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Tables of Contents for The Systematic Identification of Organic Compounds
Chapter/Section Title
Page #
Page Count
Chapter 1 Introduction
1
7
1.1 The Systematic Identification of Organic Compounds: The Need for Organic Qualitative Analysis
1
2
1.2 Suggestions to Students and Instructors
3
2
1.3 Laboratory Safety and First Aid
5
3
Chapter 2 Identification of Unknowns
8
26
2.1 Preliminary Examination
12
1
2.2 Physical Constants
12
1
2.3 Molecular Weight Determination
12
1
2.4 Molecular Formula Determination
13
1
2.5 Solubility Tests
13
1
2.6 Infrared and Nuclear Magnetic Resonance, and Spectra Analyses
14
1
2.7 Classification Tests
14
3
2.8 Preparation of a Satisfactory Derivatives
17
4
2.9 Mixtures
21
1
2.10 Report Forms
22
12
Chapter 3 Preliminary Examination, Physical Properties, and Purity Determination
34
48
3.1 Preliminary Examination
35
2
3.1.1 Physical State
35
1
3.1.2 Color
35
1
3.1.3 Odor
35
1
3.1.4 Ignition Test
36
1
3.1.5 Summary and Applications
37
1
3.2 Determination of Physical Properties
37
21
3.2.1 Melting Points
37
7
3.2.2 Boiling Points
44
6
3.2.3 Specific Gravity
50
6
3.2.4 Index of Refraction of Liquids
56
2
3.3 Introduction to Chromatography
58
13
3.3.1 Thin-Layer Chromatography
59
4
3.3.2 Gas Chromatography
63
8
3.4 Optical Rotation
71
7
3.4.1 Preparation of the Solution
71
1
3.4.2 Filling the Polarimeter Tube
71
1
3.4.3 The Use of the Polarimeter
72
2
3.4.4 Expression of Results
74
1
3.4.5 Enantiomeric Excess (Optical Purity) and Resolution
75
3
3.5 Recrystallization
78
4
Chapter 4 Determination of Molecular Formula
82
12
4.1 Qualitative Elemental Analysis
83
7
4.1.1 Fusion of Organic Compounds with Sodium
83
7
4.2 Quantitative Elemental Analysis
90
4
4.2.1 Combustion and Related Analyses
90
3
4.2.2 Formula Determination by Mass Spectrometry
93
1
Chapter 5 Classification of Organic Compounds by Solubility
94
24
5.1 Solubility in Water, Aqueous Acids and Bases, and Ether
95
20
5.1.1 Determination of Solubilities
97
1
5.1.2 Theory of Solubility
98
5
5.1.3 Theory of Acid-Base Solubility
103
3
5.1.4 Solubility in Water
106
1
5.1.5 Solubility in 5% Hydrochloric Acid Solution
106
1
5.1.6 Solubility in 5% Sodium Hydroxide and 5% Sodium Bicarbonate Solutions
107
3
5.1.7 Solubility of Amphoteric Compounds
110
1
5.1.8 Solubility in Cold, Concentrated Sulfuric Acid
111
1
5.1.9 Borderlines Between Solubility Classes
112
3
5.2 Solubility in Organic Solvents
115
3
Chapter 6 Spectrometric Methods
118
82
6.1 Mass Spectrometry
119
7
6.2 Infrared (IR) Spectrometry
126
29
6.3 Nuclear Magnetic Resonance Spectrometry
155
20
6.4 Ultraviolet Spectrometry
175
13
6.5 Problems
188
12
Chapter 7 Chemical Tests for Functional Groups
200
101
7.1 Acid Anhydrides
204
7
7.2 Acyl Halides
211
2
7.3 Alcohols
213
15
7.4 Aldehydes
228
8
7.5 Amides
236
2
7.6 Amines and Amine Salts
238
15
7.7 Amino Acids
253
2
7.8 Carbohydrates
255
9
7.9 Carboxylic Acids
264
1
7.10 Esters
265
1
7.11 Ethers
266
4
7.12 Halides
270
5
7.13 Hydrocarbons-Alkanes
275
1
7.14 Hydrocarbons-Alkenes
276
7
7.15 Hydrocarbons-Alkynes
283
1
7.16 Hydrocarbons-Aromatic
284
5
7.17 Ketones
289
1
7.18 Nitriles
290
1
7.19 Nitro Compounds
291
3
7.20 Phenols
294
5
7.21 Sulfonamides, Sulfonic Acids, Sulfonyl Chlorides
299
2
Chapter 8 The Preparation of Derivatives
301
90
8.1 Carboxylic Acids, Acid Anhydrides, Acid Halides
304
10
8.2 Alcohols
314
5
8.3 Aldehydes and Ketones
319
6
8.4 Amides
325
6
8.5 Amines
331
8
8.6 Amino Acids
339
6
8.7 Carbohydrates
345
3
8.8 Esters
348
11
8.9 Ethers--Aliphatic
359
1
8.10 Ethers--Aromatic
360
4
8.11 Halides--Alkyl
364
5
8.12 Halides--Aromatic
369
3
8.13 Hydrocarbon--Aromatic
372
3
8.14 Nitriles
375
5
8.15 Nitro Compounds
380
1
8.16 Phenols
381
4
8.17 Sulfonic Acids, Sulfonyl Chlorides, Sulfonamides
385
6
Chapter 9 Structural Problems-Solution Methods and Exercises
391
50
9.1 Compounds with Structures Previously Described in the Literature
391
11
9.2 Determination of the Structures of New Compounds Not Described in the Chemical Literature
402
3
9.3 Problems
405
36
Chapter 10 Separation of Mixtures
441
36
10.1 Preliminary Examinations of Mixtures
442
2
10.2 Distillation and Sublimation
444
8
10.2.1 Distillation
444
5
10.2.2 Steam Distillation
449
2
10.2.3 Sublimation
451
1
10.3 Extractions: Separations Based Upon Salt Formation
452
9
10.3.1 Extraction of Water Insoluble Mixtures
454
3
10.3.2 Extraction of Water Soluble Mixtures
457
4
10.4 Chromatography
461
16
10.4.1 Column Chromatography
463
8
10.4.2 High-Performance Liquid Chromatography (HPLC)
471
3
10.4.3 Gas Chromatography
474
3
Chapter 11 Chemical Literature
477
7
11.1 Handbooks
478
1
11.2 Compendia
479
1
11.3 Spectral Collections
480
1
11.4 Journals
481
1
11.5 Abstracts and Indexes
482
1
11.6 Monographs
483
1
Appendix I Handy Tables for the Organic Laboratory
484
8
Composition and Properties of Common Acids and Bases
485
1
Composition of Common Buffer Solutions
486
1
Pressure-Temperature Nomograph for Vacuum Distillations
486
1
Elution Solvents for Chromatography
487
1
Salt-Ice Mixtures for Cooling Baths
488
1
Liquid Media for Heating Baths
489
1
Solvents for Extraction of Aqueous Solutions
489
1
Drying Agents for Organic Solvents
490
1
More Powerful Dehydrating Agents for Organic Liquids
491
1
Appendix II Equipment and Chemicals for the Laboratory
492
8
Apparatus
492
7
Individual Desk Equipment
492
1
Suggested Locker Equipment
492
1
Suggested Supplementary Kit
493
1
Suggested Supplementary Microscale Kit
493
1
General Laboratory Equipment
493
1
Special Laboratory Equipment
494
1
Items Obtained on Temporary Loan from Instructor or Stockroom
494
1
Waste Containers Needed in the Laboratory
494
1
Chemicals Needed in the Laboratory
495
1
Organic Compounds
495
1
Inorganic Compounds
496
1
Acids and Bases
497
1
Solutions
497
1
Indicators
498
1
Other Items
498
1
Unknowns
499
1
Appendix III Tables of Derivatives
500
 
Acid Anhydrides (Liquids)
501
1
Acid Anhydrides (Solids)
502
3
Acyl Halides (Liquids)
505
4
Acyl Halides (Solids)
509
2
Alcohols (Liquids)
511
4
Alcohols (Solids)
515
2
Aldehydes (Liquids)
517
3
Aldehydes (Solids)
520
3
Amides (Liquids)
523
1
Amides (Solids)
524
17
Amines-Primary and Secondary (Liquids)
541
4
Amines-Primary and Secondary (Solids)
545
11
Amines-Tertiary (Liquids)
556
3
Amines-Tertiary (Solids)
559
2
Amino Acids
561
2
Carbohydrates
563
2
Carboxylic Acids (Liquids)
565
2
Carboxylic Acids (Solids)
567
9
Esters (Liquids)
576
17
Esters (Solids)
593
7
Ethers-Aromatic (Liquids)
600
2
Ethers-Aromatic (Solids)
602
1
Halides-Alkyl, Cycloalkyl, and Aralkyl (Liquids)
603
2
Halides-Aromatic (Liquids)
605
1
Halides-Aromatic (Solids)
606
1
Hydrocarbons-Aromatic (Liquids)
607
1
Hydrocarbons-Aromatic (Solids)
608
1
Ketones (Liquids)
609
4
Ketones (Solids)
613
5
Nitriles (Liquids)
618
5
Nitriles (Solids)
623
8
Nitro Compounds (Liquids)
631
1
Nitro Compounds (Solids)
632
2
Phenols (Liquids)
634
2
Phenols (Solids)
636
10
Sulfonamides
646
4
Sulfonic Acids
650
3
Sulfonyl Chlorides
653