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Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach TABLE OF CONTENTS SECTION 1. A. B. C. DESK EQUIPMENT, SHELF REAGENTS, AND SOLVENTS List of Equipment for Individual Desks Miniscale Experiments 1 Microscale Experiments 2 Optional Equipment Miniscale Experiments 4 Microscale Experiments 4 Shelf Reagents and Solvents 4 SECTION 2. CHEMICALS AND SPECIAL EQUIPMENT, BY CHAPTERS CH 3 Solids: Recrystallization and Melting Points 3.2 Recrystallization 5 3.3 Physical Constants: Melting Points 5 CH 4 Liquids: Distillation and Boiling Points 4.2 Boiling Points of Pure Liquids 6 4.3 and 4.4 Simple and Fractional Distillation 8 4.6 Steam Distillation: Isolation of Citral from Lemon Grass Oil 8 CH 5 Extraction 5.3 Base and Acid Extractions 8 5.4 Isolation of Trimyristin from Nutmeg 9 CH 6 Chromatography 6.2 Thin-Layer Chromatography Separation of Spinach Pigments by TLC 9 Separation of Syn- and Anti-Azobenzenes by TLC 9 6.3 Column Chromatography 10 6.4 Gas-Liquid Chromatography Part A. Qualitative and Quantitative Analyses of a Mixture of Compounds by GLC 10 Part B. Determining GLC Response Factors 10 CH 7 Stereoisomers 7.2 Separation of Diastereomeric 1,2-Cyclohexanediols 10 7.3 Isomerization of Dimethyl Maleate to Dimethyl Fumarate 11 7.4 Properties of the Enantiomers of Carvones 11 7.6 Resolution of Racemic 1-Phenylethanamine 11 CH 9 Alkanes 9.2 Chlorination Using Sulfuryl Chloride 12 i ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach 9.3 Bromination. Selectivity of Hydrogen Atom Abstraction 12 CH 10 Alkenes 10.2 Dehydrohalogenation of Alkyl Halides Part A. Elimination with Alcoholic Potassium Hydroxide 13 Part B. Elimination with Potassium tert-Butoxide 13 Qualitative Tests 13 10.3 Dehydration of Alcohols Part A. Dehydration of 4-Methyl-2-pentanol 13 Part B. Dehydration of Cyclohexanol 13 Qualitative Tests 13 10.5 Addition of Hydrobromic Acid to Alkenes 13 Qualitative Tests 14 10.6 Bromination of Alkenes 14 10.7 Acid-Catalyzed Hydration of Alkenes 14 10.8 Hydroboration-Oxidation of Alkenes 15 CH 11 Alkynes 11.2 Dehydrohalogenation of 1,2-Dihaloalkanes 15 Qualitative Tests 15 11.3 Addition Reactions of Alkynes 16 11.4 Terminal Alkynes as Acids 16 CH 12 Dienes: The Diels-Alder Reaction 12.3 Applications of Diels-Alder Reactions Part A. Reaction of 1,3-Butadiene and Maleic Anhydride 16 Part B. Reaction of 1,3-Cyclopentadiene and Maleic Anhydride 16 Part C.1 1,4-Cyclohexene-cis-1,2-dicarboxylic Acid 16 Qualitative Tests 16 Part C.2 Bicyclo[2.2.1]hept-5-ene-endo-2,3-dicarboxylic Acid 17 Qualitative Tests 17 CH 13 Kinetic and Thermodynamic Control of a Reaction 13.2 Formation of Semicarbazones under Kinetic and Thermodynamic Control Part A. Preparation of Cyclohexanone Semicarbazone 17 Part B. Preparation of 2-Furaldehyde Semicarbazone 17 Part C. Reactions of Semicarbazide with Cyclohexanone and 2-Furaldehyde in Phosphate Buffer Solution 17 Part D. Reactions of Semicarbazide with Cyclohexanone and 2-Furaldehyde in Bicarbonate Buffer Solution 17 ii ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach Part E. Tests of Reversibility of Semicarbazone Formation 18 CH 14 Nucleophilic Aliphatic Substitution: Preparation of Alkyl Halides 14.4 Preparation of 1-Bromobutane: An SN2 Reaction 18 14.5 Preparation of 2-Chloro-2-methylbutane: An SN1 Reaction 18 Qualitative Tests 18 14.6 Chemical Kinetics: Evidence for Nucleophilic Substitution Mechanisms 18 CH 15 Arenes. Electrophilic Aromatic Substitution 15.2 Friedel-Crafts Alkylation of p-Xylene with 1-Bromopropane 19 15.3 Friedel-Crafts Acylation of m-Xylene with Phthalic Anhydride 19 15.4 Nitration of Bromobenzene Part A. Nitration 20 Part B. Thin-Layer Chromatography 20 Part C. Column Chromatography 20 15.5 Relative Rates of Electrophilic Aromatic Substitution Part A. Qualitative Measurements 20 Part B. Quantitative Measurements 21 CH 16 Oxidation of Alcohols and Carbonyl Compounds 16.2 Preparation of Aldehydes and Ketones by Oxidation of Alcohols Part A. Oxidation of Cyclododecanol to Cyclododecanone 21 Part B. Oxidation of 4-Chlorobenzyl Alcohol to 4-Chlorobenzoic Acid 21 16.3 Base-Catalyzed Oxidation-Reduction of Aldehydes: The Cannizzaro Reaction 22 CH 17 Reduction Reactions of Double Bonds: Alkenes, Carbonyl Compounds, and Imines 17.2 Catalytic Hydrogenation of the Carbon-Carbon Double Bond: Qualitative Tests 22 23 17.3 Reduction of Imines: Preparation of Amines 23 17.4 Reduction of Carbonyl Compounds: Preparation of Alcohols 23 17.5 Enzymatic Reduction: A Chiral Alcohol from a Ketone 23 Qualitative Test 24 17.6 Determining Optical Purity 24 CH 18 Reactions of Carbonyl Compounds 18.2 The Wittig and Related Reactions Part A. Preparation of (Z)- and (E)-Stilbenes by a Wittig Reaction 24 Qualitative Tests 24 iii ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach Part B. Preparation of a Stilbene by the Horner-Wadsworth-Emmons Reaction 25 Qualitative Tests 25 18.3 Reactions of Stabilized Carbanions from Carbonyl Compounds Qualitative Tests 25 25 18.4 Conjugate Addition to an α,β-Unsaturated Ketone 25 Qualitative Tests 26 CH 19 Organometallic Chemistry 19.2 Grignard Reagents: Preparation 26 19.4 Grignard Reagents: Reactions Part A. Preparation of Triphenylmethanol 27 Part B. Preparation of Benzoic Acid 27 Part C. Preparation of 2-Methyl-3-heptanol 27 CH 20 Carboxylic Acids and Their Derivatives 20.2 Esters and the Fischer Esterification 28 20.3 Amides and Insect Repellents 28 20.4 Amides and Chemiluminescence Part A. Preparation of Luminol 28 Part B. Chemiluminescence 29 CH 21 Multistep Organic Synthesis 21.2 Sulfanilamide: Discovery and Synthesis of the First Antibiotic Part A. Preparation of Aniline 29 Part B. Preparation of Acetanilide 29 Part C. Preparation of 4-Acetamidobenzenesulfonyl Chloride 29 Part D. Preparation of 4-Acetamidobenzenesulfonamide 29 Part E. Preparation of Sulfaniliamide 29 Solubility Tests 30 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene Part B. Preparation of 4-Bromoacetanilide 30 Part C. Preparation of 4-Bromo-2-chloroacetanilide 30 Part D. Preparation of 4-Bromo-2-chloroaniline 30 Part E. Preparation of 4-Bromo-2-chloro-6-iodoaniline 30 Part F. Preparation of 4-Bromo-2-chloro-6-iodobenzene 31 21.4 Lidocaine: Synthesis of an Anesthetic Agent Part A. Preparation of 2,6-Dimethylaniline 31 Part B. Preparation of α-Chloro-2,6-dimethylacetanilide 31 iv ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach Part C. Preparation of Lidocaine 31 CH 22 Polymers 22.2 Chain-Reaction Polymerization Part A. Removal of the Inhibitor from Commercial Styrene 32 Part B. Polymerization of Pure Styrene 32 Part C. Step-Growth Polymerization 32 22.3 Step-Growth Polymerization 32 CH 23 Carbohydrates 23.3 Disaccharides: Hydrolysis of Sucrose 33 23.4 Carbohydrates: Their Characterization and Identification 33 CH 24 α-Amino Acids and Peptides Part A. Preparation of N-tert-Butoxycarbonyl-L-Alanine 33 Part B. Preparation of Methyl L-Phenylalaninate Hydrochloride 34 Part C. Preparation of Methyl N-tert-Butoxycarbonyl L-Alanyl-L-phenylalaninate 34 Part D. Preparation of Methyl L-Alanyl-L-phenylalaninate Trifluoroacetate CH 25 Identifying Organic Compounds SECTION 3. 34 35 ANSWERS TO PRE-LAB EXERCISES CH 3 Solids: Recrystallization and Melting Points 3.2 Recrystallization. Part A. Solvent Selection 38 3.2 Recrystallization. Part B. Recrystallizing Impure Solids (Miniscale) 38 3.2 Recrystallization. Part B. Recrystallizing Impure Solids (Microscale) 39 3.3 Physical Constants: Melting Points 39 CH 4 Liquids: Distillation and Boiling Points 4.2 Boiling Points of Pure Liquids (Miniscale) 40 4.2 Boiling Points of Pure Liquids (Microscale) 41 4.3 and 4.4 Simple and Fractional Distillation (Miniscale) 41 4.3 Simple Distillation (Microscale) 42 4.6 Steam Distillation: Isolation of Citral from Lemon Grass Oil 43 CH 5 Extraction 5.3 Base Extraction. Part A One-Base Extraction 44 5.3 Base Extraction. Part B Two-Base Extraction 45 5.3 Base Extraction. Part C Acid and Base Extraction 46 5.4 Isolation of Trimyristin from Nutmeg (Miniscale) 47 5.4 Isolation of Trimyristin from Nutmeg (Microscale) 48 v ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach CH 6 Chromatography 6.2 Thin-Layer Chromatography Part A. Separation of Spinach Pigments by TLC 48 Part B. Separation of Syn- and Anti-Azobenzenes by TLC 49 6.3 Column Chromatography 49 6.4 Gas-Liquid Chromatography Part A. Qualitative and Quantitative Analysis of a Mixture of Compounds by GLC 50 Part B. Determining GLC Response Factors 51 CH 7 Stereoisomers 7.2 Separation of Diastereomeric 1,2-Cyclohexanediols 51 7.3 Isomerization of Dimethyl Maleate to Dimethyl Fumarate 52 7.4 Properties of the Enantiomers of Carvone 52 7.6 Resolution of Racemic 1-Phenylethanamine 53 CH 9 Alkanes 9.2 Chlorination Using Sulfuryl Chloride (Miniscale) 53 9.2 Chlorination Using Sulfuryl Chloride (Microscale) 54 9.3 Bromination. Selectivity of Hydrogen Atom Abstraction 54 CH 10 Alkenes 10.2 Base-Promoted Elimination of an Alkyl Halide (Miniscale) 55 10.2 Base-Promoted Elimination of an Alkyl Halide (Microscale) 56 10.3 Dehydration of Alcohols 56 10.5 Addition of Hydrobromic Acid to 1-Hexene 57 10.6 Bromination of (E)-Stilbene 58 10.7 Hydration of Norbornene 58 10.8 Hydroboration-Oxidation of (+)-α-Pinene 59 CH 11 Alkynes 11.2 Dehydrobromination of Meso-Stilbene Dibromide 60 11.3 Preparation of 3- Hydroxy-3-methyl-2-butanone 60 11.4 Formation of a Silver Acetylide and Its Decomposition 61 CH 12 Dienes. The Diels-Alder Reaction 12.3 Diels-Alder Reaction. Part A. Reaction of 1,3-Butadiene and Maleic Anhydride 61 12.3 Diels-Alder Reaction. Part B. Reaction of 1,3-Cyclopentadiene and Maleic Anhydride (Miniscale) 62 12.3 Diels-Alder Reaction. Part B. Reaction of 1,3-Cyclopentadiene and vi ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach Maleic Anhydride (Microscale) 62 12.3 Diels-Alder Reaction. Part C. Hydrolysis of Anhydrides 63 CH 13 Kinetic and Thermodynamic Control of a Reaction 13.3 Formation of Semicarbazones under Kinetic and Thermodynamic Control 64 CH 14 Nucleophilic Aliphatic Substitution: Preparation of Alkyl Halides 14.4 Preparation of 1-Bromobutane: An SN2 Reaction 64 14.5 Preparation of 2-Chloro-2-methylbutane: An SN1 Reaction 65 14.7 Chemical Kinetics: Evidence for Nucleophilic Substitution Mechanisms 66 CH 15 Arenes. Electrophilic Aromatic Substitution 15.2 Friedel-Crafts Alkylation of p-Xylene with 1-Bromopropane 66 15.3 Friedel-Crafts Acylation of m-Xylene with Phthalic Anhydride 67 15.4 Nitration of Bromobenzene. Part A. Nitration 67 15.4 Nitration of Bromobenzene. Part B. Thin-Layer Chromatography 68 15.4 Nitration of Bromobenzene. Part C. Column Chromatography 68 15.5 Relative Rates of Electrophilic Aromatic Substitution Qualitative Measurements. Part A. Qualitative Analysis 69 Quantitative Measurements. Part B. Quantitative Analysis 69 CH 16 Oxidation of Alcohols and Carbonyl Compounds 16.2 Oxidation of Alcohols. Part A. Oxidation of Cyclododecanol to Cyclododecanone 70 16.2 Oxidation of Alcohols. Part B. Oxidation of 4-Chlorobenzyl Alcohol to 4-Chlorobenzoic Acid 70 16.4 Base-Catalyzed Oxidation-Reduction of Aldehydes: The Cannizzaro Reaction 70 CH 17 Reduction Reactions of Double Bonds; Alkenes, Carbonyl Compounds, and Imines 17.2 Hydrogenation of 4-Cyclohexene-cis-1,2-dicarboxylic Acid 71 17.3 Formation and Reduction of N-Cinnamylidene-m-nitroaniline 72 17.4 Reduction 9-Fluorenone 73 17.5 Enzymatic Reduction of Methyl Acetoacetate 74 17.6 74 Determining Optical Purity of Methyl (S)-(+)-3-Hydroxybutanoate CH 18 Reactions of Carbonyl Compounds 18.2 The Wittig and Horner-Wadsworth-Emmons Reactions. Part A. Synthesis of (Z)- and (E)-Stilbenes by a Wittig Reaction 75 18.2 The Wittig and Horner-Wadsworth-Emmons Reactions. Part B. Synthesis of a Stilbene by the Horner-Wadsworth-Emmons Reaction 76 vii ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach 18.3 Preparation of trans-p-Anisalacetophenone 76 18.4 Preparation of 4,4-Dimethyl-2-cyclohexen-1-one 76 CH 19 Organometallic Chemistry 19.2 Preparation of Grignard Reagents 77 19.4 Reactions of Grignard Reagents. Part A. Preparation of Triphenylmethanol 78 19.4 Reactions of Grignard Reagents. Part B. Preparation of Benzoic Acid 79 19.4 Reactions of Grignard Reagents. Part C. Preparation of 2-Methyl-3-heptanol 80 CH 20 Carboxylic Acids and Their Derivatives 20.2 Preparation of Benzocaine 81 20.3 Preparation of N,N-Diethyl-m-Toluamide 82 20.4 Preparation and Chemiluminescence of Luminol 82 CH 21 Multistep Organic Synthesis 21.2 Synthesis of Sulfanilamide. Part A. Preparation of Aniline 83 21.2 Synthesis of Sulfanilamide. Part B. Preparation of Acetanilide 84 21.2 Synthesis of Sulfanilamide. Part C. Preparation of 4-Acetamidobenzenesulfonyl Chloride 84 21.2 Synthesis of Sulfanilamide. Part D. Preparation of 4-Acetamidobenzenesulfonilamide 85 21.2 Synthesis of Sulfanilamide. Part E. Preparation of Sulfanilamide 85 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene. Part B. Preparation of 4-Bromoacetanilide 86 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene. Part C. Preparation of 4-Bromo-2-chloroacetanilide 86 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene. Part D. Preparation of 4-Bromo-2-chloroaniline 87 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene. Part E. Preparation of 4-Bromo-2-chloro-6-iodoaniline 87 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene. Part F. Preparation of 1-Bromo-3-chloro-5-iodoaniline 88 21.4 Synthesis of Lidocaine. Part A. Preparation of 2,6-Dimethylaniline 88 21.4 Synthesis of Lidocaine. Part B. Preparation of α-Chloro-2,6-dimethyl acetanilide 88 21.4 Synthesis of Lidocaine. Part C. Preparation of Lidocaine 89 CH 22 Polymers 22.3 Preparation of Polystyrene 90 22.3 Preparation of Nylon-6,10 90 viii ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach CH 23 Carbohydrates 23.3 Hydrolysis of Sucrose 91 23.4 Classification Tests for Carbohydrates 91 23.4 Formation of Osazones 91 CH 24 α-Amino Acids and Peptides 24.3 Synthesis of the Protected Dipeptide Ala–Phe-OMe. Part A. Preparation of N-tert-Butoxycarbonyl-L-Alanine 92 24.3 Synthesis of the Protected Dipeptide Ala–Phe-OMe. Part B. Preparation of Methyl L-Phenylalaninate Hydrochloride 92 24.3 Synthesis of the Protected Dipeptide Ala–Phe-OMe. Part C. Preparation of Methyl N-tert-Butoxycarbonyl-L-Alanyl-L-Phenylalaninate 93 24.3 Synthesis of the Protected Dipeptide Ala–Phe-OMe. Part D. Preparation of Methyl L-Alanyl-L-Phenylalaninate Trifluoroacetate SECTION 4. 94 ANSWERS TO EXERCISES CH 3 Solids: Recrystallization and Melting Points 3.2 Recrystallization 95 3.3 Physical Constants: Melting Points 99 CH 4 Liquids: Distillation and Boiling Points 4.2 Boiling Points of Pure Liquids 101 4.3 Simple Distillation 101 4.4 Fractional Distillation 102 4.6 Steam Distillation: Isolation of Citral from Lemon Grass Oil 105 CH 5 Extraction 5.3 Base and Acid Extractions 106 5.4 Isolation of Trimyristin from Nutmeg 109 CH 6 Chromatography 6.2 Thin-Layer Chromatography 110 6.3 Column Chromatography 110 6.4 Gas Chromatography 112 CH 7 Stereoisomers 7.2 Separation of Diastereomeric 1,2-Cyclohexanediols 113 7.3 Isomerization of Dimethyl Maleate to Dimethyl Fumarate 114 7.4 Properties of the Enantiomers of Carvone 115 7.6 Resolution of Racemic 1-Phenylethanamine 117 CH 8 Spectral Methods 8.2 Infrared (IR) Spectroscopy 118 ix ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach 8.3 Nuclear Magnetic Resonance (NMR) Spectroscopy Proton Magnetic Resonance (1H NMR) Spectroscopy 120 Carbon-13 Nuclear Magnetic Resonance (13C NMR) Spectroscopy 123 8.4 Ultraviolet and Visible Spectroscopy 123 8.5 Mass Spectrometry 124 CH 9 Alkanes 9.2 Chlorination Using Sulfuryl Chloride 125 9.3 Bromination. Selectivity of Hydrogen Atom Abstraction 130 CH 10 Alkenes 10.2 Base-Promoted Elimination of an Alkyl Halide 133 10.3 Dehydration of Alcohols 136 10.5 Addition Reactions of Alkenes 142 10.6 Bromination of Alkenes 145 10.7 Acid-Catalyzed Hydration of Alkenes 148 10.8 Hydroboration-Oxidation of Alkenes 150 CH 11 Alkynes 11.2 Dehydrohalogenation of 1,2-Dihaloalkanes 153 11.3 Addition Reactions of Alkynes 155 11.4 Terminal Alkynes as Acids 158 CH 12 Dienes. The Diels-Alder Reaction 12.3 Diels-Alder Reactions 159 CH 13 Kinetic and Thermodynamic Control of a Reaction 13.3 Formation of Semicarbazones under Kinetic and Thermodynamic Control 166 CH 14 Nucleophilic Aliphatic Substitution: Preparation of Alkyl Halides 14.4 Preparation of 1-Bromobutane: An SN2 Reaction 171 14.5 Preparation of 2-Chloro-2-methylbutane: An SN1 Reaction 174 14.6 Chemical Kinetics: Evidence for Nucleophilic Substitution Mechanisms 177 CH 15 Arenes. Electrophilic Aromatic Substitution 15.2 Friedel-Crafts Alkylation of p-Xylene with 1-Bromopropane 179 15.3 Friedel-Crafts Acylation of m-Xylene with Phthalic Anhydride 183 15.4 Nitration of Bromobenzene 185 15.5 Relative Rates of Electrophilic Aromatic Substitution 188 CH 16 Oxidation of Alcohols and Carbonyl Compounds 16.2 Preparation of Aldehydes and Ketones by Oxidation of Alcohols, Part A. 193 16.2 Preparation of Aldehydes and Ketones by Oxidation of Alcohols, Part B. 194 x ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Table of Contents Experimental Organic Chemistry: A Miniscale and Microscale Approach 16.3 Base-Catalyzed Oxidation-Reduction of Aldehydes by the Cannizzaro Reaction 196 CH 17 Reduction Reactions of Double Bonds: Alkenes, Carbonyl Compounds, and Imines 17.2 Catalytic Hydrogenation of the Carbon-Carbon Double Bond 199 17.3 Reduction of Imines: Preparation of Amines 202 17.4 Reduction of Carbonyl Compounds: Preparation of Alcohols 206 17.5 Enzymatic Reduction: A Chiral Alcohol from a Ketone 208 17.6 Determining Optical Purity 210 CH 18 Reactions of Carbonyl Compounds 18.2 The Wittig and Related Reactions 211 18.3 Reaction of Stabilized Carbanions from Carbonyl Compounds 215 18.4 Conjugate Addition to an α,β-Unsaturated Ketone 218 CH 19 Organometallic Chemistry 19.2 Grignard Reagents: Preparation 221 19.5 Grignard Reagents: Reactions 224 CH 20 Carboxylic Acids and Their Derivatives 20.2 Esters and the Fischer Esterificaiton 229 20.3 Amides and Insect Repellents 231 20.4 Amides and Chemiluminescence 233 CH 21 Multistep Organic Synthesis 21.2 Sulfanilamide: Discovery and Synthesis of the First Antibiotic 235 21.3 Synthesis of 1-Bromo-3-chloro-5-iodobenzene 244 21.4 Lidocaine: Synthesis of an Anesthetic Agent 251 CH 22 Polymers 22.4 Chain-Reaction Polymerization 255 22.3 Step-Growth Polymerization 257 CH 23 Carbohydrates 23.3 Disaccharides: Hydrolysis of Sucrose 259 23.4 Carbohydrates: Their Characterization and Identification 263 CH 24 α-Amino Acids and Peptides 265 CH 26 The Literature of Organic Chemistry 273 xi ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Section 1. Desk Equipment, Shelf Reagents, and Solvents Experimental Organic Chemistry: A Miniscale and Microscale Approach SECTION 1. DESK EQUIPMENT, SHELF REAGENTS, AND SOLVENTS A. List of Equipment for Individual Desks Miniscale Experiments 6 Beakers, 100-, 150-, 250-, 400-, 600-, 800-mL 1 Board, asbestos, 15 x 15 cm 1 Bottle, wash, 250-mL 6 Bottles, 2 wide- and 4 narrow-mouth 2 Brushes, test tube 2 Burners, 1 micro 3 Clamps, jaw 4 Clips, Keck 2 Cylinders, graduated, 10-, 100-mL 1 Disk, evaporating, 15-cm 2 Flasks, Erlenmeyer, 50-mL 2 Flasks, Erlenmeyer, 125-mL 1 Flask, Erlenmeyer, 250-mL 3 Flasks, filtering, 50-, 125-, 250-mL 1 Funnels, Büchner, 43-, 71-mm 1 Funnel, glass, short-stemmed 1 Funnel, Hirsch 2 Funnels, separatory, 60-, 125-mL 1 Gauze, wire 1 Holder, test tube 1 Matches, box Paper, filter, 4.25-, 7.0-cm, 1 box ea. 1 Pan, 2-L 10 Pipets, Pasteur 1 Pipet, graduated, 10-mL 1 Rack, test tube 1 Rubber policeman 1 Spatula, porcelain 1 Spatula, semi-micro Sponge, copper, or stainless steel, 1/2 ea. 12 Test tubes, Pyrex, 18 x 150-mm 12 Test tubes, Pyrex, 13 x 100-mm 12 Test tubes, soft glass, 10 x 75-mm 1 ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Section 1. Desk Equipment, Shelf Reagents, and Solvents Experimental Organic Chemistry: A Miniscale and Microscale Approach 2 Test tubes, side-arm, 18 x 150-mm 1 Test tube, graduated, 10-mL 1 Thermometer, 360 °C 2 Towels 1 Tube, drying Tubing, rubber, 12 ft 2 Watchglasses, 50-mm 1 Standard taper Glassware Kit, containing the following items: 1 Adapter, thermometer 1 Adapter, vacuum 1 Claisen head 1 Column/Condenser, fractionating 1 Condenser, water-cooled 4 Flasks, round-bottom, 10-mL, 25-mL, 50-mL, 125-mL 1 Funnel, separatory, 125-mL Lubricant, stopcock, 1 tube 1 Stillhead 1 Stopper 1 Sleeve, rubber Microscale Experiments 6 Beakers, 100-, 150-, 250-, 400-, 600-, 800-mL 1 Board, asbestos, 15 x 15-cm 1 Bottle, wash, 250-mL 6 Bottles, 2 wide- and 4 narrow-mouth 2 Brushes, test tube 2 Burners, 1 micro 2 Clamps, jaw 1 Cylinder, graduated, 100-mL 1 Disk, evaporating, 15-cm 2 Flasks, Erlenmeyer, 50-mL 2 Flasks, Erlenmeyer, 125-mL 1 Flask, Erlenmeyer, 250-mL 3 Flasks, filtering, 50-, 125-, 250-mL 1 Funnels, Büchner, 43-, 71-mm 1 Funnel, glass, short-stemmed 1 Funnel, Hirsch 2 ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Section 1. Desk Equipment, Shelf Reagents, and Solvents Experimental Organic Chemistry: A Miniscale and Microscale Approach 2 Funnels, separatory, 60-, 125-mL 1 Gauze, wire 1 Holder, test tube 1 Matches, box Paper, filter, 4.25-, 7.0-cm, 1 box ea. 1 Pan, 2-L 10 Pipets, Pasteur 1 Pipet, graduated, 10-mL 1 Rack, test tube 1 Rubber policeman 1 Spatula, porcelain 1 Spatula, semi-micro Sponge, copper, or stainless steel, 1/2 ea. 12 Test tubes, Pyrex, 18 x 150-mm 12 Test tubes, Pyrex, 13 x 100-mm 12 Test tubes, soft glass, 10 x 75-mm 2 Test tubes, side-arm, 18 x 150-mm 1 Test tube, graduated, 10-mL 1 Thermometer, 360 °C 2 Towels 1 Tube, drying Tubing, rubber, 12 ft 2 Watchglasses, 50-mm 1 Standard taper Glassware Kit, containing the following items: 1 Adapter, thermometer 1 Claisen head 1 Condenser, air 1 Condenser, reflux 2 Flasks, round-bottom, 10-mL, 25-mL Lubricant, stopcock, 1 tube 1 Stillhead, Hickman with port 1 Stopper 1 Sleeve, rubber 1 Tube, drying 1 Vial, conical 3 ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert Section 1. Desk Equipment, Shelf Reagents, and Solvents B. Experimental Organic Chemistry: A Miniscale and Microscale Approach Optional Equipment Miniscale Experiments 2 Heating mantles, 50-mL, 125-mL, or 1 oil bath or sand bath 1 Magnetic stirrer 1 Stirbar 2 Disposable syringes, 5-, 10-mL, and needles 1 Variable transformer 1 Laboratory jack Microscale Experiments 1 oil bath or sand bath 1 Magnetic stirrer 1 Spinvane 3 Disposable syringes, 1-, 2-, 5-mL, and needles 1 Variable transformer 1 Laboratory Jack C. Shelf Reagents and Solvents Inorganic: Ammonium hydroxide, 15 M, (28% NH3), sp gr 0.90 Hydrochloric acid, concentrated, 12 M, (37% HCl), sp gr 1.10 Hydrochloric acid, dilute, 3 M, (10% HCl), 258 mL conc. HCl/L Nitric acid, concentrated, 16 M, (71% HNO3), sp gr 1.42 Sodium bicarbonate, 1.2 M, (10% NaHCO3), 100 g, NaHCO3/L Sodium carbonate, 1 M (10% Na2CO3); 106 g Na2CO3/L or 286 g Na2CO3.10 H2O/L Sodium chloride, saturated; 380 g NaCl/L Sodium hydroxide, 3 M, (12% NaOH), sp gr 1.11; 120 g NaOH/L Sulfuric acid, concentrated, 18 M (96% H2SO4), sp gr 1.84 Organic: Dichloromethane Diethyl ether, absolute Diethyl ether, solvent grade Ethanol, absolute Ethanol, 95% Petroleum ether, bp 60–80 °C 4 ©2011 Brooks/Cole – Cengage Learning Full file at http://testbank360.eu/solution-manual-experimental-organic-chemistry-5th-edition-gilbert
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