Correlation Guide for Laboratory Techniques in Organic Chemistry, 4th Edition. with Modern Projects and Experiments in Organic Chemistry
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1 1 Correlation Guide for Laboratory Techniques in Organic Chemistry, 4th Edition with Modern Projects and Experiments in Organic Chemistry Miniscale and Standard Taper Microscale, 2nd edition Note to users of the 2nd edition of Modern Projects and Experiments in Organic Chemistry regarding a change in Pasteur pipet nomenclature in the 4th edition of Laboratory Techniques in Organic Chemistry: We have introduced a second type of the Pasteur pipet filtration method. A Pasteur filter pipet, as described in the 2nd edition, is called a Pasteur filter-tip pipet in the 4th edition (see page 60); and the term Pasteur filter pipet is now used for a microscale gravity filtration apparatus, with the cotton packed at the top of the tip instead of the bottom (see Section 9.3). We have also replaced Technique with Chapter in the 4th edition of Laboratory Techniques in Organic Chemistry. Experiment 1: Extraction of Caffeine from Tea Miniscale procedure: Miniscale Vacuum Filtration Apparatus: Section 9.4, Figure 9.6 Boiling Stones: Section 6.1 Microscale procedure: Microscale Vacuum Filtration Apparatus: Section 9.4, Figures 9.8 and 9.9 Microscale Extraction: Sections 10.6, 10.6a, and 10.6c Pasteur Filter-tip Pipets: Section 5.3, Figure 5.9 Pasteur Filter Pipet ( microfunnel in the procedure): Section 9.3, Figures 9.3 and 9.4. Alternatively, filtration and drying can be done simultaneously by Section 11.2, Method 2, Figure 11.4a. Experiment 2: Purification and Thin-Layer Chromatographic Analysis of Caffeine Sand Bath for Heating: Section 6.2, Figure 6.4 Sublimation: Chapter 16 Preparation of micropipets for TLC: Section 18.2
2 2 Preparation of TLC plate: Sections Analysis of TLC plate: Section 18.5; Figure 18.7 Iodine visualization of TLC plate: Section 18.4 (Note: Method differs from TOC, 2nd ed.) Experiment 3: Synthesis of Ethanol by Fermentation of Sucrose Boiling Points: Section 12.1 Miniscale Simple Distillation: Section 12.3a; apparatus: Figure 12.7 Miniscale Fractional Distillation: Section 12.4; apparatus: Figure Azeotropic Distillation: Section 12.5 Experiment 4: Synthesis of Salicylic Acid Miniscale Reflux: Section 7.1; apparatus: Figure 7.1a Boiling Stones: Section 6.1 Heating Methods: Section 6.2 Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4 Melting Points and Melting Ranges: Chapter 14; procedure: Section 14.3 Interpreting IR Spectra: Section Microscale Reflux: Section 7.1; apparatus: Figure 7.1b Boiling Stones: Section 6.1 Heating Methods: Section 6.2 Microscale Vacuum Filtration Apparatus: Section 9.4; filtration apparatus: Figures 9.8 and 9.9 Melting Points and Melting Ranges: Chapter 14; procedure: Section 14.3 Interpreting IR Spectra: Sections
3 3 Experiment 5: Analgesics and Synthesis of Aspirin Mixed Solvent Recrystallization: Chapter 15.4 Recrystallization: Sections 15.3 and 15.5; apparatus for vacuum filtration: Figure 15.4 Fluted Filter Paper: Section 9.1 Melting Points and Melting Ranges: Chapter 14; procedure: Section 14.3 Interpreting IR Spectra: Sections Heating Methods: Section 6.2 Mixed Solvent Recrystallization: Section 15.4 Recrystallization: Sections 15.3 and ; Figures 15.5 and 15.6 Melting Points and Melting Ranges: Chapter 14; procedure: Section 14.3 Interpreting IR Spectra: Sections Experiment 6: Isolation of Essential Oils from Plants 6.1 (S)-(+)-Carvone from Caraway Seeds Miniscale Steam Distillation: Section 12.6, Figure How to Select a Recrystallization Solvent: Section 15.4 Miniscale Recrystallization: Sections 15.1, 15.3, and 15.4 Melting Points and Melting Ranges: Chapter 14; procedure: Sections 14.3 and 14.5 Gas Chromatography: Chapter 20 Polarimetry: Sections
4 4 6.2 Isolation of (R)-(+)-Limonene from Orange Peels Miniscale Steam Distillation: Section 12.6, Figure Polarimetry: Sections Experiment 7: Computational Chemistry Chapter 8 in the 4th edition of Laboratory Techniques in Organic Chemistry has an expanded set of questions. Experiment 8: Radical Halogenation Reactions 8.1 Radical Chlorination Reactions Microscale Extraction: Sections 10.6, 10.6a 10.6b Pasteur Filter-tip Pipets: Section 5.3, Figure Photobromination of 1,2-Diphenylethane Removal of Noxious Vapors: Section 7.6; apparatus: Figure 7.18 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Experiment 9: Nucleophilic Substitution Reactions 9.1 S N 1/ S N 2 Reactivity of alkyl Halides No techniques called out. 9.2 Synthesis and Identification of Alkyl Bromides from Unknown Alcohols Miniscale Reflux: Section 7.1, Figure 7.1a Miniscale Simple Distillation: Section 12.3a; apparatus: Figure 12.7
5 5 Microscale Extractions: Sections 10.6, 10.6a, and 10.6c Pasteur Filter-tip Pipets: Section 5.3, Figure 5.9 Miniscale Short-Path Distillation: Section 12.3b; apparatus: Figure 12.8 Experiment 10: E2 Elimination of 2-Bromoheptane: Influence of the Base Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4b Pasteur Filter-tip Pipets: Section 5.3, Figure 5.9 Microscale Extraction: Sections 10.6a 10.6b Experiment 11: Dehydration of Alcohols 11.1 Acid-Catalyzed Dehydration of 2-Methyl-2-butanol Miniscale Fractional Distillation: Section 12.4; apparatus: Figure Pasteur Filter-tip Pipets: Section 5.3, Figure Acid-Catalyzed Dehydration of 2-Methylcyclohexanol Microscale Distillation: Section 12.3c; apparatus: Figure Pasteur Filter-tip Pipets: Section 5.3, Figure 5.9 Experiment 12: Synthesis of Esters from Alcohols 12.1 Synthesis of Isopentyl Acetate Miniscale Reflux: Section 7.1: apparatus: Figure 7.1a
6 6 Miniscale Simple Distillation: Section 12.3a; apparatus: Figure 12.7 Microscale Reflux: Section 7.1; apparatus: Figure 7.1b Microscale Extraction: Sections 10.6, 10.6a 10.6b Microscale Distillation: Section 12.3c; apparatus: Figure or Figure Optional Experiment Microscale Boiling Point Determination: Section 12.1; apparatus: Figure Synthesis of Benzocaine Recrystallization from Mixed Solvent Pairs: Section 15.4 Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4 Recrystallization from Mixed Solvent Pairs: Section 15.4 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5
7 Determination of the Equilibrium Constant for an Esterification Reaction Microscale Extraction: Sections 10.6, 10.6a 10.6b Pasteur Filter-tip Pipets: Section 5.3, Figure 5.9 Experiment 13: Green Chemistry: Oxidation of Cyclohexanol Using Sodium Hypochlorite Miniscale Steam Distillation: Section 12.6, Figure Microscale Extraction: Sections 10.6, 10.6a, and 10.6c Experiment 14: Oxidation of Cinnamyl Alcohol using Pyridinium Chlorochromate ; visualization: Section 18.4 Liquid Chromatography: Chapter 19; column preparation/procedure: Sections Experiment 15: Grignard Syntheses 15.1 Synthesis of Phenylmagnesium Bromide for Use as a Synthetic Intermediate
8 8 Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4a and Figure 7.2a or 7.2b Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4b 15.2 Synthesis of 1.1-Diphenylethanol Microscale Extraction: Sections 10.6, 10.6a 10.6b Microscale Gravity Filtration: Section 9.3; Pasteur filter pipet: Figures 9.3 and Synthesis of Benzoic Acid Microscale Extraction: Sections 10.6, 10.6a 10.6b Microscale Vacuum Filtration Apparatus: Section 9.4, Figures 9.8 and 9.9 Experiment 16: Addition Reactions of Alkenes 16.1 Free-Radical Versus ionic Addition of Hydrobromic Acid Microscale Extraction: Sections 10.6, 10.6a 10.6b 16.2 Stereochemistry of Bromine Addition to trans-cinnamic Acid
9 9 Miniscale Reflux: Section 7.1; apparatus: Figure 7.1a Mixed Solvent Recrystallization: Section 15.4 Microscale Reflux: Chapter 7.1; apparatus: Figure 7.1b Mixed Solvent Recrystallization: Section 15.4 Microscale Vacuum Filtration Apparatus: Section 9.4, Figures 9.8 and 9.9 Experiment 17: Synthesis of Polystyrene Liquid Chromatography: Chapter 19; column preparation/procedure: Sections Experiment 18: Phase Transfer Catalysis Miniscale Reflux: Section 7.1; apparatus: Figure 7.1a Microscale Reflux: Section 7.1; apparatus: Figure 7.1b Microscale Extraction: Sections 10.6, 10.6a, and 10.6c Experiment 19: Diels-Alder Reaction Removal of Noxious Vapors: Section 7.6; apparatus: Figure 7.16 Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4
10 10 Removal of Noxious Vapors: Section 7.6; apparatus: Figure 7.18 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Experiment 20: Selectivity in the Bromination of Acetanilide and 4-Methylacetanlide Removal of Noxious Vapors: Section 7.6; apparatus: Figure 7.18 Mixed Solvent Recrystallization: Section 15.4 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Experiment 21: Acylation of Ferrocene Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4b Liquid Chromatography: Section 19.5a, Figure 19.7 Experiment 22: Akylation of 1,4-Dimethoxybenzene
11 11 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Microscale Extraction: Sections 10.6, 10.6a 10.6b Experiment 23: Kinetic versus Equilibrium Control in the Alkylation of Chlorobenzene Microscale Extraction: Sections 10.6, 10.6a, and 10.6c Experiment 24: Reduction Reactions of 3-Nitroacetophenone 24.1 Reduction of 3-Nitroacetophenone Using Sodium Borohydride Microscale Gravity Filtration: Section 9.3; Pasteur filter pipet: Sections 9.3 and Reduction of 3-Nitroacetophenone Using Tin and Hydrochloric Acid Microscale Vacuum Filtration Apparatus: Section 9.4, Figures 9.8 and 9.9 Experiment 25: Horner-Emmons-Wittig Synthesis of Methyl-E-4-Methoxycinnamate Mixed Solvent Recrystallization: Section 15.4 Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4
12 12 Mixed Solvent Recrystallization: Section 15.4 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Experiment 26: Synthesis of Triphenylmethane Dyes: Crystal Violet and Malachite Green Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4a and Figure 7.2a or 7.2b Experiment 27: Enolate Chemistry: Synthesis of trans-1,2-dibenzoylcyclopropane Miniscale Reaction Apparatus: Section 7.2; Figure 7.2a Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4 Microscale Reaction Apparatus: Sections 7.2, Figure 7.3a Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Experiment 28: Amide Chemistry 28.1 Synthesis of Benzoylamino Acids from Glycine, Alanine, and Valine Miniscale and s 28.2 Synthesis of a Mosquito Repellant: N,N-Diethyl-meta-Toluamide (DEET)
13 13 Removal of Noxious Vapors: Section 7.6; apparatus: Figure 7.16 Liquid Chromatography: Chapter 19; column preparation/procedure: Sections Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4b Removal of Noxious Vapors: Section 7.6; apparatus: Figure 7.18 Microscale Extraction: Sections 10.6, 10.6a, and 10.6c Flash Chromatography: Chapter 19; column preparation/procedure: Sections Project 1: Identification of a White Solid: A Team Approach Melting Points and Melting Ranges: Chapter 14; procedure: Sections 14.3 and 14.5 Optional Experiment Project 2: Using Extraction to Separate a Mixture 2.1 Separation and Purification of the Compounds in the Unknown Mixture: First Week
14 14 Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4 Miniscale Vacuum Filtration Apparatus: Section 9.4, Figure Melting Points, Purity, and Identification of the Compounds in the Unknown Mixture: Second Week Melting Points and Melting Ranges: Chapter 14; procedure: Sections 14.3 and 14.5 Project 3: Hydrolysis of an Unknown Ester 3.1 Hydrolysis and Azeotropic Distillation: First Week Boiling Stones: Section 6.1 Miniscale Reflux: Section 7.1; apparatus: Section 7.1a Azeotropic Distillation: Section 12.5 Miniscale Simple Distillation: Section 12.3a; apparatus: Figure Recrystallization and Extraction: Second Week Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure 15.4 Miniscale Vacuum Filtration Apparatus: Section 9.4; apparatus: Figure Distillation, Boiling Points, and Melting Points: Third Week Miniscale Simple Distillation: Section 12.3a; apparatus: Figure 12.7 Melting Points and Melting Ranges: Chapter 14; procedure: Section Identification of the Unknown Ester: Third Week
15 15 Refractometry: Section 13.3 Project 4: Interconversion of 4-tert-Butylcyclohexanol and 4-tert-Butylcyclohexanone 4.1 Green Chemistry: Sodium Hypochlorite Oxidation of 4-tert-Butylcyclohexanol Miniscale Simple Distillation: Section 12.3a; apparatus: Figure Sodium Borohydride Reduction of 4-tert-Butylcyclohexanone Gas Chromatography: Chapter 19; analysis of chromatogram: Sections 19.7 and 19.8 Microscale Extraction: Sections 10.6, 10.6a 10.6b
16 16 Project 5: Synthesis of 1-Bromobutane and the Grignard Synthesis of an Alcohol 5.1 Synthesis of 1-Bromobutane from 1-Butanol Miniscale Reflux: Section 7.1; apparatus: Figure 7.1a Miniscale Steam Distillation: Section 12.6, Figure Miniscale Simple Distillation: Section 12.3a; apparatus: Figure Grignard Synthesis of Secondary and Tertiary Alcohols Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4a and Figure 7.2a or 7.2b Miniscale Reaction Apparatus: Section 7.3; Figure 7.4a Miniscale Simple Distillation: Section 12.3a; apparatus: Figure 12.7 Project 6: E1/E2 Elimination Reactions 6.1 Acid-Catalyzed Dehydration of 2-Methyl-2-Butanol Miniscale Fractional Distillation: Section 12.4; apparatus: Figure Synthesis of 2-Chloro-2-methyl butane
17 17 Miniscale Short-Path Distillation: Section 12.3b; apparatus: Figure Base-Catalyzed Dehydrochlorination of 2-Chloro-2-methylbutane Miniscale Fractional Distillation: Section 12.4; apparatus: Figure Project 7: Synthesis and Hydroboration-Oxidation of 1-Phenylcyclohexene 7.1 Grignard Synthesis of 1-Phenylcyclohexene Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4a and Figure 7.2a or 7.2b Recovery of an Organic Product: Section Acid-Catalyzed Dehydration of 1-Phenylcyclohexanol 7.3 Hydroboration-Oxidation of 1-Phenylcyclohexanol Microscale Extraction: Sections 10.6, 10.6a, and 10.6c 7.4 Computational Chemistry Experiment Computational Chemistry: Chapter 8 Spin-Spin Coupling (Splitting): Section
18 18 Project 8: Electrophilic Aromatic Substitution 8.1 Synthesis of Diacetylferrocene Anhydrous Reaction Conditions: Section 7.3; apparatus: Figure 7.4b Microscale Extraction: Sections 10.6, 10.6a, and 10.6c 8.2 Purification by Column Chromatography Preparation and Elution of a Microscale Column: Section 19.5a; apparatus: Figure Optional Column Chromatography for Isolation of the Minor Diacetylferrocene Isomer Liquid Chromatography: Chapter 19; column preparation/procedure: Sections , Figure 19.2 or 19.4 Project 9: Stereochemistry of Electrophilic Addition to an Alkene 9.1 Synthesis of Cyclohex-4-ene-cis-1,2-dicarboxylic Acid Removal of Noxious Vapors: Section 7.6; apparatus: Figure Bromination of Cyclohex-4-ene-cis-1,2-dicarboxylic Acid Miniscale Vacuum Filtration Apparatus: Section 9.4, Figure Synthesis of Dimethyl 4,5-Dibromocyclohexane-cis-1,2-dicarboxylate
19 19 Project 10: Diels-Alder Cycloadditions of Dienophiles to Dimethyl-1,3-Butadiene 10.1 Competition Reactions of 2,3-Dimethyl-1,3-butadiene and 1,3-Cyclohexadiene with Maleic Acid Gas Chromatography: Chapter 20; determining chromatographic conditions: Section 20.5; analysis of chromatogram: Sections 20.4, 20.7, and Competition Reactions of 2,3-Dimethyl-1,3-butadiene with Diethyl-trans-2-Butenedioate and Diethyl-cis-2-Butenedioate Gas Chromatography: Chapter 20; determining chromatographic conditions: Section 20.5; analysis of chromatogram: Sections 20.4, 20.7, and Competition Reactions of 2,3-Dimethyl-1,3-butadiene with Dimethyl-cis-2-Butenedioate and Dimethyl 2-Butynedioate Gas Chromatography: Chapter 20; determining chromatographic conditions: Section 20.5; analysis of chromatogram: Sections 20.4, 20.7, and Designing and Carrying Out a Synthesis of Dimethyl 4,5-Dimethylbenzene-1,2-dicarboxylate by Diels-Alder and Dehydrogenation Chemistry Gas Chromatography: Chapter 20; determining chromatographic conditions: Section 20.5; analysis of chromatogram: Sections 20.4, 20.7, and 20.8
20 20 Project 11: Aldol-Dehydration Chemistry Using Unknown Aldehydes and Ketones 11.1 Preparation and Characterization of the Aldol-Dehydration Product How to Select a Recrystallization Solvent: Section 15.4 Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Figure Preparation and Characterization of Solid Derivatives of the Unknown Aldehyde and Unknown Ketone How to Select a Recrystallization Solvent: Section 15.4 Microscale Recrystallization: Sections 15.3 and 15.6; filtration apparatus: Figure 15.5 Project 12: Biochemical Catalysis and the Stereochemistry of Borohydride Reduction 12.1 Thiamine-Catalyzed Benzoin Condensation Miniscale Recrystallization: Sections 15.3 and 15.5; filtration apparatus: Section 15.4 Interpreting IR Spectra: Sections Stereoselectivity of the Borohydride Reduction of Benzoin Mixed Solvent Recrystallization: Section 15.4
21 21 Project 13: Designing a Multistep Synthesis Students need to submit a list of reagents and additional equipment needed for their syntheses. Project 14: Sugars: Glucose Pentaacetates 14.1 Synthesis of α-d-glucose Pentaacetate and β-d-glucose Pentaacetate 14.2 Investigation of Kinetic and Equilibrium Control in the Glucose Pentaacetate System 14.3 Computational Chemistry Experiment Project 15: Enantioselective Synthesis by Enzymatic Hydrolysis Using Pig-Liver Esterase 15.1 Synthesis of Dimethyl Cyclohex-4-ene-cis-1,2-dicarboxylate by Diels-Alder Cycloaddition and Esterification Removal of Noxious Vapors: Section 7.6; apparatus: Figure Synthesis of (±)-Methyl Hydrogen Cyclohex-4-ene-cis-1,2-dicarboxylate NMR Spectroscopy: Chapter 22; sample preparation: Sections 22.2; interpreting spectra: Sections Enantioselective Enzymatic Hydrolysis of Dimethyl Cyclohex-4-ene-cis-1,2-dicarboxylate
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