Preface Introduction Laboratory Safety Chemistry and the Environment The Effect of ph on a Food Preservative. Learning Basic Operations. Separating the Components of Panacetin. Extraction and Evaporation. Identifying a Constituent of Panacetin. Recrystallization and Melting-Point Measurement. Synthesis of Salicylic Acid from Wintergreen Oil. Heating under Reflux. Preparation of Synthetic Banana Oil. Simple Distillation, Gas Chromatography. Separation of Petroleum Hydrocarbons. Fractional Distillation. A Green Synthesis of Camphor. Addition, Sublimation. Identification of a Petroleum Hydrocarbon. Boiling Point, Refractive Index. Isolation and Isomerization of Lycopene from Tomato Paste. Column Chromatography, UV-VIS. Isolation and Identification of the Major Constituent of Clove Oil. Steam Distillation, Infrared. Introduction; Laboratory Safety; Chemistry and the Environment; Minlab: Making Useful Laboratory Items; OP-1: Cleaning and Drying Glassware; OP-4: Weighing; OP-5: Measuring Volume; OP-6: Making Transfers; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; Appendix: Laboratory Equipment; Appendix: Writing a Laboratory Report Chemistry and the Environment; The Effect of ph on a Food Preservative; Minilab: Extraction of Iodine by Dichloromethane; OP-4: Weighing; OP-5: Measuring Volume; OP-6: Making Transfers; OP-7a: Heat Sources; OP-16: Vacuum Filtration; OP- 18a: Liquid Liquid Extraction; OP-19: Evaporation; OP-26: Washing and Drying Solids Separating the Components of Panacetin; Minilab: Purification of an Unknown Compound by Recrystallization; OP-4: Weighing; OP-7a: Heat Sources; OP-26: Washing and Drying Solids; OP- 28a: Recrystallization from a Single Solvent; OP-33: Melting Point; Appendix: The Chemical Literature Synthesis and Spectral Analysis of Aspirin; Minilab: Developing and Testing a Hypothesis; OP-2: Using Specialized Glassware; OP-4: Weighing; OP-7a: Heat Sources; OP-7b: Smooth Boiling Devices; OP-7c: Heating Under Reflux; OP-16: Vacuum Recrystallization; OP-33: Melting Point; Appendix: Calculations for Organic Synthesis; Appendix: Planning an Experiment Synthesis of Salicylic Acid from Wintergreen Oil; Minilab: Preparation of Acetate Esters; OP-2: Using Specialized Glassware; OP-4: Weighing; OP-6: Making Transfers; OP-7: Heating; OP-10: Mixing; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-30a: Distillation of Liquids; OP-37: Gas Chromatography; Appendix: Planning an Experiment Minilab: Gas Chromatographic Analysis of Commercial Xylene; OP-4: Weighing; OP-7: Heating; OP-32: Fractional Distillation; OP-37: Gas Chromatography Minilab: Isolation of an Expectorant from Cough Capsules; OP-4: Weighing; OP-8: Cooling; OP-10: Mixing; OP-11: Addition of Reactants; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-29: Sublimation; OP-33: Melting Point Minilab: A Missing-Label Puzzle; OP-4: Weighing; OP-5: Measuring Volume; OP-30: Simple Distillation; OP-34: Boiling Point; OP-35: Refractive Index Minilab: Paper Chromatography of Dyes in Commercial Drink Mixes; OP-6: Making Transfers; OP-17: Centrifugation; OP-18c: Liquid Solid Extraction; OP-19: Evaporation; OP-21a: Liquid Solid Column Chromatography; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-41a: UV VIS Spectra Minilab: Gas Chromatographic Analysis of an Essential Oil from Orange Peel; OP-4: Weighing; OP-18: Extraction; OP-19: Evaporation; OP-20: Steam Distillation; OP-25: Drying Liquids; OP-39: Infrared
Identification of Unknown Ketones. Thin-Layer Chromatography, NMR. The Optical Activity of α-pinene: A Chemical Mystery. Vacuum Distillation, Optical Rotation. Investigation of a Chemical Bond by Infrared Properties of Common Functional Groups Thin-Layer Chromatographic Analysis of Drug Components Separation of an Alkane Clathrate Isomers and Isomerization Reactions Structures and Properties of Stereoisomers Bridgehead Reactivity in an S N 1 Solvolysis Reaction Minilab: Identification of an Unknown Felt-Tip-Pen Ink by TLC; OP-4: Weighing; OP-5: Measuring Volume; OP-16: Vacuum Filtration; OP-22: Thin-Layer Chromatography; OP-26: Washing and Drying Solids; OP-28b: Recrystallization from Mixed Solvents; OP-33: Melting Point; OP-40a: 1 H NMR ; Bibliography Minilab: Optical Rotation of Turpentine; OP-4: Weighing; OP-10: Mixing; OP-31: Vacuum Distillation; OP-34: Boiling Point; OP-36: Optical Rotation Minilab: The Structures of Organic Molecules; OP-39: Infrared Minilab: Who Else Has My Compound?; Qualitative Organic Analysis; OP-5: Measuring Volume; OP-30: Simple Distillation; OP-34: Boiling Point; OP-39: Infrared Minilab: Identification of an Unknown Felt-Tip-Pen Ink by TLC; ; OP-6: Making Transfers; OP-22: Thin-Layer Chromatography OP-10: Mixing; OP-16: Vacuum Filtration; OP-18: Extraction; OP- 19: Evaporation; OP-25: Drying Liquids; OP-26: Washing and Drying Solids; OP-39: Infrared Minilab: Isomers and Molecular Structure; OP-10: Mixing; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-33: Melting Point OP-7: Heating; OP-10: Mixing; OP-18: Extraction; OP-19: Evaporation; OP-25: Drying Liquids; OP-34: Boiling Point; OP- 35: Refractive Index; OP-36: Optical Rotation; OP-37: Gas Chromatography; OP-39: Infrared Minilab: Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions; Minilab: An S N 1 Reaction of Bromotriphenylmethane; OP-5: Measuring Volume; OP-7: Heating; OP-10: Mixing Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile Dehydration of Methylcyclohexanols and the Evelyn Effect Testing Markovnikov s Rule Stereochemistry of Bromine Addition to trans -Cinnamic Acid A Green Synthesis of Adipic Acid Minilab: An S N 1 Reaction of Bromotriphenylmethane; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-33: Melting Point; OP-38: High-Performance Liquid Chromatography; OP-40: Nuclear Magnetic Resonance Minilab: Preparation and Properties of a Gaseous Alkene; ; OP-10: Mixing; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-30: Simple Distillation; OP- 37: Gas Chromatography Minilab: Addition of Iodine to α-pinene; OP-7: Heating; OP-8: Cooling; OP-10: Mixing; OP-11: Addition of Reactants; OP-14: Trapping Gases; OP-18: Extraction; OP-18b: Salting Out; OP-19: Evaporation; OP-25: Drying Liquids; OP-30: Simple Distillation; OP:34: Boiling Point; OP-39: Infrared Minilab: Unsaturation in Commercial Products; OP-10: Mixing; OP-11: Addition of Reactants; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-33: Melting Point Minilab: The Nylon Rope Trick; OP-6: Making Transfers; OP-7: Heating; OP-8: Cooling; OP-10: Mixing; OP-16: Vacuum Recrystallization; OP-33: Infrared
Minilab: An S N 1 Reaction of Bromotriphenylmethane; Minilab: Free-Radical Stability; OP-6: Making Transfers; OP-7: Heating; OP-10: Mixing; OP-11: Addition of Reactants; OP-14: Trapping Gases; OP-15: Gravity Filtration; OP-16: Vacuum Filtration; OP- 19: Evaporation; OP-26: Washing and Drying Solids; OP-27: Cleaning and Drying Gases; OP-28: Recrystallization; OP-33: Preparation of Bromotriphenylmethane and the Trityl Free Radical Melting Point Minilab: The Nylon Rope Trick; OP-7: Heating; OP-10: Mixing; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; Chain-Growth Polymerization of Styrene and Methyl Methacrylate OP-30: Simple Distillation; OP-39: Infrared OP-17: Centrifugation; OP-32: Fractional Distillation; OP-34: Synthesis of Ethanol by Fermentation Boiling Point Minilab: Nucleophilic Substitution Rates of Alcohols; OP-7: Heating; OP-10: Mixing; OP-14: Trapping Gases; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-30: Simple Reaction of Butanols with Hydrobromic Acid Distillation; OP-34: Boiling Point; OP-39: Infrared Minilab: Oxidation of Alcohols by Potassium Permanganate; Borohydride Reduction of Vanillin to Vanillyl Alcohol Synthesis of Triphenylmethanol and the Trityl Carbocation An Unexpected Reaction of 2,3-Dimethyl-2,3-butanediol Identification of a Conjugated Diene from Eucalyptus Oil Spectral Identification of Monoterpenes Synthesis and Spectral Analysis of Aspirin Directive Effects in the Bromination of Vanillin Mechanism of the Nitration of Arenes by Nitronium Fluoborate Friedel Crafts Acylation of Anisole Minilab: Preparation of a Fluorescent Dye; OP-7: Heating; OP- 10: Mixing; OP-11: Addition of Reactants; OP-12a: Using Drying Tubes; OP-16: Vacuum Filtration; OP-17: Centrifugation; OP-19: Evaporation; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP- 33: Melting Point; OP-39: Infrared Minilab: Photoreduction of Benzophenone; Qualitative Organic Analysis; OP-7: Heating; OP-10: Mixing; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-30: Simple Distillation; OP- 34: Boiling Point; OP-39: Infrared ; OP-40: Nuclear Magnetic Resonance Minilab: Diels Alder Reaction of Maleic Anhydride and Furan; OP-7: Heating; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-33: Melting Point; OP 37: Gas Chromatography; OP-39: Infrared Minilab: Identification of an Unknown Arene by NMR ; Minilab: Interpretation of a Mass Spectrum; OP-39: Infrared ; OP-40: Nuclear Magnetic Resonance ; OP-41: Ultraviolet Visible Minilab: Interpretation of a Mass Spectrum; OP-7: Heating; OP- 10: Mixing; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-39: Infrared ; OP-40: Nuclear Magnetic Resonance Minilab: Free-Radical Stability; OP-10: Mixing; OP-16: Vacuum Recrystallization; OP-33: Melting Point Minilab: Nitration of Naphthalene; OP-18: Extraction; OP-19: Evaporation; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-37: Gas Chromatography Minilab: Preparation of Carbocations by the Friedel Crafts Reaction; OP-7: Heating; OP-10: Mixing; OP-11: Addition of Reactants; OP-12: Excluding Water from Reaction Mixtures; OP- 14: Trapping Gases; OP-16: Vacuum Filtration; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-26: Washing and Drying Solids; OP-33: Melting Point; OP-39: Infrared
Determination of the Structure of a Natural Product in Anise Oil Identification of an Oxygen-Containing Organic Compound Oxidation of the Insect Repellent 6-12 Isomerization of a Cyclic Ketone A Wittig Reaction of trans -Cinnamaldehyde Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone Electronic Effect of a para -Iodo Substituent Synthesis and Identification of an Unknown Carboxylic Acid Preparation of the Insect Repellent N,N -Diethyl-meta -toluamide Synthesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant Preparation of Para Red and Related Azo Dyes Isolation and Identification of the Major Constituent of Clove Oil; Minilab: Air Oxidation of Fluorene to 9-Fluorenone; OP-7: Heating; OP-10: Mixing; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-33: Melting Point; OP-39: Infrared Minilab: Oxidation of Alcohols by Potassium Permanganate; Minilab: Identification of an Unknown Arene by NMR ; ; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-30: Simple Distillation; OP-33: Melting Point; OP-34: Boiling Point; OP-39: Infrared ; OP-40: Nuclear Magnetic Resonance ; Appendix: Properties of Organic Compounds OP-10: Mixing; OP-11: Addition of Reactants; OP-18: Extraction; OP-19: Evaporation; OP-25: Drying Liquids; OP-30: Simple Distillation; OP-39: Infrared Isomers and Isomerization Reactions; Qualitative Organic Analysis; OP-7: Heating; OP-8: Cooling; OP-10: Mixing; OP-18: Extraction; OP-19: Evaporation; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-39: Infrared ; OP-40: Nuclear Magnetic Resonance Minilab: A Nucleophilic Addition-Elimination Reaction of Benzil; OP-7: Heating; OP-10: Mixing; OP-16: Vacuum Filtration; OP-18: Extraction; OP-19: Evaporation; OP-25: Drying Liquids; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-33: Melting Point Minilab: Preparation of Aldol Condensation Products; OP-8: Cooling; OP-10: Mixing; OP-16: Vacuum Filtration; OP-17: Centrifugation; OP-18: Extraction; OP-19: Evaporation; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-31: Vacuum Distillation; OP-33: Melting Point; OP-40: Nuclear Magnetic Resonance Minilab: Acid-Base Strengths of Organic Compounds; OP-7: Heating; OP-8: Cooling; OP-10: Mixing; OP-16: Vacuum Recrystallization Identification of a Conjugated Diene from Eucalyptus Oil; Minilab: Hydrolysis Rates of Esters; OP-10: Mixing: OP-15: Gravity Filtration; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-33: Melting Point; Appendix: Properties of Organic Compounds Minilab: Preparation of Benzamide; OP-7: Heating; OP-8: Cooling; OP-10: Mixing; OP-11: Addition of Reactants; OP-14: Trapping Gases; OP-18: Extraction; OP-19: Evaporation; OP-21: Column Chromatography; OP-24: Washing Liquids; OP-25: Drying Liquids; OP-37: Gas Chromatography; OP-39: Infrared ; OP-40: Nuclear Magnetic Resonance Minilab: Synthesis of Dimedone Derivatives of Benzaldehyde; OP-7: Heating; OP-10: Mixing: OP-13: Excluding Air from Reaction Mixtures; OP-16: Vacuum Filtration; OP-19: Evaporation; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-33: Melting Point; OP-40: Nuclear Magnetic Resonance Minilab: A Diazonium Salt Reaction of 2-Aminobenzoic Acid; OP- 8: Cooling; OP-10: Mixing; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids
Reaction of Phthalimide with Sodium Hypochlorite Identification of an Unknown Amine Preparation and Mass Spectrum of 2-Phenylindole Nucleophilic Strength and Reactivity in S N Ar Reactions Structure of an Unknown D-Hexose Fatty Acid Content of Commercial Cooking Oils Structure of an Unknown Dipeptide Multistep Synthesis of Benzilic Acid from Benzaldehyde Using the Chemical Literature in an Organic Synthesis A Research Project in Organic Chemistry Minlab: Making Useful Laboratory Items Minilab: Extraction of Iodine by Dichloromethane Minilab: Purification of an Unknown Compound by Recrystallization Minilab: Developing and Testing a Hypothesis Minilab: Preparation of Acetate Esters Minilab: Gas Chromatographic Analysis of Commercial Xylene Minilab: Isolation of an Expectorant from Cough Capsules Minilab: A Missing-Label Puzzle Minilab: Paper Chromatography of Dyes in Commercial Drink Mixes Minilab: Gas Chromatographic Analysis of an Essential Oil from Orange Peel Minilab: Identification of an Unknown Felt-Tip Pen Ink by TLC Minilab: Optical Rotation of Turpentine Minilab: The Structures of Organic Molecules Minilab: Who Else Has My Compound? Minilab: Isomers and Molecular Structure Minilab: Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions Minilab: An S N 1 Reaction of Bromotriphenylmethane Minilab: Preparation and Properties of a Gaseous Alkene Minilab: Beckmann Rearrangement of Benzophenone Oxime; OP-7: Heating; OP-8: Cooling; OP-9: Temperature Monitoring; OP-10: Mixing; OP-16: Vacuum Filtration; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-33: Melting Point ; OP-26: Washing and Drying Solids; OP-28: Recrystallization; OP-30: Simple Distillation; OP-33: Melting Point; OP-34: Boiling Point; OP-39: Infrared ; Appendix: Properties of Organic Compounds Minilab: Dyeing with Indigo; OP-7: Heating; OP-9: Temperature Monitoring; OP-10: Mixing; OP-15: Gravity Filtration; OP-16: Vacuum Recrystallization; OP-29: Sublimation; OP-33: Melting Point; OP- 42: Mass OP-5: Measuring Volume; OP-10: Mixing; OP-41b: Colorimetry Minilab: Reactions of Monosaccharides with Phenols; OP-7: Heating; OP-8: Cooling; OP-10: Mixing; OP-16: Vacuum Recrystallization; OP-33: Melting Point; OP-36: Optical Rotation Minilab: Isolation of Trimyristin from Nutmeg; Minilab: Preparation of a Soap Using a Phase-Transfer Catalyst; OP-7: Heating; OP-18: Extraction; OP-19: Evaporation; OP-25: Drying Liquids; OP-37: Gas Chromatography Minilab: Isolation of a Protein from Milk; OP-3: Using Glass Rod and Tubing; OP-18: Extraction; OP-19: Evaporation; OP-22: Thin- Layer Chromatography; OP-23: Paper Chromatography; OP-24: Washing Liquids Minilab: A Spontaneous Reaction of Benzaldehyde; OP-7: Heating; OP-10: Mixing; OP-15: Gravity Filtration; OP-16: Vacuum Recrystallization; OP-33: Melting Point; OP-39: Infrared Appendix: Keeping a Laboratory Notebook; Appendix: The Chemical Literature; Bibliography Introduction; Appendix: Keeping a Laboratory Notebook; Appendix: The Chemical Literature Introduction Preparation of Bromotriphenylmethane and the Trityl Free Radical
Minilab: Addition of Iodine to α-pinene Minilab: Unsaturation in Commercial Products Minilab: Free-Radical Stability Minilab: The Nylon Rope Trick Minilab: Nucleophilic Substitution Rates of Alcohols Minilab: Photoreduction of Benzophenone Minilab: Oxidation of Alcohols by Potassium Permanganate Minilab: Preparation of a Fluorescent Dye Minilab: Diels Alder Reaction of Maleic Anhydride and Furan Identification of a Conjugated Diene from Eucalyptus Oil Minilab: Identification of an Unknown Arene by NMR Minilab: Interpretation of a Mass Spectrum Minilab: Nitration of Naphthalene Minilab: Preparation of Carbocations by the Friedel Crafts Reaction Minilab: Air Oxidation of Fluorene to 9-Fluorenone Minilab: A Nucleophilic Addition Elimination Reaction of Benzil Minilab: Preparation of Aldol Condensation Products Minilab: A Spontaneous Reaction of Benzaldehyde Minilab: Acid Base Strengths of Organic Compounds Minilab: Hydrolysis Rates of Esters Minilab: Preparation of Benzamide Minilab: Synthesis of Dimedone Derivatives of Benzaldehyde Minilab: A Diazonium Salt Reaction of 2-Aminobenzoic Acid Minilab: Beckmann Rearrangement of Benzophenone Oxime Minilab: Dyeing with Indigo Minilab: Reactions of Monosaccharides with Phenols Minilab: Isolation of Trimyristin from Nutmeg Minilab: Preparation of a Soap Using a Phase-Transfer Catalyst Minilab: Isolation of a Protein from Milk OP-1: Cleaning and Drying Glassware OP-2: Using Specialized Glassware OP-3: Using Glass Rod and Tubing OP-4: Weighing OP-5: Measuring Volume OP-6: Making Transfers OP-7: Heating OP-8: Cooling OP-9: Temperature Monitoring OP-10: Mixing OP-11: Addition of Reactants OP-12: Excluding Water from Reaction Mixtures OP-13: Excluding Air from Reaction Mixtures OP-14: Trapping Gases OP-15: Gravity Filtration OP-16: Vacuum Filtration OP-17: Centrifugation OP-18: Extraction OP-19: Evaporation OP-20: Steam Distillation OP-21: Column Chromatography OP-22: Thin-Layer Chromatography OP-23: Paper Chromatography OP-24: Washing Liquids Synthesis of Dimedone and Measurement of its Tautomeric Equilibrium Constant Identification of an Oxygen-Containing Organic Compound; Identification of an Unknown Amine; Appendix: Properties of Organic Compounds
OP-25: Drying Liquids OP-26: Washing and Drying Solids OP-27: Cleaning and Drying Gases OP-28: Recrystallization OP-29: Sublimation OP-30: Simple Distillation OP-31: Vacuum Distillation OP-32: Fractional Distillation OP-33: Melting Point OP-34: Boiling Point OP-35: Refractive Index OP-36: Optical Rotation OP-37: Gas Chromatography OP-38: High-Performance Liquid Chromatography OP-39: Infrared OP-40: Nuclear Magnetic Resonance OP-41: Ultraviolet Visible OP-42: Mass Appendix: Laboratory Equipment Appendix: Keeping a Laboratory Notebook Appendix: Writing a Laboratory Report Appendix: Calculations for Organic Synthesis Appendix: Planning an Experiment Appendix: Properties of Organic Compounds Appendix: The Chemical Literature Bibliography Bibliography Experiments Recommended to be Purchased Together: Basic Operations Set Learning Basic Operations. The Effect of ph on a Food Preservative Extraction and Evaporation. Separating the Components of Panacetin Recrystallization and Melting-Point Measurement. Identifying a Constituent of Panacetin Heating under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil Set Properties of Common Functional Groups Identification of an Oxygen-Containing Organic Compound Appendix: Properties of Organic Compounds