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Tables of Contents for Microscale Organic Laboratory
Chapter/Section Title
Page #
Page Count
Introduction
1
4
General Rules for the Microscale Laboratory
3
1
The Organic Chemistry Laboratory
4
1
Safety
5
11
Making the Laboratory a Safer Place
5
2
Nature of Hazards
5
1
Reduction of Risks
6
1
Precautionary Measures
7
1
Thinking about the Risks in Using Chemicals
7
9
Disposal of Chemicals
8
1
Material Safety Data Sheets
8
4
Alternate Sources of Information
12
1
Estimating the Risks from Vapors
12
1
Concluding Thoughts
13
3
Introduction to Microscale Organic Laboratory Equipment and Techniques
16
17
Microglassware Equipment
17
2
Standard Taper Joints
17
1
Conical Vials
18
1
Condensers
18
1
Distillation Heads
18
1
Recrystallization Tubes
18
1
Miscellaneous Items
18
1
Gas Chromatographic Fraction Collection Items
19
1
Standard Experimental Apparatus
19
6
Heating and Stirring Arrangements
19
1
Sand Bath Technique/Hotplate Calibration
19
1
Metal Heat-Transfer Devices
20
1
Stirring
20
1
Reflux Apparatus
20
2
Distillation Apparatus
22
1
Moisture-Protected Reaction Apparatus
23
1
Specialized Pieces of Equipment
24
1
Microscale Laws
25
4
Rules of the Trade for Handling Organic Materials at the Microscale Level
25
1
Rules for Working with Liquids at the Microscale Level
26
3
Rules for Working with Solids at the Microscale Level
29
1
The Laboratory Notebook
29
1
Example of a Laboratory Notebook Entry
30
2
Calculation of Yields
32
1
Determination of Physical Properties
33
11
Liquids
34
1
Ultramicro-Boiling Point
34
2
Density
36
2
Refractive Index
38
2
Solids
40
1
Melting Points
40
1
Simple Capillary Melting Point
40
1
Evacuated Melting Points
40
2
Mixture Melting Points
42
2
Microscale Laboratory Techniques
44
55
Microscale Separation of Liquid Mixtures by Preparative Gas Chromatography
44
1
GC Instrumentation
45
5
Procedure for Preparative Collection
49
1
Distillation
50
1
Distillation
50
1
Simple Distillation at the Semimicroscale Level
50
3
Fractional Semimicroscale Distillation
53
2
Solvent Extraction
55
1
Solubility
55
3
Partition Coefficient
58
2
Extraction
60
6
Liquid-Liquid Extraction
60
1
Microscale Extraction
61
2
Separatory Funnel---Semimicroscale, Macroscale Extraction
63
1
Continuous Liquid-Liquid Extraction
64
1
Separation of Acids and Bases
65
1
Salting Out
66
1
Solid-Liquid Extraction
67
1
Drying Agents
67
2
Solid-Phase Extraction
69
2
Crystallization
71
1
General Crystallization Procedure
71
2
Simple Crystallization
73
1
Filtration Techniques
74
3
Use of the Hirsch Funnel
74
1
A Hirsch Funnel Alternative---Nail-filter Funnel
75
1
Craig Tube Crystallizations
75
2
Chromatography
77
1
Technique 6A Column, Flash, High-Performance Liquid, Paper, and Thin-Layer Chromatography
77
1
Column Chromatography
78
4
Packing the Column
79
1
Sample Application
79
1
Elution of the Column
80
1
Fraction Collection
80
1
Flash Chromatography
81
1
Thin-Layer Chromatography
82
3
Paper Chromatography
85
1
High-Performance Liquid Chromatography
85
1
Technique 6B Concentration of Solutions
86
1
Distillation
86
1
Evaporation with Nitrogen Gas
87
1
Removal of Solvent Under Reduced Pressure
87
3
Collection and Control of Gaseous Products
90
1
Water Insoluble Gases
90
1
Trapping By-product Gases
91
1
Measurement of Specific Rotation
92
1
Theory
92
1
The Polarimeter
93
2
High Performance Polarimeters and Optical Rotary Dispersion
95
1
Applications to Structure Determination in Natural Products
95
1
Inaccurate Measurements
95
1
Sublimation
96
1
Sublimation Theory
96
1
Experimental Set-up
97
1
Precautions
97
2
Microscale Organic Laboratory Experiments
99
280
Introduction
99
1
Measurement of Physical Properties
100
6
The Separation of a 25-L Mixture of Heptanol (bp 153 C and Cyclohexanol (bp 160 C) by Gas Chromatography
106
6
Distillation
112
11
Simple Distillation at the Semimicroscale Level: Separation of Ethyl Acetate from trans-1,2-Dibenzoylethylene
112
3
Fractional Semimicroscale Distillation: Separation of Hexane and Toluene
115
2
Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning Band Column
117
3
Fractional Semimicroscale Distillation: The Separation of 2-Methylpentane and Cyclohexane Using a Spinning Band in a Hickman-Hinkle Still
120
3
Solvent Extraction
123
10
Determination of a Partition Coefficient for the System Benzoic Acid, Methylene Chloride, and Water
123
5
Solvent Extraction I: The System; Benzoic Acid, Methylene Chloride, and 10% Sodium Bicarbonate Solution; An Example of Acid-Base Extraction Techniques
128
1
Solvent Extraction II: A Three Component Mixture; An Example of the Separation of an Acid, a Base, and a Neutral Substance
129
4
Reduction of Ketones Using a Metal Hydride Reagent: Cyclohexanol and cis- and trans-4-tert-Butylcyclohexanol
133
12
Cyclohexanol
135
4
cis- and trans-4-tert-Butylcyclohexanol
139
6
Photochemical Isomerization of an Alkene: cis-1,2-Dibenzoylethylene
145
10
Purification of trans-1,2-Dibenzoylethylene
148
1
Isomerization of an Alkene: Thin-Layer Chromatographic Analysis
149
5
Isomerization of an Alkene: Nuclear Magnetic Resonance Analysis
154
1
The Cannizzaro Reaction with 4-Chlorobenzaldehyde: 4-Chlorobenzoic Acid and 4-Chlorobenzyl Alcohol
155
10
The Esterification Reaction: Ethyl Laurate, Isopentyl Acetate, and the Use of Acidic Resins
165
19
Ethyl Laurate
176
2
Isopentyl Acetate, Semimicroscale Preparation
178
1
Esterification by Acidic Resins
179
5
Semimicroscale Preparations
The E1 Elimination Reaction: Dehydration of 2-Butanol to Yield 1-Butene, trans-2-Butene, and cis-2-Butene
184
8
The E2 Elimination Reaction: Dehydrohalogenation of 2-Bromobutane to Yield 1-Butene, trans-2-Butene, and cis-2-Butene
192
7
The Isolation of Natural Products
199
19
Isolation and Characterization of an Optically Active Natural Product: Usnic Acid
199
5
Isolation and Characterization of a Natural Product: Caffeine and Caffeine 5-Nitrosalicylate
204
9
Isolation of a Natural Product by Steam Distillation: Cinnamaldehyde from Cinnamon
213
5
Reductive Catalytic Hydrogenation of an Alkene: Octane
218
5
Hydroboration-Oxidation of an Alkene: Octanol
223
7
Diels-Alder Reaction: 4-Cyclohexene-cis-1,2-dicarboxylic Acid Anhydride
230
11
Optional Semimicroscale Preparation
Diels-Alder Reaction: 9, 10-Dihydroanthracene-9, 10-,-succinic Acid Anhydride
241
5
Optional Semimicroscale and Macroscale Preparations
Grignard Reaction with a Ketone: Triphenylmethanol
246
8
Grignard Reaction with an Aldehyde: 4-Methyl-3-heptanol
254
5
The Perkin Reaction: Condensation of Rhodanine with an Aromatic Aldehyde to Yield o-Chlorobenzylidene Rhodanine
259
5
Optional Semimicroscale Preparation
Alkene Preparation by the Wittig Reaction: (E)-Stilbene; 1-Methylene-4-tert-butylcyclohexane; and trans-9-(2-Phenylethenyl)anthracene
264
15
(E)-Stilbene by the ``Instant Ylide'' Method
269
2
(E)-Stilbene by the Horner-Wadsworth-Emmons Reaction
271
2
Methylene-4-tert-butylcyclohexane
273
2
trans-9-(2-Phenylethenyl)anthracene
275
4
Aldol Reaction: Dibenzalacetone
279
7
Optional Semimicroscale Preparation
Quantitative Analysis of Grignard Reagents: 1-Methylbutylmagnesium Bromide and Phenylmagnesium Bromide
286
4
1-Methylbutylmagnesium Bromide
288
1
Phenylmagnesium Bromide
288
2
Williamson Synthesis of Ethers: Propyl p-Tolyl Ether and Methyl p-Ethylphenyl Ether
290
12
Propyl p-Tolyl Ether, Optional Macroscale Preparation
291
4
Methyl p-Ethylphenyl Ether
295
7
Optional Semimicroscale and Macroscale Preparations
Amide Synthesis: Acetanilide and N,N'-Diacetyl-1,4-phenylenediamine
302
7
Acetanilide, Optional Semimicroscale Preparation
304
2
N,N'-Diacetyl-1,4-phenylenediamine
306
3
Imide Synthesis: N-Phenylmaleimide
309
5
Maleanilic Acid
311
1
N-Phenylmaleimide
312
2
Synthesis of Cyclic Carboxylic Acid Anhydrides: Succinic Anhydride and Phthalic Anhydride
314
5
Succinic Anhydride
316
1
Phthalic Anhydride
317
2
Diazonium Coupling Reaction: Methyl Red
319
5
Friedel-Crafts Acylation: Acetylferrocene and Diacetylferrocene
324
6
Halogenation: Electrophilic Aromatic Substitution to Yield 4-Bromoacetanilide
330
5
Nitration: 2,5-Dichloronitrobenzene; N,N'-Diacetyl-2,3-dinitro-1,4-phenylenediamine; 5-Nitrosalicylic Acid; and 2- and 4-Nitrophenol
335
10
Semimicroscale Preparation of Anhydrous Nitric Acid
2,5-Dichloronitro-benzene
338
1
N,N'-Diacetyl-2,3-dinitro-1,4-phenylenediamine
339
1
5-Nitrosalicylic Acid
340
2
2- and 4-Nitrophenol
342
3
Nucleophilic Aromatic Substitution: 2,4-Dinitrophenylthiocyanate
345
4
Halogenation Using N-Bromosuccinimide: 9-Bromoanthracene
349
4
Hypochlorite Oxidation of an Alcohol: Cyclohexanone
353
3
Chromium Trioxide---Resin or Hypochlorite Oxidation of an Alcohol: 9-Fluorenone
356
6
9-Fluorenone: CrO3 Oxidation of 9-Fluorenol
357
2
9-Fluorenone: NaOCI Oxidation of 9-Fluorenol
359
3
Hypochlorite Oxidation of Methyl Ketones by the Haloform Reaction: Benzoic Acid and p-Methoxybenzoic Acid
362
5
Benzoic Acid
363
2
p-Methoxybenzoic Acid
365
2
Optional Semimicroscale Preparation
Conversion of Cyclohexyl Bromide to Cyclohexene---an E2 Elimination Reaction: Factors Affecting the Rate of a Chemical Reaction
367
12
Advanced Microscale Organic Laboratory Experiments
379
40
Introduction
379
1
Diborane Reductions: Thioxanthene and Xanthene
380
8
Thioxanthene
382
2
Xanthene
384
4
Heterocyclic Ring Synthesis: Benzimidazole
388
3
Heterocyclic Ring Synthesis: 4-Hydroxycoumarin and Dicoumarol
391
6
4-Hydroxycoumarin
394
1
Dicoumarol
395
2
Grignard and Aryl Halide Cross-Coupling Reaction: 1-Methyl-2-(methyl-d3)-benzene
397
6
Oxidative Coupling of 2-Naphthol: 1,1'-Bi-2-Naphthol
403
5
Beckmann Rearrangement: Benzanilide
408
6
Preparation of an Enol Acetate: Cholesta-3,5-dien-3-ol Acetate
414
5
Sequential Syntheses: The Transition from Macro to Micro
419
113
Introduction
419
2
The Synthesis of Hexaphenylbenzene
421
32
Experiment [A1a] The Benzoin Condensation of Benzaldehyde: Benzoin
426
5
Semimicroscale Preparation and Optional Microscale Preparations
Copper(II) Ion Oxidation of Benzoin: Benzil
431
4
Semimicroscale Preparation and Optional Microscale Preparation
Tetraphenylcyclopentadienone
Optional Microscale Preparation
435
4
(E)-Stilbene
Semimicroscale Preparation
439
2
Bromination of (E)-Stilbene: meso-Stilbene Dibromide
Semimicroscale Preparation and Optional Macroscale and Microscale Preparations
441
5
Dehydrohalogenation of meso-Stilbene Dibromide: Diphenylacetylene
Semimicroscale Preparation and Optional Macroscale and Microscale Preparations
446
3
Hexaphenylbenzene
449
4
The Stepwise Synthesis of Nylon-6,6
453
8
Oxidation of Cyclohexanol: Adipic Acid
Macroscale Preparation
454
3
Preparation of an Acid Chloride: Adipoyl Chloride
Semimicroscale Preparation
457
3
Preparation of a Polyamide: Nylon-6,6
460
1
The Synthesis of Sulfanilamide
461
10
Acetylation of Aniline: 2,2,2-Trifluoroacetanilide
Semimicroscale Preparation
463
3
Chlorosulfonation of 2,2,2-Trifluoroacetanilide: p-(Trifluoroacetamido) benzenesulfonyl Chloride
Semimicroscale Preparation
466
2
Preparation of an Arene Sulfonamide: Sulfanilamide
Semimicroscale Preparation
468
3
The Synthesis of 2'-Bromostyrene
471
17
The Verley-Doebner Modification of the Knoevenagel Reaction: trans-Cinnamic Acid
Semimicroscale Preparation
474
4
Bromination of trans-Cinnamic Acid: erythro-2,3-Dibromo-3-phenylpropanoic Acid
Semimicroscale Preparation
478
4
An Elimination Reaction with erythro-2,3-Dibromo-3-phenylpropanoic Acid: 2'-Bromostyrene
Semimicroscale Preparation
482
6
The Synthesis of Piperonylonitrile from Piperonyl Alcohol
488
15
Piperonal
Macroscale Preparation and Optional Microscale Preparations
489
6
Piperonal O-(2,4-Dinitrophenyl)-oxime
Semimicroscale Preparation and Optional Microscale Preparation
495
4
Piperonylonitrile
499
4
Introduction of Photochromism: The Synthesis of a Photochromic Imine
503
29
An Aldol Reaction: trans-4-Nitrochalcone
Semimicroscale Preparation
507
5
erythro-2,3-Dibromo-3-(4-nitrophenyl)propiophenone
Semimicroscale Preparation
512
5
trans-2-(4-Nitrophenyl)-3-benzoylaziridine
Semimicroscale Preparation
517
8
A Photochromic Imine: 2-exo-6-exo-2,4-Diphenyl-6-(4-nitrophenyl)-1,3-diazabicyclo[3.1.0]hex-3-ene
525
7
Spectroscopic Identification of Organic Compounds
532
86
Introduction to Infrared Spectroscopy
532
1
Introduction to Group Frequencies
533
1
Interpretation of Infrared Spectra
533
1
Strategies for Interpreting Infrared Spectra
534
2
A Survey of Group Frequencies Identified in Organic Molecules
536
8
Group Frequencies of the Hydrocarbons are Listed as Follows: Alkanes
536
1
Alkenes C=C Stretching
536
1
Alkene C---H
536
2
Alkynes
538
1
Arenes
538
1
Group Frequencies of Carbonyl Groups C=O
538
1
The major factors perturbing carbonyl frequencies
539
1
Group frequencies of the heteroatom functional groups
Alcohols
539
1
Aldehydes
540
1
Ketones
540
1
Esters
540
1
Acyl Halides
540
1
Carboxylic Acids
541
1
Anhydrides
541
1
Ethers
541
1
Primary Amines
542
1
Nitriles
542
1
Primary amides
542
1
Secondary amides
542
1
Isocyanates
543
1
Thiols
543
1
Alkyl halides
543
1
Aryl halides (Chlorobenzene)
544
1
Infrared Spectroscopy: Instrumentation and Sample Handling
544
10
Instrumentation
544
1
Sample Handling in the Infrared
545
1
Liquid Samples
545
1
Solution Spectra and Spectra of Materials Boiling Below 100, C
545
1
Solid Samples
545
9
Nuclear Magnetic Resonance Spectroscopy: Introduction to Nuclear Magnetic Resonance
554
9
Nuclear Spin
554
1
Instrumentation
555
2
Chemical Shift
557
1
Spin-Spin Coupling
558
3
Intensities
561
1
Second-Order Effects
561
2
Interpretation of 1H NMR Spectra
563
10
1H Chemical Shifts
565
1
Spin-Spin Coupling
566
1
Geminal Coupling
566
1
Vicinal Coupling
567
1
Long-Range Coupling
568
1
Examples of Complex, Yet First-Order, Coupling
568
1
Ethyl Vinyl Ether
568
2
Allyl Acetate
570
3
13C NMR Spectroscopy
573
6
Two-Dimensional Nuclear Magnetic Resonance Spectroscopy
579
2
Nuclear Magnetic Resonance Spectroscopy Sampling
581
4
Ultraviolet-Visible Spectroscopy: Introduction to Absorption Spectroscopy
585
15
UV-Vis Spectroscopy
586
2
Applications to Organic Molecules
588
7
Instrumentation
595
3
Sample Preparation
598
2
Mass Spectrometry
600
2
Instrumentation
602
6
Ion Source
602
1
Mass Analyzer
603
2
Detector
605
1
Tuning the Mass Spectrometer
605
1
Sample Introduction
605
1
Gas Chromatography/Mass Spectrometry
606
1
Capillary Columns
606
2
Split Injection
608
1
Split/Splitless Injection
608
1
Features of the Mass Spectrum
608
5
Terms
609
1
Isotope Peaks
609
2
Recognizing the Molecular Ion
611
1
Mass Spectral Interpretation
612
1
Case Study: Synthesis of Methyl Benzoate
613
5
Qualitative Identification of Organic Compounds
618
34
Organic Qualitative Analysis
618
23
Preliminary Tests
619
3
Separation of Impurities
622
1
Detection of Elements Other Than Carbon, Hydrogen, and Oxygen
622
4
Solubility Characteristics
626
2
The Classification Tests
628
13
Preparation of Derivatives
641
11
Carboxylic Acids
642
1
Alcohols
643
1
Aldehydes and Ketones
644
1
Amines
645
1
Acid Chlorides and Anhydrides
646
1
Aromatic Hydrocarbons
647
1
Nitriles
647
1
Phenols
647
1
Aliphatic Hydrocarbons, Halogenated Hydrocarbons, Amides, Nitro Compounds, Ethers, and Esters
648
4
Glossary
652
3
Index
655