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