D E TA I L E D C O N T E N T S

Structure and Bonding | !

!-! Atomic Structure: The Nucleus )

!-" Atomic Structure: Orbitals (
!-# Atomic Structure: Electron Configurations $
CHAPTER
!-$ Development of Chemical Bonding Theory

!
*
!-% Describing Chemical Bonds: Valence Bond Theory !%
!-& sp# Hybrid Orbitals and the Structure of Methane !"
!-' sp# Hybrid Orbitals and the Structure of Ethane !)
!-( sp" Hybrid Orbitals and the Structure of Ethylene !(
!-) sp Hybrid Orbitals and the Structure of Acetylene !*
!-!* Hybridization of Nitrogen, Oxygen, Phosphorus, and Sulfur !#
!-!! Describing Chemical Bonds: Molecular Orbital Theory "%
!-!" Drawing Chemical Structures "!

SOMETHING EXTRA Organic Foods: Risk versus Benefit "'

Summary "$
Key words "$
Working Problems "*
Exercises "*a

Polar Covalent Bonds; Acids and Bases | "#

"-! Polar Covalent Bonds: Electronegativity

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"#
©Kostyantyn
Ivanyshen/

"-" Polar Covalent Bonds: Dipole Moments )!

"-# Formal Charges ))
CHAPTER
"-$ Resonance

"
)$
"-% Rules for Resonance Forms )*
"-& Drawing Resonance Forms )&
"-' Acids and Bases: The Brønsted–Lowry Definition ("

vii

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 viii $%&'(&')

"-( Acid and Base Strength ((

"-) Predicting Acid–Base Reactions from pKa Values ($
"-!* Organic Acids and Organic Bases (*
"-!! Acids and Bases: The Lewis Definition '%
"-!" Noncovalent Interactions between Molecules '(

SOMETHING EXTRA Alkaloids: From Cocaine

to Dental Anesthetics '$

Summary '#
Key words '#
Exercises '&

Organic Compounds: Alkanes and

Their Stereochemistry | *+
#-! Functional Groups
Shutterstock.com

$%
©tactilephoto/

#-" Alkanes and Alkane Isomers $$

#-# Alkyl Groups *%
CHAPTER
#-$ Naming Alkanes

)
*)
#-% Properties of Alkanes *#
#-& Conformations of Ethane #%
#-' Conformations of Other Alkanes #"

SOMETHING EXTRA Gasoline #$

Summary #*
Key words #*
Exercises ##

Organic Compounds: Cycloalkanes and

Their Stereochemistry | #,
$-! Naming Cycloalkanes &%
Indiapicture /

$-" Cis–Trans Isomerism in Cycloalkanes &"

Alamy

$-# Stability of Cycloalkanes: Ring Strain &'

CHAPTER
$-$ Conformations of Cycloalkanes

(
&*
$-% Conformations of Cyclohexane &&
$-& Axial and Equatorial Bonds in Cyclohexane !%!

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 $%&'(&') ix

$-' Conformations of Monosubstituted Cyclohexanes !%(

$-( Conformations of Disubstituted Cyclohexanes !%*
$-) Conformations of Polycyclic Molecules !!%

SOMETHING EXTRA Molecular Mechanics !!)

Summary !!(
Key words !!(
Exercises !!(a

Stereochemistry at Tetrahedral Centers | !!-

%-! Enantiomers and the Tetrahedral Carbon

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!!$
©Bart Brouwer/

%-" The Reason for Handedness in Molecules: Chirality !!*

%-# Optical Activity !"!
CHAPTER
%-$ Pasteur’s Discovery of Enantiomers

'
!")
%-% Sequence Rules for Specifying Configuration !"(
%-& Diastereomers !)!
%-' Meso Compounds !))
%-( Racemic Mixtures and the Resolution of Enantiomers !)'
%-) A Review of Isomerism !)#
%-!* Chirality at Nitrogen, Phosphorus, and Sulfur !(%
%-!! Prochirality !(!
%-!" Chirality in Nature and Chiral Environments !('

SOMETHING EXTRA Chiral Drugs !(*

Summary !(#
Key words !(#
Exercises !(#a

An Overview of Organic Reactions | !.,

&-! Kinds of Organic Reactions

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!(&
©Aspen Photo/

&-" How Organic Reactions Occur: Mechanisms !'!

&-# Radical Reactions !'"
CHAPTER
&-$ Polar Reactions

$
!''
&-% An Example of a Polar Reaction: Addition of HBr to Ethylene !'&
&-& Using Curved Arrows in Polar Reaction Mechanisms !$"

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 x $%&'(&')

&-' Describing a Reaction: Equilibria, Rates, and Energy Changes !$'

&-( Describing a Reaction: Bond Dissociation Energies !$&
&-) Describing a Reaction: Energy Diagrams and Transition States !*!
&-!* Describing a Reaction: Intermediates !*(
&-!! A Comparison Between Biological Reactions
and Laboratory Reactions !**

SOMETHING EXTRA Where Do Drugs Come From? !*&

Summary !#!
Key words !#!
Exercises !#!a

Practice Your Scientific Analysis and Reasoning I

The Chiral Drug Thalidomide | !#"

Alkenes: Structure and Reactivity | !#-

'-! Industrial Preparation and Use of Alkenes

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!#$
©JIANHAO

'-" Calculating Degree of Unsaturation !#*

GUAN/

'-# Naming Alkenes !#&

CHAPTER
'-$ Cis–Trans Isomerism in Alkenes

*
!&"
'-% Alkene Stereochemistry and the E,Z Designation !&(
'-& Stability of Alkenes !&#
'-' Electrophilic Addition Reactions of Alkenes "%!
'-( Orientation of Electrophilic Additions: Markovnikov’s Rule "%'
'-) Carbocation Structure and Stability "%#
'-!* The Hammond Postulate "!!
'-!! Evidence for the Mechanism of Electrophilic
Additions: Carbocation Rearrangements "!(

SOMETHING EXTRA Bioprospecting: Hunting

for Natural Products "!*

Summary "!#
Key words "!#
Exercises "!&

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 $%&'(&') xi

Alkenes: Reactions and Synthesis | ""+

(-! Preparing Alkenes: A Preview of Elimination Reactions ""!

Science Faction/
Getty Images
Ed Darack/

(-" Halogenation of Alkenes: Addition of X" """

(-# Halohydrins from Alkenes: Addition of HOX ""'
CHAPTER
(-$ Hydration of Alkenes: Addition of H"O by Oxymercuration

#
""*
(-% Hydration of Alkenes: Addition of H"O by Hydroboration ")%
(-& Reduction of Alkenes: Hydrogenation ")'
(-' Oxidation of Alkenes: Epoxidation and Hydroxylation ")&
(-( Oxidation of Alkenes: Cleavage to Carbonyl Compounds "("
(-) Addition of Carbenes to Alkenes: Cyclopropane Synthesis "('
(-!* Radical Additions to Alkenes: Chain-Growth Polymers "(*
(-!! Biological Additions of Radicals to Alkenes "'!
(-!" Reaction Stereochemistry: Addition of H"O to an Achiral Alkene "'"
(-!# Reaction Stereochemistry: Addition of H"O to a Chiral Alkene "''

SOMETHING EXTRA Terpenes: Naturally Occurring Alkenes "'*

Summary "'&
Key words "'&
Learning Reactions "$%
Summary of Reactions "$%
Exercises "$"

Alkynes: An Introduction to Organic Synthesis | "*/

)-! Naming Alkynes

Shutterstock.com

"$(
©Igor Bulgarin/

)-" Preparation of Alkynes: Elimination Reactions of Dihalides "$'

)-# Reactions of Alkynes: Addition of HX and X" "$'
CHAPTER
)-$ Hydration of Alkynes

&
"$#
)-% Reduction of Alkynes "*"
)-& Oxidative Cleavage of Alkynes "*'
)-' Alkyne Acidity: Formation of Acetylide Anions "*'
)-( Alkylation of Acetylide Anions "**
)-) An Introduction to Organic Synthesis "*&

SOMETHING EXTRA The Art of Organic Synthesis "#)

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 xii $%&'(&')

Summary "#(
Key words "#(
Summary of Reactions "#'
Exercises "#$a

Organohalides | "#0
Sebastián Crespo

!*-! Names and Structures of Alkyl Halides "##

Photography/
Getty Images

!*-" Preparing Alkyl Halides from Alkanes: Radical Halogenation "&%

!*-# Preparing Alkyl Halides from Alkenes: Allylic Bromination "&"
CHAPTER
!*-$ Stability of the Allyl Radical: Resonance Revisited

!%
"&(
!*-% Preparing Alkyl Halides from Alcohols "&*
!*-& Reactions of Alkyl Halides: Grignard Reagents "&#
!*-' Organometallic Coupling Reactions )%%
!*-( Oxidation and Reduction in Organic Chemistry )%)

SOMETHING EXTRA Naturally Occurring Organohalides )%'

Summary )%*
Key words )%*
Summary of Reactions )%*
Exercises )%#

Reactions of Alkyl Halides: Nucleophilic

Substitutions and Eliminations | /+,
!!-! The Discovery of Nucleophilic Substitution Reactions )!%
Martin Harvey/
Getty Images

!!-" The SN" Reaction )!)

!!-# Characteristics of the SN" Reaction )!$
CHAPTER
!!-$ The SN! Reaction

!!
)")
!!-% Characteristics of the SN! Reaction )"*
!!-& Biological Substitution Reactions )))
!!-' Elimination Reactions: Zaitsev’s Rule ))'
!!-( The E" Reaction and the Deuterium Isotope Effect ))#
!!-) The E" Reaction and Cyclohexane Conformation )(!
!!-!* The E! and E!cB Reactions )()
!!-!! Biological Elimination Reactions )('
!!-!" A Summary of Reactivity: SN!, SN", E!, E!cB, and E" )('

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 $%&'(&') xiii

SOMETHING EXTRA Green Chemistry )(*

Summary )(&
Key words )(&
Summary of Reactions )'%
Exercises )'%a

Practice Your Scientific Analysis and Reasoning II

From Mustard Gas to Alkylating Anticancer Drugs | /-!

Structure Determination: Mass Spectrometry

and Infrared Spectroscopy | /-.
!"-! Mass Spectrometry of Small Molecules:
MakiEni’s photo/
Getty Images

Magnetic-Sector Instruments )''

!"-" Interpreting Mass Spectra )'*
CHAPTER !"-# Mass Spectrometry of Some Common Functional Groups )$"

!" !"-$ Mass Spectrometry in Biological Chemistry:

Time-of-Flight (TOF) Instruments )$*
!"-% Spectroscopy and the Electromagnetic Spectrum )$#
!"-& Infrared Spectroscopy )*!
!"-' Interpreting Infrared Spectra )*)
!"-( Infrared Spectra of Some Common Functional Groups )*$

SOMETHING EXTRA X-Ray Crystallography )#(

Summary )#'
Key words )#'
Exercises )#'

Structure Determination: Nuclear Magnetic

Resonance Spectroscopy | /#*
!#-! Nuclear Magnetic Resonance Spectroscopy
Shutterstock.com

)#$
©EM Karuna/

!#-" The Nature of NMR Absorptions )#&

!#-# The Chemical Shift )&"
CHAPTER
!#-$ Chemical Shifts in !H NMR Spectroscopy

!)
)&(
!#-% Integration of !H NMR Absorptions: Proton Counting )&$

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 xiv $%&'(&')

!#-& Spin–Spin Splitting in !H NMR Spectra )&*

!#-' !H NMR Spectroscopy and Proton Equivalence (%"
!#-( More Complex Spin–Spin Splitting Patterns (%(
!#-) Uses of !H NMR Spectroscopy (%*
!#-!* !#C NMR Spectroscopy: Signal Averaging and FT–NMR (%#
!#-!! Characteristics of !#C NMR Spectroscopy (!%
!#-!" DEPT !#C NMR Spectroscopy (!)
!#-!# Uses of !#C NMR Spectroscopy (!$

SOMETHING EXTRA Magnetic Resonance Imaging (MRI) (!*

Summary (!#
Key words (!#
Exercises (!&

Conjugated Compounds and Ultraviolet

Spectroscopy | ."+
!$-! Stability of Conjugated Dienes: Molecular Orbital Theory
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("!
©DemarK/

!$-" Electrophilic Additions to Conjugated Dienes:

Allylic Carbocations ("'
CHAPTER !$-# Kinetic versus Thermodynamic Control of Reactions ("#

!( !$-$
!$-%
The Diels–Alder Cycloaddition Reaction
Characteristics of the Diels–Alder Reaction
()%
()!
!$-& Diene Polymers: Natural and Synthetic Rubbers ()*
!$-' Ultraviolet Spectroscopy ()#
!$-( Interpreting Ultraviolet Spectra: The Effect of Conjugation ((!
!$-) Conjugation, Color, and the Chemistry of Vision (("

SOMETHING EXTRA Photolithography (((

Summary (($
Key words (($
Summary of Reactions ((*
Exercises ((*a

Practice Your Scientific Analysis and Reasoning III

Photodynamic Therapy (PDT) | ..#

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 $%&'(&') xv

Benzene and Aromaticity | .-!

!%-! Naming Aromatic Compounds

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('"
©Handmade

!%-" Structure and Stability of Benzene ('$

Pictures/

!%-# Aromaticity and the Hückel $n ! " Rule ('&

CHAPTER
!%-$ Aromatic Ions

!'
($!
!%-% Aromatic Heterocycles: Pyridine and Pyrrole ($(
!%-& Polycyclic Aromatic Compounds ($*
!%-' Spectroscopy of Aromatic Compounds ($&

SOMETHING EXTRA Aspirin, NSAIDs, and COX-" Inhibitors (*(

Summary (*$
Key words (*$
Exercises (**

Chemistry of Benzene: Electrophilic

Aromatic Substitution | .0#
!&-! Electrophilic Aromatic Substitution Reactions: Bromination (*&
Library / Alamy
Niday Picture

!&-" Other Aromatic Substitutions (#"

!&-# Alkylation and Acylation of Aromatic Rings:
CHAPTER The Friedel–Crafts Reaction (##

!$ !&-$
!&-%
Substituent Effects in Electrophilic Substitutions
Trisubstituted Benzenes: Additivity of Effects '%)
(&)

!&-& Nucleophilic Aromatic Substitution '%'

!&-' Benzyne '%#
!&-( Oxidation of Aromatic Compounds '!%
!&-) Reduction of Aromatic Compounds '!)
!&-!* Synthesis of Polysubstituted Benzenes '!(

SOMETHING EXTRA Combinatorial Chemistry '!&

Summary '"!
Key words '"!
Summary of Reactions '""
Exercises '"(

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 xvi $%&'(&')

Alcohols and Phenols | -"-

!'-! Naming Alcohols and Phenols

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'"$
©JManuel

!'-" Properties of Alcohols and Phenols '"#

Murillo/

!'-# Preparation of Alcohols: A Review '))

CHAPTER
!'-$ Alcohols from Carbonyl Compounds: Reduction

!*
')'
!'-% Alcohols from Carbonyl Compounds: Grignard Reaction ')&
!'-& Reactions of Alcohols '()
!'-' Oxidation of Alcohols ''%
!'-( Protection of Alcohols '')
!'-) Phenols and Their Uses '''
!'-!* Reactions of Phenols ''*
!'-!! Spectroscopy of Alcohols and Phenols ''&

SOMETHING EXTRA Ethanol: Chemical, Drug, Poison '$)

Summary '$(
Key words '$(
Summary of Reactions '$'
Exercises '$*

Ethers and Epoxides; Thiols and Sulfides | -*#

!(-! Names and Properties of Ethers

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'$&
©Heiko Kiera/

!(-" Preparing Ethers '*%

!(-# Reactions of Ethers: Acidic Cleavage '*)
CHAPTER
!(-$ Reactions of Ethers: Claisen Rearrangement

!#
'*'
!(-% Cyclic Ethers: Epoxides '**
!(-& Reactions of Epoxides: Ring-Opening '*#
!(-' Crown Ethers '#)
!(-( Thiols and Sulfides '#(
!(-) Spectroscopy of Ethers '##

SOMETHING EXTRA Epoxy Resins and Adhesives '&!

Summary '&"
Key words '&"
Summary of Reactions '&)
Exercises '&(a

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