The Systematic Identification of Organic Compounds
The Systematic Identification of Organic Compounds Seventh Edition
Ralph L. Shriner Christine K.F. Hermann Terence C. Morrill David Y. Curtin Reynold...
The Systematic Identification of Organic Compounds Seventh Edition
Ralph L. Shriner Christine K.F. Hermann Terence C. Morrill David Y. Curtin Reynold C. Fuson
John Wiley & Sons, Inc. NewYork • Chichester • Weinheim • Brisbane • Singapore • Toronto
Contents Chapter 1 1.1 1.2 1.3
The Systematic Identification of Organic Compounds: The Need for Organic Qualitative Analysis Suggestions to Students and Instructors Laboratory Safety and First Aid
Preliminary Examination Physical Constants Molecular Weight Determination Molecular Formula Determination Solubility Tests Infrared and Nuclear Magnetic Resonance, and Spectra Analyses Classification Tests Preparation of a Satisfactory Derivatives Mixtures Report Forms
Chapter 3
P r e l i m i n a r y E x a m i n a t i o n , P h y s i c a l P r o p e r t i e s , and P u r i t y
1 3 5
8 12 12 12 13 13 14 14, 17 21 22
34
Determination 3.1
3.2
3.3
3.4
3.5
Preliminary Examination 3.1.1 Physical State 3.1.2 Color 3.1.3 Odor 3.1.4 Ignition Test 3.1.5 Summary and Applications Determination of Physical Properties 3.2.1 Melting Points 3.2.2 Boiling Points 3.2.3 Specific Gravity 3.2.4 Index of Refraction of Liquids Introduction to Chromatography 3.3.1 Thin-Layer Chromatography 3.3.2 Gas Chromatography Optical Rotation 3.4.1 Preparation of the Solution 3.4.2 Filling the Polarimeter Tube 3.4.3 The Use of the Polarimeter 3.4.4 Expression of Results 3.4.5 Enantiomeric Excess (Optical Purity) and Resolution Recrystallization
Qualitative Elemental Analysis 4.1.1 Fusion of Organic Compounds with Sodium Quantitative Elemental Analysis 4.2.1 Combustion and Related Analyses 4.2.2 Formula Determination by Mass Spectrometry
Chapter 5 5.1
5.2
Classification
of O r g a n i c C o m p o u n d s by S o l u b i l i t y
Solubility in Water, Aqueous Acids and Bases, and Ether 5.1.1 Determination of Solubilities 5.1.2 Theory of Solubility 5.1.3 Theory of Acid-Base Solubility 5.1.4 Solubility in Water 5.1.5 Solubility in 5% Hydrochloric Acid Solution 5.1.6 Solubility in 5% Sodium Hydroxide and 5% Sodium Bicarbonate Solutions 5.1.7 Solubility of Amphoteric Compounds 5.1.8 Solubility in Cold, Concentrated Sulfuric Acid 5.1.9 Borderlines Between Solubility Classes Solubility in Organic Solvents
Chapter 6 6.1 6.2 6.3 6.4 6.5
D e t e r m i n a t i o n of M o l e c u l a r F o r m u l a
Spectrometric Methods
Mass Spectrometry Infrared (IR) Spectrometry Nuclear Magnetic Resonance Spectrometry Ultraviolet Spectrometry Problems
Chapter 7
C h e m i c a l Tests for F u n c t i o n a l G r o u p s
Compounds with Structures Previously Described in the Literature Determination of the Structures of New Compounds Not Described in the Chemical Literature Problems
C h a p t e r 10
xi
391
391 402 405
S e p a r a t i o n of M i x t u r e s
441
Preliminary Examinations of Mixtures Distillation and Sublimation 10.2.1 Distillation 10.2.2 Steam Distillation 10.2.3 Sublimation 10.3 Extractions: Separations Based Upon Salt Formation 10.3.1 Extraction of Water Insoluble Mixtures 10.3.2 Extraction of Water Soluble Mixtures 10.4 Chromatography 10.4.1 Column Chromatography 10.4.2 High-Performance Liquid Chromatography (HPLC) 10.4.3 Gas Chromatography
442 444 444 449 451 452 454 457 461 463 471 474
10.1 10.2
xii
Contents
C h a p t e r 11 11.1 11.2 11.3 11.4 11.5 11.6
Chemical Literature
Handbooks Compendia Spectral Collections Journals Abstracts and Indexes Monographs
Appendix I
Handy Tables for the O r g a n i c L a b o r a t o r y
477 478 479 480 481 482 483
484
Composition and Properties of Common Acids and Bases Composition of Common Buffer Solutions Pressure-Temperature Nomograph for Vacuum Distillations Elution Solvents for Chromatography Salt-Ice Mixtures for Cooling Baths Liquid Media for Heating Baths Solvents for Extraction of Aqueous Solutions Drying Agents for Organic Solvents More Powerful Dehydrating Agents for Organic Liquids
485 486 486 487 488 489 489 490 491
A p p e n d i x II
492
E q u i p m e n t and C h e m i c a l s for the L a b o r a t o r y
Apparatus Individual Desk Equipment Suggested Locker Equipment Suggested Supplementary Kit Suggested Supplementary Microscale Kit General Laboratory Equipment Special Laboratory Equipment Items Obtained on Temporary Loan from Instructor or Stockroom Waste Containers Needed in the Laboratory Chemicals Needed in the Laboratory Organic Compounds Inorganic Compounds Acids and Bases Solutions Indicators Other Items Unknowns
