Designed as a lab manual for undergraduate organic chemistry courses
Balanced Approach-offers professors a large selection of experiments to choose from, giving them maximum versatility and choice, and the option of using microscale glassware, macroscale glassware, or a combination of both, for the duration of the course
Offers both standard and Discovery-Based Experiments-of t...show morehe 53 macroscale experiments and 38 microscale experiments, 18 are discovery-based, in which students answer questions using experimental data while mastering laboratory techniques
13 Multiweek Projects foster teamwork and allow students the opportunity to think through an experiment and draw their own conclusions about the process, often creating their own experimental design
All experiments have been class tested at Carleton College, Vassar College, and Bowling Green State University
Morrill, Terrence : Rochester Institute of Technology
Neckers, Douglas C. : Bowling Green State University
View Table of Contents
Preface Introduction: Getting Acquainted with the Laboratory
Experimental Organic Chemistry Laboratory Safety Cleanup Following an Experiment Desk Equipment Introduction to Macroscale and Microscale Laboratory Work Using Handbooks Your Laboratory Notebook
1. Extraction of Caffeine from Tea 2. Purification and Thin-Layer Chromatographic Analysis of Caffeine 3. Synthesis of Ethanol by Fermentation of Sucrose 4. Synthesis of Salicylic Acid 5. Synthesis of Aspirin Optional Experiment: Thin-Layer Chromatographic Analysis of Analgesics 6. Radical Chlorination Reactions 7. Isolation of Essential Oils and the Theory of Odor Isolation of S-(+)-Carvone from Caraway Seeds Isolation of R-(+)-Limonene from Orange Peels 8. Nucleophilic Substitution Reactions SN1/SN2 Reactivity of Alkyl Halides Preparation and Identification of Alkyl Bromides Synthesized from Unknown Alcohols 9. Addition Reactions of Alkenes Free Radical versus Ionic Addition of Hydrobromic Acid to Alkenes Dimerization of 2-Methylpropene (Isobutylene) Stereochemistry of Bromine Addition to trans-Cinnamic Acid 10. Dehydrohalgenation of 2-Bromoheptane: Variation of Promoting Base 11. Dehydration of Alcohols Synthesis of Cyclohexene by Acid-Catalyzed Dehydration of Cyclohexanol Dehydration of 2-Methylcyclohexanol 12. Ether Syntheses Williamson Ether Synthesis of Ethoxybutane Synthesis and Analysis of a Propyl Benhydryl Ether 13. Grignard Syntheses Synthesis of Phenylmagnesium Bromide and Its Use as a Synthetic Intermediate Grignard Synthesis of a Triphenylmethane Dye: Crystal Violet or Malachite Green 14. Phase Transfer Catalysis Williamson Ether Synthesis of Bis-4-Chlorobenzyl Ether Using Phase Transfer Catalysis Synthesis of Butyl Benzoate Using Phase Transfer Catalysis 15. Oxidation Reactions Oxidation of Cyclohexanol Using Sodium Hypochlorite General Method for Oxidizing Secondary Alcohols to Ketones Oxidation of Cinnamyl Alcohol Using Pyridinium Chlorochromate 16. Diels-Alder Reactions Synthesis of Dimethyl 3,4,5,6-Tetraphenylphthalate from 2,3,4,5-Tetraphenylcyclopentadienone and Dimethyl Acetylene Dicarboxylate Synthesis of 4-Cyclohexene-cis-1,2-Dicarboxylic Acid from Butadiene Sulfone and Maleic Anhydride 17. Electrophilic Aromatic Substitution Iodination of 1,2,4,5-Tetramethylbenzene Using Iodine and Periodic Acid Bromination of Acetanilide Optional Experiment: Removal of the Acetyl Protecting Group: Synthesis of a Bromoaniline Rates of Electrophilic Aromatic Substitution 18. Acylation and Alkylation of Aromatic Compounds Acylation of Ferrocene Synthesis of 4,4´-Di-tert-Butylbiphenyl Synthesis of 1,4-Di-tert-Butyl-2,5-Dimethoxybenzene 19. Reduction Reactions of 3-Nitroacetophenone Reduction of 3-Nitroacetophenone Using Tin and Hydrochloric Acid Reduction of 3-Nitroacetophenone Using Sodium Borohydride 20. Photochemistry: Photoreduction of Benzophenone and Rearrangement to Benzpinacolone 21. Aldol Condensation: Reaction of Benzaldehyde and Acetone 22. Synthesis of 2,3,4,5-Tetraphenylcyclopentadienone 23. Horner-Emmons-Wittig Synthesis of Methyl 4-Methoxy-E-cinnamate 24. Kinetic versus Thermodynamic Control in Chemical Reactions Semicarbazones of Cyclohexanone and 2-Furaldehyde Friedel-Crafts Alkylation of Chlorobenzene Optional Experiments 25. Synthesis of Esters Synthesis of Isopentyl Acetate (Banana Oil) Optional Experiments: Propyl Ethanoate (Propyl Acetate) and 2-Methyl-1-Propyl Propanoate (Isobutyl Propionate) Synthesis and Identification of an Ester from an Unknown Alcohol and Acetic Acid Amide Chemistry Synthesis of Hippuric Acid Optional Experiment: Solubilities of Benzoic Acid and Hippuric Acid Synthesis of a Mosquito Repellent: N,N-Diethyl-meta-Toluamide (Deet) 27. Polyphosphoric Acid-Catalyzed Beckmann Rearrangement of Acetophenone Oxime 28. Synthesis of trans-1,2-Dibenzocyclopropane by Ring Closure 29. Polymer Chemistry Synthesis of Polystyrene Optional Experiment Biodegradable Starch Films
1. Hydrolysis of an Unknown Ester Hydrolysis and Azeotropic Distillation Extraction and Recrystallization Distillation, Melting Points, and Identification 2. Synthesis of 1-Bromobutane and a Grignard Synthesis of an Alcohol Synthesis of 1-Bromobutane from 1-Butanol Optional Syntheses of Alkyl Halides Grignard Synthesis of Secondary and Tertiary Alcohols Optional Synthesis 3. Synthesis and Dehydration of 3,3-Dimethyl-2-Butanol Synthesis of 3,3-Dimethyl-2-Butanol by Reduction with Sodium Borohydride Acid-Catalyzed Dehydration of 3,3-Dimethyl-2-Butanol with Rearrangement 4. Interconversion of 4-tert-Butylcyclohexanol and 4-tert-Butylcyclohexanone Sodium Hypochlorite Oxidation of 4-tert-Butylcyclohexanol to 4-tert-Butylchclohexanone Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone Optional GC or NMR Experiment 5. Aldol Condensation Using an Unknown Aldehyde and an Unknown Ketone: Derivative Formation and Identification of Unknowns Preparation of Aldol Condensation Product Characterization of the Aldol Product 6. Benzoin Chemistry: Synthesis of an Anticonvulsant Drug Using Biochemical Catalysis Thiamine-Catalyzed Benzoin Condensation Oxidation of Benzoin Synthesis of 5,5-Diphenylhydantoin, an Anticonvulsant Drug 7. Synthesis of Benzocaine 8. Resolution of R,S-Benzoylamino Acids Papain Resolution of R,S-Benzoylamino Acids Synthesis of the R,S-Benzoylamino Acid Synthesis of the S-Benzoylamino Acid Anilide: Enzymatic Resolution Optical Activity of S-Benzoylamino Acid Anilide Further Experiments 9. Multistep Synthesis of Para Red From Acetanilide Two-Step Synthesis of p-Nitroaniline Preparation of Diazonium Salts 10. Syntheses Starting with Alkyl Halides 11. Diels-Alder Cycloadditions of Various Dienophiles to 2,3-Dimethyl-1,3-Butadiene Synthesis of cis-4,5-Dimethyl-1,2,3,6-Tetrahydrophthalic Anhydride Addition of Various Dienophiles to 2,3-Dimethyl-1,3-Butadiene 12. Multistep Synthesis of N-Phenyltetraphenylphthalimide Synthesis of Tetraphenylcyclopentadienone Synthesis of Dimethyl Tetraphenylphthalate Synthesis of Tetraphenylphthalic Acid Synthesis of Tetraphenylphthalic Anhydride Synthesis of N-Phenyl-3,4,5,6-Tetraphenylphthalimide 13. Sugars: The Glucose Pentaacetates Preparation of Stereoisomers of D-Glucose 1H NMR Analysis of a- and b-D-Glucose Pentaacetates Optical Activity of Sugars Further Investigations
III. Organic Qualitative Analysis
1. Identification of Unknowns 2. Physical Properties 3. Classification by Solubility and Elemental Analysis by Sodium Fusion Classification by Solubility Elemental Analysis by Sodium Fusion 4. Infrared, Nuclear Magnetic Resonance, and Mass Spectrometric Analysis Using Spectrometric Data 5. Classification Tests for Functional Groups Alcohols Aldehydes and Ketones Alkenes Alkyl Halides Amines Aromatic Hydrocarbons (Arenes) Aryl Halides Carboxylic Acids Carboxylic Acid Derivatives Amides, Acyl Chlorides, Esters, and Nitriles Ethers Phenols 6. Synthesis of Solid Derivatives Alcohols Aldehydes and Ketones Amines Carboxylic Acids: Amides, Anilides, Toluidides Phenols 7. Separation of Mixtures Assaying the Number of Compounds Separating the Mixture Model Extraction Procedure 8. Summary of Identification Procedure for an Unknown Compound 9. Summary of Analysis of a Mixture of Unknown Compounds
IV. Spectrometric Methods
1. Infrared Spectrometry Theory of Molecular Vibration Infrared Spectrum Infrared Instrumentation Techniques of Sample Preparation Interpreting Infrared Spectra 2. NMR Spectrometry 3. Mass Spectrometry 4. Ultraviolet and Visible Spectrometry
V. Techniques of the Organic Laboratory
1. Safety Causes of Laboratory Accidents Safety Features of Your Laboratory Preventing Accidents What to Do if an Accident Occurs Chemical Toxicology Where to Find Chemical Safety Information Protecting The Environment 2. Laboratory Glassware Standard Taper Glassware Microscale Glassware Cleaning Your Glassware Pasteur Filter Pipets 3. Heating Methods Boiling Stones Heating Devices Refluxing a Reaction Mixture 4. Extraction and Drying Agents Extraction: The Theory Macroscale Extractions Additional Information about Extractions Summary of Macroscale Extraction from Water to an Organic Solution Microscale Extractions Drying Organic Liquids Methods for Separating Drying Agents and Organic Liquids Recovery of the Organic Product from the Dried Extraction Solution 5. Recrystallization Theory of Recrystallization Selecting a Proper Recrystallization Solvent Macroscale Procedure for Recrystallizing a Solid Summary of the Macroscale Recrystallization Procedure Microscale Recrystallization Summary of the Microscale Recrystallization Procedures What to Do If No Crystals Appear in the Cooled Solution Pointers for Successful Recrystallizations 6. Melting Points and Melting Ranges Melting Point Theory Apparatus for Determining Melting Ranges Determining Melting Ranges Mixture Melting Points Thermometer Calibration Summary of Melting-Point Determination 7. Boiling Points, Distillation, and Azeotropes Boiling Points Boiling Points and Separation of Mixtures Simple Distillation Fractional Distillation Azeotropic Distillation Steam Distillation Vacuum Distillation 8. Sublimation Assembling the Apparatus for a Sublimation Carrying Out a Microscale Sublimation 9. Refractometry Theory of Refractometry The Refractometer Steps in Determining a Refractive Index Temperature Correction 10. Thin-Layer Chromatography Principles of Thin-Layer Chromatography Plates for Thin-Layer Chromatography Sample Application Choices of Developing Solvent Visualization Techniques Summary of TLC Procedure 11. Gas-Liquid Chromatography Instrumentation Columns and Liquid Stationary Phases Detectors Interpreting Chromatograms Practical GC Operating Procedures Identification of Components and Qualitative Analysis 12. Liquid Chromatography Adsorbents Elution Solvents Choosing a Column Making a Macroscale Column Elution Techniques Microscale Column Chromatography Summary of Column Chromatography Techniques Dry Column Chromatography Flash Chromatography High-Performance Liquid Chromatography 13. Polarimetry Mixtures of Optical Isomers: Separation/Resolution Polarimetric Instrumentation Specific Rotation Using the Polarimeter Enantiomeric Excess (Optical Purity)
Appendix A Derivative Tables for Organic Qualitative Analysis Appendix B The Literature of Organic Chemistry Index
Other Editions of Experimental Organic Chemistry : A Balanced Approach : Macroscale And Microscale : Flexible Connector Version / With Cd-rom:
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