Organic Chemistry 12th edition by Solomons Graham, Craig Fryhle, Scott Snyder 1119243700 9781119243700

Organic Chemistry 12th edition by Solomons T.W. Graham, Craig B. Fryhle, Scott A. Snyder – Ebook PDF Instant Download/DeliveryISBN: 1119243700, 9781119243700 

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ISBN-10 :  1119243700 

ISBN-13 :  9781119243700

Author:  Solomons T.W. Graham, Craig B. Fryhle, Scott A. Snyder 

The 12th edition of Organic Chemistry continues Solomons/Fryhle/Snyder’s tradition of excellence in teaching and preparing students for success in the organic classroom and beyond.

A central theme of the authors’ approach to organic chemistry is to emphasize the relationship between structure and reactivity. To accomplish this, the content is organized in a way that combines the most useful features of a functional group approach with one largely based on reaction mechanisms. The authors’ philosophy is to emphasize mechanisms and their common aspects as often as possible, and at the same time, use the unifying features of functional groups as the basis for most chapters. The structural aspects of the authors’ approach show students what organic chemistry is. Mechanistic aspects of their approach show students how it works. And wherever an opportunity arises, the authors’ show students what it does in living systems and the physical world around us.

Organic Chemistry 12th Table of contents:

CHAPTER 1: THE BASICS
1.1 LIFE AND THE CHEMISTRY OF CARBON COMPOUNDS—WE ARE STARDUST
1.2 ATOMIC STRUCTURE
1.3 CHEMICAL BONDS: THE OCTET RULE
1.4 HOW TO WRITE LEWIS STRUCTURES
1.5 FORMAL CHARGES AND HOW TO CALCULATE THEM
1.6 ISOMERS: DIFFERENT COMPOUNDS THAT HAVE THE SAME MOLECULAR FORMULA
1.7 HOW TO WRITE AND INTERPRET STRUCTURAL FORMULAS
1.8 RESONANCE THEORY
1.9 QUANTUM MECHANICS AND ATOMIC STRUCTURE
1.10 ATOMIC ORBITALS AND ELECTRON CONFIGURATION
1.11 MOLECULAR ORBITALS
1.12 THE STRUCTURE OF METHANE AND ETHANE: sp3 HYBRIDIZATION
1.13 THE STRUCTURE OF ETHENE (ETHYLENE): sp2 HYBRIDIZATION
1.14 THE STRUCTURE OF ETHYNE (ACETYLENE): sp HYBRIDIZATION
1.15 A SUMMARY OF IMPORTANT CONCEPTS THAT COME FROM QUANTUM MECHANICS
1.16 HOW TO PREDICT MOLECULAR GEOMETRY: THE VALENCE SHELL ELECTRON PAIR REPULSION MODEL
1.17 APPLICATIONS OF BASIC PRINCIPLES
SUMMARY AND REVIEW TOOLS
KEY TERMS AND CONCEPTS
PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 2: FAMILIES OF CARBON COMPOUNDS
2.1 HYDROCARBONS: REPRESENTATIVE ALKANES, ALKENES, ALKYNES, AND AROMATIC COMPOUNDS
2.2 POLAR COVALENT BONDS
2.3 POLAR AND NONPOLAR MOLECULES
2.4 FUNCTIONAL GROUPS
2.5 ALKYL HALIDES OR HALOALKANES
2.6 ALCOHOLS AND PHENOLS
2.7 ETHERS
2.8 AMINES
2.9 ALDEHYDES AND KETONES
2.10 CARBOXYLIC ACIDS, ESTERS, AND AMIDES
2.11 NITRILES
2.12 SUMMARY OF IMPORTANT FAMILIES OF ORGANIC COMPOUNDS
2.13 PHYSICAL PROPERTIES AND MOLECULAR STRUCTURE
2.14 SUMMARY OF ATTRACTIVE ELECTRIC FORCES
2.15 INFRARED SPECTROSCOPY: AN INSTRUMENTAL METHOD FOR DETECTING FUNCTIONAL GROUPS
2.16 INTERPRETING IR SPECTRA
2.17 APPLICATIONS OF BASIC PRINCIPLES
SUMMARY AND REVIEW TOOLS
KEY TERMS AND CONCEPTS
PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 3: ACIDS AND BASES
3.1 ACID–BASE REACTIONS
3.2 HOW TO USE CURVED ARROWS IN ILLUSTRATING REACTIONS
3.3 LEWIS ACIDS AND BASES
3.4 HETEROLYSIS OF BONDS TO CARBON: CARBOCATIONS AND CARBANIONS
3.5 THE STRENGTH OF BRØNSTED–LOWRY ACIDS AND BASES: Ka AND pKa
3.6 HOW TO PREDICT THE OUTCOME OF ACID–BASE REACTIONS
3.7 RELATIONSHIPS BETWEEN STRUCTURE AND ACIDITY
3.8 ENERGY CHANGES
3.9 THE RELATIONSHIP BETWEEN THE EQUILIBRIUM CONSTANT AND THE STANDARD FREE-ENERGY CHANGE, ΔG°
3.10 ACIDITY: CARBOXYLIC ACIDS VERSUS ALCOHOLS
3.11 THE EFFECT OF THE SOLVENT ON ACIDITY
3.12 ORGANIC COMPOUNDS AS BASES
3.13 A MECHANISM FOR AN ORGANIC REACTION
3.14 ACIDS AND BASES IN NONAQUEOUS SOLUTIONS
3.15 ACID–BASE REACTIONS AND THE SYNTHESIS OF DEUTERIUM- AND TRITIUM-LABELED COMPOUNDS
3.16 APPLICATIONS OF BASIC PRINCIPLES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 4: NOMENCLATURE AND CONFORMATIONS OF ALKANES AND CYCLOALKANES
4.1 INTRODUCTION TO ALKANES AND CYCLOALKANES
4.2 SHAPES OF ALKANES
4.3 HOW TO NAME ALKANES, ALKYL HALIDES, AND ALCOHOLS: THE IUPAC SYSTEM
4.4 HOW TO NAME CYCLOALKANES
4.5 HOW TO NAME ALKENES AND CYCLOALKENES
4.6 HOW TO NAME ALKYNES
4.7 PHYSICAL PROPERTIES OF ALKANES AND CYCLOALKANES
4.8 SIGMA BONDS AND BOND ROTATION
4.9 CONFORMATIONAL ANALYSIS OF BUTANE
4.10 THE RELATIVE STABILITIES OF CYCLOALKANES: RING STRAIN
4.11 CONFORMATIONS OF CYCLOHEXANE: THE CHAIR AND THE BOAT
4.12 SUBSTITUTED CYCLOHEXANES: AXIAL AND EQUATORIAL HYDROGEN GROUPS
4.13 DISUBSTITUTED CYCLOALKANES: CIS–TRANS ISOMERISM
4.14 BICYCLIC AND POLYCYCLIC ALKANES
4.15 CHEMICAL REACTIONS OF ALKANES
4.16 SYNTHESIS OF ALKANES AND CYCLOALKANES
4.17 HOW TO GAIN STRUCTURAL INFORMATION FROM MOLECULAR FORMULAS AND THE INDEX OF HYDROGEN DEFICIENCY
4.18 APPLICATIONS OF BASIC PRINCIPLES
SUMMARY AND REVIEW TOOLS
PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC A: 13C NMR SPECTROSCOPY—A PRACTICAL INTRODUCTION
A.1 ONE SIGNAL FOR EACH DISTINCT CARBON
A.2 CHEMICAL SHIFT—LOCATION OF THE SIGNAL DEPENDS ON ELECTRONIC ENVIRONMENT
A.3 HOW TO USE C NMR TO ELUCIDATE STRUCTURE
CHAPTER 5: STEREOCHEMISTRY
5.1 CHIRALITY AND STEREOCHEMISTRY
5.2 ISOMERISM: CONSTITUTIONAL ISOMERS AND STEREOISOMERS
5.3 ENANTIOMERS AND CHIRAL MOLECULES
5.4 MOLECULES HAVING ONE CHIRALITY CENTER ARE CHIRAL
5.5 MORE ABOUT THE BIOLOGICAL IMPORTANCE OF CHIRALITY
5.6 HOW TO TEST FOR CHIRALITY: PLANES OF SYMMETRY
5.7 NAMING ENANTIOMERS: THE R,S-SYSTEM
5.8 PROPERTIES OF ENANTIOMERS: OPTICAL ACTIVITY
5.9 RACEMIC FORMS
5.10 THE SYNTHESIS OF CHIRAL MOLECULES
5.11 CHIRAL DRUGS
5.12 MOLECULES WITH MORE THAN ONE CHIRALITY CENTER
5.13 FISCHER PROJECTION FORMULAS
5.14 STEREOISOMERISM OF CYCLIC COMPOUNDS
5.15 RELATING CONFIGURATIONS THROUGH REACTIONS IN WHICH NO BONDS TO THE CHIRALITY CENTER ARE BROKEN
5.16 SEPARATION OF ENANTIOMERS: RESOLUTION
5.17 COMPOUNDS WITH CHIRALITY CENTERS OTHER THAN CARBON
5.18 CHIRAL MOLECULES THAT DO NOT POSSESS A CHIRALITY CENTER
SUMMARY AND REVIEW TOOLS
PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 6: NUCLEOPHILIC REACTIONS
6.1 ALKYL HALIDES
6.2 NUCLEOPHILIC SUBSTITUTION REACTIONS
6.3 NUCLEOPHILES
6.4 LEAVING GROUPS
6.5 KINETICS OF A NUCLEOPHILIC SUBSTITUTION REACTION: AN SN2 REACTION
6.6 A MECHANISM FOR THE SN2 REACTION
6.7 TRANSITION STATE THEORY: FREE-ENERGY DIAGRAMS
6.8 THE STEREOCHEMISTRY OF SN2 REACTIONS
6.9 THE REACTION OF TERT-BUTYL CHLORIDE WITH WATER: AN SN1 REACTION
6.10 A MECHANISM FOR THE SN1 REACTION
6.11 CARBOCATIONS
6.12 THE STEREOCHEMISTRY OF SN1 REACTIONS
6.13 FACTORS AFFECTING THE RATES OF SN1 AND SN2 REACTIONS
6.14 ORGANIC SYNTHESIS: FUNCTIONAL GROUP TRANSFORMATIONS USING SN2 REACTIONS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
NOTES
CHAPTER 7: ALKENES AND ALKYNES I
7.1 INTRODUCTION
7.2 THE (E)–(Z) SYSTEM FOR DESIGNATING ALKENE DIASTEREOMERS
7.3 RELATIVE STABILITIES OF ALKENES
7.4 CYCLOALKENES
7.5 SYNTHESIS OF ALKENES: ELIMINATION REACTIONS
7.6 DEHYDROHALOGENATION
7.7 THE E2 REACTION
7.8 THE E1 REACTION
7.9 ELIMINATION AND SUBSTITUTION REACTIONS COMPETE WITH EACH OTHER
7.10 ELIMINATION OF ALCOHOLS: ACID-CATALYZED DEHYDRATION
7.11 CARBOCATION STABILITY AND THE OCCURRENCE OF MOLECULAR REARRANGEMENTS
7.12 THE ACIDITY OF TERMINAL ALKYNES
7.13 SYNTHESIS OF ALKYNES BY ELIMINATION REACTIONS
7.14 TERMINAL ALKYNES CAN BE CONVERTED TO NUCLEOPHILES FOR CARBON–CARBON BOND FORMATION
7.15 HYDROGENATION OF ALKENES
7.16 HYDROGENATION: THE FUNCTION OF THE CATALYST
7.17 HYDROGENATION OF ALKYNES
7.18 AN INTRODUCTION TO ORGANIC SYNTHESIS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 8: ALKENES AND ALKYNES II
8.1 ADDITION REACTIONS OF ALKENES
8.2 ELECTROPHILIC ADDITION OF HYDROGEN HALIDES TO ALKENES: MECHANISM AND MARKOVNIKOV’S RULE
8.3 STEREOCHEMISTRY OF THE IONIC ADDITION TO AN ALKENE
8.4 ADDITION OF WATER TO ALKENES: ACID-CATALYZED HYDRATION
8.5 ALCOHOLS FROM ALKENES THROUGH OXYMERCURATION–DEMERCURATION: MARKOVNIKOV ADDITION
8.6 ALCOHOLS FROM ALKENES THROUGH HYDROBORATION–OXIDATION: ANTI-MARKOVNIKOV SYN HYDRATION
8.7 HYDROBORATION: SYNTHESIS OF ALKYLBORANES
8.8 OXIDATION AND HYDROLYSIS OF ALKYLBORANES
8.9 SUMMARY OF ALKENE HYDRATION METHODS
8.10 PROTONOLYSIS OF ALKYLBORANES
8.11 ELECTROPHILIC ADDITION OF BROMINE AND CHLORINE TO ALKENES
8.12 STEREOSPECIFIC REACTIONS
8.13 HALOHYDRIN FORMATION
8.14 DIVALENT CARBON COMPOUNDS: CARBENES
8.15 OXIDATION OF ALKENES: SYN 1,2-DIHYDROXYLATION
8.16 OXIDATIVE CLEAVAGE OF ALKENES
8.17 ELECTROPHILIC ADDITION OF BROMINE AND CHLORINE TO ALKYNES
8.18 ADDITION OF HYDROGEN HALIDES TO ALKYNES
8.19 OXIDATIVE CLEAVAGE OF ALKYNES
8.20 HOW TO PLAN A SYNTHESIS: SOME APPROACHES AND EXAMPLES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 9: NUCLEAR MAGNETIC RESONANCE AND MASS SPECTROMETRY
9.1 INTRODUCTION
9.2 NUCLEAR MAGNETIC RESONANCE (NMR) SPECTROSCOPY
9.3 HOW TO INTERPRET PROTON NMR SPECTRA
9.4 SHIELDING AND DESHIELDING OF PROTONS: MORE ABOUT CHEMICAL SHIFT
9.5 CHEMICAL SHIFT EQUIVALENT AND NONEQUIVALENT PROTONS
9.6 SPIN–SPIN COUPLING: MORE ABOUT SIGNAL SPLITTING AND NONEQUIVALENT OR EQUIVALENT PROTONS
9.7 PROTON NMR SPECTRA AND RATE PROCESSES
9.8 CARBON-13 NMR SPECTROSCOPY
9.9 TWO-DIMENSIONAL (2D) NMR TECHNIQUES
9.10 AN INTRODUCTION TO MASS SPECTROMETRY
9.11 FORMATION OF IONS: ELECTRON IMPACT IONIZATION
9.12 DEPICTING THE MOLECULAR ION
9.13 FRAGMENTATION
9.14 ISOTOPES IN MASS SPECTRA
9.15 GC/MS ANALYSIS
9.16 MASS SPECTROMETRY OF BIOMOLECULES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC B: NMR THEORY AND INSTRUMENTATION
B.1 NUCLEAR SPIN: THE ORIGIN OF THE SIGNAL
B.2 DETECTING THE SIGNAL: FOURIER TRANSFORM NMR SPECTROMETERS
B.3 THE CHEMICAL SHIFT
B.4 SHIELDING AND DESHIELDING OF PROTONS: INDUCED MAGNETIC FIELDS
B.5 SPLITTING TREE DIAGRAMS AND THE ORIGIN OF SIGNAL SPLITTING
B.6 FACTORS THAT MAY COMPLICATE H NMR ANALYSES
CHAPTER 10: RADICAL REACTIONS
10.1 INTRODUCTION: HOW RADICALS FORM AND HOW THEY REACT
10.2 HOMOLYTIC BOND DISSOCIATION ENERGIES (DH°)
10.3 REACTIONS OF ALKANES WITH HALOGENS
10.4 CHLORINATION OF METHANE: MECHANISM OF REACTION
10.5 HALOGENATION OF HIGHER ALKANES
10.6 THE GEOMETRY OF ALKYL RADICALS
10.7 REACTIONS THAT GENERATE TETRAHEDRAL CHIRALITY CENTERS
10.8 ALLYLIC SUBSTITUTION AND ALLYLIC RADICALS
10.9 BENZYLIC SUBSTITUTION AND BENZYLIC RADICALS
10.10 RADICAL ADDITION TO ALKENES: THE ANTI-MARKOVNIKOV ADDITION OF HYDROGEN BROMIDE
10.11 RADICAL POLYMERIZATION OF ALKENES: CHAIN-GROWTH POLYMERS
10.12 OTHER IMPORTANT RADICAL REACTIONS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC C: CHAIN‐GROWTH POLYMERS
C.1 STEREOCHEMISTRY OF CHAIN‐GROWTH POLYMERIZATION
CHAPTER 11: ALCOHOLS AND ETHERS
11.1 STRUCTURE AND NOMENCLATURE
11.2 PHYSICAL PROPERTIES OF ALCOHOLS AND ETHERS
11.3 IMPORTANT ALCOHOLS AND ETHERS
11.4 SYNTHESIS OF ALCOHOLS FROM ALKENES
11.5 REACTIONS OF ALCOHOLS
11.6 ALCOHOLS AS ACIDS
11.7 CONVERSION OF ALCOHOLS INTO ALKYL HALIDES
11.8 ALKYL HALIDES FROM THE REACTION OF ALCOHOLS WITH HYDROGEN HALIDES
11.9 ALKYL HALIDES FROM THE REACTION OF ALCOHOLS WITH PBr3 or SOCl2
11.10 TOSYLATES, MESYLATES, AND TRIFLATES: LEAVING GROUP DERIVATIVES OF ALCOHOLS
11.11 SYNTHESIS OF ETHERS
11.12 REACTIONS OF ETHERS
11.13 EPOXIDES
11.14 REACTIONS OF EPOXIDES
11.15 ANTI 1,2-DIHYDROXYLATION OF ALKENES VIA EPOXIDES
11.16 CROWN ETHERS
11.17 SUMMARY OF REACTIONS OF ALKENES, ALCOHOLS, AND ETHERS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 12: ALCOHOLS FROM CARBONYL COMPOUNDS
12.1 STRUCTURE OF THE CARBONYL GROUP
12.2 OXIDATION–REDUCTION REACTIONS IN ORGANIC CHEMISTRY
12.3 ALCOHOLS BY REDUCTION OF CARBONYL COMPOUNDS
12.4 OXIDATION OF ALCOHOLS
12.5 ORGANOMETALLIC COMPOUNDS
12.6 PREPARATION OF ORGANOLITHIUM AND ORGANOMAGNESIUM COMPOUNDS
12.7 REACTIONS OF ORGANOLITHIUM AND ORGANOMAGNESIUM COMPOUNDS
12.8 ALCOHOLS FROM GRIGNARD REAGENTS
12.9 PROTECTING GROUPS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEM
SOLUTIONS TO PROBLEMS
QUIZ
SAMPLE PROBLEMS
SOLUTIONS TO SAMPLE PROBLEMS
FIRST REVIEW PROBLEM SET
ANSWERS TO FIRST REVIEW PROBLEM SET
CHAPTER 13: CONJUGATED UNSATURATED SYSTEMS
13.1 INTRODUCTION
13.2 THE STABILITY OF THE ALLYL RADICAL
13.3 THE ALLYL CATION
13.4 RESONANCE THEORY REVISITED
13.5 ALKADIENES AND POLYUNSATURATED HYDROCARBONS
13.6 1,3-BUTADIENE: ELECTRON DELOCALIZATION
13.7 THE STABILITY OF CONJUGATED DIENES
13.8 ULTRAVIOLET–VISIBLE SPECTROSCOPY
13.9 ELECTROPHILIC ATTACK ON CONJUGATED DIENES: 1,4-ADDITION
13.10 THE DIELS–ALDER REACTION: A 1,4-CYCLOADDITION REACTION OF DIENES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 14: AROMATIC COMPOUNDS
14.1 THE DISCOVERY OF BENZENE
14.2 NOMENCLATURE OF BENZENE DERIVATIVES
14.3 REACTIONS OF BENZENE
14.4 THE KEKULÉ STRUCTURE FOR BENZENE
14.5 THE THERMODYNAMIC STABILITY OF BENZENE
14.6 MODERN THEORIES OF THE STRUCTURE OF BENZENE
14.7 HÜCKEL’S RULE: THE 4n + 2 π ELECTRON RULE
14.8 OTHER AROMATIC COMPOUNDS
14.9 HETEROCYCLIC AROMATIC COMPOUNDS
14.10 AROMATIC COMPOUNDS IN BIOCHEMISTRY
14.11 SPECTROSCOPY OF AROMATIC COMPOUNDS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC D: ELECTROCYCLIC AND CYCLOADDITION REACTIONS
D.1 INTRODUCTION
D.2 ELECTROCYCLIC REACTIONS
D.3 THE COPE AND CLAISEN REARRANGEMENTS
D.4 CYCLOADDITION REACTIONS
CHAPTER 15: REACTIONS OF AROMATIC COMPOUNDS
15.1 ELECTROPHILIC AROMATIC SUBSTITUTION REACTIONS
15.2 A GENERAL MECHANISM FOR ELECTROPHILIC AROMATIC SUBSTITUTION
15.3 HALOGENATION OF BENZENE
15.4 NITRATION OF BENZENE
15.5 SULFONATION OF BENZENE
15.6 FRIEDEL–CRAFTS REACTIONS
15.7 SYNTHETIC APPLICATIONS OF FRIEDEL–CRAFTS ACYLATIONS: THE CLEMMENSEN AND WOLFF–KISHNER REDUCTIONS
15.8 EXISTING SUBSTITUENTS DIRECT THE POSITION OF ELECTROPHILIC AROMATIC SUBSTITUTION
15.9 ACTIVATING AND DEACTIVATING EFFECTS: HOW ELECTRON-DONATING AND ELECTRON-WITHDRAWING GROUPS AFFECT THE RATE OF AN EAS REACTION
15.10 DIRECTING EFFECTS IN DISUBSTITUTED BENZENES
15.11 REACTIONS OF BENZENE RING CARBON SIDE CHAINS
15.12 SYNTHETIC STRATEGIES
15.13 THE SNAr MECHANISM: NUCLEOPHILIC AROMATIC SUBSTITUTION BY ADDITION-ELIMINATIONSNAr
15.14 BENZYNE: NUCLEOPHILIC AROMATIC SUBSTITUTION BY ELIMINATION–ADDITION
15.15 REDUCTION OF AROMATIC COMPOUNDS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 16: ALDEHYDES AND KETONES
16.1 INTRODUCTION
16.2 NOMENCLATURE OF ALDEHYDES AND KETONES
16.3 PHYSICAL PROPERTIES
16.4 SYNTHESIS OF ALDEHYDES
16.5 SYNTHESIS OF KETONES
16.6 NUCLEOPHILIC ADDITION TO THE CARBON–OXYGEN DOUBLE BOND: MECHANISTIC THEMES
16.7 THE ADDITION OF ALCOHOLS: HEMIACETALS AND ACETALS
16.8 THE ADDITION OF PRIMARY AND SECONDARY AMINES
16.9 THE ADDITION OF HYDROGEN CYANIDE: CYANOHYDRINS
16.10 THE ADDITION OF YLIDES: THE WITTIG REACTION
16.11 OXIDATION OF ALDEHYDES
16.12 THE BAEYER–VILLIGER OXIDATION
16.13 CHEMICAL ANALYSES FOR ALDEHYDES AND KETONES
16.14 SPECTROSCOPIC PROPERTIES OF ALDEHYDES AND KETONES
16.15 SUMMARY OF ALDEHYDE AND KETONE ADDITION REACTIONS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 17: CARBOXYLIC ACIDS AND THEIR DERIVATIVES
17.1 INTRODUCTION
17.2 NOMENCLATURE AND PHYSICAL PROPERTIES
17.3 PREPARATION OF CARBOXYLIC ACIDS
17.4 ACYL SUBSTITUTION: NUCLEOPHILIC ADDITION–ELIMINATION AT THE ACYL CARBON
17.5 ACYL CHLORIDES
17.6 CARBOXYLIC ACID ANHYDRIDES
17.7 ESTERS
17.8 AMIDES
17.9 DERIVATIVES OF CARBONIC ACID
17.10 DECARBOXYLATION OF CARBOXYLIC ACIDS
17.11 POLYESTERS AND POLYAMIDES: STEP-GROWTH POLYMERS
17.12 SUMMARY OF THE REACTIONS OF CARBOXYLIC ACIDS AND THEIR DERIVATIVES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC E: STEP‐GROWTH POLYMERS
E.1 POLYAMIDES
E.2 POLYESTERS
E.3 POLYURETHANES
E.4 PHENOL–FORMALDEHYDE POLYMERS
CHAPTER 18: REACTIONS AT THE α CARBON OF CARBONYL COMPOUNDS
18.1 THE ACIDITY OF THE α HYDROGENS OF CARBONYL COMPOUNDS: ENOLATE ANIONS
18.2 KETO AND ENOL TAUTOMERS
18.3 REACTIONS VIA ENOLS AND ENOLATES
18.4 LITHIUM ENOLATES
18.5 ENOLATES OF β-DICARBONYL COMPOUNDS
18.6 SYNTHESIS OF METHYL KETONES: THE ACETOACETIC ESTER SYNTHESIS
18.7 SYNTHESIS OF SUBSTITUTED ACETIC ACIDS: THE MALONIC ESTER SYNTHESIS
18.8 FURTHER REACTIONS OF ACTIVE HYDROGEN COMPOUNDS
18.9 SYNTHESIS OF ENAMINES: STORK ENAMINE REACTIONS
18.10 SUMMARY OF ENOLATE CHEMISTRY
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 19: CONDENSATION AND CONJUGATE ADDITION REACTIONS OF CARBONYL COMPOUNDS
19.1 INTRODUCTION
19.2 THE CLAISEN CONDENSATION: A SYNTHESIS OF β-KETO ESTERS
19.3 β-DICARBONYL COMPOUNDS BY ACYLATION OF KETONE ENOLATES
19.4 ALDOL REACTIONS: ADDITION OF ENOLATES AND ENOLS TO ALDEHYDES AND KETONES
19.5 CROSSED ALDOL CONDENSATIONS
19.6 CYCLIZATIONS VIA ALDOL CONDENSATIONS
19.7 ADDITIONS TO α,β-UNSATURATED ALDEHYDES AND KETONES
19.8 THE MANNICH REACTION
19.9 SUMMARY OF IMPORTANT REACTIONS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC F: THIOLS, SULFUR YLIDES, AND DISULFIDES
F.1 PREPARATION OF THIOLS
F.2 PHYSICAL PROPERTIES OF THIOLS
F.3 THE ADDITION OF SULFUR YLIDES TO ALDEHYDES AND KETONES
F.4 THIOLS AND DISULFIDES IN BIOCHEMISTRY
SPECIAL TOPIC G: THIOL ESTERS AND LIPID BIOSYNTHESIS
G.1 THIOL ESTERS
G.2 BIOSYNTHESIS OF FATTY ACIDS
G.3 BIOSYNTHESIS OF ISOPRENOID COMPOUNDS
G.4 BIOSYNTHESIS OF STEROIDS
G.5 CHOLESTEROL AND HEART DISEASE
CHAPTER 20: AMINES
20.1 NOMENCLATURE
20.2 PHYSICAL PROPERTIES AND STRUCTURE OF AMINES
20.3 BASICITY OF AMINES: AMINE SALTS
20.4 PREPARATION OF AMINES
20.5 REACTIONS OF AMINES
20.6 REACTIONS OF AMINES WITH NITROUS ACID
20.7 REPLACEMENT REACTIONS OF ARENEDIAZONIUM SALTS
20.8 COUPLING REACTIONS OF ARENEDIAZONIUM SALTS
20.9 REACTIONS OF AMINES WITH SULFONYL CHLORIDES
20.10 SYNTHESIS OF SULFA DRUGS
20.11 ANALYSIS OF AMINES
20.12 ELIMINATIONS INVOLVING AMMONIUM COMPOUNDS
20.13 SUMMARY OF PREPARATIONS AND REACTIONS OF AMINES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
PREPARATION AND REACTIONS OF AMINES
SOLUTIONS TO PROBLEMS
QUIZ
SPECIAL TOPIC H: ALKALOIDS
H.1 ALKALOIDS CONTAINING A PYRIDINE OR REDUCED PYRIDINE RING
H.2 LKALOIDS CONTAINING AN ISOQUINOLINE OR REDUCED ISOQUINOLINE RING
H.3 ALKALOIDS CONTAINING INDOLE OR REDUCED INDOLE RINGS
CHAPTER 21: TRANSITION METAL COMPLEXES
21.1 ORGANOMETALLIC COMPOUNDS IN PREVIOUS CHAPTERS
21.2 TRANSITION METAL ELEMENTS AND COMPLEXES
21.3 HOW TO COUNT ELECTRONS IN A METAL COMPLEX
21.4 MECHANISTIC STEPS IN THE REACTIONS OF SOME TRANSITION METAL COMPLEXES
21.5 HOMOGENEOUS HYDROGENATION: WILKINSON’S CATALYST
21.6 CROSS-COUPLING REACTIONS
21.7 OLEFIN METATHESIS
21.8 TRANSITION METALS IN NATURE: VITAMIN B12 AND VANADIUM HALOPEROXIDASES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
SECOND REVIEW PROBLEM SET
ANSWERS TO SECOND REVIEW PROBLEM SET
CHAPTER 22: CARBOHYDRATES
22.1 INTRODUCTION
22.2 MONOSACCHARIDES
22.3 MUTAROTATION
22.4 GLYCOSIDE FORMATION
22.5 OTHER REACTIONS OF MONOSACCHARIDES
22.6 OXIDATION REACTIONS OF MONOSACCHARIDES
22.7 REDUCTION OF MONOSACCHARIDES: ALDITOLS
22.8 REACTIONS OF MONOSACCHARIDES WITH PHENYLHYDRAZINE: OSAZONES
22.9 SYNTHESIS AND DEGRADATION OF MONOSACCHARIDES
22.10 THE D FAMILY OF ALDOSESD
22.11 FISCHER’S PROOF OF THE CONFIGURATION OF D-(+)-GLUCOSED
22.12 DISACCHARIDES
22.13 POLYSACCHARIDES
22.14 OTHER BIOLOGICALLY IMPORTANT SUGARS
22.15 SUGARS THAT CONTAIN NITROGEN
22.16 GLYCOLIPIDS AND GLYCOPROTEINS OF THE CELL SURFACE: CELL RECOGNITION AND THE IMMUNE SYSTEM
22.17 CARBOHYDRATE ANTIBIOTICS
22.18 SUMMARY OF REACTIONS OF CARBOHYDRATES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SUMMARY OF SOME REACTIONS OF MONOSACCHARIDES
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 23: LIPIDS
23.1 INTRODUCTION
23.2 FATTY ACIDS AND TRIACYLGLYCEROLS
23.3 TERPENES AND TERPENOIDS
23.4 STEROIDS
23.5 PROSTAGLANDINS
23.6 PHOSPHOLIPIDS AND CELL MEMBRANES
23.7 WAXES
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 24: AMINO ACIDS AND PROTEINS
24.1 INTRODUCTION
24.2 AMINO ACIDS
24.3 SYNTHESIS OF α-AMINO ACIDS
24.4 POLYPEPTIDES AND PROTEINS
24.5 PRIMARY STRUCTURE OF POLYPEPTIDES AND PROTEINS
24.6 EXAMPLES OF POLYPEPTIDE AND PROTEIN PRIMARY STRUCTURE
24.7 POLYPEPTIDE AND PROTEIN SYNTHESIS
24.8 SECONDARY, TERTIARY, AND QUATERNARY STRUCTURES OF PROTEINS
24.9 INTRODUCTION TO ENZYMES
24.10 LYSOZYME: MODE OF ACTION OF AN ENZYME
24.11 SERINE PROTEASES
24.12 HEMOGLOBIN: A CONJUGATED PROTEIN
24.13 PURIFICATION AND ANALYSIS OF POLYPEPTIDES AND PROTEINS
24.14 PROTEOMICS
SUMMARY AND REVIEW TOOLS
PROBLEMS
LEARNING GROUP PROBLEMS
SOLUTIONS TO PROBLEMS
QUIZ
CHAPTER 25: NUCLEIC ACIDS AND PROTEIN SYNTHESIS
25.1 INTRODUCTION
25.2 NUCLEOTIDES AND NUCLEOSIDES
25.3 LABORATORY SYNTHESIS OF NUCLEOSIDES AND NUCLEOTIDES
25.4 DEOXYRIBONUCLEIC ACID: DNA
25.5 RNA AND PROTEIN SYNTHESIS
25.6 DETERMINING THE BASE SEQUENCE OF DNA: THE CHAIN-TERMINATING (DIDEOXYNUCLEOTIDE) METHOD
25.7 LABORATORY SYNTHESIS OF OLIGONUCLEOTIDES
25.8 POLYMERASE CHAIN REACTION
25.9 SEQUENCING OF THE HUMAN GENOME: AN INSTRUCTION BOOK FOR THE MOLECULES OF LIF

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