Microscale Organic Laboratory: with Multistep and Multiscale Syntheses, 4th Edition,9780471321859

Microscale Organic Laboratory: with Multistep and Multiscale Syntheses, 4th Edition

by ; ;
Edition: 4th
ISBN13: 9780471321859
ISBN10: 0471321850
Format: Hardcover
Pub. Date: 2000-01-01
Publisher(s): Wiley
List Price: $232.90

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Summary

This is a laboratory text for the mainstream organic chemistry course taught at both two and four year schools, featuring both microscale experiments and options for scaling up appropriate experiments. It provides complete coverage of organic laboratory experiments and techniques with a strong emphasis on modern laboratory instrumentation, a sharp focus on safety in the lab, excellent pre- and post-lab exercises, and multi-step experiments. There is also another text available by the same authors titled Microscale Techniques for the Organic Lab, Second Edition which has more material on techniques and spectroscopy, but has no experiments.

Table of Contents

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

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