Organic chemistry
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1988
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| 245 | 1 | 0 | |a Organic chemistry |c John McMurry |
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Datensatz im Suchindex
| _version_ | 1804118755212525568 |
|---|---|
| adam_text | Organic
Chemistry
SECOND EDITION
G Marc Loudon
Purdue University
The Benjamin/Cummings Publishing Company, Inc
Menlo Park, California • Reading, Massachusetts
Don Mills, Ontario • Wokingham, U K • Amsterdam • Sydney
Singapore • Tokyo • Madrid • Bogota • Santiago • San Juan
Contents
in Brief
:HA PTEH 1 Introduction to Structure and Bonding 1
2 Electronic Structure of Atoms and Molecules 35
3 Alkanes and the Functional Groups 54
4 Introduction to Alkenes Equilibria and Reaction Rates 88
5 Addition Reactions of Alkenes 135
6 Introduction to Stereochemistry 181
7 Cyclic Compounds Stereochemistry and Chemical
Reactions 220
8 Introduction to Alkyl Halides, Alcohols, Ethers, Thiols and
Sulfides 272
9 Substitution and Elimination Reactions of Alkyl Halides 319
10 Chemistry of Alcohols, Glycols, and Thiols 368
11 Chemistry of Ethers, Epoxides, and Sulfides 417
112 Infrared Spectroscopy and Mass Spectrometry 450
13 Nuclear Magnetic Resonance Spectroscopy 490
M Chemistry of Alkynes 548
15 Dienes, Resonance, and Aromaticity 581
16 Chemistry of Benzene and Its Derivatives 638
17 Allylic and Benzylic Reactivity 685
— 1£ Chemistry of Aryl Halides, Vinylic Halides, and Phenols 715
19 Chemistry of Aldehydes and Ketones Carbonyl-Addition
Reactions 757
20 Chemistry of Carboxylic Acids 816
21 Chemistry of Carboxylic Acid Derivatives 856
22 Chemistry of Enols, Enolate Ions, and a,/3-Unsaturatec!
Carbonyl Compounds 919
23 Chemistry of Amines 985
• 24 Chemistry of Naphthalene and the Aromatic
Heterocycles 1043
25 Pericyclic Reactions 1091
26 Amino Acids, Peptides, and Proteins 1132
27 Carbohydrates and Nucleic Acids 1196
Appendices A-1
Ciredlotts c-1
Index 1-1
xvii
Contents
in Detail
CHAPTER 1 Introduction to Structure
and Bonding 1
1 1 INTRODUCTION 1
A Why Study Organic Chemistry? 1
B Emergence of Organic Chemistry 2
1 2 CLASSICAL THEORIES OF CHEMICAL
BONDING 3
A The Ionic Bond_ 4
B The Covalent Bond 6T——
C The Polar Covalent Bond 9
1 3 LEWIS ACIDS AND BASES: THE ARROW
FORMALISM FOR LEWIS ACID-BASE
REACTIONS 12
/14 BR0NSTED-LOWRY ACJDS AND BASES: THE
ARROW FORMALISM FOR DISPLACEMENT
REACTIONS 14
1)5 A REVIEW OF THE ARROW FORMALISM
1 6 STRUCTURES OF COVALENT COMPOUNDS
A Methods for Determining Molecular Structure
B Prediction of Molecular Geometry 20
1 7 RESONANCE STRUCTURES 25
KEY IDEAS IN CHAPTER 1 27
ADDITIONAL PROBLEMS 28
xviii
CHAPTER 2 Electronic Structures of
Atoms and Molecules 35
2:1 THE WAVE NATURE OF THE ELECTRON
22 ELECTRONIC STRUCTURE OF THE
HYDROGEN ATOM 36 •
2 3 ELECTRONIC STRUCTURES OF MORE
COMPLEX ATOMS 41
2 4 ELECTRONIC STRUCTURES OF MOLECULES
MOLECULAR ORBITALS 44
2 5 MOLECULAR ORBITAL THEORY AND LEWIS
STRUCTURES 47
*26 HYBRID ORBITALS 48
A Bonding in Methane 48
B Bonding in Ammonia 49
KEY IDEAS IN CHAPTER 2 50
ADDITIONAL PROBLEMS 51
CHAPTER 3 Alkanes and the Functional
Groups 54
3 1 NORMAL ALKANES 56
3 2 STRUCTURAL ISOMERS RULES FOR
ALKANE NOMENCLATURE 58
A Nomenclature of Alkanes 58
B Classification of Carbon Substitution 62
Contents in Detail x/x
3 3 CYCLOALKANES SKELETAL STRUCTURES
3 4 PHYSICAL PROPERTIES OF ALKANES 65
A Boiling Points 65
B Melting Points 68
C Other Physical Properties 69
3 5 CONFORMATIONS OF ALKANES ROTATION
ABOUT CARBON-CARBON SINGLE BONDS
A Conformation of Ethane 69
B Conformations of Butane 72
3 6 COMBUSTION OF ALKANES ELEMENTAL
ANALYSIS 75
3 7 OCCURRENCE AND USE OF ALKANES 78
3 8 FUNCTIONAL GROUPS THE R NOTATION
KEY IDEAS IN CHAPTER 3 83
ADDITIONAL PROBLEMS 84
CHAPTER 4 Introduction to Alkenes
Equilibria and Reaction
Rates 88
4 1 STRUCTURE AND BONDING IN ALKENES
A Carbon Hybridization in Alkenes the
7r-Bond 89
B Cis-Transjsomensm 92
4 2 NOMENCLATURE OTAtKENES 94
A Common and Systematic Nomenclature
B Nomenclature of Stereoisomers: The Cahn^
Ingold-Prelog E,Z System 96
4 3 PHYSICAL PROPERTIES OF ALKENES 101
4 4 RELATIVE STABILITIES OF ALKENE ISOMERS
A Free Energy and Chemical Equilibrium
B Heats of Formation -104
C Relative Stabilities of Alkene Isomers
4 5 ADDITION OF HYDROGEN HALIDES TO
ALKENES • 108
A Carbocations as Intermediates in the
Addition of Hydrogen Halides to Alkenes
B Structure and Stability of Carbocations
C Summary: Mechanism of Hydrogen-Halide
Addition to Alkenes 112
4 6 REARRANGEMENT OF CARBOCATIONS
4 7 REACTION RATES TRANSITION-STATE
THEORY AND HAMMOND S POSTULATE
A Transition-State Theory 117
B Multistep Reactions 119
C Use of Transition-State Theory Hammond s
Postulate 121
4 8 HYDRATION OF ALKENES CATALYSIS 123
KEY IDEAS IN CHAPTER 4 127
ADDITIONAL PROBLEMS 128
CHAPTER 5 Addition Reactions of
Alkenes 135
5 1 HALOGENATION OF ALKENES 135
A Addition of Chlorine and Bromine to Alkenes
B Halohydrin Formation 137
5 2 WRITING ORGANIC REACTIONS 138
5 3 CONVERSION OF ALKENES INTO ALCOHOLS
A Hydroboration-Oxidation of Alkenes 139
B Oxymercuration-Reduction of Alkenes
C Comparison of Methods of Alcohol (
Synthesis 145
5 4 CONVERSION OF ALKENES INTO GLYCOLS
5 5 OZONOLYSIS OF ALKENES 148
5;6 SUMMARY OF ELECTROPHILIC ADDITION
REACTIONS 151
5 7 CATALYTIC HYDROGENATION OF ALKENES
A Conversion of Alkenes into Alkanes 152
B Heats of Hydrogenation 153
5 8 ADDITION OF HYDROGEN BROMIDE TO
ALKENES: THE PEROXIDE EFFECT FREE-
RADICAL CHAIN REACTIONS 154
A Homolysis vs Heterolysis Free Radicals
B Free-Radical Addition of HBr to Alkenes
Free-Radical Chain Reactions 157
xx Contents in Detail
C Structure and Stability of Free Radicals
Explanation of the Peroxide Effect 160
D Bond Dissociation Energies Absence of the
Peroxide Effect in Addition of HCI and HI to
Alkenes 163
5 9 INDUSTRIAL USE AND PREPARATION OF
ALKENES OTHER TYPES OF FREE-RADICAL
REACTIONS 1 66
A Free-Radical Polymerization of Alkenes
B Industrial Source of Alkenes Thermal
Cracking of Alkanes 168
5 10 ELEMENTAL ANALYSIS OF ALKENES
UNSATURATION NUMBER 170
KEY IDEAS IN CHAPTER 5 171
ADDITIONAL PROBLEMS 172
CHAPTER 6 Introduction to
Stereochemistry 181
6 1 ENANTIOMERS AND CHIRALITY -182
6 2 NOMENCLATURE OF ENANTIOMERS; THE
R,S SYSTEM 186
6 3 PHYSICAL PROPERTIES OF ENANTIOMERS;
OPTICAL ACTIVITY 188
A Polarized Light 188
B Optical Activity 190
C Optical Activities of Enantiomers 190
6 4 RACEMATES 193- -
6 5 DETERMINATION OF ABSOLUTE
CONFIGURATION STEREOCHEMICAL
CORRELATION 1 94
6 6 DIASTEREOMERS ANALYSIS OF ISOMERISM
6 7 MESO COMPOUNDS 199 ,
6 8 CONFORMATIONAL STEREOISOMERS
AMINE INVERSION : 201
A Chiral Molecules without Asymmetric Atoms
B Asymmetric Nitrogen: Amine Inversion
6 9 FISCHER PROJECTIONS 205
6 10 CHIRALTY, OPTICAL ACTIVITY, AND THE
POSTULATION OF TETRAHEDRAL CARBON
KEY IDEAS IN CHAPTER 6 213
ADDITIONAL PROBLEMS 214
CHAPTER 7 Cyclic Compounds
Stereochemistry and
Chemical Reactions 220
7 1 RELATIVE STABILITIES OF THE
•MONOCYCLIC ALKANES 221
7 2 CONFORMATIONS OF CYCLOHEXANE 223
7 3 MONOSUBSTITUTED CYCLOHEXANES
CONFORMATIONAL ANALYSIS 227
7 4 DISUBSTITUTED CYCLOHEXANES CIS-
TRANS ISOMERISM IN CYCLIC COMPOUNDS
7 5 PLANAR REPRESENTATION OF CYCLIC
COMPOUNDS 235
7 6 CYCLOPENTANE, CYCLOBUTANE, AND
CYCLOPROPANE 237
A Conformation of Cyclopentane 237
B Cyclobutane and Cyclopropane 237
7 7 BICYCLIC AND POLYCYCLIC COMPOUNDS
A Classification and Nomenclature 240
B Cis and Trans Ring Fusion 242
C Trans-Cycloalkenes Bredt s Rule 244
D Steroids 245
7 8 STEREOCHEMISTRY AND CHEMICAL
REACTIONS 247
A Reactions of Achiral Compounds that Give
Enantiomeric Pairs of Products 247
B Reactions that Give Diastereomeric Products
C Reactions of Enantiomers 249
1 D Reactions of Diastereomers 251
7 9 CHIRALITY IN NATURE 252 -
7 10 STEREOCHEMISTRY OF ALKENE ADDITION
REACTIONS 253
A Syn and Anti Addition Stereochemistry of
Hydroboration 253
B Reactions at Asymmetric Carbons
Oxidation of Organoboranes 255
C Use of Stereochemistry to Investigate
Reaction Mechanism Stereochemistry of
Alkene Bromination 256
D Stereochemistry of Other Addition
Reactions 260
KEY IDEAS IN CHAPTER 7 262
ADDITIONAL PROBLEMS 263
Contents in Detail xx/
CHAPTER 8 Introduction to Alkyl
Halides, Alcohols, Ethers,
Thiols and Sulfides 272
8 1 NOMENCLATURE 273
A Nomenclature of Alkyl Halides 274
B Nomenclature of Alcohols and Thiols 275
C Nomenclature of Ethers and Sulfides 279
8 2 STRUCTURES 281
8 3 PHYSICAL PROPERTIES POLARITY AND
HYDROGEN BONDING 282
A Boiling Points of Ethers and Alkyl Halides:
Effect of Polarity 282
B Boiling Points of Alcohols: Effect of
Hydrogen Bonding 284
8 4 SOLVENTS IN ORGANIC CHEMISTRY 287
A Classification of Solvents 287
B Solubility 288
C Crown Ethers and lonophorous Antibiotics
8 5 REVIEW OF BR0NSTED ACIDITY AND
BASICITY 295
A Dissociation Constants and pKa 295
B Factors that Determine Acid Strength
8 6 ACIDITY OF ALCOHOLS AND THIOLS 298
A Formation of Alkoxides and Mercaptides
B InductiveJEffects on Alcohol Acidity 300
C Effect of Branching-on Alcohol Acidity Role
of the Solvent, in Acidity 302
8 7 BASICITY OF ALCOHOLS AND ETHERS
304 • • i
8 8 ORGANOMETALLIC COMPOUNDS
GRIGNARD AND ORGANOLITHIUM
REAGENTS 306
A Formation of Grignard and Organolithium
Reagents 307
B Protonolysis of Grignard and Organolithium
Reagents 307
8 9 INDUSTRIAL PREPARATION AND USE OF
ALKYL HALIDES, ALCOHOLS AND ETHERS
A Industrial Preparation of Alkyl Halides Free-
Radical Halogenation 309
B Uses of Hailogen-Containing Compounds
C Production and Use of Alcohols and Ethers
D Safety Hazards of Ethers 313
KEY IDEAS IN CHAPTER 8 314
ADDITIONAL PROBLEMS 315
CHAPTER 9 Substitution and Elimination
Reactions of Alkyl Halides
9 1 NUCLEOPHILIC SUBSTITUTION REACTIONS:
INTRODUCTION 320
9 2 EQUILIBRIUM IN NUCLEOPHILIC
SUBSTITUTION REACTIONS 321
9 3 THE Sn2 REACTION 323
A Reaction Rates and Mechanism 323
B Stereochemistry of the Sn2 Reaction 327
C Effect of Alkyl Halide Structure on the SN2
Reaction 329
D Effect of Leaving-Group and Nucleophile
• Basicities on the SN2 Reaction Solvent
Effects 330
E Summary of the SN2 Reaction 333
9 4 THE E2 REACTION 333
A The E2 Reaction: Rate Law and Mechanism
B Effect of Leaving Group on the E2 Reaction
-Isotope Effects 334
C Competition between the E2 and SN2
Reactions 336
D Double Bond Position (Regiochemistry) in
the E2 Reaction Products 339 •
E Stereochemistry of the E2 Reaction 342
F Summary of the E2 Reaction q 344
9 5 SUBSTITUTION REACTIONS OF TERTIARY
ALKYL HALIDES THE SN1 REACTION 344
A Rate Law and Mechanism of the SN1
Reaction 344
B Rate-Determining and Product-Determining
Steps The E1 Reaction 346
C Effect of Leaving Group on the SN1-E1
Reaction Lewis-Acid Catalysis 350
D Solvent Effects on the SN1 Reaction 351
E Stereochemistry of the SN1 Reaction 352
F Summary of the SN1 and E1 Reactions
xxii Contents in Detail
9 6 SUBSTITUTION AND ELIMINATION
REACTIONS OF ALKYL HALIDES: SUMMARY
9 7 DIVALENT CARBON: CARBENES 356
KEY IDEAS IN CHAPTER 9 359
ADDITIONAL PROBLEMS 360
CHAPTER 10 Chemistry of Alcohols,
Glycols, and Thiols 368
10 1 DEHYDRATION OF ALCOHOLS 368
A Conversion of Alcohols into Alkenes
B Pinacol Rearrangement 372
10 2 REACTION OF ALCOHOLS WITH
HYDROGEN HALIDES 373
10 3 SULFONATE AND INORGANIC ESTER
DERIVATIVES OF ALCOHOLS 377
A Sulfonate Ester Derivatives of Alcohols
B Esters Derived from Alcohols and Strong
Inorganic Acids 379
10 4 REACTION OF ALCOHOLS-WITH THIONYL •
CHLORIDE AND PHOSPHORUS
TRIBROMIDE 380
10 5 • CONVERSION OF ALCOHOLSJNTO ALKYL
HALIDES: SUMMARY 382 - -
10 6 OXIDATION OF ALCOHOLS OXIDATION AND
REDUCTION IN ORGANIC CHEMISTRY
383
A Conversion of Alcohols into Carbonyl
Compounds with Chromium (VI) 384
B Oxidation and Reduction in Organic
Chemistry 386
C Other Methods for Oxidizing Alcohols
D Oxidative Cleavage of Glycols 392
10 7 BIOLOGICAL OXIDATION OF ETHANOL
A0 8 CHEM CM_ MAD STEREOCHEMICAL GROUP
EQUW/ALENCE 397
A Stereochemistry of the Alcohol
Dehydrogenase Reaction 397
B Chemical Equivalence and Nonequivalence
10 9 OXIDATION OF THIOLS 404
10 10 SYNTHESIS OF ALCOHOLS AND GLYCOLS
DESIGN OF ORGANIC SYNTHESIS 406
A Synthesis of Alcohols and Glycols 406
B Design of Organic Synthesis 407
KEY IDEAS IN CHAPTER 10 409
ADDITIONAL PROBLEMS 410
CHAPTER 77 Chemistry of Ethers,
Epoxides, and Sulfides
11 1 SYNTHESIS OF ETHERS AND SULFIDES
A Williamson Ether Synthesis 418
B Alkoxymercuration-Reduction of Alkenes
11 2 SYNTHESIS OF EPOXIDES 420 -
A Oxidation of Alkenes with Peroxyacids
B Cyclization of Halohydrins 422
11 3 CLEAVAGE OF ETHERS AND SULFIDES
A Cleavage of Ethers by Acids 424
B: Cleavage of Sulfides by Raney Nickel
11 4 NUCLEOPHILIC SUBSTITUTION REACTIONS
OF EPOXIDES 427
A Hydrolysis of Epoxides Conversion of
1 Epoxides into Glycols 427
B Synthesis of Primary Alcohols: Reaction of
Ethylene Oxide with Grignard Reagents
11 5 OXONIUM AND SULFONIUM SALTS 433
A Reactions of Oxonium and Sulfonium Salts
B S-Adenosylmethionine: Nature s Methyl
Donor , 434
• 11 6 NEIGHBORING-GROUP PARTICIPATION
11 7 OXIDATION OF ETHERS AND SULFIDES
11 8 ORGANIC SYNTHESIS: THE THREE
FUNDAMENTAL OPERATIONS 439
KEY IDEAS IN CHAPTER 11 442
ADDITIONAL PROBLEMS 443
Contents in Detail xxi ii
CHAPTER 12 Infrared Spectroscopy and
Mass Spectrometry 450
12 1 INTRODUCTION TO SPECTROSCOPY
A Electromagnetic Radiation 451
B Absorption Spectroscopy 452
12 2 INFRARED SPECTROSCOPY 454
A The Infrared Spectrum 454
B Physical Basis of IR Spectroscopy 455
C Infrared Absorption and Chemical Structure
458
D Factors that Determine IR Absorption
Position 458
E Factors that Determine IR Absorption
Intensity 461
12 3 FUNCTIONAL-GROUP INFRARED
ABSORPTIONS 463
A IR Spectra of Alkanes, Alkyl Halides, and
Alkenes 463
B IR Spectra of Alcohols and Ethers 465
12 4 EXPERIMENTAL ASPECTS OF INFRARED
SPECTROSCOPY 467
12 5 INTRODUCTION TO MASS SPECTROMETRY
A The Mass Spectrum 468
B Isotopic Peaks 470
C Fragmentation 474
D: Identifying the Molecular Ion 478 -
E The Mass Spectrometer _ 479
KEY IDEAS IN CHAPTER 12 481
ADDITIONAL PROBLEMS 482
CHAPTER 13 Nuclear Magnetic
Resonance Spectroscopy
13 1 INTRODUCTION TO NMR SPECTROSCOPY
13 2 THE NMR SPECTRUM: CHEMICAL SHIFT
AND INTEGRAL 494
A The NMR Spectrum 494
B Relationship of Chemical Shift and Integral
to Structure 496
C Solving Unknown Structures with NMR
(Part 1) 500
D Physical Basis of the Chemical Shift
13 3 THE NMR SPECTRUM: SPIN-SPIN
SPLITTING 502
A The n+1 Splitting Rule 503
B Physical Basis of Splitting 506
C Multiple Splitting/Splitting Diagrams
D Solving Unknown Structures with NMR
(Part 2) 512
13 4 INTERPRETING COMPLEX NMR SPECTRA
HIGH-FIELD NMR 514
13 5 FUNCTIONAL GROUP NMR ABSORPTION 517
A NMR Spectra of Alkenes 517
B NMR Spectra of Alkanes and Cycloalkanes
C NMR Spectra of Alkyl Halides and Ethers
D NMR Spectra of Alcohols 522
13 6 USE OF DEUTERIUM IN PROTON NMR
13 7 NMR SPECTROSCOPY OF DYNAMIC
SYSTEMS 525
13 8 NMR OF NUCLEI OTHER THAN HYDROGEN
CARBON-13 NMR 528
13 9 SOLVING STRUCTURE PROBLEMS WITH
SPECTROSCOPY 533
13 10 NMR INSTRUMENTATION NEWER USES
OF NMR 536
KEY IDEAS IN CHAPTER 13 537
ADDITIONAL PROBLEMS 538
•CHAPTER 14 Chemistry of Alkynes
14 1 NOMENCLATURE OF ALKYNES 548
14 2 STRUCTURE AND BONDING IN ALKYNES
14 3 PHYSICAL PROPERTIES OF ALKYNES
A Boiling Points and Solubilities 553
B IR Spectroscopy of Alkynes 553
C NMR Spectroscopy of Alkynes 554
14 4 ADDITIONS TO THE TRIPLE BOND:
INTRODUCTION 556
XX/V Contents in Detail
14 5 CONVERSION OF ALKYNES INTO
ALDEHYDES AND KETONES 557
A Hydration of Alkynes 557
B Hydroboration of Alkynes 561
14 6 REDUCTION OF ALKYNES 562
A Catalytic Hydrogenation of Alkynes 562 -
B Reduction of Alkynes with Alkali Metals in
Ammonia 563
14 7 ACIDITY OF 1-ALKYNES 566
A Carbanions Acetylide Anions 566
B Acetylenic Anions as Nucleophiles • 569
14 8 ORGANIC SYNTHESIS USING ALKYNES
570 j
14 9 PHEROMONES • 572
14 10 OCCURRENCE AND USE OF ALKYNES
KEY IDEAS IN CHAPTER 14 574
ADDITIONAL PROBLEMS 575
CHAPTER 15 Dienes, Resonance, and
Aromaticity 581
15 1 STRUCTURE AND STABILITY OF DIENES
A - Structure and Stability of Conjugated
Dienes 582
;B Structure and~Stability-of Cumulated
Dienes 584
ULTRAVIOLET SPECTROSCOPY
A The UV Spectrum 586
B Physical Basis of UV Spectroscopy 588
C UV Spectroscopy of Conjugated Alkenes
THE DIELS-ALDER REACTION
A
B
C
D
Reactions of Conjugated Dienes with
Alkenes 592
Effect of Diene Conformation on the Diels-
Alder Reaction 594
Stereochemistry of the Diels-Alder
Reaction 596
15 5 USES OF CONJUGATED DIENES: DIENE
POLYMERS 608
15 6 RESONANCE 609
A Writing Resonance Structures 609
B Relative Importance of Resonance
Structures 610
C Use of Resonance Structures
15 7 AROMATICITY 615
A Benzene: a Puzzling Alkene
B Structure of Benzene 617
C Stability of Benzene 620
D Aromaticity The Hiickel 4n + 2 Rule
E Electronic Basis of the 4n + 2 Rule 626
KEY IDEAS IN CHAPTER 15 629
ADDITIONAL PROBLEMS 630
CHAPTER 16 Chemistry of Benzene and
Its Derivatives 638
Uses of the Diels-Alder Reaction 599
ADDITION OF HYDROGEN HALIDES TO
CONJUGATED DIENES 600
A 1,2- and 1,4-Addition Allylic Cations
B Kinetic and Thermodynamic Control
16 1 NOMENCLATURE OF BENZENE
DERIVATIVES 638
16 2- PHYSICAL PROPERTIES OF BENZENE
DERIVATIVES 641
16:3 SPECTROSCOPY OF BENZENE
DERIVATIVES 642
A IR Spectroscopy 642
B NMR Spectroscopy 643
• C UV Spectroscopy 647
16 4 ELECTROPHILIC AROMATIC SUBSTITUTION
REACTIONS OF BENZENE 648
A Halogenation of Benzene 648
B Electrophilic Aromatic Substitution 650
C Nitration of Benzene 651
D Sulfonation of Benzene 652
E Friedel-Crafts Acylation of Benzene
F Friedel-Crafts Alkylation of Benzene
16 5 ELECTROPHILIC AROMATIC SUBSTITUTION
REACTIONS OF SUBSTITUTED BENZENES
A Directing Effects of Substituents 658
B Activating and Deactivating Effects of
Substituents 664
Contents in Detail xxv
C Use of Electrophilic Aromatic Substitution
Reactions in Organic Synthesis 668
16 6 HYDROGENATION OF BENZENE
DERIVATIVES 672
16 7 SOURCE AND INDUSTRIAL USE OF
AROMATIC HYDROCARBONS 673
16 8 BIOLOGICAL CONVERSION OF AROMATIC
COMPOUNDS INTO EPOXIDES THE
CANCER CONNECTION 674
KEY IDEAS IN CHAPTER 16 675
ADDITIONAL PROBLEMS 676
CHAPTER 17 Allylic and Benzylic
Reactivity 685
17 1 ALLYLIC AND BENZYLIC CARBOCATIONS
SN1 REACTIONS 686
17 2 ALLYLIC AND BENZYLIC RADICALS ALLYLIC
AND BENZYLIC BROMINATION 690
17 3 ALLYLIC AND BENZYLIC GRIGNARD
REAGENTS 694
17 4 ALLYLIC AND BENZYLIC SN2 REACTIONS
17 5 SIDE-CHAIN OXIDATION OF
ALKYLBENZENES 698
17 6 THE ISOPRENE RULE BIOSYNTHESIS OF
TERPENES 699
A Essential Oils and Terpenes 699
B Biosynthesis of Terpenes 701
KEY IDEAS-IN CHARIER 17 705
ADDITIONAL PROBLB/is ^706—
CHAPTER 18 Chemistry of Aryl Halides
Vinylic Halides, and
Phenois 715
18 1 LACK OF REACTIVITY OF VINYLIC AND
ARYL HALIDES IN SN2 REACTIONS 716
18 2 ELIMINATION REACTIONS OF VINYLIC
HALIDES 718 •
18 3 LACK OF REACTIVITY OF VINYLIC AND
ARYL HALIDES IN SN1 AND E1 REACTIONS
18 4 NUCLEOPHILIC SUBSTITUTION REACTIONS
OF ARYL HALIDES 721
A Nucleophilic Aromatic Substitution 721
B Substitution by Elimination-Addition:
Benzyne 725
C Substitution Reactions of Aryl Halides:
Summary 728
18 5 ARYL AND VINYLIC GRIGNARD REAGENTS
18 6 ACIDITY OF PHENOLS 729
A Resonance Effects on Acidity 729
B Formation and Use of Phenoxides 732
18 7 OTHER REACTIONS OF PHENOLS 735
A Oxidation of Phenols to Quinones 735
B Electrophilic Aromatic Substitution
Reactions of Phenols 739
C Lack of Reactivity of the Phenolic Carbon-
Oxygen Bond 742
18 8 INDUSTRIAL PREPARATION AND USE OF
PHENOL 743
KEY IDEAS IN CHAPTER 18 745
ADDITIONAL PROBLEMS 747
CHAPTER 19 Chemistry of Aldehydes
and Ketones Carbonyl-
Addition Reactions 757
19 1 NOMENCLATURE OF ALDEHYDES AND
KETONES 758
A Common Nomenclature 758
B Systematic Nomenclature 760
19 2 PHYSICAL PROPERTIES OF ALDEHYDES
AND KETONES , 763
19 3 SPECTROSCOPY OF ALDEHYDES AND
KETONES 764
A IR Spectroscopy 764
B NMR Spectroscopy 765
C UV Spectroscopy 766
D Mass Spectrometry 768
19 4 SYNTHESIS OF ALDEHYDES AND KETONES
19 5 INTRODUCTION TO ALDEHYDE AND
KETONE REACTIONS 770
19 6 BASICITY OF ALDEHYDES AND KETONES
19 7 REVERSIBLE ADDITION REACTIONS OF
ALDEHYDES AND KETONES 773
A Mechanisms of, Carbonyl-Addition
Reactions 774 -
B Equilibrium in Carbonyl-Addition Reactions
xxv/ Contents in Detail
19 8 REDUCTION OF ALDEHYDES AND
KETONES TO ALCOHOLS 780
19 9 REACTION OF ALDEHYDES AND KETONES
WITH GRIGNARD REAGENTS 784
19 10 ACETALS PROTECTING GROUPS 787
A Preparation and Hydrolysis of Acetals
B Protecting Groups 791
19 11 REACTIONS OF ALDEHYDES AND
KETONES WITH AMINES 792
A Imine Formation with Primary Amines
B Enamine Formation with Secondary
Amines 796
19 12 REDUCTION OF CARBONYL GROUPS TO
METHYLENE GROUPS 798
19 13 CONVERSION OF ALDEHYDES AND
KETONES INTO ALKENES: THE WITTIG
ALKENE SYNTHESIS 800
19 14 OXIDATION OF ALDEHYDES 804
19 15 MANUFACTURE AND USE OF ALDEHYDES
AND KETONES 805
KEY IDEAS IN CHAPTER19 806
ADDITIONAL PROBLEMS 807
CHAPTER 20 Chemistry of Carboxylic
Acids 816
20 1 NOMENCLATURE~OF-©ARBOXYLIC ACIDS
817 —
A Common Nomenclature • 817
B - Systemic Nomenclature 819
20 2 STRUCTURE AND PHYSICAL PROPERTIES
OF CARBOXYLIC ACIDS 821
x20 3 SPECTROSCOPY OF CARBOXYLIC ACIDS
822
• A IR Spectroscopy 822
B NMR Spectroscopy 823
20 4 ACIDITY AND BASICITY OF CARBOXYLIC
ACIDS 824
A Acidity of Carboxylic and Sulfonic Acids
B 828 Basicity of Carboxylic Acids
FATTY ACIDS, SOAPS, AND DETERGENTS
20 6 SYNTHESIS OF CARBOXYLIC ACIDS 831
20 7 INTRODUCTION TO CARBOXYLIC ACID
REACTIONS 832
20 8 CONVERSION OF CARBOXYLIC ACIDS INTO
ESTERS 833
A Acid-Catalyzed Esterification 833
B Esterification by Alkylation • 837
20 9 CONVERSION OF CARBOXYLIC ACIDS INTO
ACID CHLORIDES AND ANHYDRIDES 839
A Synthesis of Acid Chlorides 839
B Synthesis of Anhydrides 841
20 10 REDUCTION OF CARBOXYLIC ACIDS TO
ALCOHOLS 843
20 11 DECARBOXYLATION OF CARBOXYLIC
ACIDS 844
KEY IDEAS IN CHAPTER 20 847
ADDITIONAL PROBLEMS 848
CHAPTER 21 Chemistry of Carboxylic
Acid Derivatives - 856
21 1 NOMENCLATURE AND CLASSIFICATION OF
CARBOXYLIC ACID DERIVATIVES 857
A Esters and Lactones 857
B Acid Halides 858 ~
C Anhydrides 859
D Nitriles 859
E Amides, Lactams, and Imides 860
F Nomenclature of Substituent Groups
G Carbonic Acid Derivatives 862
21 2 STRUCTURE OF CARBOXYLIC ACID
DERIVATIVES 863
21 3 PHYSICAL PROPERTIES OF CARBOXYLIC
ACID DERIVATIVES 864
A Esters 864
B Anhydrides and Acid Chlorides 864
C Nitriles 865
D Amides 865
21 4 SPECTROSCOPY OF CARBOXYLIC ACID
DERIVATIVES 866
A IR Spectroscopy 866
B NMR Spectroscopy 868
C Solving Structural Problems Involving
Nitrogen-Containing Compounds 870
Contents in Detail xxvii
21 5 BASICITY OF CARBOXYLIC ACID
DERIVATIVES 870
21 6 INTRODUCTION TO THE REACTIONS OF
CARBOXYLIC ACID DERIVATIVES 872
21 7 HYDROLYSIS OF CARBOXYLIC ACID
DERIVATIVES 873
A Hydrolysis and Cleavage of Esters 873
B Mechanisms of Substitution at the Carbonyl
Group 877
C HydrolysiS of Amides 878
D Hydrolysis of Nitriles 879
E Hydrolysis of Acid Chlorides and
Anhydrides 881
F Relative Carbonyl Reactivity of Carboxylic
Acid Derivatives 881
21 8 REACTION OF CARBOXYLIC ACID
DERIVATIVES WITH NUCLEOPHILES 884
A Reactions of Acid Chlorides with
Nucleophiles 884
B Reactions of Anhydrides with Nucleophiles
C Reactions of Esters* with Nucleophiles
21 9 REDUCTION OF CARBOXYLIC ACID
DERIVATIVES 890
A Reduction of Esters to Primary Alcohols
B Reduction of Amides to Amines- 891
C Reduction of Nitriles to Primary Amines
_ 893_
D Reduction of Acid-Chlorides to Aldehydes
E Relative Reactivity of Carbonyl Compounds
with Nucleophiles 897 -
21 10 REACTIONS OF CARBOXYLIC ACID
DERIVATIVES WITH ORGANOMETALLIC
REAGENTS 897
A Reaction of Esters with Grignard
Reagents 897
B Reaction of Acid Chlorides with Lithium
Dialkylcuprates 899
21 11 SYNTHESIS OF CARBOXYLIC ACID
DERIVATIVES 900
21 12 OCCURRENCE AND USE OF CARBOXYLIC
ACIDS AND THEIR DERIVATIVES 902
A Nylon and Polyesters 902
B Waxes, Fats, and Phospholipids 905
KEY IDEAS IN CHAPTER 21 907*
ADDITIONAL PROBLEMS 908
CHAPTER 22 Chemistry of Enols,
Enolate Ions, and
a,p-Unsaturated Carbonyl
Compounds 919
22 1 ACIDITY OF CARBONYL COMPOUNDS
ENOLATE IONS 920
A Formation of Enolate Ions 920
B Introduction to Reactions of Enolate Ions
22 2 ENOLIZATION OF CARBONYL COMPOUNDS
22 3 a-HALOGENATION OF CARBONYL
COMPOUNDS 927
A Acid-Catalyzed a-Halogenation of
Aldehydes and Ketones 927
B Halogenation~of Aldehydes and Ketones in
Base: the Haloform Reaction 929
C a-Bromination of Carboxylic Acids: the Hell—
Volhard-Zelinsky Reaction 931
D Reactions of a-Halo Carbonyl Compounds
22 4 ALDOL CONDENSATION 933
A Base-Catalyzed Aldol Condensation
B Acid-Catalyzed Aldol Condensation 935
C Special Types of Aldol Condensations
D Synthesis with the Aldol Condensation
22 5 CONDENSATION REACTIONS INVOLVING
ESTER ENOLATE IONS 940
A Claisen Condensation 941
B Dieckmann Condensation 944
C Crossed Claisen Condensation 944
D Synthesis with the Claisen Condensation
22 6 ALKYLATION OF ESTER ENOLATE IONS
A! Malonic Ester Synthesis 948
B Direct Alkylation of Enolate Ions Derived
from Simple Monoesters 950
C Acetoacetic Ester Synthesis 952
22 7 BIOSYNTHESIS OF COMPOUNDS DERIVED
FROM ACETATE 955
xxviii Contents in Detail
A Biosynthesis of Fatty Acids 955
B Biosynthesis of Aromatic Compounds:
Polyketides 957
22 8 CONJUGATE-ADDITION REACTIONS 959
A Conjugate Addition to «,/3-Unsaturated
Carbonyl Compounds 959
B Conjugate Addition vs Carbonyl-Group
Reactions 962
C Conjugate Addition of Enolate Ions:
Michael Addition 964
22 9 REDUCTION OF a,/3-UNSATURATED
CARBONYL COMPOUNDS 966
22 10 REACTIONS OF a,/3-UNSATURATED
CARBONYL COMPOUNDS WITH
ORGANOMETALLIC REAGENTS 967
A Addition of Organolithium Reagents to the
-Carbonyl Group 967
B Conjugate Addition of Lithium
Dialkylcuprate Reagents 968
22 11 ORGANIC SYNTHESIS WITH CONJUGATE
ADDITION REACTIONS 970
KEY IDEAS IN CHAPTER 22 972
ADDITIONAL PROBLEMS 973
CHAPTER 23 Chemistry of Amines
23 1 NOMENCLATURE OF AMINES 986
A CommorT Nomenclature 986
B Systematic Nomenclature 987 _
23 2 STRUCTURE OF AMINES -989
23 3 PHYSICAL PROPERTIES OF AMINES 990
•23 4 SPECTROSCOPY OF AMINES 990
A IR Spectroscopy 990
B NMR Spectroscopy * 991
C Mass Spectrometry 992
23 5 BASICITY AND ACIDITY OF AMINES 993
A Basicity of Amines 993
B Substituent Effects on Amine Basicity
C Separations Using Amine Basicity 998
D Use of Amine Basicity in Optical Resolution
E Acidity of Amines 1000
F Summary of Acidity and Basicity 1000
23 6 QUATERNARY AMMONIUM SALTS 1001
23 7 ALKYLATION AND ACYLATION REACTIONS
OF AMINES 1001
A Direct Alkylation of Amines 1002
B Reductive Amination 1003
C Acylation of Amines 1005
23 8 HOFMANN ELIMINATION OF QUATERNARY
AMMONIUM HYDROXIDES 1005
23 9 AROMATIC SUBSTITUTION REACTIONS OF
ANILINE DERIVATIVES 1009
23 10 REACTIONS OF AMINES WITH NITROUS
ACID REACTIONS OF DIAZONIUM IONS
A Reactions of Alkanediazonium Salts
B Substitution Reactions of Aryldiazonium
Salts 1014
C Aromatic Substitution with Diazonium Ions
D Reactions of Secondary and Tertiary
Amines with Nitrous Acid 1019
23 11 SYNTHESIS OF AMINES 1020-
A Gabriel Synthesis of Primary Amines
B Reduction of Nitro Compounds 1021
C Hofmann and Curtius Rearrangements
D Synthesis of Amines: Summary 1027
23 12 OCCURRENCE AND USE OF AMINES
A Industrial Use of Amines and Ammonia
B Naturally Occurring Amines 1028
KEY- IDEAS IN CHAPTER 23 1031
ADDITIONAL PROBLEMS 1032
CHAPTER 24 Chemistry of Naphthalene
and the Aromatic
Heterocycles 1043
24 1 CHEMISTRY OF NAPHTHALENE 1044
A Physical Properties and Structure 1044
B Nomenclature of Naphthalene Derivatives
C Electrophilic Aromatic Substitution
Reactions of Naphthalene and Its
Derivatives 1047
Contents in Detail xx/x
24 2 INTRODUCTION TO THE AROMATIC
HETEROCYCLES 1051
A Nomenclature 1051
B Structure and Aromaticity 1052
C Basicity and Acidity of the Nitrogen
Heterocycles 1054
24 3 CHEMISTRY OF FURAN, PYRROLE, AND-
THIOPHENE 1057
A Electrophilic Aromatic Substitution 1057
B Addition Reactions of Furan 1060
C Side-Chain Reactions 1061
24 4 CHEMISTRY OF INDOLE, BENZOFURAN,
AND BENZOTHIOPHENE 1062
A Electrophilic Aromatic Substitution- 1062
B Synthesis of Indoles 1063
24 5 CHEMISTRY OF PYRIDINE AND QUINOLINE
A Electrophilic Aromatic Substitution 1067
B Nucleophilic Aromatic Substitution 1070
C Pyridinium Salts and Their Reactions
1073
D Side-Chain Reactions of Pyridine
Derivatives 1074
E Synthesis of Quinolines 1076
24 6 OCCURRENCE OF HETEROCYCLIC
COMPOUNDS 1078
KEY IDEAS IN CHAPTER 24 1079
ADDITIONAL PROBLEMS 1080
CHAPTER 25 Pericyclic Reactions
25 1 MOLECULAR ORBITALS OF CONJUGATED
it - ELECTRON SYSTEMS 1094
A Molecular Orbitals of Conjugated Alkenes
B Molecular Orbitals of Conjugated Ions and
Radicals 1097
C Excited States 1099
25 2 ELECTROCYCLIC REACTIONS 1100
A Stereochemistry of Electrocyclic Reactions
B Excited-State Electrocyclic Reactions
C Selection Rules and Microscopic
Reversibility 1103
25 3 CYCLOADDITION REACTIONS 1105
25 4 SIGMATROPIC REACTIONS 1109
A Classification and Stereochemistry of
Sigmatropic Reactions [1,3] and [1,5]
Sigmatropic Rearrangements 1109
B [3,3] Sigmatropic Rearrangements: Cope
and Claisen Rearrangements 1116
C Summary: Selection Rules for Sigmatropic
Reactions 1118
25 5 SUMMARY OF THE PERICYCLIC SELECTION
RULES 1119
25 6 FLUXIONAL MOLECULES 1120
25 7 PERICYCLIC REACTIONS IN BIOLOGY;
FORMATION OF VITAMIN D 1121
KEY IDEAS IN CHAPTER 25 1123
ADDITIONAL PROBLEMS 1124
CHAPTER 26 Amino Acids, Peptides,
and Proteins 1132
26 1 NOMENCLATURE OF AMINO ACIDS AND
PEPTIDES 1133
A Nomenclature of Amino Acids 1133
B Nomenclature of Peptides 1135
26 2 STEREOCHEMISTRY OF THE a-AMINO
ACIDS 1138
26 3 UV SPECTRA OF AMINO ACIDS AND
PEPTIDES 1138
26 4 ACID^BASE PROPERTIES OF AMINO ACIDS
AND PEPTIDES 1139
A Zwitterionic Structures of Amino Acids and
Peptides 1139
B Isoelectric Points of Amino Acids and
Peptides 1141
C Separations of Amino Acids and Peptides
Using Acid-Base Properties 1143
26 5 SYNTHESIS AND OPTICAL RESOLUTION OF
a-AMINO ACIDS 1146
A Alkylation of Ammonia 1146
B Alkylation of Aminomalonate Derivatives
C Strecker Synthesis 1147
D Optical Resolution of a-Amino Acids
26 6 REACTIONS OF AMINO ACIDS 1149
A Acylation and Esterification 1149
B Reaction with Ninhydrin 1150
xxx Contents in Detail
26 7 ANALYTICALLY IMPORTANT REACTIONS OF
PEPTIDES 1152
A Hydrolysis of Peptides Amino Acid
Analysis 1152
B Sequential Degradation of Peptides
C Specific Cleavage of Peptides 1157
26 8 SYNTHESIS OF PEPTIDES 1162 •
A Strategy of Peptide Synthesis 1162
B Solid-Phase Peptide Synthesis 1163
26 9 STRUCTURES OF PEPTIDES AND
PROTEINS 1168
A Primary Structure 1168
—A B Secondary Structure 1170
C Tertiary and Quaternary Structures
26 10 ENZYMES: BIOLOGICAL CATALYSTS
26 11 OCCURRENCE OF PEPTIDES AND
PROTEINS 1182
KEY IDEAS IN CHAPTER 26 1183
ADDITIONAL PROBLEMS 1184
CHAPTER 27 Carbohydrates and Nucleic
Acids 1196
27 1 • CLASSIFICATION AND PROPERTIES OF
SUGARS 1198 -
27 2 STRUCTURES OF THE MONOSACCHARIDES
A Stereochemistry and Configuration
1198 •
B Cyclic Structures of the Monosaccharides
27 3 MUTAROTATION OF SUGARS 1207
27 4 BASE-CATALYZED (SOMERIZATION OF
SUGARS 1210
27 5 GLYCOSIDES 1212
27 6 ETHER AND ESTER DERIVATIVES OF
SUGARS 1215
27 7 OXIDATION AND REDUCTION REACTIONS
OF SUGARS 1217
A Oxidation to Aldonic Acids 1217 -
B Oxidation to Aldaric Acids 1218
C Periodate Oxidation 1220
D Reduction to Alditols 1221
27 8 SYNTHESIS OF SUGARS FROM OTHER
SUGARS 1221
A Kiliani-Fischer Synthesis: Increasing the
Length of an Aldose Chain 1221
B Ruff and Wohl Degradations: Decreasing
the Length of an Aldose Chain 1223
27 9 PROOF OF GLUCOSE STEREOCHEMISTRY
A Which Diastereomer? The Fischer Proof
B Which Enantiomer? The Absolute
Configuration of Glucose 1228
27 10 DISACCHARIDES AND POLYSACCHARIDES
A Disaccharides 1229
B Polysaccharides 1232
27 11 NUCLEOSIDES, NUCLEOTIDES, AND
NUCLEIC ACIDS 1236
A Nucleosides and Nucleotides _ 1236
B Structures of DNA and RNA1238
C DNA, RNA, and the Genetic Code
D DNA Modification and Chemical
Carcinogenesis 1245
KEY IDEAS IN CHAPTER 27 1248
ADDITIONAL PROBLEMS 1249
APPENDICES A-1
Appendix I Nomenclature of Organic Compounds
1 A-1
Appendix II Important Infrared Absorptions A-2
Apendix III Important NMR Chemical Shifts A-4
|
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| indexdate | 2024-07-09T16:15:20Z |
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| spelling | McMurry, John Verfasser aut Organic chemistry John McMurry 2. ed. Pacific Grove, Cal. Brooks/Cole 1988 getr. Zähl. Ill. txt rdacontent n rdamedia nc rdacarrier Organische chemie gtt Chemistry, Organic Organische Chemie (DE-588)4043793-0 gnd rswk-swf 1\p (DE-588)4151278-9 Einführung gnd-content 2\p (DE-588)4123623-3 Lehrbuch gnd-content Organische Chemie (DE-588)4043793-0 s DE-604 HEBIS Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=002846070&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | McMurry, John Organic chemistry Organische chemie gtt Chemistry, Organic Organische Chemie (DE-588)4043793-0 gnd |
| subject_GND | (DE-588)4043793-0 (DE-588)4151278-9 (DE-588)4123623-3 |
| title | Organic chemistry |
| title_auth | Organic chemistry |
| title_exact_search | Organic chemistry |
| title_full | Organic chemistry John McMurry |
| title_fullStr | Organic chemistry John McMurry |
| title_full_unstemmed | Organic chemistry John McMurry |
| title_short | Organic chemistry |
| title_sort | organic chemistry |
| topic | Organische chemie gtt Chemistry, Organic Organische Chemie (DE-588)4043793-0 gnd |
| topic_facet | Organische chemie Chemistry, Organic Organische Chemie Einführung Lehrbuch |
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