Microscale Techniques for the Organic Laboratory

ISBN-10: 0471249092

ISBN-13: 9780471249092

Edition: 2nd 2002 (Revised)

Authors: Dana W. Mayo, Peter K. Trumper, Ronald M. Pike

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Description:

This is a laboratory text for the mainstream organic chemistry course, featuring both microscale techniques and spectroscopy. It provides complete coverage of organic laboratory techniques.
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Book details

List price: $97.95
Edition: 2nd
Copyright year: 2002
Publisher: John Wiley & Sons, Incorporated
Publication date: 6/29/2001
Binding: Paperback
Pages: 352
Size: 7.00" wide x 9.50" long x 0.50" tall
Weight: 1.606
Language: English

Introduction
General Rules for the Microscale Laboratory
The Organic Chemistry Laboratory
Safety
Making the Laboratory a Safer Place
Nature of Hazards
Reduction of Risks
Precautionary Measures
Thinking about the Risks in Using Chemicals
Disposal of Chemicals
Material Safety Data Sheets
Alternate Sources of Information
Estimating the Risks from Vapors
Concluding Thoughts
Introduction to Microscale Organic Laboratory Equipment and Techniques
Microglassware Equipment
Standard Taper Joints
Conical Vials
Condensers
Distillation Heads
Recrystallization Tubes
Miscellaneous Items
Gas Chromatographic Fraction Collection Items
Standard Experimental Apparatus
Heating and Stirring Arrangements
Sand Bath Technique/Hotplate Calibration
Metal Heat-Transfer Devices
Stirring
Reflux Apparatus
Distillation Apparatus
Moisture-Protected Reaction Apparatus
Specialized Pieces of Equipment
Microscale Laws
Rules of the Trade for Handling Organic Materials at the Microscale Level
Rules for Working with Liquids at the Microscale Level
Rules for Working with Solids at the Microscale Level
The Laboratory Notebook
Example of a Laboratory Notebook Entry
Calculation of Yields
Determination of Physical Properties
Liquids
Ultramicro-Boiling Point
Density
Refractive Index
Solids
Melting Points
Simple Capillary Melting Point
Evacuated Melting Points
Mixture Melting Points
Microscale Laboratory Techniques
Microscale Separation of Liquid Mixtures by Preparative Gas Chromatography
GC Instrumentation
Procedure for Preparative Collection
The Separation of a 25-[mu]L Mixture of Heptanol (bp 153 [degree]C) and Cyclohexanol (bp 160 [degree]C) by Gas Chromatography
The Separation of a 40-[mu]L Mixture of (1S)-(--)--[alpha]-Pinene (bp 156 [degree]C) and (1S)-(--)-[beta]-Pinene (bp 165 [degree]C) by Gas Chromatography
The Separation of a 40-[mu]L Mixture of 2-Heptanone (bp 149-150 [degree]C) and Cyclohexanol (bp 160-161 [degree]C) by Gas Chromatography
The Separation of a 40-[mu]L Mixture of d-Limonene (bp 175-176 [degree]C) and Cyclohexyl acetate (bp 173 [degree]C) by Gas Chromatography
Techniques 2 and 3: Distillation
Simple Distillation at the Semimicroscale Level
Simple Semimicroscale Distillation: Separation of Hexane and Toluene
Fractional Semimicroscale Distillation
Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning-Band Column
Fractional Semimicroscale Distillation: Separation of 2-Methylpentane and Cyclohexane Using a Spinning-Band in a Hickman-Hinkle Still
Solvent Extraction
Solubility
Partition Coefficient
Extraction
Liquid-Liquid Extraction
Microscale Extraction
Separatory Funnel--Semimicroscale Macroscale Extraction
Continuous Liquid-Liquid Extraction
Separation of Acids and Bases
Salting Out
Solid-Liquid Extraction
Drying Agents
Solid-Phase Extraction
Crystallization
General Crystallization Procedure
Simple Crystallization
Filtration Techniques
Use of the Hirsch Funnel
A Hirsch Funnel Alternative--Nail-filter Funnel
Craig Tube Crystallizations
Chromatography
Column, Flash, High-Performance, Liquid, Paper, and Thin-Layer Chromatography
Column Chromatography
Packing the Column
Sample Application
Elution of the Column
Fraction Collection
Flash Chromatography
Thin-Layer Chromatography
Paper Chromatography
High-Performance Liquid Chromatography
Concentration of Solutions
Distillation
Evaporation with Nitrogen Gas
Removal of Solvent Under Reduced Pressure
Collection and Control of Gaseous Products
Water Insoluble Gases
Trapping Byproduct Gases
Measurement Of Specific Rotation
Theory
The Polarimeter
Inaccurate Measurements
High-Performance Polarimeters and Optical Rotary Dispersion
Applications to Structure Determination in Natural Products
Sublimation
Sublimation Theory
Experimental Set-up
Precautions
Introduction to Infrared Spectroscopy
Introduction to Group Frequencies: Interpretation of Infrared Spectra
Strategies for Interpreting Infrared Spectra
A Survey of Group Frequencies Identified in Organic Molecules
Group Frequencies of the Hydrocarbons
Alkanes
Alkenes C=C Stretching
Alkene C--H
Alkynes
Arenes
Group Frequencies of Carbonyl Groups
Factors that Raise the C=O Frequency
Factors that Lower the C=O Frequency
Group Frequencies of the Heteroatom Functional Groups
Hexane
Alcohols
Aldehydes
Ketones
Esters
Acyl Halides
Carboxylic Acids
Anhydrides
Ethers
Primary Amines
Nitriles
Primary Amides
Secondary Amides
Isocyanates
Thiols
Alkyl Halides
Aryl Halides (Chlorobenzene)
Infrared Spectroscopy: Instrumentation and Sample Handling
Instrumentation
Sample Handling in the Infrared
Liquid Samples
Solution Spectra and Spectra of Materials Boiling Below 100 [degree]C
Solid Samples
Infrared Analysis: Reduction of Ketones Using a Metal Hydride Reagent: Cyclohexanone to Cyclohexanol
A Spectral Comparison of Reactant and Product
Infrared Analysis: An Additional Example of the Reduction of t-Butylcyclohexanone
Introduction to Nuclear Magnetic Resonance Spectroscopy
Nuclear Spin
Instrumentation
Chemical Shift
Spin-Spin Coupling
Intensities
Second-Order Effects
Interpretation of [superscript 1]H NMR Spectra
[superscript 1]H Chemical Shifts
Spin-Spin Coupling
Geminal Coupling
Vicinal Coupling
Long-Range Coupling
Examples of Complex, Yet First-Order, Coupling
Ethyl Vinyl Ether
Allyl Acetate
4-tert-Butylcyclohexanol
[superscript 13]C NMR Spectroscopy
Two-Dimensional Nuclear Magnetic Resonance Spectroscopy
Nuclear Magnetic Resonance Spectroscopy Sampling
Introduction to Ultraviolet-Visible Spectroscopy Absorption Spectroscopy: Theory
UV-Vis Spectroscopy
Applications to Organic Molecules
Instrumentation
Sample Preparation
Introduction to Mass Spectrometry
Instrumentation
Ion Source
Mass Analyzer
Detector
Tuning the Mass Spectrometer
Sample Introduction
Gas Chromatography/Mass Spectrometry
Capillary Columns
Split Injection
Split/Splitless Injection
Features of the Mass Spectrum
Terms
Isotope Peaks
Recognizing the Molecular Ion
Mass Spectral Interpretation
Case Study: Synthesis of Methyl Benzoate
Qualitative Identification of Organic Compounds Organic Qualitative Analysis
Preliminary Tests
Separation of Impurities
Detection of Elements Other Than Carbon, Hydrogen, and Oxygen
Solubility Characteristics
The Classification Tests
Preparation of Derivatives
Carboxylic Acids
Alcohols
Aldehydes and Ketones
Amines
Acid Chlorides and Anhydrides
Aromatic Hydrocarbons
Nitriles
Phenols
Aliphatic Hydrocarbons, Halogenated, Hydrocarbons, Amides, Nitro Compounds, Ethers, and Esters
Glossary
Index
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