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PART 1 Introduction to Basic Laboratory Techniques |
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1 | (150) |
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Introduction to Microscale Laboratory |
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2 | (11) |
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13 | (8) |
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21 | (11) |
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Semimicroscale Crystallization---Erlenmeyer Flask and Hirsch Funnel |
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22 | (3) |
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Microscale Crystallization---Craig Tube |
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25 | (2) |
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Selecting a Solvent to Crystallize a Substance |
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27 | (1) |
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28 | (1) |
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Critical Thinking Application |
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29 | (3) |
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32 | (10) |
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33 | (3) |
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Distribution of a Solute between Two Immiscible Solvents |
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36 | (1) |
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How Do You Determine Which One Is the Organic Layer? |
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37 | (1) |
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Use of Extraction to Isolate a Neutral Compound from a Mixture Containing an Acid or Base Impurity |
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38 | (2) |
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Critical Thinking Application |
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40 | (2) |
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42 | (9) |
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Thin-Layer Chromatography |
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43 | (2) |
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Selecting the Correct Solvent for Thin-Layer Chromatography |
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45 | (1) |
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Monitoring a Reaction with Thin-Layer Chromatography |
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46 | (2) |
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48 | (3) |
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Simple and Fractional Distillation |
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51 | (6) |
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Simple and Fractional Distillation (Semimicroscale Procedure) |
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53 | (3) |
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Simple and Fractional Distillation (Microscale Procedure) |
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56 | (1) |
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Infrared Spectroscopy and Boiling-Point Determination |
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57 | (6) |
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61 | (2) |
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63 | (8) |
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67 | (4) |
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Isolation of the Active Ingredient in an Analgesic Drug |
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71 | (4) |
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75 | (7) |
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Acetaminophen (Microscale Procedure) |
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76 | (2) |
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Acetaminophen (Semimicroscale Procedure) |
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78 | (2) |
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80 | (2) |
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TLC Analysis of Analgesic Drugs |
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82 | (8) |
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87 | (3) |
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Isolation of Caffeine from Tea or Coffee |
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90 | (13) |
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Extraction of Caffeine from Tea with Methylene Chloride |
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93 | (2) |
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Extraction of Caffeine from Tea or Coffee Using Solid Phase Extraction (SPE) |
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95 | (4) |
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Esters---Flavors and Fragrances |
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99 | (4) |
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Isopentyl Acetate (Banana Oil) |
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103 | (9) |
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Isopentyl Acetate (Microscale Procedure) |
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104 | (2) |
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Isopentyl Acetate (Semimicroscale Procedure) |
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106 | (2) |
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Terpenes and Phenylpropanoids |
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108 | (4) |
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Essential Oils: Extraction of Oil of Cloves by Steam Distillation and Liquid Carbon Dioxide |
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112 | (12) |
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Oil of Cloves (Microscale Procedure) |
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113 | (2) |
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Oil of Cloves (Semimicroscale Procedure) |
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115 | (1) |
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Extraction of Oil of Cloves with Liquid Carbon Dioxide---A Demonstration |
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116 | (3) |
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Stereochemical Theory of Odor |
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119 | (5) |
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Spearmint and Caraway Oil: (+)-and (--)-Carvones |
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124 | (12) |
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132 | (4) |
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Isolation of Chlorophyll and Carotenoid Pigments from Spinach |
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136 | (9) |
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Ethanol and Fermentation Chemistry |
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142 | (3) |
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145 | (6) |
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PART 2 Introduction to Molecular Modeling |
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151 | (24) |
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Molecular Modeling and Molecular Mechanics |
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152 | (4) |
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An Introduction to Molecular Modeling |
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156 | (12) |
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The Conformations of n-Butane: Local Minima |
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157 | (1) |
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Cyclohexane Chair and Boat Conformations |
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158 | (1) |
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Substituted Cyclohexane Rings |
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159 | (1) |
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159 | (1) |
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Computational Chemistry---ab Initio and Semiempirical Methods |
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160 | (8) |
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168 | (7) |
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Heats of Formation: Isomerism, Tautomerism, and Regioselectivity |
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169 | (2) |
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Heats of Reaction: SN1 Reaction Rates |
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171 | (1) |
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Density--Electrostatic Potential Maps---Acidities of Carboxylic Acids |
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172 | (1) |
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Density--Electrostatic Potential Maps: Carbocations |
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173 | (1) |
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Density--LUMO Maps: Reactivities of Carbonyl Groups |
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173 | (2) |
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PART 3 Properties and Reactions of Organic Compounds |
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175 | (272) |
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Reactivities of Some Alkyl Halides |
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176 | (4) |
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Nucleophilic Substitution Reactions: Competing Nucleophiles |
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180 | (10) |
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Competitive Nucleophiles with 1-Butanol or 2-Butanol |
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183 | (3) |
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Competitive Nucleophiles with 2-Methyl-2-Propanol |
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186 | (1) |
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187 | (3) |
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Hydrolysis of Some Alkyl Chlorides |
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190 | (5) |
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Synthesis of n-Butyl Bromide and t-Pentyl Chloride |
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195 | (9) |
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197 | (2) |
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n-Butyl Bromide (Semimicroscale Procedure) |
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199 | (1) |
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t-Pentyl Chloride (Microscale Procedure) |
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200 | (1) |
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t-Pentyl Chloride (Semimicroscale Procedure) |
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201 | (1) |
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t-Pentyl Chloride (Macroscale Procedure) |
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202 | (2) |
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Elimination Reactions: Dehydration and Dehydrohalogenation |
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204 | (7) |
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Dehydration of 1-Butanol and 2-Butanol |
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207 | (1) |
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Dehydrobromination of 1-Bromobutane and 2-Bromobutane |
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208 | (3) |
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211 | (6) |
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4-Methylcyclohexene (Microscale Procedure) |
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213 | (1) |
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4-Methylcyclohexene (Semimicroscale Procedure) |
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214 | (3) |
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Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene |
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217 | (7) |
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Relative Reactivities of Several Aromatic Compounds |
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224 | (4) |
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Nitration of Methyl Benzoate |
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228 | (11) |
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233 | (6) |
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Methyl Stearate from Methyl Oleate |
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239 | (10) |
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243 | (6) |
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249 | (2) |
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Preparation of a Detergent |
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251 | (13) |
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Petroleum and Fossil Fuels |
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255 | (9) |
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Gas-Chromatographic Analysis of Gasolines |
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264 | (10) |
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268 | (6) |
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Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination |
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274 | (10) |
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Chiral Reduction of Ethyl Acetoacetate |
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275 | (4) |
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NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate |
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279 | (5) |
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Nitration of Aromatic Compounds Using a Recyclable Catalyst |
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284 | (4) |
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An Oxidation--Reduction Scheme: Borneol, Camphor, Isoborneol |
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288 | (14) |
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Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid |
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302 | (12) |
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Preparation of Benzoin by Thiamine Catalysis |
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303 | (6) |
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309 | (2) |
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Preparation of Benzilic Acid |
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311 | (3) |
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Tetraphenylcyclopentadienone |
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314 | (3) |
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Triphenylmethanol and Benzoic Acid |
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317 | (11) |
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322 | (3) |
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325 | (3) |
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Aqueous-Based Organozinc Reactions |
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328 | (3) |
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Resolution of (±)-α-Phenylethylamine and Determination of Optical Purity |
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331 | (8) |
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Resolution of (±)-α-Phenylethylamine |
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334 | (3) |
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Determination of Optical Purity Using NMR and a Chiral Resolving Agent |
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337 | (2) |
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The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones) |
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339 | (5) |
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Preparation of an α,β-Unsaturated Ketone via Michael and Aldol Condensation Reactions |
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344 | (4) |
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Enamine Reactions: 2-Acetylcyclohexanone |
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348 | (11) |
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1,4-Diphenyl-1,3-butadiene |
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359 | (11) |
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Benzyltriphenylphosphonium Chloride (Wittig Salt) |
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362 | (1) |
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Preparation of 1,4-Diphenyl-1,3-Butadiene Using Sodium Ethoxide to Generate the Ylide |
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362 | (2) |
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Preparation of 1,4-Diphenyl-1,3-Butadiene Using Potassium Phosphate to Generate the Ylide |
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364 | (3) |
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367 | (3) |
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370 | (3) |
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Methyl Salicylate (Oil of Wintergreen) |
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373 | (10) |
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Pheromones: Insect Attractants and Repellents |
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377 | (6) |
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N,N-Diethyl-m-Toluamide: The Insect Repellent ``OFF'' |
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383 | (9) |
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388 | (4) |
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Sulfa Drugs: Preparation of Sulfanilamide |
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392 | (14) |
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397 | (9) |
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Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene |
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406 | (13) |
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407 | (2) |
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409 | (1) |
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410 | (2) |
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Infrared Spectra of Polymer Samples |
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412 | (2) |
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Diels--Alder Reaction and Insecticides |
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414 | (5) |
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The Diels--Alder Reaction of Cyclopentadiene with Maleic Anhydride |
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419 | (5) |
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Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone |
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424 | (13) |
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Photoreduction of Benzophenone |
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425 | (6) |
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Synthesis of β-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol |
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431 | (2) |
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Fireflies and Photochemistry |
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433 | (4) |
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437 | (7) |
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The Chemistry of Sweeteners |
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441 | (3) |
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Analysis of a Diet Soft Drink by HPLC |
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444 | (3) |
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PART 4 Identification of Organic Substances |
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447 | (48) |
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Identification of Unknowns |
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448 | (47) |
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454 | (6) |
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Tests for the Elements (N, S, X) |
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460 | (6) |
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466 | (4) |
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470 | (7) |
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477 | (2) |
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479 | (3) |
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482 | (4) |
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486 | (5) |
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491 | (4) |
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PART 5 Project-Based Experiments |
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495 | (46) |
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A Separation and Purification Scheme |
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496 | (2) |
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Preparation of a C-4 or C-5 Acetate Ester |
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498 | (4) |
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Extraction of Essential Oils from Caraway, Cinnamon, Cloves, Cumin, or Fennel by Steam Distillation |
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502 | (8) |
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Isolation of Essential Oils by Steam Distillation |
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504 | (3) |
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Identification of the Constituents of Essential Oils by Gas Chromatography--Mass Spectrometry |
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507 | (1) |
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Investigation of the Essential Oils of Herbs and Spices---A Mini--Research Project |
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508 | (2) |
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Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol |
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510 | (5) |
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Friedel--Crafts Acylation |
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515 | (7) |
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The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry |
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522 | (2) |
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The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy |
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524 | (3) |
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527 | (2) |
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Synthesis of Substituted Chalcones: A Guided-Inquiry Experience |
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529 | (4) |
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Michael and Aldol Condensation Reactions |
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533 | (3) |
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Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem |
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536 | (2) |
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538 | (3) |
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541 | (416) |
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542 | (16) |
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The Laboratory Notebook, Calculations, and Laboratory Records |
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558 | (8) |
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Laboratory Glassware: Care and Cleaning |
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566 | (8) |
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How to Find Data for Compounds: Handbooks and Catalogs |
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574 | (7) |
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Measurement of Volume and Weight |
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581 | (8) |
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Heating and Cooling Methods |
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589 | (9) |
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598 | (18) |
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616 | (11) |
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Physical Constants of Solids: The Melting Point |
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627 | (10) |
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637 | (10) |
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Crystallization: Purification of Solids |
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647 | (22) |
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Extractions, Separations, and Drying Agents |
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669 | (25) |
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Physical Constants of Liquids: The Boiling Point and Density |
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694 | (9) |
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703 | (12) |
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Fractional Distillation, Azeotropes |
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715 | (17) |
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Vacuum Distillation, Manometers |
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732 | (13) |
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745 | (5) |
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750 | (6) |
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756 | (21) |
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Thin-Layer Chromatography |
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777 | (15) |
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High-Performance Liquid Chromatography (HPLC) |
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792 | (5) |
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797 | (21) |
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818 | (9) |
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827 | (6) |
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833 | (35) |
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Nuclear Magnetic Resonance Spectroscopy (Proton NMR) |
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868 | (38) |
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Carbon-13 Nuclear Magnetic Resonance Spectroscopy |
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906 | (18) |
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924 | (18) |
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Guide to the Chemical Literature |
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942 | (15) |
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957 | (22) |
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Tables of Unknowns and Derivatives |
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958 | (13) |
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Procedures for Preparing Derivatives |
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971 | (5) |
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976 | (3) |
| Index |
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979 | |
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