Microscale and Miniscale Organic Chemistry Laboratory Experiments

✍ Scribed by Allen M Schoffstall, Barbara A Gaddis, Melvin L Druelinger, Allen Schoffstall, Barbara Gaddis, Melvin Druelinger

• Publisher: McGraw-Hill Science/Engineering/Math
• Year: 2003
• Tongue: English
• Leaves: 688
• Edition: 2
• Category: Library

✦ Synopsis

This book offers a comprehensive introductory treatment of the organic laboratory techniques for handling glassware and equipment, safety in the laboratory, micro- and miniscale experimental procedures, theory of reactions and techniques, relevant background information, applications and spectroscopy.

✦ Table of Contents

Title
Contents
Introduction
Important Features of the Organic Lab
Goals for the Organic Laboratory
Working in the Laboratory
Laboratory Safety
Material Safety Data Sheet (MSDS)
Your Laboratory Notebook
How to Be a Successful Organic Laboratory Student
Laboratory Reports
Chapter One Techniques in the Organic Chemistry Laboratory
Technique A Glassware and Equipment: Heating and Cooling
Microscale Glassware and Related Equipment
Miniscale Glassware
Additional Glassware and Equipment
How to Clean Glassware
How to Heat and Cool Glass Reaction Vessels
Technique B Weighing and Measuring
How to Weigh Solids and Liquids
Introduction to Measuring Volumes of Liquids
How to Use a Calibrated Glass Pipet
How to Use an Automatic Delivery Pipet
How to Use a Syringe
Exercise B.1: Determining Density of an Aqueous Solution
Exercise B.2: Determining Density of an Organic Liquid
Exercise B.3: Calibrating a Pasteur Pipet
Technique C Melting Points
Mixed Melting Behavior
Melting Behavior of Solids
Calibration of the Thermometer
Apparatus for Measuring Melting Points
How to Determine a Melting Point
Exercise C.1: Calibration of a Thermometer
Exercise C.2: Melting Point of an Unknown Solid
Exercise C.3: Mixed Melting Point
Technique D Boiling Points
Intermolecular Attractions
How to Do a Microscale Boiling Point Determination
How to Do a Miniscale Boiling Point Determination
Exercise D.1: Determining the Micro Boiling Point of an Unknown Liquid
Exercise D.2: Determining the Boiling Point of an Unknown Liquid
Technique E Index of Refraction
How to Use the Abbe Refractometer
Exercise E.1: Measuring the Refractive Index of an Unknown Liquid
Technique F Recrystallization, Filtration, and Sublimation
Solvents for Recrystallization
Choosing a Solvent
Choosing a Solvent Pair
How to Do a Microscale Recrystallization
How to Do a Miniscale Recrystallization
Important Tips Concerning Recrystallization
Introduction to Filtration
How to Use a Microscale Filter Pipet
How to Do a Miniscale Suction Filtration
How to Do a Miniscale Gravity Filtration
Important Tips Concerning Filtration
Introduction to Sublimation
Exercise F.1: Recrystallizing an Impure Solid (microscale)
Exercise F.2: Recrystallizing an Impure Solid (miniscale)
Exercise F.3: Recrystallizing an Impure Solid with Hot Gravity Filtration
Exercise F.4: Purifying an Unknown Solid by Solvent-Pair Recrystallization
Exercise F.5: Sublimation of Caffeine
Exercise F.6: Sublimation of Caffeine
Technique G Distillation and Reflux
Microscale Apparatus for Simple Distillation and Assembly
How to Do a Simple Microscale Distillation
Important Tips Concerning Microscale Distillation
Miniscale Apparatus for Simple Distillation
How to Do a Simple Miniscale Distillation
Important Tips Concerning Miniscale Distillation
Introduction to Reflux
How to Do a Microscale Reaction with Reflux
How to Do a Miniscale Reaction with Reflux
Important Tips on Reflux
Evaporation of Solvents
Exercise G.1: Distilling a Mixture of Cyclohexane and Toluene (microscale)
Exercise G.2: Distilling a Mixture of Cyclohexane and Toluene (miniscale)
Technique H Fractional Distillation and Steam Distillation
How to Do a Miniscale Fractional Distillation
Practical Tips about Miniscale Fractional Distillation
Introduction to Steam Distillation
Exercise H.1: Miniscale Fractional Distillation of a Mixture of Cyclohexane and Toluene
Exercise H.2: Microscale Fractional Distillation of Cyclohexane and Toluene
Exercise H.3: Steam Distillation of Lemon Grass Oil (miniscale)
Technique I Extraction and Drying
How to Do a Microscale Extraction
How to Do a Miniscale Extraction
Important Tips Concerning Extraction
Drying and Drying Agents
How to Do Microscale Drying
How to Do Miniscale Drying
Important Tips Concerning Drying Agents
Exercise I.1: Determining the Distribution Coefficient of Caffeine (microscale)
Exercise I.2: Determining the Distribution Coefficient of Caffeine (miniscale)
Exercise I.3: Using Distribution Coefficients to Identify an Unknown Solid (microscale)
Technique J Gas-Liquid Chromatography
Gas-Liquid Chromatography Basics
Quantitative Analysis
How to Use the Gas Chromatograph
Exercise J.1: Determining Relative Detector Response Factors in GC
Exercise J.2: Determining Mass Percent of a Mixture Using GC
Exercise J.3: Determining Mass Percent of a Mixture of Alcohols
Technique K Thin-Layer, Column, and High-Performance Liquid Chromatography
Introduction to Thin-Layer Chromatography (TLC)
Introduction to Column Chromatography
How to Do a Miniscale Gravity Column Chromatography
How to Do Microscale Column Chromatography
Introduction to High-Performance Liquid Chromatography (HPLC)
Exercise K.1: Analysis of Analgesic Tablets by TLC
Exercise K.2: Separating Ferrocene and Acetylferrocene Using Column Chromatography (microscale)
Exercise K.3: Separating Ferrocene and Acetylferrocene Using Column Chromatography (miniscale)
Exercise K.4: HPLC Analysis of Benzaldehyde and Benzyl Alcohol
Technique L Polarimetry
Optical Purity and Enantiomeric Excess
How to Measure Optical Rotation
Exercise L.1: Determining the Optical Purity of an Unknown Liquid
Exercise L.2: Determining the Melting Points of Enantiomers and Racemates
Chapter Two Spectroscopic Methods and Molecular Modeling
Technique M Infrared Spectroscopy
General Approach to Solving an IR Spectrum
Recording an IR Spectrum
How to Prepare a Sample for IR Analysis
Important Tips Concerning IR
Exercise M.1: Recording the IR Spectrum of an Organic Liquid
Exercise M.2: Recording the IR Spectrum of an Organic Solid
Exercise M.3: Spectroscopic Identification of Unknowns
Technique N Nuclear Magnetic Resonance Spectroscopy
Chemical Shifts in 1H NMR Spectroscopy
Equivalence of Protons in 1H NMR Spectroscopy
Integration in 1H NMR Spectroscopy
Splitting (coupling) in 1H NMR Spectroscopy
Coupling Constants
Protons in a Chiral Environment
Diastereotopic Protons in Alkenes
Protons on Heteroatoms
Solvents for 1H NMR Spectroscopy
How to Prepare a Sample for 60–90 MHz CW 1H NMR Spectroscopy
How to Prepare a Sample for FT NMR
Structural Identification from the NMR Spectrum
Introduction to 13C NMR Spectroscopy
Solvents for 13C NMR Spectroscopy
How to Prepare a Sample for 13C NMR Spectroscopy
General Approach to Determining an Unknown Structure
Exercise N.1: Recording a 1H NMR Spectrum
Exercise N.2: Recording a 13C NMR Spectrum
Exercise N.3: 1H NMR Spectral Problems
Exercise N.4: 13C NMR Spectral Problems
Exercise N.5: Spectral Identification Using 1H and 13C NMR
Technique O Ultraviolet and Visible Spectroscopy
Uses of UV-Visible Spectroscopy
How to Operate a Spectronic 20
How to Operate a UV-Visible Spectrometer
Technique P Mass Spectrometry
Principles of Mass Spectrometry
Fragmentation Patterns
Molecular Ion Peak
Isotopes
Gas Chromatography/Mass Spectrometry (GC/MS)
Strategy for Solving Structural Problems Using MS, IR, and NMR
Mass Spectrometric Analysis Guidelines
Exercise P.1: Solving Problems in Mass Spectrometry
Technique Q Molecular Modeling
Organic Molecular Models
Drawing Organic Molecules Using Computer Software
Molecular Modeling Using Computer Software
Molecular Mechanics
Quantum Mechanics
Exercises
Exercise Q.1: Conformational Analysis of Butane and Other Molecules
Exercise Q.2: Conformational Analysis of Propane
Exercise Q.3: Conformational Analysis of 2-Methylbutane
Exercise Q.4: Identifying Reactive Sites
Exercise Q.5: Heats of Formation and Dipole Moments
Exercise Q.6: LUMO Energies of Alkenes
Exercise Q.7: Conformational Analysis of 3-Fluoropropene
Chapter Three Applications Using Laboratory Resources and Techniques
Experiment 3.1 Scavenger Hunt: Introduction to Chemical Data Reference Books and Calculations
Part A: Scavenger Hunt in the Chemical Reference Books
Part B: Scavenger Hunt and Stoichiometric Calculations
Experiment 3.2 Identification of Organic Liquids by Physical Properties
General Directions
Part A: Boiling Point Determination
Part B: Refractive Index Determination
Experiment 3.3 Relationships Between Structure and Physical Properties
Part A: Determination of the Effect of Structure on Boiling Point
Part B: Determination of the Effect of Structure on Refractive Index
Part C: Determination of the Effect of Structure on Melting Point
Experiment 3.4 Properties of Solvents and Recrystallization of Organic Solids
Part A: Selecting an Appropriate Solvent
Part B: Microscale Recrystallization of an Organic Solid
Experiment 3.5 Separations Based upon Acidity and Basicity
Part A: Determination of Solubilities
Part B: Microscale Separation of Naphthalene, Benzoic Acid, and Ethyl 4-Aminobenzoate
Part C: Miniscale Separation of Benzoic Acid and Ethyl 4-Aminobenzoate
Experiment 3.6 Isolation of a Natural Product
Part A: Miniscale Extraction of Caffeine from Tea Leaves
Part B: Miniscale Extraction of Caffeine from Instant Coffee
Part C: Miniscale Isolation of Caffeine from NoDoz
Part D: Miniscale Isolation of Cholesterol from Simulated Gallstones
Experiment 3.7 Solvent and Polarity Effects in Thin-layer Chromatography (TLC)
Part A: Determining the Effect of Polarity on Elution
Part B: Separation and Identification of Components of a Mixture of trans-Stilbene, 9-Fluorenone, and Benzoic Acid
Experiment 3.8 Purification and Analysis of a Liquid Mixture: Simple and Fractional Distillation
Part A: Microscale Distillation
Part B: Microscale Fractional Distillation
Part C: Miniscale Distillation
Part D: Miniscale Fractional Distillation
Chapter Four Alcohols and Alkyl Halides
Experiment 4.1 Synthesis of an Alkyl Halide from an Alcohol
Experiment 4.2 Selectivity of Free Radical Chlorination of 2,3-Dimethylbutane
Chapter Five Synthesis of Alkenes
Experiment 5.1 Alkenes Via Acid-catalyzed Dehydration of Alcohols
Part A: Microscale Synthesis of Alkenes Via Acid-catalyzed Dehydration of 3-Methyl-3-pentanol
Part B: Miniscale Synthesis of Alkenes Via Acid-catalyzed Dehydration of 3,3-Dimethyl-2-butanol
Part C: Microscale Synthesis of Alkenes Via Acid-catalyzed Dehydration of an Unknown Alcohol
Experiment 5.2 Alkenes Via Base-Induced Elimination of Alkyl Halides
Chapter Six Alkene Addition Reactions
Experiment 6.1 Catalytic Hydrogenation of Alkenes
Part A: Microscale Hydrogenation of 1-Decene
Part C: Microscale Partial Hydrogenation of Olive Oil
Part B: Microscale Hydrogenation of Allylbenzene
Experiment 6.2 Hydration of Alkenes
Part A: Microscale Hydration of 2-Ethyl-1-butene
Part B: Microscale Hydration of Norbornene
Part C: Miniscale Hydration of Norbornene
Experiment 6.3 Preparation of Alcohols from Alkenes by Hydroboration-oxidation
Part A: Microscale Hydroboration-oxidation of 3,3-Dimethyl-1-butene
Part B: Miniscale Hydroboration-oxidation of 3,3-Dimethyl-1-butene
Experiment 6.4 Addition Polymers: Preparation of Polystyrene and Polymethyl Methacrylate
Part A: Miniscale Polymerization of Styrene (Bulk Method)
Part B: Microscale Polymerization of Styrene (Solution Method)
Part C: Miniscale Polymerization of Methyl Methacrylate (Bulk Method)
Chapter Seven Stereochemistry
Experiment 7.1 Stereochemistry of Alkenes and Derivatives
Part A: Microscale Cis-Trans Isomerization of an Alkene
Part B: Microscale Addition of Bromine to Fumaric Acid
Part C: Determining the Mechanism of the Isomerization of Dimethyl Maleate to Dimethyl Fumarate (Miniscale)
Chapter Eight Introduction to Nucleophilic Substitution Reactions
Experiment 8.1 Relative Rates of Nucleophilic Substitution Reactions
Part A: Determination of Factors Affecting the Relative Rates of SN2 Reactions
Part B: Determination of Factors Affecting the Relative Rates of SN1 Reactions
Experiment 8.2 Nucleophilic Aliphatic Substitution: Synthesis of 1-Bromobutane
Part A: Microscale Synthesis of 1-Bromobutane
Part B: Miniscale Synthesis of 1-Bromobutane
Chapter Nine Dienes and Conjugation
Experiment 9.1 Dienes and the Diels-Alder Reaction
Part A: Microscale Reaction of 1,3-Butadiene with Maleic Anhydride
Part B: Miniscale Reaction of 2,3-Dimethyl-1,3-butadiene with Maleic Anhydride
Part C: Microscale Reaction of Cyclopentadiene with Maleic Anhydride
Part D: Miniscale Reaction of Cyclopentadiene with Maleic Anhydride
Part E: Miniscale Reaction of Anthracene with Maleic Anhydride
Chapter Ten Qualitative Organic Analysis I
Experiment 10.1 Qualitative Analysis of Alkyl Halides, Alkenes, Dienes, and Alkynes
Chapter Eleven Reactions of Aromatic Side Chains
Experiment 11.1 Benzylic Oxidation: Benzoic Acid from Toluene; A Phthalic Acid from an Unknown Xylene
Part A: Microscale Oxidation of Toluene to Benzoic Acid
Part B: Microscale Oxidation of a Xylene to a Phthalic Acid
Chapter Twelve Electrophilic Aromatic Substitution
Experiment 12.1 Activating and Deactivating Effects of Aromatic Substituents: Relative Rates of Bromination
Experiment 12.2 Nitration of Methyl Benzoate or an Unknown
Part A: Microscale Nitration of Methyl Benzoate
Part B: Miniscale Nitration of Methyl Benzoate
Part C: Miniscale Nitration of an Unknown Aromatic Compound
Experiment 12.3 Friedel-Crafts Acylation Reactions
Part A: Microscale Procedure for Acetylation of Biphenyl
Part B: Microscale Procedure for Acetylation of Phenanthrene with TLC Analysis
Part C: Microscale Benzoylation of Ferrocene with Column Chromatography
Experiment 12.4 Aromatic Bromination
Part A: Microscale Bromination of Acetanilide
Part B: Microscale Bromination of p-Methylacetanilide with TLC and Column Chromatography or HPLC Analysis
Part C: Experimental Design of a Procedure for Bromination of an Acetanilide Derivative
Chapter Thirteen Combined Spectroscopy and Advanced Spectroscopy
Experiment 13.1 Infrared and Nuclear Magnetic Resonance Spectroscopy of Alcohols, Ethers, and Phenols
Part A: Experimental Procedure for Infrared Spectroscopy
Part B: Experimental Procedure for IR and NMR Spectroscopy
Part C: Exercises for IR and NMR Spectroscopy
Experiment 13.2 Combined Spectral Analysis: Infrared, Ultraviolet, and Nuclear Magnetic Resonance Spectroscopy and Mass Spectrometry
Solved Examples of the Use of Combined Spectroscopy
Part A: Purification of the Unknown
Part B: Preparation of the Sample and Spectroscopic Analysis
Part C: Spectroscopic Exercises
Chapter Fourteen Organometallics
Experiment 14.1 Grignard Synthesis: Preparation of Triphenylmethanol and 3-Methyl-2-phenyl- 2-butanol
Part A: Microscale Synthesis of Triphenylmethanol from Benzophenone
Part B: Miniscale Synthesis of Triphenylmethanol from Ethyl Benzoate
Part C: Microscale Synthesis of 3-Methyl-2-phenyl-2-butanol
Experiment 14.2 Using Indium Intermediates: Reaction of Allyl Bromide with an Aldehyde
Chapter Fifteen Alcohols and Diols
Experiment 15.1 Stereoselective Reduction of Ketones with Sodium Borohydride
Part A: Microscale Reduction of Benzil
Part B: Microscale Reduction of (1R)-(+)-Camphor
Experiment 15.2 Experimental Design for an Alcohol Oxidation
Experiment 15.3 Photochemical Oxidation of Benzyl Alcohol
Chapter Sixteen Ethers
Experiment 16.1 Ether Synthesis by SN2 Displacement
Part A: Microscale Preparation of an Alkyl Halophenyl Ether
Part B: Miniscale Preparation of Benzyl tert-Butyl Ether
Experiment 16.2 Nucleophilic Aliphatic Substitution Puzzle: Substitution Versus Elimination
Chapter Seventeen Aldehydes and Ketones
Experiment 17.1 Stereoselective Synthesis of Alkenes
Part A: Microscale Wittig Synthesis of trans-9-(2-phenylethenyl)anthracene
Part B: Miniscale Wittig Synthesis of trans-9-(2-phenylethenyl)anthracene
Part C: Microscale Horner-Emmons Reaction of Diethylbenzyl Phosphonate and Benzaldehyde
Experiment 17.2 Conversion of Cyclohexanone to Caprolactam
Part A: Microscale Conversion of Cyclohexanone to Caprolactam
Part B: Miniscale Conversion of Cyclohexanone to Caprolactam
Experiment 17.3 Pinacol Rearrangement and Photochemical Synthesis of Benzopinacol
Part A: Microscale Synthesis of Pinacolone
Part B: Miniscale Photoreduction of Benzophenone
Part C: Miniscale Synthesis of Benzopinacolone
Chapter Eighteen Enols, Enolates, and Enones
Experiment 18.1 Preparation of ,a-Unsaturated Ketones Via Mixed Aldol Condensation Part A: Miniscale Synthesis of 1,9-Diphenyl-1,3,6,8- nonatetraen-5-one (Dicinnamalacetone) Part B: Microscale Synthesis of Dibenzalacetone (1,5-Diphenyl-1,4-pentadien-3-one) Part C: Identification of a Mixed Aldol Product from the Miniscale Condensation of an Unknown Aromatic Aldehyde with a Ketone Experiment 18.2 Reduction of Conjugated Ketones with Sodium Borohydride Part A: Microscale Reduction of 2-Cyclohexenone Part B: Microscale Reduction of trans-4-Phenyl-3-buten-2-one Experiment 18.3 Identification of Products of Catalytic Transfer Hydrogenation of an Enone Part A: Microscale Reaction of 2-Cyclohexenone Part B: Miniscale Reaction of 2-Cyclohexenone Chapter Nineteen Carboxylic Acids Experiment 19.1 Synthesis and Identificatoin of an Unknown Carboxylic Acid Experiment 19.2 Synthesis of trans-Cinnamic Acid Via the Haloform Reaction Chapter Twenty Carboxylic Acid Esters Experiment 20.1 Combinatorial Chemistry and the Synthesis of Fruity Esters Part A: Combinatorial Selection Part B: Microscale Synthesis of an Ester Experiment 20.2 Synthesis of Esters by Baeyer-Villiger Oxidation Part A: Microscale Oxidation of an Unknown Cyclic Ketone Part B: Miniscale Oxidation of Cyclohexanone Chapter Twenty-One Dicarbonyl Compounds Experiment 21.1 Base-Catalyzed Condensations of Dicarbonyl Compounds Part A: Microscale Preparation of Coumarin or a Coumarin Derivative Part B: Miniscale Preparation of Coumarin or a Coumarin Derivative Experiment 21.2 Reactions of Diketones: Synthesis of 2,5-Dimethyl- 1-phenylpyrrole and Preparation of an Unknown Pyrrole Part A: Microscale Synthesis of 2,5-Dimethyl-1-phenylpyrrole Part B: Microscale Preparation of an Unknown Pyrrole Chapter Twenty-Two Amines Experiment 22.1 Relating Color to Structure: Synthesis of Azo Dyes Part A: Miniscale Diazotization of an Aromatic Amine Part B.1: Miniscale Coupling with a Phenol Part B.2: Miniscale Coupling with an Amine Part C: Direct Dyeing with an Azo Dye Part D: Recording the UV-Visible Spectrum of the Prepared Dyes Part E: Determining the pH Indicator Range of the Prepared Dyes Part F: Determining Antibacterial Properties of the Dye Experiment 22.2 Synthesis of Pyrazole and Pyrimidine Derivatives Part A: Microscale Synthesis of a Five-Member Ring Heterocycle from Hydrazine and an Unknown Diketone Part B: Miniscale Synthesis of a Five-Member Ring Heterocycle from Hydrazine and an Unknown Diketone Part C: Microscale Synthesis of a Substituted Pyrimidine Part D: Miniscale Synthesis of a Substituted Pyrimidine Experiment 22.3 Synthesis of Heterocyclic Compounds Part A: Miniscale Reaction of Benzaldehyde and Pyrrole Part B: Microscale Reaction of o-Phenylenediamine and Formic Acid Experiment 22.4 Synthesis of Heterocycles and Kinetics by Spectroscopic Analysis Part A: Miniscale Preparation of Lophines (2-Aryl-4,5-diphenylimidazoles) Part B: Miniscale Synthesis of Substituted Lophinyl (2-Aryl-4,5-diphenylimidazole) Dimers Part C: Kinetics of the Recombination Reaction Chapter Twenty-Three Aryl Halides Experiment 23.1 Nucleophilic Aromatic Substitution Part A: Microscale Reaction of Sodium Ethoxide with 1-Bromo-2,4-dinitrobenzene Part B: Microscale Reaction of Sodium Ethoxide with p-Fluoronitrobenzene Chapter Twenty-Four Phenols Experiment 24.1 Exploring Structure-function Relationships of Phenols: Synthesis of Salicylic Acid, Aspirin, and Vanillin Derivatives Part A: Miniscale Reactions of Vanillin PartB: Miniscale Hydrolysis of Methyl Salicylate Part C: Miniscale Synthesis of Acetylsalicylic Acid Chapter Twenty-Five Carbohydrates Experiment 25.1 Classification of Sugars and Identification of an Unknown Sugar General Instructions for the Microscale Identification of an Unknown Sugar Part A: Osazone Formation Part B: Chemical Tests Experiment 25.2 Esterification of Sugars: Preparation of Sucrose Octaacetate and- and a-D-Glucopyranose Pentaacetate
Part A: Miniscale Preparation of D-Sucrose Octaacetate
Part B: Microscale Preparation of β-D-Glucopyranose Pentaacetate
Part C: Microscale Conversion of β-D-Glucopyranose Pentaacetate to the a-Anomer
Part D: Miniscale Preparation of α-D-Glucose Pentaacetate and Measurement of Optical Rotation
Chapter Twenty-Six Lipids
Experiment 26.1 Soap from a Spice: Isolation, Identification, and Hydrolysis of a Triglyceride
Part A: Miniscale Isolation of a Triglyceride from Nutmeg
Part B: Microscale Hydrolysis of a Triglyceride
Part C: Determination of Properties of the Soap from Nutmeg
Experiment 26.2 Preparation of Esters of Cholesterol and Determination of Liquid Crystal Behavior
Chapter Twenty-Seven Amino Acids and Derivatives
Experiment 27.1 Conversion of an Amino Acid to a Sunscreen: Multistep Preparation of Benzocaine or a Benzocaine Analog
Part A: Miniscale Synthesis of p-Methylacetanilide
Part B: Miniscale Synthesis of p-Acetamidobenzoic Acid
Part C: Miniscale Synthesis of p-Aminobenzoic Acid
Part D: Microscale Esterification of p-Aminobenzoic Acid
Part E: Determining the Effectiveness of the p-Aminobenzoic Acid Ester as a Sunscreen
Chapter Twenty-Eight Qualitative Organic Analysis II
Experiment 28.1 Designing a Classification Scheme for Characterizing an Organic Compound
Part A: Microscale Solubility Tests
Part B: Microscale Chemical Tests
Part C: Microscale Classification of an Unknown Compound
Experiment 28.2 Experimental Methods of Qualitative Organic Analysis
Introduction to Qualitative Organic Analysis
Overall Approach to Identifying the Unknown
Step 1: Purify
Step 2: Determine the Physical Properties
Step 3: Examine the Physical State
Step 4: Perform Solubility Tests
Step 5: Identify the Functional Groups Present
Step 6: Select an Appropriate Derivative
Step 7: Prepare and Purify the Derivative
Step 8: Identify the Unknown
Experimental Procedure
Part A: Purification of the Unknown
Part B: Solubility Tests
Part C: Chemical Tests (Arranged Alphabetically)
Part D: Derivatives
Part E Qualitative Organic Analysis of Unknowns
Part E.1: Qualitative Analysis of Aldehydes and Ketones
Part E.2: Qualitative Analysis of Alcohols and Phenols
Part E.3: Qualitative Analysis of Amines and Carboxylic Acids
Part E.4: Qualitative Analysis of a General Unknown
Part E.5: Qualitative Analysis and Spectroscopic Analysis of a General Unknown
Chapter Twenty-Nine Projects
Experiment 29.1 Multistep Synthesis of 1-Bromo-3-chloro-5-iodobenzene from Aniline
Part A: Synthesis of Acetanilide from Aniline
Part B: Miniscale Synthesis of 4-Bromoacetanilide from Acetanilide
Part C: Synthesis of 4-Bromo-2-chloroacetanilide from 4-Bromoacetanilide
Part D: Synthesis of 4-Bromo-2-chloroaniline from 4-Bromo- 2-chloroacetanilide
Part F: Synthesis of 1-Bromo-3-chloro-5-iodobenzene from 4-Bromo-2-chloro-6-iodoaniline
Part E: Miniscale Synthesis of 4-Bromo-2-chloro-6-iodoaniline from 4-Bromo-2-chloroaniline
Experiment 29.2 Multistep Synthesis of Sulfanilamide Derivatives as Growth Inhibitors
Part A: Preparation of Acetanilide
Part B: Preparation of p-Acetamidobenzenesulfonyl Chloride
Part C: Reaction of p-Acetamidobenzenesulfonyl Chloride with an Amine
Part D: Hydrolysis of the Acetamido Group
Part E: Bacterial Testing of Antibiotic Susceptibility
Part A: Miniscale Synthesis of Acetanilide
Part B: Miniscale Synthesis of p-Acetamidobenzenesulfonyl Chloride
Part C: Miniscale Synthesis of Sulfonamides
Part D: Miniscale Synthesis of Sulfanilamides
Part E: Bacterial Testing of Antiobiotic Susceptibility
Experiment 29.3 Structural Determination of Isomers Using Decoupling and Special NMR Techniques
Part A: Homonuclear Decoupling of a Known Alkene and Determination of Coupling Constants
Part B: Characterization of an Unknown Compound Using Homonuclear Decoupling in 1H NMR
Part C: Characterization of an Unknown Compound Using 1H NMR, 13C NMR, 1H-1H (COSY) and HETCOR (1H-13C COSY)
Experiment 29.4 The Library-Laboratory Connection
Part A: Chemical Abstracts (CA) and Beilstein
Part B: Searching Science Library Databases
Part C: Searching on the Web
Experiment 29.5 Stereochemistry, Molecular Modeling, and Conformational Analysis
Part A: Molecular Models Using a Model Kit
Part B: Computer Modeling
Part C: Conformational Analysis of Rotational Isomers
Part D: Using Molecular Modeling to Analyze Rotational Conformations of Stereoisomers
Appendix A Tables of Derivatives for Qualitative Organic Analysis
Appendix B Laboratory Skills and Calculations
Appendix C Designing a Flow Scheme
Appendix D Material Safety Data Sheet
Appendix E Tables of Common Organic Solvents and Inorganic Solutions
Index