTION
Problem 15-17
Problem 15-18
15-12 The Diels–Alder as an Example of a Pericyclic Reaction
15-12A Conservation of Orbital Symmetry in the Diels–Alder Reaction
15-12B The “Forbidden” [2 + 2] Cycloaddition
15-12C Photochemical Induction of Cycloadditions
Problem 15-19
Problem 15-20
15-13 Ultraviolet Absorption Spectroscopy
15-13A Spectral Region
15-13B Ultraviolet Light and Electronic Transitions
15-13C Obtaining an Ultraviolet Spectrum
Problem 15-21
15-13D Interpreting UV–Visible Spectra
SOLUTION
Problem 15-22
15-14 Colored Organic Compounds
Problem 15-23
15-15 UV-Visible Analysis in Biology and Medicine
Essential Terms
Essential Problem-Solving Skills in Chapter 15
Study Problems
16 Aromatic Compounds
Goals for Chapter 16
16-1 Introduction: The Discovery of Benzene
16-2 The Structure and Properties of Benzene
16-3 The Molecular Orbitals of Benzene
16-4 The Molecular Orbital Picture of Cyclobutadiene
16-5 Aromatic, Antiaromatic, and Nonaromatic Compounds
16-6 Hückel’s Rule
Problem 16-6
16-7 Molecular Orbital Derivation of Hückel’s Rule
Problem 16-9
16-8 Aromatic Ions
16-8A The Cyclopentadienyl Ions
Problem 16-10
Problem 16-11
16-8B The Cycloheptatrienyl Ions
16-8C The Cyclooctatetraene Dianion
Problem 16-12
Problem 16-13
Problem 16-14
Problem 16-15
16-8D Summary of Annulenes and Their Ions
16-9 Heterocyclic Aromatic Compounds
16-9A Pyridine
16-9B Pyrrole
Problem 16-16
16-9C Pyrimidine and Imidazole
Problem 16-17
Problem 16-18
16-9D Furan and Thiophene
Problem 16-19
Problem 16-20
16-10 Polynuclear Aromatic Hydrocarbons
16-11 Aromatic Allotropes of Carbon
16-11A Allotropes of Carbon: Diamond
16-11B Graphite
16-11C Fullerenes
16-12 Fused Heterocyclic Compounds
Problem 16-22
16-13 Nomenclature of Benzene Derivatives
Problem 16-23
Problem 16-24
16-14 Physical Properties of Benzene and Its Derivatives
16-15 Spectroscopy of Aromatic Compounds
Essential Terms
Essential Problem-Solving Skills in Chapter 16
Study Problems
17 Reactions of Aromatic Compounds
Goals for Chapter 17
17-1 Electrophilic Aromatic Substitution
Problem 17-1
17-2 Halogenation of Benzene
17-3 Nitration of Benzene
Problem 17-3
17-4 Sulfonation of Benzene
Problem 17-4
17-5 Nitration of Toluene: The Effect of Alkyl Substitution
17-6 Activating, Ortho, Para-Directing Substituents
17-6A Alkyl Groups
Problem 17-5
Problem 17-6
17-6B Substituents with Nonbonding Electrons
Alkoxy Groups
Problem 17-7
Amine Groups
Problem 17-8
Problem 17-9
17-7 Deactivating, Meta-Directing Substituents
Summary Deactivating, Meta-Directors
Problem 17-10
17-8 Halogen Substituents: Deactivating, but Ortho, Para-Directing
Problem 17-11
Summary Directing Effects of Substituents
17-9 Effects of Multiple Substituents on Electrophilic Aromatic Substitution
Problem 17-12
SOLUTION
Problem 17-13
Problem 17-14
17-10 The Friedel–Crafts Alkylation
Problem 17-15
Problem 17-16
17-11 The Friedel–Crafts Acylation
17-11A Mechanism of Acylation
Summary Comparison of Friedel–Crafts Alkylation and Acylation
17-11B The Clemmensen Reduction: Synthesis of Alkylbenzenes
17-11C The Gatterman–Koch Formylation: Synthesis of Benzaldehydes
Problem 17-20
17-12 Nucleophilic Aromatic Substitution
17-12A The Addition–Elimination Mechanism
Problem 17-21
17-12B The Benzyne Mechanism: Elimination–Addition
Problem 17-22
Problem 17-23
Problem 17-24
17-13 Aromatic Substitutions Using Organometallic Reagents
17-13A Couplings Using Organocuprate Reagents
Problem 17-25
Problem 17-26
17-13B The Heck Reaction
Problem 17-27
Problem 17-28
17-13C The Suzuki Reaction (Suzuki Coupling)
Problem 17-29
Problem 17-30
17-14 Addition Reactions of Benzene Derivatives
17-14A Chlorination
17-14B Catalytic Hydrogenation of Aromatic Rings
17-14C Birch Reduction
Problem 17-31
Problem 17-32
17-15 Side-Chain Reactions of Benzene Derivatives
17-15A Permanganate Oxidation
Problem 17-33
17-15B Side-Chain Halogenation
Problem 17-34
Problem 17-35
Problem 17-36
17-15C Nucleophilic Substitution at the Benzylic Position
First-Order Reactions
Problem 17-37
Second-Order Reactions
Problem 17-38
Problem 17-39
17-16 Reactions of Phenols
17-16A Oxidation of Phenols to Quinones
Problem 17-40
17-16B Electrophilic Aromatic Substitution of Phenols
Problem 17-41
Problem 17-42
Problem-Solving Strategy Synthesis Using Electrophilic Aromatic Substitution
Problem 17-43
Problem 17-44
Problem 17-45
Problem 17-46
Problem 17-47
Problem 17-48
Problem 17-49
Summary Reactions of Aromatic Compounds
Summary Electrophilic Aromatic Substitution of Benzene
Summary Substitutions of Aryl Halides
Essential Terms
Essential Problem-Solving Skills in Chapter 17
Study Problems
18 Ketones and Aldehydes
Goals for Chapter 18
18-1 Carbonyl Compounds
18-2 Structure of the Carbonyl Group
18-3 Nomenclature of Ketones and Aldehydes
18-4 Physical Properties of Ketones and Aldehydes
18-5 Spectroscopy of Ketones and Aldehydes
18-5A Infrared Spectra of Ketones and Aldehydes
18-5B Proton NMR Spectra of Ketones and Aldehydes
18-5C Carbon NMR Spectra of Ketones and Aldehydes
18-5D Mass Spectra of Ketones and Aldehydes
Problem 18-2
McLafferty Rearrangement of Ketones and Aldehydes
Problem 18-3
Problem 18-4
18-5E Ultraviolet Spectra of Ketones and Aldehydes
The π→π* Transition
The n→π* Transition
Problem 18-5
18-6 Industrial Importance of Ketones and Aldehydes
18-7 Review of Syntheses of Ketones and Aldehydes
18-7A Ketones and Aldehydes from Oxidation of Alcohols (Section 11-2)
18-7B Ketones and Aldehydes from Ozonolysis of Alkenes (Section 8-15B)
18-7C Phenyl Ketones and Aldehydes: Friedel–Crafts Acylation (Section 17-11)
18-7D Ketones and Aldehydes from Hydration of Alkynes (Section 9-9F)
Catalyzed by Acid and Mercuric Salts
Hydroboration–Oxidation of Alkynes
SOLUTION
Problem 18-6
18-8 Synthesis of Ketones from Carboxylic Acids
Problem 18-7
18-9 Synthesis of Ketones and Aldehydes from Nitriles
Problem 18-8
Problem 18-9
18-10 Synthesis of Aldehydes and Ketones from Acid Chlorides and Esters
Problem 18-10
Summary Syntheses of Ketones and Aldehydes
18-11 Reactions of Ketones and Aldehydes: Introduction to Nucleophilic Addition
Problem 18-11
Problem 18-12
18-12 Hydration of Ketones and Aldehydes
Problem 18-13
Problem 18-14
18-13 Formation of Cyanohydrins
Problem 18-15
Problem 18-16
18-14 Formation of Imines
Problem 18-17
Problem 18-18
Problem 18-19
Problem 18-20
18-15 Condensations with Hydroxylamine and Hydrazines
Summary Condensations of Amines with Ketones and Aldehydes
Problem 18-21
Problem 18-22
Problem 18-23
18-16 Formation of Acetals
Problem 18-24
18-17 Use of Acetals as Protecting Groups
18-18 The Wittig Reaction
Problem 18-30
Problem 18-31
18-19 Oxidation of Aldehydes
Problem 18-34
18-20 Reductions of Ketones and Aldehydes
18-20A Hydride Reductions (Review)
18-20B Catalytic Hydrogenation
18-20C Deoxygenation of Ketones and Aldehydes
Clemmensen Reduction (Review)
Wolff–Kishner Reduction
Problem 18-35
Problem 18-36
Summary Reactions of Ketones and Aldehydes
Summary Nucleophilic Addition Reactions of Aldehydes and Ketones
Essential Terms
Essential Problem-Solving Skills in Chapter 18
Study Problems
19 Amines
Goals for Chapter 19
19-1 Introduction
19-2 Nomenclature of Amines
19-2A Common Names
Problem 19-1
19-2B IUPAC Names
Problem 19-2
Problem 19-3
19-3 Structure of Amines
Problem 19-4
19-4 Physical Properties of Amines
Problem 19-5
19-5 Basicity of Amines
19-6 Factors that Affect Amine Basicity
19-7 Salts of Amines
19-8 Spectroscopy of Amines
19-8A Infrared Spectroscopy
Problem 19-7
19-8B Proton NMR Spectroscopy
19-8C Carbon NMR Spectroscopy
Problem 19-8
Problem 19-9
19-8D Mass Spectrometry
Problem 19-10
19-9 Reactions of Amines with Ketones and Aldehydes (Review)
19-10 Aromatic Substitution of Arylamines and Pyridine
19-10A Electrophilic Aromatic Substitution of Arylamines
19-10B Electrophilic Aromatic Substitution of Pyridine
Problem 19-11
Problem 19-12
19-10C Nucleophilic Aromatic Substitution of Pyridine
Problem 19-13
Problem 19-14
19-11 Alkylation of Amines by Alkyl Halides
Problem 19-15
Problem 19-16
19-12 Acylation of Amines by Acid Chlorides
SOLUTION
Problem 19-17
19-13 Formation of Sulfonamides
Problem 19-18
Problem 19-19
19-14 Amines as Leaving Groups: The Hofmann Elimination
SOLUTION
Problem 19-20
19-15 Oxidation of Amines; The Cope Elimination
SOLUTION
Problem 19-21
Problem 19-22
19-16 Reactions of Amines with Nitrous Acid
19-17 Reactions of Arenediazonium Salts
19-18 Synthesis of Amines by Reductive Amination
19-19 Synthesis of Amines by Acylation–Reduction
SOLUTION
Problem 19-27
19-20 Syntheses Limited to Primary Amines
19-20A Direct Alkylation and Gabriel Synthesis
Problem 19-28
Problem 19-29
19-20B Reduction of Azides and Nitriles
Formation and Reduction of Azides
Formation and Reduction of Nitriles
Problem 19-30
19-20C Reduction of Nitro Compounds
Problem 19-31
Summary
Essential Terms
Essential Problem-Solving Skills in Chapter 19
Study Problems
20 Carboxylic Acids
Goals for Chapter 20
20-1 Introduction
20-2 Nomenclature of Carboxylic Acids
20-2A Common Names
20-2B IUPAC Names
20-2C Nomenclature of Dicarboxylic Acids
Common Names of Dicarboxylic Acids
IUPAC Names of Dicarboxylic Acids
Problem 20-1
Problem 20-2
20-3 Structure and Physical Properties of Carboxylic Acids
20-4 Acidity of Carboxylic Acids
20-4A Measurement of Acidity
20-4B Substituent Effects on Acidity
Problem 20-3
20-5 Salts of Carboxylic Acids
20-6 Commercial Sources of Carboxylic Acids
20-7 Spectroscopy of Carboxylic Acids
20-7A Infrared Spectroscopy
Problem 20-7
20-7B NMR Spectroscopy
Problem 20-8
20-7C Ultraviolet Spectroscopy
20-7D Mass Spectrometry
Problem 20-9
Problem 20-10
20-8 Synthesis of Carboxylic Acids
20-8A Review of Previous Syntheses
20-8B Carboxylation of Grignard Reagents
20-8C Formation and Hydrolysis of Nitriles
Problem 20-11
Summary
20-9 Reactions of Carboxylic Acids and Derivatives; Nucleophilic Acyl Substitution
20-10 Condensation of Acids with Alcohols: The Fischer Esterification
Problem 20-12
Problem 20-13
Problem 20-14
Problem 20-15
Problem 20-16
SOLUTION
Problem 20-17
20-11 Esterification Using Diazomethane
20-12 Condensation of Acids with Amines: Direct Synthesis of Amides
Problem 20-18
20-13 Reduction of Carboxylic Acids
20-14 Alkylation of Carboxylic Acids to Form Ketones
Problem 20-20
Problem 20-21
20-15 Synthesis and Use of Acid Chlorides
*Problem 20-22
Problem 20-23
Problem 20-24
Summary
Summary
Essential Terms
Essential Problem-Solving Skills in Chapter 20
Study Problems
21 Carboxylic Acid Derivatives
Goals for Chapter 21
21-1 Introduction
21-2 Structure and Nomenclature of Acid Derivatives
21-2A Esters of Carboxylic Acids
Lactones
21-2B Amides
Lactams
21-2C Nitriles
21-2D Acid Halides
21-2E Acid Anhydrides
21-2F Nomenclature of Multifunctional Compounds
Problem 21-1
21-3 Physical Properties of Carboxylic Acid Derivatives
21-3A Boiling Points and Melting Points
21-3B Solubility
21-4 Spectroscopy of Carboxylic Acid Derivatives
21-4A Infrared Spectroscopy
Esters
Problem 21-2
Problem 21-3
Amides
Lactones and Lactams
Nitriles
Acid Halides and Anhydrides
Problem 21-4
21-4B NMR Spectroscopy
Proton NMR
Carbon NMR
Problem 21-5
21-5 Interconversion of Acid Derivatives by Nucleophilic Acyl Substitution
21-5A Reactivity of Acid Derivatives
21-5B Favorable Interconversions of Acid Derivatives
Problem 21-6
21-5C Leaving Groups in Nucleophilic Acyl Substitutions
Problem 21-7
Problem 21-8
Problem 21-9
Problem 21-10
Problem 21-11
21-6 Transesterification
Problem-Solving Strategy Proposing Reaction Mechanisms
Base-Catalyzed Transesterification
Problem 21-12
Acid-Catalyzed Transesterification
Problem 21-13
Problem 21-14
Problem 21-15
21-7 Hydrolysis of Carboxylic Acid Derivatives
21-7A Hydrolysis of Acid Halides and Anhydrides
21-7B Hydrolysis of Esters
Problem 21-16
Problem 21-17
Problem 21-18
21-7C Hydrolysis of Amides
Problem 21-19
Problem 21-20
Problem 21-21
21-7D Hydrolysis of Nitriles
Problem 21-22
Problem 21-23
21-8 Reduction of Acid Derivatives
21-8A Reduction to Alcohols
21-8B Reduction to Aldehydes
21-8C Reduction to Amines
Problem 21-25
21-9 Reactions of Acid Derivatives with Organometallic Reagents
21-10 Summary of the Chemistry of Acid Chlorides
21-11 Summary of the Chemistry of Anhydrides
21-12 Summary of the Chemistry of Esters
21-13 Summary of the Chemistry of Amides
21-14 Summary of the Chemistry of Nitriles
21-15 Thioesters
21-16 Esters and Amides of Carbonic Acid
Problem 21-40
Problem 21-41
Essential Terms
Essential Problem-Solving Skills in Chapter 21
Study Problems
22 Condensations and Alpha Substitutions of Carbonyl Compounds
Goals for Chapter 22
22-1 Introduction
22-2 Enols and Enolate Ions
22-2A Keto–Enol Tautomerism
Problem 22-1
Problem 22-2
22-2B Formation and Stability of Enolate Ions
Problem 22-3
22-3 Alkylation of Enolate Ions
Problem 22-4
Problem 22-5
22-4 Formation and Alkylation of Enamines
Problem 22-6
Problem 22-7
Problem 22-8
Problem 22-9
22-5 Alpha Halogenation of Ketones
22-5A Base-Promoted α Halogenation
SOLUTION
Problem 22-10
Multiple Halogenation
Problem 22-11
22-5B The Haloform Reaction
Problem 22-12
Problem 22-13
Problem 22-14
22-5C Acid-Catalyzed Alpha Halogenation
SOLUTION
Problem 22-15
Problem 22-16
22-6 Alpha Bromination of Acids: The HVZ Reaction
Problem 22-17
22-7 The Aldol Condensation of Ketones and Aldehydes
22-7A Base-Catalyzed Aldol Condensations
SOLUTION
Problem 22-18
Problem 22-19
Problem 22-20
22-7B Acid-Catalyzed Aldol Condensations
Problem 22-21
22-8 Dehydration of Aldol Products
Problem 22-22
Problem 22-23
Problem 22-24
22-9 Crossed Aldol Condensations
Problem 22-25
Problem 22-26
Problem 22-27
Problem 22-28
Problem 22-29
22-10 Aldol Cyclizations
Problem 22-30
Problem 22-31
22-11 Planning Syntheses Using Aldol Condensations
Problem 22-32
Problem 22-33
22-12 The Claisen Ester Condensation
SOLUTION
Problem 22-34
Problem 22-35
Problem 22-36
SOLUTION
Problem 22-37
Problem 22-38
22-13 The Dieckmann Condensation: A Claisen Cyclization
Problem 22-39
Problem 22-40
22-14 Crossed Claisen Condensations
Problem 22-41
Problem 22-42
SOLUTION
Problem 22-43
Problem 22-44
Problem 22-45
22-15 Syntheses Using β-Dicarbonyl Compounds
22-16 The Malonic Ester Synthesis
SOLUTION
Problem 22-47
Problem 22-48
22-17 The Acetoacetic Ester Synthesis
SOLUTION
Problem 22-49
Problem 22-50
Problem 22-51
22-18 Conjugate Additions: The Michael Reaction
SOLUTION
Problem 22-52
Problem 22-53
Problem 22-54
Problem 22-55
Problem 22-56
22-19 The Robinson Annulation
Problem 22-57
Problem 22-58
Problem 22-59
Summary
Essential Terms
Essential Problem-Solving Skills in Chapter 22
Study Problems
23 Carbohydrates and Nucleic Acids
Goals for Chapter 23
23-1 Introduction
23-2 Classification of Carbohydrates
Problem 23-1
23-3 Monosaccharides
23-3A Classification of Monosaccharides
Problem 23-2
Problem 23-3
23-3B The d and l Configurations of Sugars
Problem 23-4
Problem 23-5
23-3C Epimers
Problem 23-6
23-4 Cyclic Structures of Monosaccharides
23-5 Anomers of Monosaccharides; Mutarotation
Problem 23-12
23-6 Reactions of Monosaccharides: Reduction
Problem 23-14
Problem 23-15
23-7 Oxidation of Monosaccharides; Reducing Sugars
23-8 Nonreducing Sugars: Formation of Glycosides
Problem 23-20
Problem 23-21
23-9 Ether and Ester Formation
Problem 23-25
Problem 23-26
Problem 23-27
23-10 Chain Shortening: The Ruff Degradation
Problem 23-29
Problem 23-30
Problem 23-31
23-11 Chain Lengthening: The Kiliani–Fischer Synthesis
Problem 23-32
Problem 23-33
Problem 23-34
Problem 23-35
Summary Reactions of Sugars
23-12 Disaccharides
23-12A The 1,4′ Linkage: Cellobiose, Maltose, and Lactose
Cellobiose: A β-1,4′ Glucosidic Linkage
Maltose: An α-1,4′ Glucosidic Linkage
Problem 23-36
Problem 23-37
Lactose: A β-1,4′ Galactosidic Linkage
Problem 23-38
23-12B The 1,6′ Linkage: Gentiobiose
Problem 23-39
23-12C Linkage of Two Anomeric Carbons: Sucrose
SOLUTION
Problem 23-40
Problem 23-41
23-13 Polysaccharides
23-13A Cellulose
Problem 23-42
23-13B Starches: Amylose, Amylopectin, and Glycogen
Amylose
Amylopectin
Glycogen
23-13C Chitin: A Polymer of N-Acetylglucosamine
23-14 Nucleic Acids: Introduction
23-15 Ribonucleosides and Ribonucleotides
Problem 23-43
Problem 23-44
23-16 The Structures of RNA and DNA
23-16A The Structure of Ribonucleic Acid
23-16B Deoxyribose and the Structure of Deoxyribonucleic Acid
23-16C Base Pairing
Problem 23-45
23-16D The Double Helix of DNA
23-17 Additional Functions of Nucleotides
Essential Terms
Essential Problem-Solving Skills in Chapter 23
Study Problems
24 Amino Acids, Peptides, and Proteins
Goals for Chapter 24
24-1 Introduction
24-2 Structure and Stereochemistry of the α−Amino Acids
24-2A The Standard Amino Acids of Proteins
Problem 24-1
Problem 24-2
24-2B Essential Amino Acids
Problem 24-3
24-2C Rare and Unusual Amino Acids
24-3 Acid–Base Properties of Amino Acids
24-4 Isoelectric Points and Electrophoresis
Problem 24-4
Problem 24-5
Problem 24-6
Problem 24-7
Problem 24-8
24-5 Synthesis of Amino Acids
24-5A Reductive Amination
Problem 24-9
24-5B Amination of an α−Halo Acid
Problem 24-10
24-5C The Strecker Synthesis
SOLUTION
Problem 24-11
Problem 24-12
Summary Syntheses of Amino Acids
24-6 Resolution of Amino Acids
Problem 24-13
24-7 Reactions of Amino Acids
24-7A Esterification of the Carboxyl Group
Problem 24-14
Problem 24-15
24-7B Acylation of the Amino Group: Formation of Amides
Problem 24-16
24-7C Reaction with Ninhydrin
Problem 24-17
Summary Reactions of Amino Acids
24-8 Structure and Nomenclature of Peptides and Proteins
24-8A Peptide Structure
24-8B Peptide Nomenclature
Problem 24-18
24-8C Disulfide Linkages
24-9 Peptide Structure Determination
24-9A Cleavage of Disulfide Linkages
24-9B Determination of the Amino Acid Composition
Sequencing the Peptide: Terminal Residue Analysis
24-9C Sequencing from the N Terminus: The Edman Degradation
Problem 24-19
Problem 24-20
Problem 24-21
24-9D C-Terminal Residue Analysis
24-9E Breaking the Peptide into Shorter Chains: Partial Hydrolysis
Problem 24-22
Problem 24-23
24-10 Laboratory Peptide Synthesis
24-10A The Individual Reactions
Attaching the Peptide to the Solid Support
Using the 9-Fluorenylmethoxycarbonyl (Fmoc) Protecting Group
Use of DCC as a Peptide Coupling Agent
Problem 24-24
24-10B An Example of Solid-Phase Peptide Synthesis
24-11 Classification of Proteins
24-12 Levels of Protein Structure
24-12A Primary Structure
24-12B Secondary Structure
24-12C Tertiary Structure
24-12D Quaternary Structure
24-13 Protein Denaturation
24-13A Reversible and Irreversible Denaturation
24-13B Prion Diseases
Essential Terms
Essential Problem-Solving Skills in Chapter 24
Study Problems
25 Lipids
Goals for Chapter 25
25-1 Introduction
25-2 Waxes
25-3 Triglycerides
Problem 25-1
25-3A Hydrogenation of Triglycerides; Trans Fats
Problem 25-2
25-3B Transesterification of Fats and Oils to Biodiesel
Problem 25-3
25-4 Saponification of Fats and Oils: Soaps and Detergents
Problem 25-4
Problem 25-5
Problem 25-6
Problem 25-7
25-5 Phospholipids
Problem 25-8
25-6 Steroids
Problem 25-9
Problem 25-10
25-7 Prostaglandins
25-8 Terpenes
25-8A Characteristics and Nomenclature of Terpenes
Problem 25-11
25-8B Classification of Terpenes
Problem 25-12
Problem 25-13
25-8C Terpenoids
Essential Terms
Essential Problem-Solving Skills in Chapter 25
Study Problems
26 Synthetic Polymers
Goals for Chapter 26
26-1 Introduction
26-2 Chain-Growth Polymers
26-2A Free-Radical Polymerization
Problem 26-1
Problem 26-2
Chain Branching by Hydrogen Abstraction
Problem 26-3
26-2B Cationic Polymerization
Problem 26-4
Problem 26-5
Problem 26-6
26-2C Anionic Polymerization
Problem 26-7
Problem 26-8
Problem 26-9
26-3 Stereochemistry of Polymers
Problem 26-10
26-4 Stereochemical Control of Polymerization: Ziegler–Natta Catalysts
26-5 Natural and Synthetic Rubbers
26-6 Copolymers of Two or More Monomers
Problem 26-12
26-7 Step-Growth Polymers
26-7A Polyamides: Nylon
Problem 26-13
26-7B Polyesters
Problem 26-14
Problem 26-15
26-7C Polycarbonates
Problem 26-16
Problem 26-17
26-7D Polyurethanes
Problem 26-18
Problem 26-19
Problem 26-20
26-8 Polymer Structure and Properties
26-8A Polymer Crystallinity
26-8B Thermal Properties
26-8C Plasticizers
26-9 Recycling of Plastics
Essential Terms
Essential Problem-Solving Skills in Chapter 26
Study Problems
Appendices
Answers to Selected Problems
Photo Credits
Index
Numbered
A
B
C
D
E
F
G
H
I
J
K
L
M
N
O
P
Q
R
S
T
U
V
W
X
Y
Z
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Test Bank for Organic Chemistry, 9th Edition, Leroy G. Wade, ISBN-10: 032197137X, ISBN-13: 9780321971371

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