Student s Study Guide and Solutions Manual for Organic Chemistry 8th Edition by Paula Yurkanis Bruice ISBN 9780134066585 0134066588

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ISBN 10: 0134066588
ISBN 13: 9780134066585
Author: Paula Yurkanis Bruice

Student s Study Guide and Solutions Manual for Organic Chemistry 8th Edition Table of contents:

PART ONEAn Introduction to the Study of Organic Chemistry

1 Remembering General Chemistry: Electronic Structure and Bonding

1.1 The Structure of an Atom

Problem 1 ♦

Problem 2 ♦

Problem 3 ♦

1.2 How the Electrons in an Atom are Distributed

Ground-State Electronic Configuration

Valence and Core Electrons

Problem 4 ♦

Problem 5 ♦

Problem 6

1.3 Covalent Bonds

Achieving a Filled Outer Shell by Losing or Gaining Electrons

Problem 7 ♦

Achieving a Filled Outer Shell by Sharing Electrons

Nonpolar and Polar Covalent Bonds

Problem 8 ♦

Problem 9 ♦

Dipole Moments of Bonds

Problem 10 Solved

Problem 11 ♦

Problem 12 Solved

Solution

Problem 13

Electrostatic Potential Maps

Problem 14 ♦

1.4 How the Structure of a Compound is Represented

Lewis Structures

Lone-Pair Electrons

Formal Charge

Problem 15 ♦

Drawing Lewis Structures

Problem 16

Problem-Solving Strategy Drawing Lewis Structures

Problem 17 Solved

Solution to 17 a.

Solution to 17 b.

Problem 18 ♦

Kekulé Structures

Condensed Structures

Problem 19 ♦

Problem 20 ♦

Problem 21 ♦

Problem 22

Skeletal Structures

Problem 23

1.5 Atomic Orbitals

s Atomic Orbitals

p Atomic Orbitals

Problem 24

1.6 An Introduction to Molecular Orbital Theory

Forming a sigma (σ) Bond

Bonding and Antibonding Molecular Orbitals

Problem 25 ♦

Forming a pi (π) Bond

The VSEPR Model

Problem 26 ♦

1.7 How Single Bonds are Formed in Organic Compounds

The Bonds in Methane

Hybrid Orbitals

Tetrahedral Carbon; Tetrahedral Bond Angle

The Bonds in Ethane

Problem 27 ♦

Problem 28

1.8 How a Double Bond is Formed: The Bonds in Ethene

Problem 29 Solved

Solution

1.9 How a Triple Bond is Formed: The Bonds in Ethyne

Problem 30

Problem 31 Solved

Solution to 31 a.

Solution to 31 b.

Problem 32

1.10 The Bonds in the Methyl Cation, the Methyl Radical, and the Methyl Anion

The Methyl Cation (C+H3)

The Methyl Radical (⋅CH3)

The Methyl Anion (:¯CH3)

1.11 The Bonds in Ammonia and in the Ammonium Ion

Problem 33 ♦

Problem 34 ♦

1.12 The Bonds in Water

Problem 35 ♦

Problem 36 Solved

Solution

1.13 The Bond in a Hydrogen Halide

Problem 37 ♦

Problem 38

1.14 Hybridization and Molecular Geometry

Problem-Solving Strategy Predicting the Orbitals and Bond Angles Used in Bonding

Problem 39

1.15 Summary: Hybridization, Bond Lengths, Bond Strengths, and Bond Angles

Bond Order

Hybridization

Problem 40 Solved

Solution

Bond Length and Bond Strength

Hybridization Affects Bond Length and Bond Strength

Hybridization Affects Bond Angles

Problem 41 ♦

Problem 42 ♦

Problem 43

Problem 44

Problem-Solving Strategy Predicting Bond Angles

Problem 45 ♦

1.16 Dipole Moments of Molecules

Problem 46 ♦

Problem 47

Problem 48 ♦

Essential Concepts

Glossary

Problems

2 Acids and Bases: Central to Understanding Organic Chemistry

2.1 An Introduction to Acids and Bases

Problem 1 ♦

Problem 2 ♦

Problem 3 ♦

Problem 4 ♦

2.2 pKa and pH

Defining Keq

Defining Ka

Defining pKa

Defining pH

Problem 5 ♦

Problem 6 ♦

Problem-Solving Strategy

Problem 7

Problem 8

Problem 9 ♦

2.3 Organic Acids and Bases

Carboxylic Acids

Alcohols

Amines

Protonated Compounds

Alcohols, Carboxylic Acids, and Amines are Acids and Bases

Problem 10 ♦

Problem 11

Problem 12 ♦

Problem-Solving Strategy Determining the Most Basic Atom in a Compound

Problem 13 ♦

Problem 14 ♦

2.4 How to Predict the Outcome of an Acid–Base Reaction

2.5 How to Determine the Position of Equilibrium

Problem 16

Problem 17

Problem 18 ♦

Problem 19 ♦

2.6 How the Structure of an Acid Affects its pKa Value

Electronegativity

Problem 20 ♦

Hybridization

Problem 21 ♦

Problem 22 ♦

Problem 23

Problem 24

Size

Problem 25 ♦

Problem 26 ♦

Problem 27 ♦

Problem 28 ♦

Problem 29 ♦

2.7 How Substituents Affect the Strength of an Acid

Problem-Solving Strategy Determining Relative Acid Strength

Problem 30 ♦

Problem 31 ♦

Problem 32 ♦

Problem 33 Solved

Solution

2.8 An Introduction to Delocalized Electrons

Inductive Electron Withdrawal

Delocalized Electrons

Problem-Solving Strategy Determining the Site of Protonation in a Compound with Delocalized Electrons

Problem 34

Problem 35 ♦

Problem 36 ♦

Problem 37

2.9 A Summary of the Factors that Determine Acid Strength

Problem 38 ♦

2.10 How pH Affects the Structure of an Organic Compound

Problem-Solving Strategy Determining the Structure at a Particular pH

Problem 39 ♦

Problem 40 ♦

Problem 41 Solved

Solution

Problem 42 ♦

Problem 43

Problem 44 Solved

Solution 44 a.

Solution 44 b.

Problem 45 ♦

Problem 46 ♦

Problem 47 Solved

Solution

Problem 48 ♦

2.11 Buffer Solutions

Problem 49 ♦

Problem 50 Solved

Solution

2.12 Lewis Acids and Bases

Problem 51

Problem 52

Essential concepts

Problems

3 An Introduction to Organic Compounds Nomenclature, Physical Properties, and Structure

3.1 Alkyl Groups

Problem 3 ♦

3.2 The Nomenclature of Alkanes

Problem 9 ♦

Problem 10 Solved

Solution

Problem 11 ♦

Problem 12 Solved

Solution to 12 a.

Problem 13

Problem 14 ♦

3.3 The Nomenclature of Cycloalkanes

Problem 15 ♦

Problem-Solving Strategy Interpreting a Skeletal Structure

Problem 16

Problem 17 ♦

Problem 18

Problem 19

3.4 The Nomenclature of Alkyl Halides

3.5 The Nomenclature of Ethers

3.6 The Nomenclature of Alcohols

Common Names

Systematic Names

Problem 23 ♦

Problem 24

Problem 25 ♦

Problem 26 ♦

3.7 The Nomenclature of Amines

3.8 The Structures of Alkyl Halides, Alcohols, Ethers, and Amines

3.9 Noncovalent Interactions

Boiling Points

London Dispersion Forces

Problem 32 ♦

Dipole–Dipole Interactions

Hydrogen Bonds

Problem-Solving Strategy Predicting Hydrogen Bonding

Problem 33 ♦

Problem 34

Problem 35 ♦

Problem 36

Melting Points

3.10  The Solubility of Organic Compounds

3.11 Rotation Occurs about Carbon–Carbon Single Bonds

3.12 Some Cycloalkanes Have Angle Strain

Problem 43 ♦

Problem-Solving Strategy Calculating the Strain Energy of a Cycloalkane

Problem 44

3.13 Conformers of Cyclohexane

3.14 Conformers of Monosubstituted Cyclohexanes

Problem 46 ♦

Problem 47 ♦

3.15 Conformers of Disubstituted Cyclohexanes

Geometric Isomers

Problem-Solving Strategy Differentiating Cis–Trans Isomers

Problem 48 ♦

3.16 Fused Cyclohexane Rings

Essential Concepts

Problems

Part Two Electrophilic Addition Reactions, Stereochemistry, and Electron Delocalization

4 Isomers: The Arrangement of Atoms in Space

4.1 Cis–Trans Isomers Result from Restricted Rotation

4.2 Using the E,Z System to Distinguish Isomers

4.3 A Chiral Object Has a Nonsuperimposable Mirror Image

Problem 13 ♦

4.4 An Asymmetric Center is a Cause of Chirality in a Molecule

Problem 14 ♦

4.5 Isomers with One Asymmetric Center

Problem 16 ♦

4.6 Asymmetric Centers and Stereocenters

Problem 17 ♦

4.7 How to Draw Enantiomers

Problem 18

Problem 19 Solved

Solution

4.8 Naming Enantiomers by the R,S System

4.9 Chiral Compounds Are Optically Active

Problem 28 ♦

Problem 29 Solved

Solution

Problem 30 ♦

Problem 31 Solved

Solution

Problem 32 ♦

4.10 How Specific Rotation Is Measured

Problem 33 ♦

Problem 34 ♦

4.11 Enantiomeric Excess

Problem 35 ♦

Problem 36 ♦

Problem 37 Solved

Solution

4.12 Compounds with More than One Asymmetric Center

4.13 Stereoisomers of Cyclic Compounds

Problem 42

Problem 43 ♦

Problem 44

Problem 45

Problem 46 ♦

Problem-Solving Strategy

Problem 47

Problem 48 ♦

4.14 Meso Compounds Have Asymmetric Centers but Are Optically Inactive

Problem-Solving Strategy

Problem 49 ♦

Problem 50 Solved

Solution

Problem 51

4.15 How to Name Isomers with More than One Asymmetric Center

4.16 Nitrogen and Phosphorus Atoms Can Be Asymmetric Centers

Problem 63

4.17 Receptors

Problem 64 ♦

4.18 How Enantiomers Can Be Separated

Essential Concepts

Problems

5 Alkenes Structure, Nomenclature, and an Introduction to Reactivity Thermodynamics and Kinetics

5.1 Molecular Formulas and the Degree of Unsaturation

Problem 1 SOLVED

Solution

Problem 2 ♦

Problem 3 SOLVED

Solution

Problem 4 ♦

Problem 5

Problem 6 ♦

5.2 The Nomenclature of Alkenes

Problem 7 ♦

Problem 8 ♦

Problem 9 ♦

5.3 The Structure of Alkenes

Problem 10 SOLVED

Solution

Problem 11 ♦

Problem-Solving Strategy

Problem 12

5.4 How An Organic Compound Reacts Depends on Its Functional Group

5.5 How Alkenes React • Curved Arrows Show the Flow of Electrons

Electrophiles

Nucleophiles

Problem 13 ♦

Problem 14

The Mechanism of a Reaction

Problem 15 SOLVED

Solution to 15 a. 

Problem 16

Problem 17

A Reaction Coordinate Diagram Describes the Reaction Pathway

5.6 Thermodynamics: How Much Product is Formed?

Gibbs Free-Energy Change

Problem 18 ♦

Problem 19 SOLVED

Solution

Problem 20

Enthalpy and Entropy

Problem 21

Problem 22 ♦

5.7 Increasing the Amount of Product Formed in a Reaction

5.8 Calculating ΔH° Values

Problem 23 ♦

5.9 Using ΔH° Values to Determine the Relative Stabilities of Alkenes

Catalytic Hydrogenation

Problem-Solving Strategy

Problem 24

Problem 25

Relative Stabilities of Alkenes

Problem 26 ♦

Problem 27 ♦

Problem 28 ♦

5.10 Kinetics: How Fast is the Product Formed?

Problem 29 ♦

Problem 30

5.11 The Rate of a Chemical Reaction

The Difference Between the Rate of a Reaction and the Rate Constant for a Reaction

The Arrhenius Equation

Problem 31 SOLVED

Solution to 31 a. 

Problem 32 ♦

Problem 33 ♦

How Are Rate Constants Related to the Equilibrium Constant?

Problem 34 ♦

5.12 A Reaction Coordinate Diagram Describes the Energy Changes That Take Place During a Reaction

Reaction Coordinate Diagram

Transition States and Intermediates

The Rate-Determining Step

Problem 35

Problem 36 ♦

Problem 37 ♦

5.13 Catalysis

Problem 38 ♦

5.14 Catalysis by Enzymes

Essential Concepts

Problems

6 The Reactions of Alkenes • The Stereochemistry of Addition Reactions

6.1 The Addition of a Hydrogen Halide to an Alkene

Problem 1

6.2 Carbocation Stability Depends on the Number of Alkyl Groups Attached to the Positively Charged Carbon

6.3 What Does the Structure of the Transition State Look Like?

Problem 5 ♦

6.4 Electrophilic Addition Reactions Are Regioselective

6.5 The Addition of Water to an Alkene

Problem 9 ♦

Problem 10 ♦

Problem 11 ♦

6.6 The Addition of an Alcohol to an Alkene

Problem 12

Problem 13 Solved

Solution

Problem 14

Problem 15

6.7 A Carbocation Will Rearrange if It Can Form a More Stable Carbocation

6.8 The Addition of Borane to an Alkene: Hydroboration–Oxidation

6.9 The Addition of a Halogen to an Alkene

Problem 20 ♦

Problem 21

6.10 The Addition of a Peroxyacid to an Alkene

Nomenclature of Epoxides

Problem 27 ♦

Problem 28 ♦

Problem 29 Solved

Solution to 29 a.

Solution to 29 b.

6.11 The Addition of Ozone to an Alkene: Ozonolysis

Problem-Solving Strategy

Solution to a.

Solution to b.

Solution to c.

Problem 30

Problem 31 ♦

Problem 32 ♦

Problem 33 Solved

Solution to 33 a.

Solution to 33 b.

Problem 34

6.12 Regioselective, Stereoselective, And Stereospecific Reactions

Problem 35 ♦

6.13 The Stereochemistry of Electrophilic Addition Reactions

The Stereochemistry of Addition Reactions That Form a Product with One Asymmetric Center

Problem 36 ♦

Problem 37

Problem 38 Solved

Solution

The Stereochemistry of Addition Reactions That Form Products with Two Asymmetric Centers

Addition Reactions That Form a Carbocation Intermediate

Problem 39 Solved

The Stereochemistry of Hydrogen Addition

Problem 40 Solved

Solution 40 a.

Solution 40 b.

The Stereochemistry of Peroxyacid Addition

Problem 41 ♦

The Stereochemistry of Hydroboration–Oxidation

Problem 42 ♦

The Stereochemistry of Addition Reactions That Form a Cyclic Bromonium or Chloronium Ion Intermediate

Problem 43

Problem 44 Solved

Solution

A Mnemonic to the Rescue

Problem-Solving Strategy

Problem 45

Problem 46

Problem 47

Problem 48

Problem 49

Problem 50 ♦

6.14 The Stereochemistry of Enzyme-Catalyzed Reactions

Problem 51 ♦

6.15 Enantiomers Can Be Distinguished by Biological Molecules

Enzymes

6.16 Reactions and Synthesis

Problem 52 Solved

Solution to 52 a.

Solution to 52 b.

Problem 53

Problem 54 ♦

Essential Concepts

Summary of Reactions

Problems

7 The Reactions of Alkynes • An Introduction to Multistep Synthesis

7.1 The Nomenclature of Alkynes

Problem 1 ♦

Problem 2 ♦

Problem 3 ♦

Problem 4 ♦

Problem 5

7.2 How to Name a Compound That Has More than One Functional Group

Problem 6 ♦

Problem 7 ♦

7.3 The Structure of Alkynes

Problem 8 ♦

7.4 The Physical Properties of Unsaturated Hydrocarbons

Problem 9 ♦

Problem 10 ♦

7.5 The Reactivity of Alkynes

π-Complex Formation

Alkynes Are Less Reactive Than Alkenes

Problem 11 Solved

Solution

7.6 The Addition of Hydrogen Halides and the Addition of Halogens to an Alkyne

Addition of a Hydrogen Halide to an Alkyne

Addition to a Terminal Alkyne

Addition to an Internal Alkyne

Addition of a Halogen to an Alkyne

Problem 12 ♦

Problem 13

7.7 The Addition of Water to an Alkyne

7.8 The Addition of Borane to an Alkyne: Hydroboration–Oxidation

Problem 17

Problem 18 ♦

7.9 The Addition of Hydrogen to an Alkyne

7.10 A Hydrogen Bonded to an sp Carbon Is “Acidic”

Problem 21

Problem 22 ♦

Problem 23 ♦

Problem-Solving Strategy

Problem 24 ♦

Problem 25 Solved

Solution

Problem 26 ♦

7.11 Synthesis Using Acetylide Ions

Problem 27 Solved

Solution

  7.12 An Introduction to Multistep Synthesis

Factors That Affect the Design of a Synthesis

Designing a Synthesis

Problem 28

Essential Concepts

Summary of Reactions

Problems

8 Delocalized Electrons Their Effect on Stability, pKa, and the Products of a ReactionAromaticity and Electronic EffectsAn Introduction to the Reactions of Benzene

8.1 Delocalized Electrons Explain Benzene’s Structure

The Puzzle of Benzene’s Structure

Kekulé, Sabatier, and X-ray Diffraction Solve the Puzzle

Problem 1 ♦

Problem 2

8.2 The Bonding in Benzene

8.3 Resonance Contributors and the Resonance Hybrid

The Difference Between a Resonance Contributor and a Resonance Hybrid

8.4 How to Draw Resonance Contributors

Rules for Drawing Resonance Contributors

Example 1

Example 2

Example 3

Example 4

Problem 3

8.5 The Predicted Stabilities of Resonance Contributors

Features That Decrease the Predicted Stability

Problem-Solving Strategy

Problem 4 ♦

Problem 5 SOLVED

Solution 

Problem 6

8.6 Delocalization Energy is the Additional Stability Delocalized Electrons Give to a Compound

Problem 7 ♦

Problem 8

Problem 9

Problem 10 ♦

8.7 Delocalized Electrons Increase Stability

Stability of Dienes

Conjugated Dienes

Allenes

Problem 11 ♦

Problem 12 ♦

Stability of Allylic and Benzylic Cations

Problem 13 ♦

 8.8 A Molecular Orbital Description of Stability

Ethene

1,3-Butadiene

Problem 14 ♦

Problem 15 ♦

1,4-Pentadiene

Problem 16 ♦

8.9 Delocalized Electrons Affect pKa Values

Acetic Acid versus Ethanol

Phenol versus Cyclohexanol

Aniline versus Cyclohexylamine

Problem-Solving Strategy

Problem 17 ♦

Problem 18 ♦

Problem 19 ♦

8.10 Electronic Effects

Inductive Electron Withdrawal

Electron Donation by Hyperconjugation

Electron Donation by Resonance

Electron Withdrawal by Resonance

Effect of Electron Donation and Electron Withdrawal on pKa Values

Problem 20 ♦

Problem 21 ♦

Problem 22 SOLVED

Problem 23

8.11      Delocalized Electrons Can Affect the Product of a Reaction

Problem 24 ♦

Problem 25 SOLVED

Solution 

Problem 26

8.12 Reactions of Dienes

Reactions of Isolated Dienes

Problem 27 ♦

Reactions of Conjugated Dienes

Problem 28 ♦

Problem 29 ♦

Problem 30

Problem 31

Problem 32 ♦

8.13     Thermodynamic Versus Kinetic Control

Kinetic and Thermodynamic Products

Mild Conditions Favor the Kinetic Product

Vigorous Conditions Favor the Thermodynamic Product

Reaction Coordinate Diagrams Explain the Temperature Dependence of the Products

The Temperature at Which a Reaction Changes from Irreversible to Reversible Depends on the Reaction

When 1,3-Butadiene Reacts with HBr, Why Is the 1,4-Addition Product the Thermodynamic Product?

Why Is the 1,2-Addition Product Always the Kinetic Product?

Problem 33 ♦

Problem 34 ♦

Identifying the Kinetic and Thermodynamic Products

Problem 35 ♦

Problem 36 SOLVED

Solution

Problem 37

Problem 38

8.14 The Diels–Alder Reaction is a 1,4-Addition Reaction

An Electron Withdrawing Group Increases the Reactivity of the Dienophile

Examples of Diels–Alder Reactions

Problem 39 ♦

A Molecular Orbital Description of the Diels–Alder Reaction

Predicting the Product When Both Reagents Are Unsymmetrically Substituted

Problem 40 ♦

Problem 41

Problem 42 ♦

Conformation of the Diene

Exo and Endo Products

Problem 43 ♦

Problem 44

Problem 45 SOLVED

Solution

The Stereochemistry of the Diels–Alder Reaction

Problem 46 ♦

8.15 Retrosynthetic Analysis of the Diels–Alder Reaction

Problem 47 ♦

8.16   Benzene is an Aromatic Compound

8.17 The Two Criteria for Aromaticity

Problem 48 ♦

Problem 49 ♦

8.18    Applying the Criteria for Aromaticity

Problem 50 ♦

Problem 51 SOLVED

Solution

Problem 52 ♦

Problem 53 ♦

Problem-Solving Strategy

Problem 54

8.19 A Molecular Orbital Description of Aromaticity

Antiaromatic Compounds

Problem 55

8.20    Aromatic Heterocyclic Compounds

Pyridine

Pyrrole, Furan, and Thiophene

Problem 56 ♦

Problem 57 ♦

Problem 58 SOLVED

Solution

Problem 59

Problem 60

8.21 How Benzene Reacts

8.22 Organizing What We Know about the Reactions of Organic Compounds

Essential Concepts

Summary of Reactions

Problems

Rules for Drawing Resonance Contributors

π Electrons Move Toward an sp2 Carbon That Is a Positively Charged Carbon

Problem 1

Problem 2

π Electrons Move Toward an sp2 Carbon That Is a Doubly Bonded Carbon

Problem 3

Problem 4

A Lone Pair Moves Toward an sp2 Carbon That Is a Doubly Bonded Carbon

ANSWERS TO PROBLEMS ON DRAWING RESONANCE CONTRIBUTORS

PARTTHREE Substitution and Elimination Reactions

9 Substitution and Elimination Reactions of Alkyl Halides

9.1 The SN2 Reaction

Experimental Evidence for the Mechanism for an SN2 Reaction

Problem 3 ♦

The Mechanism for an SN2 Reaction

How the Mechanism Accounts for the Experimental Evidence

Problem 4 ♦

Problem 5 ♦

Problem 6 ♦ SOLVED

Solution to 6 a.

Problem 7 SOLVED

Solution

Problem 8

9.2 Factors that Affect SN2 Reactions

The Leaving Group in an SN2 Reaction

Problem 9 ♦

The Nucleophile in an SN2 Reaction

Effect of Basicity on Nucleophilicity

Effect of Solvent on Nucleophilicity

Problem 10 ♦

Why Is the Nucleophilicity Affected by the Solvent?

Problem 11 ♦

Problem 12 ♦

Nucleophilicity Is Affected by Steric Effects

Problem 13 SOLVED

Solution

Problem 14 ♦

A Wide Variety of Compounds Can Be Synthesized by SN2 Reactions

Problem 15 ♦

Problem 16 SOLVED

Solution

Problem 17

9.3 The SN1 Reaction

Experimental Evidence for the Mechanism for an SN1 Reaction

The Mechanism for an SN1 Reaction

How the Mechanism Accounts for the Experimental Evidence

Most SN1 Reactions Lead to Partial Racemization

Problem 18 ♦

9.4 Factors that Affect SN1 Reactions

The Leaving Group in an SN1 Reaction

The Nucleophile in an SN1 Reaction

Problem 19 ♦

9.5 Competition Between SN2 and SN1 Reactions

Problem-Solving Strategy

Problem 20

Problem 21 ♦

9.6 Elimination Reactions of Alkyl Halides

9.7 The E2 Reaction

An E2 Reaction is Regioselective

Alkyl Chlorides, Alkyl Bromides, and Alkyl Iodides Preferentially Form the More Stable Product

Zaitsev’s Rule

Problem 22 ♦

Limitations of Zaitsev’s Rule

Alkyl Fluorides Preferentially Form the Less Stable Alkene

Carbocation and Carbanion Stability

Summary of the Regioselectivity of E2 Reactions

Problem 23 ♦

Relative Reactivities in an E2 Reaction

Problem 24 ♦

Problem 25 ♦

9.8 The E1 Reaction

The E1 Reaction Is Regioselective

The Leaving Group in E2 and E1 Reactions

Problem 26 ♦

Problem 27 ♦

Problem 28 ♦

Problem-Solving Strategy Proposing a Mechanism

Problem 29

9.9 Competition Between E2 and E1 Reactions

Problem 30

Problem 31 SOLVED

Solution

Problem 32

9.10 E2 and E1 Reactions are Stereoselective

The Stereoisomers Formed in an E2 Reaction

Syn and Anti Elimination

A Reactant with Two Hydrogens on the β-Carbon-Carbon

A Reactant with One Hydrogen on the β-Carbon

Problem-Solving Strategy Determining the Major Product of an E2 Reaction

Problem 33 ♦

The Stereoisomers Formed in an E1 Reaction

Problem 34 SOLVED

Solution

Problem 35

9.11 Elimination from Substituted Cyclohexanes

E2 Reactions of Substituted Cyclohexanes

Problem 36 ♦

Problem 37 ♦

E1 Reactions of Substituted Cyclohexanes

Problem 38

9.12 Predicting the Products of the Reaction of an Alkyl Halide with a Nucleophile/Base

SN2/E2 Reactions of Primary Alkyl Halides

Steric Hindrance Favors the Elimination Product

SN2/E2 Reactions of Secondary Alkyl Halides

A Strong Base Favors the Elimination Product

A Bulky Base Favors the Elimination Product

A High Temperature Favors the Elimination Product

E2 Reaction of a Tertiary Alkyl Halide

SN1/E1 Reactions of Tertiary Alkyl Halides

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