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- Herausgeber: John Wiley & Sons
- Kategorie: Wissenschaft und neue Technologien
- Sprache: Englisch
Provides an in-depth study of organic compounds that bridges the gap between general and organic chemistry
Organic Chemistry: Concepts and Applications presents a comprehensive review of organic compounds that is appropriate for a two-semester sophomore organic chemistry course. The text covers the fundamental concepts needed to understand organic chemistry and clearly shows how to apply the concepts of organic chemistry to problem-solving. In addition, the book highlights the relevance of organic chemistry to the environment, industry, and biological and medical sciences. The author includes multiple-choice questions similar to aptitude exams for professional schools, including the Medical College Admissions Test (MCAT) and Dental Aptitude Test (DAT) to help in the preparation for these important exams.
Rather than categorize content information by functional groups, which often stresses memorization, this textbook instead divides the information into reaction types. This approach bridges the gap between general and organic chemistry and helps students develop a better understanding of the material. A manual of possible solutions for chapter problems for instructors and students is available in the supplementary websites. This important book:
• Provides an in-depth study of organic compounds with division by reaction types that bridges the gap between general and organic chemistry
• Covers the concepts needed to understand organic chemistry and teaches how to apply them for problem-solving
• Puts a focus on the relevance of organic chemistry to the environment, industry, and biological and medical sciences
• Includes multiple choice questions similar to aptitude exams for professional schools
Written for students of organic chemistry, Organic Chemistry: Concepts and Applications is the comprehensive text that presents the material in clear terms and shows how to apply the concepts to problem solving.
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Seitenzahl: 821
Veröffentlichungsjahr: 2019
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Table of Contents
Cover
Preface
About This Book
To the Student of Organic Chemistry
To the Instructor
About the Companion Website
1 Bonding and Structure of Organic Compounds
1.1 Introduction
1.2 Electronic Structure of Atoms
1.3 Chemical Bonds
1.4 Chemical Formulas
1.5 The Covalent Bond
1.6 Bonding – Concept Summary and Applications
1.7 Intermolecular Attractions
1.8 Intermolecular Interactions – Concept Summary and Applications
End of Chapter Problems
2 Carbon Functional Groups and Organic Nomenclature
2.1 Introduction
2.2 Functional Groups
2.3 Saturated Hydrocarbons
2.4 Organic Nomenclature
2.5 Structure and Nomenclature of Alkanes
2.6 Unsaturated Hydrocarbons
2.7 Structure and Nomenclature of Alkenes
2.8 Structure and Nomenclature of Substituted Benzenes
2.9 Structure and Nomenclature of Alkynes
End of Chapter Problems
3 Heteroatomic Functional Groups and Organic Nomenclature
3.1 Properties and Structure of Alcohols, Phenols, and Thiols
3.2 Nomenclature of Alcohols
3.3 Nomenclature of Thiols
3.4 Structure and Properties of Aldehydes and Ketones
3.5 Nomenclature of Aldehydes
3.6 Nomenclature of Ketones
3.7 Structure and Properties of Carboxylic Acids
3.8 Nomenclature of Carboxylic Acids
3.9 Structure and Properties of Esters
3.10 Structure and Properties of Acid Chlorides
3.11 Structure and Properties of Anhydrides
3.12 Structure and Properties of Amines
3.13 Structure and Properties of Amides
3.14 Structure and Properties of Nitriles
3.15 Structure and Properties of Ethers
3.16 An Overview of Spectroscopy and the Relationship to Functional Groups
End of Chapter Problems
4 Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities
4.1 Introduction
4.2 Structural Isomers
4.3 Conformational Isomers of Alkanes
4.4 Conformational Isomers of Cycloalkanes
4.5 Geometric Isomers
4.6 Stability of Alkanes
4.7 Stability of Alkenes
4.8 Stability of Alkynes
End of Chapter Problems
5 Stereochemistry
5.1 Introduction
5.2 Chiral Stereoisomers
5.3 Significance of Chirality
5.4 Nomenclature of the Absolute Configuration of Chiral Molecules
5.5 Properties of Stereogenic Compounds
5.6 Compounds with More Than One Stereogenic Carbon
5.7 Resolution of Enantiomers
End of Chapter Problems
6 An Overview of the Reactions of Organic Chemistry
6.1 Introduction
6.2 Acid–Base Reactions
6.3 Addition Reactions
6.4 Reduction Reactions
6.5 Oxidation Reactions
6.6 Elimination Reactions
6.7 Substitution Reactions
6.8 Pericyclic Reactions
6.9 Catalytic Coupling Reactions
End of Chapter Problems
7 Acid–Base Reactions in Organic Chemistry
7.1 Introduction
7.2 Lewis Acids and Bases
7.3 Relative Strengths of Acids and Conjugate Bases
7.4 Predicting the Relative Strengths of Acids and Bases
7.5 Factors That Affect Acid and Base Strengths
7.6 Applications of Acid–Bases Reactions in Organic Chemistry
End of Chapter Problems
8 Addition Reactions Involving Alkenes and Alkynes
8.1 Introduction
8.2 The Mechanism for Addition Reactions Involving Alkenes
8.3 Addition of Hydrogen Halide to Alkenes (Hydrohalogenation of Alkenes)
8.4 Addition of Halogens to Alkenes (Halogenation of Alkenes)
8.5 Addition of Halogens and Water to Alkenes (Halohydrin Formation)
8.6 Addition of Water to Alkenes (Hydration of Alkenes)
8.7 Addition of Carbenes to Alkenes
8.8 The Mechanism for Addition Reactions Involving Alkynes
8.9 Applications of Addition Reactions to Synthesis
End of Chapter Problems
9 Addition Reactions Involving Carbonyls and Nitriles
9.1 Introduction
9.2 Mechanism for Addition Reactions Involving Carbonyl Compounds
9.3 Addition of HCN to Carbonyl Compounds
9.4 Addition of Water to Carbonyl Compounds
9.5 Addition of Alcohols to Carbonyl Compounds
9.6 Addition of Ylides to Carbonyl Compounds (The Wittig Reaction)
9.7 Addition of Enolates to Carbonyl Compounds
9.8 Addition of Amines to Carbonyl Compounds
9.9 Mechanism for Addition Reactions Involving Imines
9.10 Mechanism for Addition Reactions Involving Nitriles
9.11 Applications of Addition Reactions to Synthesis
End of Chapter Problems
10 Reduction Reactions in Organic Chemistry
10.1 Introduction
10.2 Reducing Agents of Organic Chemistry
10.3 Reduction of C=O and C=S Containing Compounds
10.4 Reduction of Imines
10.5 Reduction of Oxiranes
10.6 Reduction of Aromatic Compounds, Alkynes, and Alkenes
End of Chapter Problems
11 Oxidation Reactions in Organic Chemistry
11.1 Introduction
11.2 Oxidation
11.3 Oxidation of Alcohols and Aldehydes
11.4 Oxidation of Alkenes Without Bond Cleavage
11.5 Oxidation of Alkenes with Bond Cleavage
11.6 Applications of Oxidation Reactions of Alkenes
11.7 Oxidation of Alkynes
11.8 Oxidation of Aromatic Compounds
11.9 Autooxidation of Ethers and Alkenes
11.10 Applications of Oxidation Reactions to Synthesis
End of Chapter Problems
12 Elimination Reactions of Organic Chemistry
12.1 Introduction
12.2 Mechanisms of Elimination Reactions
12.3 Elimination of Hydrogen and Halide (Dehydrohalogenation)
12.4 Elimination of Water (Dehydration)
12.5 Applications of Elimination Reactions to Synthesis
End of Chapter Problems
13 Spectroscopy Revisited, A More Detailed Examination
13.1 Introduction
13.2 The Electromagnetic Spectrum
13.3 UV‐Vis Spectroscopy and Conjugated Systems
13.4 Infrared Spectroscopy
13.5 Mass Spectrometry
13.6 Nuclear Magnetic Resonance (NMR) Spectroscopy
End of Chapter Problems
14 Free Radical Substitution Reactions Involving Alkanes
14.1 Introduction
14.2 Types of Alkanes and Alkyl Halides
14.3 Chlorination of Alkanes
14.4 Bromination of Alkanes
14.5 Applications of Free Radical Substitution Reactions
14.6 Free Radical Inhibitors
14.7 Environmental Impact of Organohalides and Free Radicals
End of Chapter Problems
15 Nucleophilic Substitution Reactions at sp3 Carbons
15.1 Introduction
15.2 The Electrophile
15.3 The Leaving Group
15.4 The Nucleophile
15.5 Nucleophilic Substitution Reactions
15.6 Bimolecular Substitution Reaction Mechanism (S
N
2 Mechanism)
15.7 Unimolecular Substitution Reaction Mechanism (S
N
1 Mechanism)
15.8 Applications of Nucleophilic Substitution Reactions – Synthesis
End of Chapter Problems
16 Nucleophilic Substitution Reactions at Acyl Carbons
16.1 Introduction
16.2 Mechanism for Acyl Substitution
16.3 Substitution Reactions Involving Acid Chlorides
16.4 Substitution Reactions Involving Anhydrides
16.5 Substitution Reactions Involving Esters
16.6 Substitution Reactions Involving Amides
16.7 Substitution Reactions Involving Carboxylic Acids
16.8 Substitution Reactions Involving Oxalyl Chloride
16.9 Substitution Reactions Involving Sulfur Containing Compounds
16.10 Applications of Acyl Substitution Reactions
End of Chapter Problems
17 Aromaticity and Aromatic Substitution Reactions
17.1 Introduction
17.2 Structure and Properties of Benzene
17.3 Nomenclature of Substituted Benzene
17.4 Stability of Benzene
17.5 Characteristics of Aromatic Compounds
17.6 Electrophilic Aromatic Substitution Reactions of Benzene
17.7 Electrophilic Aromatic Substitution Reactions of Substituted Benzene
17.8 Applications – Synthesis of Substituted Benzene Compounds
17.9 Electrophilic Substitution Reactions of Polycyclic Aromatic Compounds
17.10 Electrophilic Substitution Reactions of Pyrrole
17.11 Electrophilic Substitution Reactions of Pyridine
17.12 Nucleophilic Aromatic Substitution
End of Chapter Problems
18 Conjugated Systems and Pericyclic Reactions
18.1 Conjugated Systems
18.2 Pericyclic Reactions
End of Chapter Problems
19 Catalytic Carbon–Carbon Coupling Reactions
19.1 Introduction
19.2 Reactions of Transition Metal Complexes
19.3 Palladium‐Catalyzed Coupling Reactions
End of Chapter Problems
20 Synthetic Polymers and Biopolymers
20.1 Introduction
20.2 Cationic Polymerization of Alkenes
20.3 Anionic Polymerization of Alkenes
20.4 Free Radical Polymerization of Alkenes
20.5 Copolymerization of Alkenes
20.6 Properties of Polymers
20.7 Biopolymers
20.8 Amino Acids, Monomers of Peptides and Proteins
20.9 Acid–Base Properties of Amino Acids
20.10 Synthesis of α‐Amino Acids
20.11 Reactions of α‐Amino Acids
20.12 Primary Structure and Properties of Peptides
20.13 Secondary Structure of Proteins
20.14 Monosaccharides, Monomers of Carbohydrates
20.15 Reactions of Monosaccharides
20.16 Disaccharides and Polysaccharides
20.17 N‐Glycosides and Amino Sugars
20.18 Lipids
20.19 Properties and Reactions of Waxes
20.20 Properties and Reactions of Triglycerides
20.21 Properties and Reactions of Phospholipids
20.22 Structure and Properties of Steroids, Prostaglandins, and Terpenes
End of Chapter Problems
Index
End User License Agreement
List of Tables
Chapter 1
Table 1.1 Comparisons of the three types of orbitals found in most organic co...
Table 1.2 Number of bonds that are possible from a neutral atom in molecules.
Chapter 2
Table 2.1 Common functional groups of organic molecules.
Table 2.2 Various uses and properties of different categories of alkanes.
Table 2.3 The IUPAC names of straight chain hydrocarbons.
Table 2.4 IUPAC names for selected heteroatomic groups.
Table 2.5 The IUPAC names of cyclic hydrocarbons.
Chapter 3
Table 3.1 Selected IR frequencies of common functional groups.
Chapter 4
Table 4.1 Conformers of cis and trans isomers of disubstituted cyclohexanes.
Chapter 5
Table 5.1 Examples of different enantiomers of drugs having different physiol...
Chapter 7
Table 7.1 p
K
a
for various acids of organic chemistry.
Chapter 11
Table 11.1 Calculating the oxidation states for methane and carbon dioxide.
Table 11.2 Calculation the oxidation states for various types of hydrocarbons...
Table 11.3 Calculation the oxidation states for molecules with oxygen.
Chapter 13
Table 13.1 Relationship between different regions of the electromagnetic spec...
Table 13.2 IR frequencies of various functional groups.
Table 13.3 Chemical shifts of different protons based on different environmen...
Table 13.4 Carbon‐13 chemical shift values based on different environments of...
Chapter 14
Table 14.1 Bond dissociation energies for different types of hydrocarbons.
Table 14.2 Bond dissociation energies for different halogens.
Table 14.3 Dissociation bond energies for different C─H bonds.
Chapter 15
Table 15.1 Common protic and aprotic organic solvents.
Chapter 17
Table 17.1 Names that are used for some monosubstituted benzene molecules.
Table 17.2 Examples of activating and deactivating substituents for electroph...
Chapter 18
Table 18.1 Relationship between number of pi (π) electrons of conjugated syst...
Chapter 20
Table 20.1 Selected polymers produced from various monomers through polymeriz...
Table 20.2 Side‐chain groups of amino acids that occur naturally.
List of Illustrations
Chapter 1
Figure 1.1 A slice through an atom showing
s
orbitals with different princip...
Figure 1.2 A slice through an atom showing
p
orbitals with different princip...
Figure 1.3 The three equivalent
p
orbitals all point in three different dire...
Figure 1.4 Two‐dimensional illustration of the atom showing the nucleus, the...
Figure 1.5 The hydrogen atom as seen on the periodic table.
Figure 1.6 The carbon atom as seen on the periodic table.
Figure 1.7 Lewis dot structures for selected atoms.
Figure 1.8 The formation of an ionic bond between lithium and fluorine.
Figure 1.9 Correct Lewis dot structure for carbon dioxide (CO
2
).
Figure 1.10 Examples of common organic molecules with different geometries a...
Figure 1.11 Two different representations of polar covalent bonds.
Figure 1.12 Examples of selected molecules in which different representation...
Figure 1.13 Lewis dot structure of nitric acid showing the formal charges.
Figure 1.14 Equivalent Lewis dot structures (resonance structures) for nitri...
Figure 1.15 A detailed description of CH
3
CH
2
CH
3
using a line‐angle represent...
Figure 1.16 A detailed description of CH
3
CH(CH
3
)CH
3
using a line‐angle repre...
Figure 1.17 Molecular orbital diagram of hydrogen molecule.
Figure 1.18 Hybridization of the 2s and 2p orbitals of carbon to form four e...
Figure 1.19 Molecular orbital diagram of one of the bonds of methane, note t...
Figure 1.20 Methane showing the tetrahedral arrangement of the four equivale...
Figure 1.21 Hybridization of the 2s and 2p orbitals of nitrogen to form four...
Figure 1.22 Ammonia showing the trigonal pyramidal arrangement of the three ...
Figure 1.23 Hybridization of the 2s and two 2p orbitals of carbon to form th...
Figure 1.24 Graphical representation of sp
2
sigma bonds and unhybridized p o...
Figure 1.25 Graphical illustration of the pi (π) bond of ethylene.
Figure 1.26 Molecular orbital diagram of the pi (π) bond of ethylene
Figure 1.27 Graphical illustration of the pi (π) orbital of ethylene showing...
Figure 1.28 Relative energies of the molecular orbitals of ethylene
Figure 1.29 Hybridization of the 2s and one 2p orbital of carbon to form two...
Figure 1.30 Representation of the sigma bonds and two unhybridized 2p orbita...
Figure 1.31 Representation of the sigma bonds and two perpendicular pi (π) b...
Figure 1.32 Illustration of the dipole–dipole attraction between two molecul...
Figure 1.33 Hydrogen bond between two methanol molecules.
Figure 1.34 Graphical illustration of the attraction between two nonpolar mo...
Figure 1.35 Boiling points of different alkanes with the same molecular weig...
Chapter 2
Figure 2.1 Examples of common compounds that have different functional group...
Figure 2.2 Commonly known compounds with functional groups identified.
Figure 2.3 Examples of acyclic saturated hydrocarbon compounds, also known a...
Figure 2.4 Examples of cyclic saturated hydrocarbon compounds (cycloalkanes)...
Figure 2.5 The process of pumping petroleum, also called crude oil, from the...
Figure 2.6 Examples of using common names for some common compounds.
Figure 2.7. Representations of benzene.
Chapter 3
Figure 3.1 Infrared spectrum of water (H─O─H).
Figure 3.2 Infrared spectrum of methanol (CH
3
─OH).
Figure 3.3 Infrared spectrum of 2‐propanone (CH3COCH3).
Chapter 4
Figure 4.1 Illustration of the dashed‐wedge representation of 2‐bromobutane....
Figure 4.2 A dashed‐wedge representation for 3,4‐dimethylhexane illustrating...
Figure 4.3 Dashed/wedge conformer that results after the rotation about the ...
Figure 4.4 Example of the orientation of molecules for the Newman projection...
Figure 4.5 The Newman projection of 3,4‐dimethylhexane shown in Figure 4.4
Figure 4.6 Newman projections of different conformers of 3,4‐dimethylhexane....
Figure 4.7 Relative energies of the various conformers of 1,2‐dibromoethane ...
Figure 4.8 Representations of trans and cis arrangements of 1,2‐dimethylcycl...
Figure 4.9 Representations of cyclobutane and
trans
and
cis
‐dimethylcyclobut...
Figure 4.10 Cyclopentane showing axial hydrogens (H
a
) and equatorial hydroge...
Figure 4.11
cis
and
trans
‐Dimethylcyclopentanes.
Figure 4.12 Different conformations of
cis
and
trans
‐1,3‐dichlorocyclopentan...
Figure 4.13 Chair and boat conformations of cyclohexane.
Figure 4.14 Illustration of the rationale for the relative stabilities of th...
Figure 4.15 Representation of the different hydrogens of cyclohexane chair c...
Figure 4.16 Conformational changes of cyclohexane from one chair conformer t...
Figure 4.17 Two chair conformers of methylcyclohexane.
Figure 4.18 Possible conformers of 1,4‐dimethylcyclohexane.
Figure 4.19 Possible conformers of 1,4‐dimethylcyclohexane in which the dash...
Figure 4.20 Different isomers (geometric isomers) of 1,2‐difluoroethene and ...
Figure 4.21 Examples of fatty acids (unsaturated fatty acids with cis double...
Figure 4.22 E and Z designation in the IUPAC nomenclature system of 1,2‐difl...
Figure 4.23 Energy profile for an exothermic reaction.
Figure 4.24 Reaction profile for the reactions of two different reactants th...
Figure 4.25 Combustion reactions of two isomers of octane showing the amount...
Figure 4.26 Reaction profile for the combustion reactions of octane (shown i...
Figure 4.27 Combustion of different alkanes, along with the amount of heat l...
Figure 4.28 Reaction profile for the catalytic hydrogenation of 3‐methyl‐1‐b...
Figure 4.29 Reaction profile for the catalytic hydrogenation of
cis
‐2‐butene...
Figure 4.30 Reaction profile for the catalytic hydrogenation of 1‐hexyne and...
Chapter 5
Figure 5.1
L
‐Alanine and
D
‐alanine are different molecules; they are mirror ...
Figure 5.2 Nonsuperimposable mirror images, also known as enantiomers.
Figure 5.3 Superimposable mirror images, or same molecules.
Figure 5.4 An example of a symmetrical molecule, which is not a stereogenic ...
Figure 5.5 Examples of chiral and achiral molecules, an asterisk indicates t...
Figure 5.6 Illustration of the dashed‐wedge representation for stereogenic m...
Figure 5.7 The Fischer projection of a specific isomer of 1‐bromo‐1‐chloroet...
Figure 5.8 Dashed/wedge and Fischer projection of 2‐bromobutane.
Figure 5.9 Hypothetical interaction between two enantiomers of a chiral drug...
Figure 5.10 Fischer projections of different stereoisomers of 2‐bromo‐3‐chlo...
Figure 5.11 Dashed‐wedge representations of the stereoisomers shown in Figur...
Figure 5.12 Dashed‐wedge representation of the stereoisomers shown in Figure...
Figure 5.13 Symmetrical analysis of isomers of 1,2‐dimethylcyclopropane.
Figure 5.14 An experimental method for the separation of a mixture of enanti...
Figure 5.15 Illustration of purification of carboxylic acid by the scheme sh...
Chapter 6
Figure 6.1 Examples of common organic acids.
Chapter 8
Figure 8.1 Energy profile for the hypothetical electrophilic addition reacti...
Figure 8.2 Relative stabilities of different types of carbocations.
Figure 8.3 Energy profile for the addition reaction of methylcyclohexene wit...
Figure 8.4 Flat carbocation showing equal probability of attack of nucleophi...
Figure 8.5 Relative stabilities of different types of radicals.
Figure 8.6 Proposed model for the electronic configuration of singlet carben...
Chapter 10
Figure 10.1 Steps for the cis hydrogenation of an alkene in the presence of ...
Chapter 11
Figure 11.1 Important biological α‐keto acids.
Chapter 12
Figure 12.1 Mechanism for a β‐elimination‐bimolecular (E2) elimination react...
Figure 12.2 Energy profile of a β‐elimination reaction. Note that this is a ...
Figure 12.3 Energy profile of E1 reaction. Note that first step is the slowe...
Chapter 13
Figure 13.1 Representation of energy in the form of a wave.
Figure 13.2 Relationship between the wavelength and the different regions of...
Figure 13.3 Ground state electronic configuration of ethylene showing the pi...
Figure 13.4 Ground state electronic configuration and excited state of ethyl...
Figure 13.5 pi (π) orbitals of 1,3‐butadiene.
Figure 13.6 UV‐Vis spectrum for isoprene, which has two double bonds in conj...
Figure 13.7 Vibrational modes and IR frequencies of carbon dioxide, which is...
Figure 13.8 IR spectrum of carbon dioxide showing the two vibrational modes....
Figure 13.9 IR spectrum of formaldehyde (HCOH).
Figure 13.10 IR spectrum of formic acid (HCO
2
H), showing the O─H and carboxy...
Figure 13.11 IR spectrum of benzoic acid, showing the OH and carboxylic acid...
Figure 13.12 IR spectrum of benzylamine, showing the N–H frequencies. Note t...
Figure 13.13 IR spectrum of benzyl alcohol, showing the O–H frequency. Note ...
Figure 13.14 Schematics showing the components of the electron impact mass s...
Figure 13.15 Electrospray ionization mass spectrometer.
Figure 13.16 Electron ionization mass spectrum of methylbromide (CH
3
Br).
Figure 13.17 Electron ionization mass spectrum of 2,4‐dimethylpentane.
Figure 13.18 Representation of spinning protons, which give rise to tiny mag...
Figure 13.19 Nonaligned nuclear spins in the absence of an external magnetic...
Figure 13.20 Representation of two possible orientations of a small bar magn...
Figure 13.21 Illustration of energy requirement for transition of various or...
Figure 13.22 Schematics of the nuclear magnetic resonance (NMR) spectrometer...
Figure 13.23 300 MHz nuclear magnetic resonance (NMR) instrument.
Figure 13.24 Methanol showing the different types of protons in different en...
Figure 13.25 NMR spectrum of methanol, showing TMS as zero on the ppm or
δ
...
Figure 13.26 Proposed NMR spectrum of
tert
‐butyl methyl ether.
Figure 13.27 300 MHz
1
H NMR spectrum of
tert
‐butyl methyl ether in CDCl
3
as ...
Figure 13.28 Proposed NMR spectrum for 1,1,2‐trichloroethane showing the dif...
Figure 13.29 Actual 300 MHz
1
H NMR spectrum for 1,1,2‐trichloroethane showin...
Figure 13.30 300 MHz
1
H NMR spectrum for 2‐methyl‐2‐propanol in CDCl
3
.
Figure 13.31 300 MHz
1
H NMR spectrum for 2‐methyl‐1‐propanol in CDCl
3
.
Figure 13.32 300 MHz
1
H NMR spectrum for 2‐butanol in CDCl
3
.
Figure 13.33 300 MHz
1
H NMR spectrum for 1‐butanol in CDCl
3
.
Figure 13.34 300 MHz
1
H NMR spectrum of benzene in CDCl
3
.
Figure 13.35 300 MHz
1
H NMR spectrum of nitrobenzene in CDCl
3
.
Figure 13.36 300 MHz
1
H NMR spectrum of 1,4‐dinitrobenzene in CDCl
3
.
Figure 13.37 300 MHz
1
H NMR spectrum of 1,2‐dinitrobenzene in acetone.
Figure 13.38 300 MHz
1
H NMR spectrum of 1,3‐dinitrobenzene in acetone.
Figure 13.39 300 MHz
1
H NMR spectrum of ethyl benzoate in CDCl
3
.
Figure 13.40 300 MHz
1
H NMR spectrum of phenyl propionate in CDCl
3
.
Figure 13.41 300 MHz
1
H NMR spectrum of benzyl alcohol in CDCl
3
.
Figure 13.42 300 MHz
1
H NMR spectrum of benzyl amine in CDCl
3
.
Figure 13.43 300 MHz
1
H NMR spectrum of benzoic acid in CDCl
3
.
Figure 13.44 300 MHz
1
H NMR spectrum of benzaldehyde acid in CDCl
3
.
Figure 13.45 300 MHz
13
C NMR spectrum of benzene in CDCl
3
.
Figure 13.46 300 MHz
13
C NMR spectrum of nitrobenzene in CDCl
3
.
Figure 13.47 300 MHz
13
C NMR spectrum of 1,3‐dinitrobenzene in CDCl
3
.
Figure 13.48 300 MHz
13
C NMR spectrum of benzyl alcohol in CDCl
3
.
Figure 13.49 300 MHz
13
C NMR spectrum of benzoic acid in CDCl
3
.
Figure 13.50 300 MHz
13
C NMR spectrum of benzaldehyde in CDCl
3
.
Chapter 14
Figure 14.1 Common alkyl halides that are used as common organic solvents.
Figure 14.2 Types of carbons and hydrogens of alkanes.
Figure 14.3 Types of carbons and hydrogens of propane.
Figure 14.4 Types of hydrogens bonded to 2‐methylpropane (isobutane).
Figure 14.5 Examples of the classification of different types of alkyl chlor...
Figure 14.6 Relative energies showing the difference in energies for differe...
Figure 14.7 Order of stability of radicals.
Figure 14.8 Relative strengths of the different types of C─H bonds, the stro...
Chapter 15
Figure 15.1 Energy profile of S
N
2 reaction of a nucleophile with an electrop...
Figure 15.2 Energy profile of S
N
2 reaction where
E
a1
represents the reaction...
Figure 15.3 Nucleophilicity trend for nucleophiles of S
N
2 reactions.
Figure 15.4 These bulky strong Lewis bases do not serve as good nucleophiles...
Figure 15.5 Solvated fluoride anion with a protic solvent, methanol.
Figure 15.6 Energy profile for a typical S
N
1 reaction, which takes place in ...
Figure 15.7 The attack of a flat carbocation by a nucleophile to give a pair...
Figure 15.8 Two different ways that a single covalent bond can be synthesize...
Figure 15.9 Two different ways of synthesizing the bond of the ether functio...
Chapter 16
Figure 16.1 Summary of the reactions of acid chlorides.
Figure 16.2 Summary of the reactions of esters.
Chapter 17
Figure 17.1 Kekulé's structure of benzene.
Figure 17.2 Model of benzene showing p orbitals and the nature of the bondin...
Figure 17.3 Common and acceptable representations of benzene.
Figure 17.4 Familiar pleasant‐smelling aromatic compounds, which all contain...
Figure 17.5 Commonly used compounds that contain the benzene ring system.
Figure 17.6 Different isomers of dimethylbenzenes.
Figure 17.7 Examples of disubstituted benzene.
Figure 17.8 Examples of disubstituted benzenes.
Figure 17.9 Common representations for the numbered relationships used in th...
Figure 17.10 Examples of common names of selected disubstituted benzenes.
Figure 17.11 Energy diagram illustrating the relationship between the stabil...
Figure 17.12 Representation of the exothermic reactions of benzene and the h...
Figure 17.13 Carbocyclic‐conjugated ions.
Figure 17.14 Examples of polycyclic molecules.
Figure 17.15 Examples of heterocyclic compounds.
Figure 17.16 Model of pyridine showing p orbitals and the nature of the bond...
Figure 17.17 Delocalization of electrons about the plane of pyrrole.
Figure 17.18 Delocalization of pi (π) and sigma electrons about the plane of...
Figure 17.19 Imidazole, a heterocyclic aromatic molecule.
Figure 17.20 Energy profile for the electrophilic substitution of naphthalen...
Figure 17.21 Direction of the dipole moment of pyrrole.
Chapter 18
Figure 18.1 Energy diagram of the relative stability of molecules with conju...
Figure 18.2 Molecular orbitals of ethylene molecule with its p electrons.
Figure 18.3 Illustration of incorrect phase of the orbitals of two ethylene ...
Figure 18.4 Illustration of correct phase of the orbitals of two ethylene mo...
Figure 18.5 Promotion of electron from the HOMO to LUMO for light.
Figure 18.6 Molecular orbitals of the ground state of 1,3‐butadiene and ethy...
Figure 18.7 Illustration of the correct phase involving the HOMO of 1,3‐buta...
Figure 18.8 Ground and excited states of 2,4‐hexadiene.
Figure 18.9 Conrotatory ring closure of ground state 1,3‐hexadiene to give t...
Figure 18.10 Disrotatory ring closure of excited 1,3‐hexadiene to give the p...
Chapter 19
Figure 19.1 A summary of the Heck catalytic coupling reactions.
Figure 19.2 A summary of the Suzuki catalytic coupling reactions.
Figure 19.3 A summary of the Stille catalytic coupling reactions.
Figure 19.4 A summary of the Negishi catalytic coupling reactions.
Chapter 20
Figure 20.1 Illustration of the molecular arrangements of crystalline and am...
Figure 20.2 Examples of a wax, a triglyceride, and a phospholipid.
Figure 20.3 Examples of a steroid, a prostaglandin, and a terpene.
Figure 20.4 Representation of soap molecules in water surrounding grease par...
Figure 20.5 Lecithin, a phospholipids, which is used for the treatment of va...
Guide
Cover
Table of Contents
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Organic Chemistry
Concepts and Applications
Allan D. Headley
Texas A&M UniversityCommerce, Texas, USA
This edition first published 2020© 2020 John Wiley & Sons, Inc.
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Library of Congress Cataloging‐in‐Publication Data
Names: Headley, Allan D., 1955– author.Title: Organic chemistry : concepts and applications / Allan D. Headley (Texas A&M University).Description: First edition. | Hoboken, NJ : Wiley, 2020. | Includes bibliographical references and index. |Identifiers: LCCN 2019018485 (print) | LCCN 2019020628 (ebook) | ISBN 9781119504627 (Adobe PDF) | ISBN 9781119504672 (ePub) | ISBN 9781119504580 (pbk.)Subjects: LCSH: Chemistry, Organic–Textbooks.Classification: LCC QD251.3 (ebook) | LCC QD251.3 .H43 2020 (print) | DDC 547–dc23LC record available at https://lccn.loc.gov/2019018485
Cover Design: WileyCover Images: Background © Sean Nel/Shutterstock, Chemical images courtesy of Allan D. Headley
Preface
About This Book
This book is written from the students' perspective. Addressing the questions that students of organic chemistry typically have, the errors they typically make, along with some fundamental misconceptions that they typically formulate, are all the focus of this textbook. A major difference between this textbook and the majority of other textbooks is with the presentation of the information. The objective of this textbook is to develop the student's ability to think critically and creatively and equally important to improve the problem‐solving skills of students. The content information is presented in such a way to assist students develop these skills. These are skills critically needed for students of science as they prepare for today's workforce. This approach also gives students the assurance that their opinions and thoughts are valued. As a result, students will become confident as they master the subject material. With this approach, students will quickly realize that it is in their best interest to develop these skills instead of relying on memorization as they approach this course and other science courses. The development of these skills will eventually prepare students to become better scientists. The problems in each chapter and at the end‐of‐chapter problems are designed to get students to solve problems by using their critical thinking skills.
For the majority of textbooks, the vast amount of organic chemistry information is dealt with primarily by categorizing the information into functional group categories. Thus, each of the approximately 20 chapters of a typical organic chemistry textbook is basically an exhaustive study of compounds with the different functional groups found in organic chemistry. This approach does not lend itself to aid students understand and master the vast content information of organic chemistry; this approach only presents large categories of information for students to handle. As a result, some students tend to rely on memorization instead of developing a scientific approach to handle all the information presented. In this textbook, the vast amount of organic chemistry information is not presented by functional group categories, but instead by reaction types; this approach presents much fewer categories of information for students to handle. In this textbook, the content information is divided into eight general categories based on reaction types, and not functional groups. An overview of the eight reaction types that are covered in the textbook is covered in Chapter 6. Since the majority of these types of reactions are the basic reactions covered in general chemistry, this approach provides a much better method to bridge the gap between general chemistry and organic chemistry. For example, there is a chapter that covers oxidation, a concept covered in general chemistry, but in this textbook, the concept of oxidation is applied to organic molecules that have different functional groups. Thus, after students have learned the concept of oxidation, they will be better prepared to apply that concept to a wide variety of organic molecules. The first part of the textbook covers relevant concepts of chemistry and the later sections deal with the applications of the concepts learned to the reactions of a wide cross section of molecules with different functional groups, hence the title of the textbook – Organic Chemistry: Concepts and Applications.
The first chapter covers the description of the atom and molecules; the next two chapters give a basic description of functional groups and the nomenclature of organic molecules so that students can readily recognize different types of molecules and learn the language of organic chemistry encountered in later chapters. The philosophy is that once students are able to recognize different functional groups, they will be better able to predict and communicate the various outcomes of different reactions encountered in organic chemistry. As a result, students will be able to apply their creative thinking skills to solve various problems encountered in this course. Since students are taught early in the textbook how to recognize the different reaction types, they will not only recognize the connection with general chemistry and organic chemistry but also how to apply the knowledge gained from general chemistry to new concepts that will be learned in organic chemistry.
Another aspect that this textbook covers is the importance and relevance of organic chemistry to our environment, the pharmaceutical and chemical industries, and biological and physical sciences. For example, in the study of the properties and the types of reactions that alkanes undergo, students will recognize the relevance of using different types of reactions to convert fossil and petroleum products into important compounds, such as polymers, pharmaceutical products, everyday household chemicals, insecticides, and herbicides. Also, the importance and significance of reactive intermediates including radicals are discussed. As a result, throughout the textbook, there are various “Did you Know?” sections. In these sections, students are shown the importance and the relevance of the content material being covered to the environment; often times, this is information that students may not have realized or know. There is a supplemental package that accompanies this text that includes multiple‐choice questions similar to those of most national standardized tests and there are answers and detailed explanations for the questions. This supplemental package is included since most students who take organic chemistry eventually take an aptitude test for professional schools, including the Medical College Admissions Test (MCAT) for medical school, Dental Aptitude Test (DAT) for dental school, Pharmacy College Admission Test (PCAT) for pharmacy school, or the GRE subject test for most graduate programs. Organic chemistry makes up a large percentage of these exams since students' critical, analytical, and creative skills are needed to be successful in organic chemistry and these programs.
In summary, this textbook offers a new approach to not only teach organic chemistry but also as a guide to assist students to become better scientists by developing their critical, analytical, and creative thinking skills. These skills will prepare students for today's job market, which relies heavily on the creative application of knowledge.
To the Student of Organic Chemistry
Chemistry is all around us and plays a very important role in just about every aspect of our everyday lives. Our society benefits from chemistry, especially organic chemistry, in many ways. A large percentage of just about everything around us is derived through a process that involves chemistry. For example, a large percentage of the clothes that we wear are synthetic polymers; the plastic containers for milk, water, and other liquids are made from polymers, which are different types of polymers from the kind that are used to make some of the clothes that we wear. So, it is important to understand and learn how chemistry can be used to benefit our everyday lives, and how chemists can utilize chemistry to improve the quality of our lives and solve various problems. In order to succeed in this course, you must have a positive attitude about chemistry. The same is true for any of your other courses and anything that you want to succeed at in life. Can you imagine an athlete who wants to be the best at his or her sport keeps saying that they just do not like the game or thinks that the game that they are playing is extremely difficult and that they will never master that particular game! I am of the impression that such an individual will not be very successful at that particular sport. As a result, this cannot be the approach to succeed at mastering something that needs to be mastered. A very positive approach must be taken in order to be successful in organic chemistry. One way of achieving the goal of benefiting the maximum from organic chemistry is to become involved in chemistry; get to know, understand, and appreciate its benefits to society. This approach will require constant and persistent work on this subject. Develop a schedule for study and try to study consistently for at least five to six hours per week. Depending on your background in chemistry, some students may require a bit more time. Most people who succeed at a particular discipline have to put aside a large percentage of time to practice and perfect their skills. Each member of the football team must practice regularly so that the team can be the best in the conference and the nation. We can learn something from their approach to achieve success – they set aside time to practice regularly. Whether the discipline is baseball, football, cheerleading, or chemistry, success appears to come from disciplined and consistent hard work. Like anything that we do in life that we are successful at, we must dedicate time in order to achieve perfection. An important aspect of time dedicated toward mastering organic chemistry is to attend classes and taking good notes. Just hearing the subject being discussed goes a long way. As you start to master the subject, you will require less time to understand the different topics of organic chemistry and you will be able to spend more time analyzing and applying the concepts learned.
There are strategies that have been proven to be useful in order to be successful in organic chemistry. It may sound simple, but the first strategy to succeed in organic chemistry is to attend lectures and it is important to attend each and every lecture. Read ahead of the lecture material that will be discussed. Sometimes, you may not fully understand the materials that you read, but the main point is to get familiar with the material so that when you get to lecture, you will have already seen some of the materials and understanding it then will be much easier. Practice, practice, practice! Work the problems at the end of the chapter and those in the chapter – do not just work problems to get the answers that are in the solutions manual, but spend most of your time understanding the concept of each problem. The problems in this textbook are designed to apply your understanding of specific concepts to solve a wide variety of problems. The problems are not designed to determine how well you have memorized the information and can reproduce it. Remember that the solutions that are found in the solutions manual are not always the only solutions; there are typically other reasonable possibilities. If your answer is different from the one shown in the solutions manual, you should use your critical thinking skills to determine why the difference before coming to a final conclusion. In working your problems, you should be able to formulate a very similar question by changing a few words or structures of molecules of the problem to get another problem that can test the same concept. You will have to think through possible solutions. It is best to work a few problems and understand the concepts involved than to work lots of problems and not fully understand the concepts or principles. In solving problems, make sure that you “work” through the problems and not just look at the problem and then look at the solutions manual for the “answer.” It is always a good practice to go over your graded exams. Some instructors offer regrades that allows students to challenge possible solutions and grading errors. Take advantage of this opportunity since it serves to reinforce your thinking ability and confidence, plus it may get you a few extra points on an exam!
It is impossible to learn chemistry and master the subject without getting questions. Scientists are curious individuals and are constantly seeking explanations for different observations. A good test of how well you are doing in this course is to determine how many questions come to you as the different topics are covered. If you read the textbook and attend lectures and have not developed a question or become curious about something, such as why does this happen, etc., you should try to carry out a deeper analysis of the topic that you are studying. The type of questions that should cross your mind should be of the curious type, the “what if” question is one that demonstrates curiosity. The next aspect of being a good scientist is to get your questions answered. Seek to get answers to your questions by first thinking through the concepts instead of just checking the solutions manual for the answers, or just getting an answer from someone without a discussion. With this approach, you have not utilized your critical and analytical thinking skills by just getting an answer. A major aspect of our work as scientists is centered on our ability to critically analyze information and formulate reasonable explanations. If you still need to get additional explanations for your questions, start seeking individuals who can assist. Most professors have posted office hours – use them. Some schools have help sessions or other forms of tutorials – capitalize on these opportunities. Some universities are very fortunate to have graduate students or tutorial study groups; these are tremendous resources to assist in getting your questions answered. Some students find it very helpful to form study groups. This approach is very helpful since you will learn from your peers. Peer‐led team learning environments are typically found in the workplace, the team approach is very useful in finding solutions to various problems. Remember that it is extremely difficult for you to succeed in this course by just working alone; this course is also intended to assist students to become good at working in teams. Molecular models and molecular modeling computer programs will play an important role in helping you to better visualize and understand most of the concepts that will be discussed in this course. There are lots of computer programs that will assist in the visualization of the actual three‐dimensional structures of molecules; some give good descriptions of the arrangements of electrons about atoms and molecules. Also, become very familiar with the periodic table and the meaning of each number on the table and the approximate location of each atom on the periodic table. This knowledge will become very useful in analyzing various properties of atoms and molecules.
There are many benefits to taking a course such as organic chemistry. Most of the principles and reactions that will be discussed in this course may not be remembered in years to come, but students will develop a more scientific mind from the various exercises, including the exams and discussions encountered throughout the course. Critical thinking, combined with a scientific approach developed in this course, is the key to being successful at your chosen profession and will be invaluable as you continue to prepare for your profession. From this course, you will not only gain knowledge of the basic principles of organic chemistry, but another major benefit, which is of equal importance, is the development and constant utilization of the critical and analytical thinking skills, which will be invaluable to assist you in solving work and life's everyday challenges. Most science students are required to take organic chemistry in order to assist in the development of better critical thinking skills. You will discover that if you take the scientific approach to learn organic chemistry, you will not have to memorize your way through this course. Instead, you will have the ability to apply the concepts learned to solve various problems and be better prepared to analyze and evaluate new information, and eventually be able to create new knowledge.
In summary, the ultimate goal of a course of this type is for students to be able to evaluate information learned and eventually to be able to generate new knowledge to benefit the society. Today's society is often described as a knowledge‐based society because of the need to have creative thinkers find innovative avenues to apply new knowledge learned. You will need to be disciplined, be ready to work hard and consistently, and not be afraid to think. This approach keeps research, innovation, and new discoveries alive. At the end of the semester, you should reflect on your accomplishments over the semester and determine if you have made any change in the way you think or approach problems and if you have become a better scientist. If you have, then you have had a very successful semester of organic chemistry!
To the Instructor
We have all heard the comment from some students of organic chemistry that there is a major disconnect between their general chemistry course and organic chemistry. One of the goals of this textbook is to address that disconnect. In this book, concepts that are learned in general chemistry are constantly being reinforced and are used as the foundation for students to gain a better understanding of concepts that are discussed in organic chemistry. Fundamental concepts are introduced early so that students can get a clear understanding of a topic that is being introduced. This approach is important so that when specific topics are re‐introduced throughout the textbook, students will be comfortable in applying the concepts learned to solve different problems.
In this book, students will find only relevant material throughout the text. Some textbooks try to introduce very advanced topics, and students at this level do not have a deep enough understanding of concepts involved to fully appreciate such advanced topics. As a result, students find such topics very confusing and often times serve as a distraction from the important topic being discussed. Information in this textbook is designed to stimulate students' critical thinking skills and to get students to apply these skills to find possible solutions to various problems. It is also designed to get students to fully develop the scientific method and to reach conclusions based on the scientific process. In this textbook, each concept is presented in a timely manner so that students are constantly building on their knowledge – most on the principles learned in general chemistry. Problems are carefully designed so that students have the opportunity to apply their critical thinking skills to determine possible solutions to problems encountered. As a result, there is no unique solution to most problems, but a discussion is given for each problem with possible solutions in the solutions manual. This approach makes students aware that there are sometimes not just one unique answer to some questions. This approach also serves to build students' confidence in making decisions about possible solutions. In this textbook, whenever a new topic is introduced, it is done so by reintroducing and building on the fundamental principles learned in general chemistry. As a result, this is a perfect textbook to bridge the gap between the courses of general chemistry and organic chemistry.
About the Companion Website
This book is accompanied by a companion website:
www.wiley.com/go/Headley_OrganicChemistry
The website includes:
Solution manual
MCQs
1Bonding and Structure of Organic Compounds
1.1 Introduction
The word “organic” was first used to describe compounds that were derived from plants or animals, but this term was later used to describe compounds that contain mostly carbon and hydrogen atoms. Today, the term organic is loosely used to describe food that is produced without the use of pesticides, hormones, antibiotics, or fertilizers.
In organic chemistry, we will carry out a detailed study of the composition, properties, and reactions of compounds that contain primarily carbon and hydrogen atoms, also known as organic compounds. Even though many organic compounds contain only carbon and hydrogen atoms, a large percentage contains other atoms, such as oxygen, nitrogen, sulfur, as well as halogens; these atoms are referred to as heteroatoms. Atoms other than carbon and hydrogen that are present in organic compounds are called heteroatoms.
Prior to the start of the nineteenth century, chemists were familiar with inorganic compounds; for example, it was known that ammonium cyanate, an inorganic compound, could be easily made by the exchange reaction shown in Reaction (1‐1).
Even though organic compounds were known, similar reactions that could be used for their synthesis were not known. Instead, organic compounds were obtained primarily from natural sources, such as extraction from plants and other natural sources. As early as 1828, a medical doctor, Friedrich Wöhler, synthesized urea, a known organic compound. The synthesis of urea was accomplished by heating ammonium cyanate (an inorganic compound), as shown by the reaction in Reaction (1‐2).
This was a major discovery that initiated the era of organic chemistry. For the first time, an organic compound could be synthesized and these types of compounds did not have to be obtained naturally. In the early 1800s, just about all compounds that were used for different reasons, mostly medical, were obtained from natural sources. Today, a large percentage of organic compounds, including urea, which is a major component of fertilizer, adhesives, and resins, are synthesized and are not obtained naturally.
DID YOU KNOW?
Fruits and vegetables that are produced without the use of pesticides or fertilizers are described as “organic.”
Organic chemistry is that branch of science that deals with the synthesis and properties of compounds that contain primarily carbon and hydrogen atoms. As mentioned earlier, many other compounds that also contain heteroatoms are also considered organic. It is truly remarkable that the millions of known organic compounds, with new ones being constantly synthesized, all contain only carbons, hydrogens, and just a few heteroatoms! Today, most of the organic compounds that are synthesized are not made from inorganic compounds, but from simpler organic compounds. Some known everyday organic compounds that are made from simple starting organic compounds are shown below.
You may be wondering where are the carbon and hydrogen atoms in these compounds since they are not shown in the structure, except for the first structure, which shows two representations of N,N‐diethyl‐3‐methylbenzamide (DEET). You will learn later in this chapter that at each intersection in the structure, there are carbon and hydrogen atoms or just carbon atoms. DEET contains carbon, hydrogen, oxygen, and nitrogen atoms. Ibuprofen, a painkiller, contains carbon, hydrogen, and oxygen atoms. The artificial sweetener, saccharin, contains carbon, hydrogen, oxygen, nitrogen, and sulfur atoms. Dichlorodiphenyltrichloroethane (DDT), which is used as an insecticide, contains carbon, hydrogen, and chlorine atoms. As mentioned earlier, these compounds are still considered organic even though they contain heteroatoms and not just carbon and hydrogen atoms. Today, a variety of useful organic compounds, like those shown above, are made from simple starting compounds and they are not obtained from natural sources. Various drugs, pesticides, herbicides, plastic bottles, and various household cleaners are examples of compounds that are synthesized from simple starting compounds. A specific branch of chemistry that deals with the synthesis of such compounds from simple starting compounds is called organic synthesis. Today’s pharmaceutical industries routinely synthesize important drugs to cure various diseases, but there are many factors that must be considered before a decision is made to synthesize a particular drug or to isolate it from nature as was typically done in the 1800s as pointed out earlier. It is extremely expensive to develop a particular drug, and isolation from natural sources has environmental impacts that must be considered.
DID YOU KNOW?
Taxol is an organic compound that is used for the cure of cancer, specifically cervical and breast cancer.
