Microscale and Miniscale Organic Chemistry Laboratory Experiments

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