John McMurry, Professor Emeritus

Index

Symbols

1,2-addition 14.2 Electrophilic Additions to Conjugated Dienes: Allylic Carbocations, 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones

1,3-diaxial interactions 4.7 Conformations of Monosubstituted Cyclohexanes

1,4-addition 14.2 Electrophilic Additions to Conjugated Dienes: Allylic Carbocations, 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones

3′ end 28.1 Nucleotides and Nucleic Acids

5′ end 28.1 Nucleotides and Nucleic Acids

α anomer 25.5 Cyclic Structures of Monosaccharides: Anomers

α helix 26.9 Protein Structure

α-amino acids 26.1 Structures of Amino Acids

α-substitution reaction Why This Chapter?

β anomer 25.5 Cyclic Structures of Monosaccharides: Anomers

β-oxidation pathway 29.3 Catabolism of Triacylglycerols: β-Oxidation

β-pleated sheet 26.9 Protein Structure

A

absolute configuration 5.5 Sequence Rules for Specifying Configuration

absorption spectrum 12.5 Spectroscopy and the Electromagnetic Spectrum

acetals, R₂C(OR′)₂ 19.10 Nucleophilic Addition of Alcohols: Acetal Formation

acetoacetic ester synthesis 22.7 Alkylation of Enolate Ions

acetylide anion 9.7 Alkyne Acidity: Formation of Acetylide Anions

achiral 5.2 The Reason for Handedness in Molecules: Chirality

acid anhydrides Why This Chapter?

acid chlorides 3.1 Functional Groups

acid halides Why This Chapter?

acidity constant (K_a) 2.8 Acid and Base Strength

activation energy, ΔG^‡ 6.9 Describing a Reaction: Energy Diagrams and Transition States

active site 6.11 A Comparison Between Biological Reactions and Laboratory Reactions

acyl (a-sil) group 19.1 Naming Aldehydes and Ketones

acyl group 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

acyl phosphates Why This Chapter?

acylated 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

acylation 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

Addition reactions 6.1 Kinds of Organic Reactions

AlCl₃-assisted 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

alcohols 3.1 Functional Groups, Why This Chapter?

Alcoholysis 21.2 Nucleophilic Acyl Substitution Reactions

aldaric acid 25.6 Reactions of Monosaccharides

Aldehydes 3.1 Functional Groups

Aldehydes (RCHO) Why This Chapter?

alditol 25.6 Reactions of Monosaccharides

aldol reaction 23.1 Carbonyl Condensations: The Aldol Reaction

aldonic acids 25.6 Reactions of Monosaccharides

aldoses 25.1 Classification of Carbohydrates

alicyclic 4.1 Naming Cycloalkanes

aliphatic 3.2 Alkanes and Alkane Isomers

alkaloids 2 Chemistry Matters —Alkaloids: From Cocaine to Dental Anesthetics

alkanes 3.2 Alkanes and Alkane Isomers

alkene Why This Chapter?

alkoxide ion, RO^– 17.2 Properties of Alcohols and Phenols

alkoxymercuration 18.2 Preparing Ethers

alkyl group 3.3 Alkyl Groups

Alkyl halides 3.1 Functional Groups, Why This Chapter?

alkylamines 24.1 Naming Amines

alkylation 9.8 Alkylation of Acetylide Anions, 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

alkyne Why This Chapter?

allyl group 7.3 Naming Alkenes

allylic 10.3 Preparing Alkyl Halides from Alkenes: Allylic Bromination

amides 3.1 Functional Groups, Why This Chapter?

amines 3.1 Functional Groups, Why This Chapter?

amino sugars 25.7 The Eight Essential Monosaccharides

Aminolysis 21.2 Nucleophilic Acyl Substitution Reactions

amplitude 12.5 Spectroscopy and the Electromagnetic Spectrum

Anabolic steroids 27.6 Steroids

anabolism 29.1 An Overview of Metabolism and Biochemical Energy

androgens 27.6 Steroids

angle strain 4.3 Stability of Cycloalkanes: Ring Strain

anomeric center 25.5 Cyclic Structures of Monosaccharides: Anomers

anomers 25.5 Cyclic Structures of Monosaccharides: Anomers

Antarafacial 30.5 Cycloaddition Reactions

anti conformation 3.7 Conformations of Other Alkanes

anti periplanar 11.8 The E2 Reaction and the Deuterium Isotope Effect

anti stereochemistry 8.2 Halogenation of Alkenes: Addition of X2

antiaromatic 15.3 Aromaticity and the Hückel 4n + 2 Rule

antibonding MO 1.11 Describing Chemical Bonds: Molecular Orbital Theory

anticodon 28.5 Translation of RNA: Protein Biosynthesis

antisense strand 28.4 Transcription of DNA

arenes 15.1 Naming Aromatic Compounds

aromatic Why This Chapter?

arylamines 24.1 Naming Amines

atactic 31.2 Stereochemistry of Polymerization: Ziegler–Natta Catalysts

atomic number (Z) 1.1 Atomic Structure: The Nucleus

Aufbau principle 1.3 Atomic Structure: Electron Configurations

axial 4.6 Axial and Equatorial Bonds in Cyclohexane

azo compounds, 24.8 Reactions of Arylamines

B

backbone 26.4 Peptides and Proteins

base peak 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

benzyl 15.1 Naming Aromatic Compounds

benzylic 11.5 Characteristics of the SN1 Reaction

benzyne 16.7 Benzyne

Bimolecular 11.2 The SN2 Reaction

Block copolymers 31.3 Copolymers

bond angle 1.6 sp3 Hybrid Orbitals and the Structure of Methane

bond dissociation energy (D) 6.8 Describing a Reaction: Bond Dissociation Energies

bond length 1.5 Describing Chemical Bonds: Valence Bond Theory

bond strength 1.5 Describing Chemical Bonds: Valence Bond Theory

bonding MO 1.11 Describing Chemical Bonds: Molecular Orbital Theory

branched-chain alkanes 3.2 Alkanes and Alkane Isomers

bromonium ion 8.2 Halogenation of Alkenes: Addition of X2

Brønsted–Lowry acid 2.7 Acids and Bases: The Brønsted–Lowry Definition

Brønsted–Lowry base 2.7 Acids and Bases: The Brønsted–Lowry Definition

C

C-terminal amino acid 26.4 Peptides and Proteins

Cahn–Ingold–Prelog rules 5.5 Sequence Rules for Specifying Configuration

Cannizzaro reaction 19.12 Biological Reductions

carbanion 10.6 Reactions of Alkyl Halides: Grignard Reagents

carbene, R₂C 8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis

carbinolamine 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation

carbocation 6.4 An Example of a Polar Reaction: Addition of HBr to Ethylene

Carbohydrates Why This Chapter?

Carbonyl condensation reactions 23.1 Carbonyl Condensations: The Aldol Reaction

carbonyl group 3.1 Functional Groups

carboxyl group 20.1 Naming Carboxylic Acids and Nitriles

carboxylation 20.5 Preparing Carboxylic Acids

carboxylic acid derivatives Why This Chapter?

carboxylic acids 3.1 Functional Groups

Carboxylic acids, RCO₂H Why This Chapter?

catabolism 29.1 An Overview of Metabolism and Biochemical Energy

cation radical 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

chain-growth polymers 8.10 Radical Additions to Alkenes: Chain-Growth Polymers, 21.9 Polyamides and Polyesters: Step-Growth Polymers, 31.1 Chain-Growth Polymers

chair conformation 4.5 Conformations of Cyclohexane

chemical shift 13.3 Chemical Shifts

chiral 5.2 The Reason for Handedness in Molecules: Chirality

chiral environment 5.12 Chirality in Nature and Chiral Environments

chirality centers 5.2 The Reason for Handedness in Molecules: Chirality

cis–trans isomers 4.2 Cis–Trans Isomerism in Cycloalkanes

citric acid cycle 29.7 The Citric Acid Cycle

Claisen condensation reaction 23.7 The Claisen Condensation Reaction

codon 28.5 Translation of RNA: Protein Biosynthesis

coenzyme 26.10 Enzymes and Coenzymes

cofactor 26.10 Enzymes and Coenzymes

combinatorial chemistry 16 Chemistry Matters —Combinatorial Chemistry

Complex carbohydrates 25.1 Classification of Carbohydrates

condensed structures 1.12 Drawing Chemical Structures

configuration 5.5 Sequence Rules for Specifying Configuration

conformational analysis 4.8 Conformations of Disubstituted Cyclohexanes

conformational isomers 3.6 Conformations of Ethane

conformations 3.6 Conformations of Ethane

conformers 3.6 Conformations of Ethane

conjugate acid 2.7 Acids and Bases: The Brønsted–Lowry Definition

conjugate addition 19.13 Conjugate Nucleophilic Addition to α,β‑Unsaturated Aldehydes and Ketones

conjugate base 2.7 Acids and Bases: The Brønsted–Lowry Definition

conjugated Why This Chapter?

conrotatory 30.2 Electrocyclic Reactions

constitutional isomers 3.2 Alkanes and Alkane Isomers

Copolymers 31.3 Copolymers

coupling 13.6 Spin–Spin Splitting in 1H NMR Spectra

coupling constant 13.6 Spin–Spin Splitting in 1H NMR Spectra

covalent bond 1.4 Development of Chemical Bonding Theory

Crown ethers 18.6 Crown Ethers

crystallites 31.7 Polymer Structure and Physical Properties

Curtius rearrangement 24.6 Synthesis of Amines

cyanohydrins 19.6 Nucleophilic Addition of HCN: Cyanohydrin Formation

cycloaddition reaction 30.5 Cycloaddition Reactions

cycloalkanes 4.1 Naming Cycloalkanes

D

D sugars 25.3 D,L Sugars

deamination 29.9 Catabolism of Proteins: Deamination

decarboxylation 22.7 Alkylation of Enolate Ions

degenerate 15.2 Structure and Stability of Benzene

degree of unsaturation 7.2 Calculating the Degree of Unsaturation

delocalized 10.4 Stability of the Allyl Radical: Resonance Revisited

delta (δ) scale 13.3 Chemical Shifts

denatured 26.9 Protein Structure

deoxy sugar 25.7 The Eight Essential Monosaccharides

deoxyribonucleic acid (DNA) Why This Chapter?

DEPT–NMR 13.12 DEPT 13C NMR Spectroscopy

deuterium isotope effect 11.8 The E2 Reaction and the Deuterium Isotope Effect

dextrorotatory 5.3 Optical Activity

Diastereomers 5.6 Diastereomers

diastereotopic 13.7 1H NMR Spectroscopy and Proton Equivalence

Dieckmann cyclization 23.9 Intramolecular Claisen Condensations: The Dieckmann Cyclization

Diels–Alder cycloaddition reaction 14.4 The Diels–Alder Cycloaddition Reaction

dienophile 14.5 Characteristics of the Diels–Alder Reaction

dipole moment 2.2 Polar Covalent Bonds and Dipole Moments

disaccharide 25.8 Disaccharides

Dispersion forces 2.12 Noncovalent Interactions between Molecules

disrotatory 30.2 Electrocyclic Reactions

disulfides 3.1 Functional Groups

disulfides (R–S–S–R′) 18.7 Thiols and Sulfides

double helix 28.2 Base Pairing in DNA

downfield 13.3 Chemical Shifts

E

E configuration 7.5 Alkene Stereochemistry and the E,Z Designation

E,Z system 7.5 Alkene Stereochemistry and the E,Z Designation

E1 reaction 11.10 The E1 and E1cB Reactions

E1cB reaction 11.10 The E1 and E1cB Reactions

E2 reaction 11.8 The E2 Reaction and the Deuterium Isotope Effect

eclipsed conformation 3.6 Conformations of Ethane

Edman degradation 26.6 Peptide Sequencing: The Edman Degradation

eicosanoids 27.4 Prostaglandins and Other Eicosanoids

Elastomers 31.7 Polymer Structure and Physical Properties

electrocyclic reaction 30.2 Electrocyclic Reactions

electromagnetic spectrum 12.5 Spectroscopy and the Electromagnetic Spectrum

electron shells 1.2 Atomic Structure: Orbitals

electron-dot structures 1.4 Development of Chemical Bonding Theory

electronegativity (EN) 2.1 Polar Covalent Bonds and Electronegativity

electrophile 6.3 Polar Reactions

electrophilic addition reaction 7.7 Electrophilic Addition Reactions of Alkenes

electrophilic aromatic substitution Why This Chapter?

electrostatic potential maps 2.1 Polar Covalent Bonds and Electronegativity

Elimination reactions 6.1 Kinds of Organic Reactions

enamines 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation

enantiomer 5.1 Enantiomers and the Tetrahedral Carbon

enantiotopic 13.7 1H NMR Spectroscopy and Proton Equivalence

endergonic 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

endo 14.5 Characteristics of the Diels–Alder Reaction

endothermic 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

enol 9.4 Hydration of Alkynes, 22.1 Keto–Enol Tautomerism

enolate ion 22.1 Keto–Enol Tautomerism

enthalpy change (ΔH) 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

entropy change (ΔS) 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

enzyme 26.10 Enzymes and Coenzymes

enzymes 6.11 A Comparison Between Biological Reactions and Laboratory Reactions

epimers 5.6 Diastereomers

epoxide 8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation

equatorial 4.6 Axial and Equatorial Bonds in Cyclohexane

esters 3.1 Functional Groups, Why This Chapter?

estrogens 27.6 Steroids

ethers 3.1 Functional Groups

Ethers (R–O–R′) Why This Chapter?

exergonic 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

exo 14.5 Characteristics of the Diels–Alder Reaction

exothermic 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

F

fatty acids 27.1 Waxes, Fats, and Oils

Fibers 31.7 Polymer Structure and Physical Properties

Fibrous proteins 26.9 Protein Structure

first-order reaction 11.4 The SN1 Reaction

Fischer esterification reaction 21.3 Reactions of Carboxylic Acids

Fischer projections 25.2 Representing Carbohydrate Stereochemistry: Fischer Projections

formal charge 2.3 Formal Charges

frequency, ν 12.5 Spectroscopy and the Electromagnetic Spectrum

Friedel–Crafts reaction 16.3 Alkylation and Acylation of Aromatic Rings: The Friedel–Crafts Reaction

frontier orbitals 30.1 Molecular Orbitals of Conjugated Pi Systems

FT–NMR 13.10 13C NMR Spectroscopy: Signal Averaging and FT–NMR

functional group 3.1 Functional Groups

furanose 25.5 Cyclic Structures of Monosaccharides: Anomers

G

Gabriel amine synthesis 24.6 Synthesis of Amines

gauche conformation 3.7 Conformations of Other Alkanes

genes 28.4 Transcription of DNA

Gibbs free-energy change (ΔG) 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

Gilman reagents (LiR₂Cu) 10.7 Organometallic Coupling Reactions

glass transition temperature, T_g 31.7 Polymer Structure and Physical Properties

Globular proteins 26.9 Protein Structure

glucocorticoids 27.6 Steroids

gluconeogenesis 29.8 Carbohydrate Biosynthesis: Gluconeogenesis

glycol 8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation

glycolysis 29.5 Catabolism of Carbohydrates: Glycolysis

glycoside 25.6 Reactions of Monosaccharides

graft copolymers 31.3 Copolymers

Grignard reaction 21.2 Nucleophilic Acyl Substitution Reactions

Grignard reagents (RMgX) 10.6 Reactions of Alkyl Halides: Grignard Reagents

ground-state electron configuration 1.3 Atomic Structure: Electron Configurations

H

halohydrin 8.3 Halohydrins from Alkenes: Addition of HO-X

Hammond postulate 7.10 The Hammond Postulate

heat of reaction 6.7 Describing a Reaction: Equilibria, Rates, and Energy Changes

hemiacetal 19.10 Nucleophilic Addition of Alcohols: Acetal Formation

Henderson–Hasselbalch equation 20.3 Biological Acids and the Henderson–Hasselbalch Equation

hertz, Hz 12.5 Spectroscopy and the Electromagnetic Spectrum

heterocycle 15.5 Aromatic Heterocycles: Pyridine and Pyrrole

Heterocyclic amines 24.1 Naming Amines

highest occupied molecular orbital (HOMO) 14.7 Ultraviolet Spectroscopy, 30.1 Molecular Orbitals of Conjugated Pi Systems

Hofmann elimination reaction 24.7 Reactions of Amines

Hofmann rearrangement 24.6 Synthesis of Amines

homopolymers 31.3 Copolymers

homotopic 13.7 1H NMR Spectroscopy and Proton Equivalence

hormones 27.6 Steroids

Hückel 4n + 2 rule 15.3 Aromaticity and the Hückel 4n + 2 Rule

Hund’s rule 1.3 Atomic Structure: Electron Configurations

hydride shift 7.11 Evidence for the Mechanism of Electrophilic Additions: Carbocation Rearrangements

hydroboration 8.5 Hydration of Alkenes: Addition of H2O by Hydroboration

hydrocarbons 3.2 Alkanes and Alkane Isomers

hydrogen bond 2.12 Noncovalent Interactions between Molecules

hydrogenated 8.6 Reduction of Alkenes: Hydrogenation

hydrolases 26.10 Enzymes and Coenzymes

Hydrolysis 21.2 Nucleophilic Acyl Substitution Reactions

hydrophilic 2.12 Noncovalent Interactions between Molecules

hydrophobic 2.12 Noncovalent Interactions between Molecules

hydroquinones 17.10 Reactions of Phenols

hydroxylation 8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation

hyperconjugation 7.6 Stability of Alkenes

I

imide 24.6 Synthesis of Amines

imines 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation

inductive effect 2.1 Polar Covalent Bonds and Electronegativity, 16.4 Substituent Effects in Electrophilic Substitutions

infrared (IR) spectroscopy 12.6 Infrared Spectroscopy

integrating 13.5 Integration of 1H NMR Absorptions: Proton Counting

intermolecular forces 2.12 Noncovalent Interactions between Molecules

ion pairs 11.4 The SN1 Reaction

ionic bond 1.4 Development of Chemical Bonding Theory

isoelectric point (pI) 26.2 Amino Acids and the Henderson–Hasselbalch Equation: Isoelectric Points

isomerases 26.10 Enzymes and Coenzymes

Isomers 3.2 Alkanes and Alkane Isomers

isotactic 31.2 Stereochemistry of Polymerization: Ziegler–Natta Catalysts

isotopes 1.1 Atomic Structure: The Nucleus

K

Kekulé structures 1.4 Development of Chemical Bonding Theory

ketals 19.10 Nucleophilic Addition of Alcohols: Acetal Formation

ketones 3.1 Functional Groups

ketones (R₂CO) Why This Chapter?

ketoses 25.1 Classification of Carbohydrates

Kiliani–Fischer synthesis 25.6 Reactions of Monosaccharides

kinetic control 14.3 Kinetic versus Thermodynamic Control of Reactions

kinetics 11.2 The SN2 Reaction

Koenigs–Knorr reaction 25.6 Reactions of Monosaccharides

L

L sugars 25.3 D,L Sugars

lactams 21.7 Chemistry of Amides

lactones 21.6 Chemistry of Esters

leaving group 11.3 Characteristics of the SN2 Reaction

levorotatory 5.3 Optical Activity

Lewis acid 2.11 Acids and Bases: The Lewis Definition

Lewis base 2.11 Acids and Bases: The Lewis Definition

Lewis structures 1.4 Development of Chemical Bonding Theory

Lindlar catalyst 9.5 Reduction of Alkynes

line-bond structures 1.4 Development of Chemical Bonding Theory

lipid bilayer 27.3 Phospholipids

Lipids Why This Chapter?

Lipoproteins 27 Chemistry Matters —Saturated Fats, Cholesterol, and Heart Disease

lone-pair electrons 1.4 Development of Chemical Bonding Theory

lowest unoccupied molecular orbital (LUMO) 14.7 Ultraviolet Spectroscopy, 30.1 Molecular Orbitals of Conjugated Pi Systems

lyases 26.10 Enzymes and Coenzymes

M

malonic ester synthesis 22.7 Alkylation of Enolate Ions

Markovnikov’s rule 7.8 Orientation of Electrophilic Additions: Markovnikov’s Rule

mass number (A) 1.1 Atomic Structure: The Nucleus

mass spectrometry (MS) 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

McLafferty rearrangement 12.3 Mass Spectrometry of Some Common Functional Groups, 19.14 Spectroscopy of Aldehydes and Ketones

melt transition temperature, T_m 31.7 Polymer Structure and Physical Properties

mercapto group 18.7 Thiols and Sulfides

meso compounds 5.7 Meso Compounds

Messenger RNA (mRNA) 28.4 Transcription of DNA

meta (m) 15.1 Naming Aromatic Compounds

metabolism 29.1 An Overview of Metabolism and Biochemical Energy

methylene group 7.3 Naming Alkenes

micelles 27.2 Soap

Michael reaction 23.10 Conjugate Carbonyl Additions: The Michael Reaction

mineralocorticoids 27.6 Steroids

molar absorptivity (ϵ) 14.7 Ultraviolet Spectroscopy

Molecular orbital (MO) theory 1.11 Describing Chemical Bonds: Molecular Orbital Theory

molecule 1.4 Development of Chemical Bonding Theory

monomers 8.10 Radical Additions to Alkenes: Chain-Growth Polymers, Why This Chapter?

monosaccharides 25.1 Classification of Carbohydrates

multiplet 13.6 Spin–Spin Splitting in 1H NMR Spectra

mutarotation 25.5 Cyclic Structures of Monosaccharides: Anomers

N

n + 1 rule 13.6 Spin–Spin Splitting in 1H NMR Spectra

N-terminal amino acid 26.4 Peptides and Proteins

Newman projection 3.6 Conformations of Ethane

nitriles 20.1 Naming Carboxylic Acids and Nitriles

node 1.2 Atomic Structure: Orbitals

nonbonding electrons 1.4 Development of Chemical Bonding Theory

noncovalent interactions 2.12 Noncovalent Interactions between Molecules

Nuclear magnetic resonance (NMR) spectroscopy Why This Chapter?

nucleophile 6.3 Polar Reactions

nucleophilic acyl substitution reaction 21.2 Nucleophilic Acyl Substitution Reactions

nucleophilic addition reaction 19.4 Nucleophilic Addition Reactions of Aldehydes and Ketones

Nucleophilic aromatic substitution 16.6 Nucleophilic Aromatic Substitution

nucleophilic substitution reactions 11.1 The Discovery of Nucleophilic Substitution Reactions

nucleoside 28.1 Nucleotides and Nucleic Acids

nucleotides 28.1 Nucleotides and Nucleic Acids

O

olefin metathesis polymerization 31.5 Olefin Metathesis Polymerization

omega-3 fatty acid 27.1 Waxes, Fats, and Oils

optically active 5.3 Optical Activity

orbital 1.2 Atomic Structure: Orbitals

Organic chemistry Why This Chapter?

organohalides Why This Chapter?

organometallic 10.6 Reactions of Alkyl Halides: Grignard Reagents

ortho (o) 15.1 Naming Aromatic Compounds

oxidation 8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation

Oxidoreductases 26.10 Enzymes and Coenzymes

oxirane 8.7 Oxidation of Alkenes: Epoxidation and Hydroxylation

oxymercuration–demercuration 8.4 Hydration of Alkenes: Addition of H2O by Oxymercuration

ozonide 8.8 Oxidation of Alkenes: Cleavage to Carbonyl Compounds

P

para (p) 15.1 Naming Aromatic Compounds

parent peak 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

Pauli exclusion principle 1.3 Atomic Structure: Electron Configurations

peptides Why This Chapter?

pericyclic reaction Why This Chapter?

periplanar 11.8 The E2 Reaction and the Deuterium Isotope Effect

phenols Why This Chapter?

phenoxide ion, ArO^– 17.2 Properties of Alcohols and Phenols

phenyl 15.1 Naming Aromatic Compounds

phospholipids 27.3 Phospholipids

phosphorane 19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction

photochemical reactions 30.3 Stereochemistry of Thermal Electrocyclic Reactions

photon 12.5 Spectroscopy and the Electromagnetic Spectrum

pi (π) bond 1.8 sp2 Hybrid Orbitals and the Structure of Ethylene

pK_a 2.8 Acid and Base Strength

Plasticizers 31.7 Polymer Structure and Physical Properties

polar covalent bonds 2.1 Polar Covalent Bonds and Electronegativity

polar reactions 6.2 How Organic Reactions Occur: Mechanisms

polarizability 6.3 Polar Reactions

Polycarbonates 31.4 Step-Growth Polymers

polycyclic molecule 4.9 Conformations of Polycyclic Molecules

polymer 8.10 Radical Additions to Alkenes: Chain-Growth Polymers, Why This Chapter?

polymerase chain reaction (PCR) 28.8 The Polymerase Chain Reaction

Polysaccharides 25.9 Polysaccharides and Their Synthesis

polyunsaturated fatty acids 27.1 Waxes, Fats, and Oils

polyurethane 31.4 Step-Growth Polymers

primary (RNH₂) 24.1 Naming Amines

primary structure 26.9 Protein Structure

principal groups Appendix A Nomenclature of Polyfunctional Organic Compounds

pro-R 5.11 Prochirality

pro-S 5.11 Prochirality

prochiral 5.11 Prochirality

prochirality center 5.11 Prochirality

progestin 27.6 Steroids

Prostaglandins 27.4 Prostaglandins and Other Eicosanoids

protecting group 17.8 Protection of Alcohols

protein Why This Chapter?

pyranose 25.5 Cyclic Structures of Monosaccharides: Anomers

Q

quadrupole mass analyzer 12.1 Mass Spectrometry of Small Molecules: Magnetic-Sector Instruments

quaternary ammonium salts 24.1 Naming Amines

quaternary structure 26.9 Protein Structure

quinone 17.10 Reactions of Phenols

R

R 3.3 Alkyl Groups

R configuration 5.5 Sequence Rules for Specifying Configuration

racemate 5.8 Racemic Mixtures and the Resolution of Enantiomers

radical 6.2 How Organic Reactions Occur: Mechanisms

radical reactions 6.2 How Organic Reactions Occur: Mechanisms

rate-determining step 11.4 The SN1 Reaction

rate-limiting step 11.4 The SN1 Reaction

Re face 5.11 Prochirality

reaction coordinate 6.9 Describing a Reaction: Energy Diagrams and Transition States

reaction intermediate 6.10 Describing a Reaction: Intermediates

reaction mechanism 6.2 How Organic Reactions Occur: Mechanisms

Rearrangement reactions 6.1 Kinds of Organic Reactions

reducing sugars 25.6 Reactions of Monosaccharides

reduction 8.6 Reduction of Alkenes: Hydrogenation, 21.2 Nucleophilic Acyl Substitution Reactions

reductive amination 24.6 Synthesis of Amines

regiospecific 7.8 Orientation of Electrophilic Additions: Markovnikov’s Rule

replication 28.3 Replication of DNA

residues 26.4 Peptides and Proteins

resonance effect 16.4 Substituent Effects in Electrophilic Substitutions

resonance forms 2.4 Resonance

resonance hybrid 2.4 Resonance

restriction endonucleases 28.6 DNA Sequencing

retrosynthetic 9.9 An Introduction to Organic Synthesis

ribonucleic acid (RNA) Why This Chapter?

Ribosomal RNA (rRNA) 28.4 Transcription of DNA

ring-current 15.7 Spectroscopy of Aromatic Compounds

ring-flip 4.6 Axial and Equatorial Bonds in Cyclohexane

Robinson annulation reaction 23.12 The Robinson Annulation Reaction

S

S configuration 5.5 Sequence Rules for Specifying Configuration

s-cis conformation 14.5 Characteristics of the Diels–Alder Reaction

Sandmeyer reaction 24.8 Reactions of Arylamines

Sanger dideoxy method 28.6 DNA Sequencing

saponification 21.6 Chemistry of Esters, 27.2 Soap

saturated 3.2 Alkanes and Alkane Isomers

sawhorse representation 3.6 Conformations of Ethane

Schiff base 29.5 Catabolism of Carbohydrates: Glycolysis

Schiff bases 19.8 Nucleophilic Addition of Amines: Imine and Enamine Formation

second-order reaction 11.2 The SN2 Reaction

secondary (R₂NH) 24.1 Naming Amines

secondary structure 26.9 Protein Structure

sense strand 28.4 Transcription of DNA

shielding 13.2 The Nature of NMR Absorptions

Si face 5.11 Prochirality

side chain 26.1 Structures of Amino Acids

sigma (σ) bonds 1.5 Describing Chemical Bonds: Valence Bond Theory

sigmatropic rearrangement 30.7 Sigmatropic Rearrangements

Simmons–Smith reaction 8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis

Simple sugars 25.1 Classification of Carbohydrates

skeletal structures 1.12 Drawing Chemical Structures

Small RNAs 28.4 Transcription of DNA

S_N1 reaction 11.4 The SN1 Reaction

S_N2 reaction 11.2 The SN2 Reaction

solvation 11.3 Characteristics of the SN2 Reaction

sp hybrid 1.9 sp Hybrid Orbitals and the Structure of Acetylene

sp² hybrid orbitals 1.8 sp2 Hybrid Orbitals and the Structure of Ethylene

sp³ hybrid orbitals 1.6 sp3 Hybrid Orbitals and the Structure of Methane

specific rotation, [α]_D 5.3 Optical Activity

spin–spin splitting 13.6 Spin–Spin Splitting in 1H NMR Spectra

staggered conformation 3.6 Conformations of Ethane

step-growth polymers 21.9 Polyamides and Polyesters: Step-Growth Polymers

Stereochemistry 3.6 Conformations of Ethane

stereoisomers 4.2 Cis–Trans Isomerism in Cycloalkanes

stereospecific 8.9 Addition of Carbenes to Alkenes: Cyclopropane Synthesis, 14.5 Characteristics of the Diels–Alder Reaction

Steric strain 3.7 Conformations of Other Alkanes, 4.3 Stability of Cycloalkanes: Ring Strain

steroids 27.6 Steroids

Stork enamine reaction 23.11 Carbonyl Condensations with Enamines: The Stork Enamine Reaction

straight-chain alkanes 3.2 Alkanes and Alkane Isomers

subordinate groups Appendix A Nomenclature of Polyfunctional Organic Compounds

substituent 3.4 Naming Alkanes

Substitution reactions 6.1 Kinds of Organic Reactions

sulfide 18.7 Thiols and Sulfides

sulfides 3.1 Functional Groups

sulfone (R₂SO₂) 18.7 Thiols and Sulfides

sulfonium ions 18.7 Thiols and Sulfides

sulfoxide (R₂SO) 18.7 Thiols and Sulfides

Suprafacial 30.5 Cycloaddition Reactions

symmetry-allowed 30.1 Molecular Orbitals of Conjugated Pi Systems

symmetry-disallowed 30.1 Molecular Orbitals of Conjugated Pi Systems

syn periplanar 11.8 The E2 Reaction and the Deuterium Isotope Effect

syn stereochemistry 8.5 Hydration of Alkenes: Addition of H2O by Hydroboration

syndiotactic 31.2 Stereochemistry of Polymerization: Ziegler–Natta Catalysts

T

tautomers 9.4 Hydration of Alkynes, 22.1 Keto–Enol Tautomerism

terpenoids 27.5 Terpenoids

tertiary (R₃N) 24.1 Naming Amines

tertiary structure 26.9 Protein Structure

thermodynamic control 14.3 Kinetic versus Thermodynamic Control of Reactions

Thermoplastics 31.7 Polymer Structure and Physical Properties

Thermosetting resins 31.7 Polymer Structure and Physical Properties

thioesters 3.1 Functional Groups, Why This Chapter?

thiolate ion 18.7 Thiols and Sulfides

thiols 3.1 Functional Groups, Why This Chapter?

Time of Flight 12.4 Mass Spectrometry in Biological Chemistry: Time-of-Flight (TOF) Instruments

torsional strain 3.6 Conformations of Ethane, 4.3 Stability of Cycloalkanes: Ring Strain

tosylate 11.1 The Discovery of Nucleophilic Substitution Reactions

transamination 29.9 Catabolism of Proteins: Deamination

transcription 28.4 Transcription of DNA

Transfer RNA (tRNA) 28.4 Transcription of DNA

transferases 26.10 Enzymes and Coenzymes

transition state 6.9 Describing a Reaction: Energy Diagrams and Transition States

translation 28.5 Translation of RNA: Protein Biosynthesis

triacylglycerols 27.1 Waxes, Fats, and Oils

turnover number 26.10 Enzymes and Coenzymes

twist-boat conformation 4.5 Conformations of Cyclohexane

U

ultraviolet (UV) spectroscopy 14.7 Ultraviolet Spectroscopy

unimolecular 11.4 The SN1 Reaction

unsaturated 7.2 Calculating the Degree of Unsaturation

upfield 13.3 Chemical Shifts

urethane 31.4 Step-Growth Polymers

uronic acid 25.6 Reactions of Monosaccharides

V

valence bond (VB) theory 1.5 Describing Chemical Bonds: Valence Bond Theory

valence shell 1.4 Development of Chemical Bonding Theory

van der Waals forces 2.12 Noncovalent Interactions between Molecules

vinyl group 7.3 Naming Alkenes

W

wavelength, λ 12.5 Spectroscopy and the Electromagnetic Spectrum

wavenumber

\tilde{v}

12.6 Infrared Spectroscopy

Waxes 27.1 Waxes, Fats, and Oils

Williamson ether synthesis 18.2 Preparing Ethers

Wittig reaction 19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction

Wohl degradation 25.6 Reactions of Monosaccharides

Wolff–Kishner reaction 19.9 Nucleophilic Addition of Hydrazine: The Wolff–Kishner Reaction

Y

ylide 19.11 Nucleophilic Addition of Phosphorus Ylides: The Wittig Reaction

Z

Z configuration 7.5 Alkene Stereochemistry and the E,Z Designation

Zaitsev’s rule 11.7 Elimination Reactions: Zaitsev’s Rule

Ziegler–Natta catalysts 31.2 Stereochemistry of Polymerization: Ziegler–Natta Catalysts

zwitterion 26.1 Structures of Amino Acids