Organic Chemistry Laboratory Standard and Microscale Experiments

, by Bell, Charles E.; Taber, Douglas; Clark, K.

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ISBN: 9780030292729 | 0030292727
Cover: Hardcover
Copyright: 8/9/2000

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Summary

Supplemental Materials

The new edition continues to offer a wide variety of organic lab experiments for both standard and microscale formats and features unusually strong coverage of spectroscopy.

Preface

xiii

Introduction

(16)

Laboratory Safety

(3)

Disposal

(1)

Laboratory Equipment and Techniques

(7)

Reports and Records

(5)

Melting Points

(6)

Melting Point of a Pure Known Compound

(1)

Melting Points as a Thermometer Calibration

(1)

Melting Point of an Unknown Compound

(2)

Recrystallization

(10)

Recrystallization of Benzoic Acid (Microscale)

(1)

Crystallization of Impure Acetanilide (Macroscale)

(1)

Preparation of Acetanilide (Microscale)

(1)

Preparation of N-Acetylanthranilic Acid: A Triboluminescent Material (Macroscale)

(2)

Extraction

(14)

Determination of a Distribution Coefficient (Macroscale)

(1)

Separation of Acidic, Basic, and Neutral Compounds (Macroscale)

(2)

Separation of Acidic, Basic, and Neutral Compounds (Microscale)

(3)

Distillation

(12)

Distillation of a Pure Compound (Macroscale)

(1)

Simple Distillation of a Mixture (Macroscale)

(1)

Fractional Distillation (Macroscale)

(1)

Fractional Distillation (Microscale)

(1)

Boiling Points (Reflux Boiling Point Method)

(1)

Micro Boiling Point Determination (Thiele--Dennis Tube Method)

(2)

Micro Boiling Point Determination (Capillary Method)

(2)

Gas Chromatography

(8)

Examination of an Unknown Mixture

(1)

GC of Fractions from Fractional Distillation

(2)

Column Chromatography

(6)

Separation of Ferrocene and Acetylferrocene (Microscale)

(1)

Isolation of Caffeine

(3)

Thin Layer Chromatography

(8)

TLC of Nitroanilines

(1)

TLC of Analgesic Drugs

(5)

High Performance Liquid Chromatography (HPLC)

(4)

Caffeine in Beverages

(3)

Steam Distillation of Essential Oils

(8)

Isolation of the Essential Oils of Caraway, Clove, or Cumin (Macroscale)

(1)

Isolation of the Essential Oil of Caraway (Microscale)

(1)

Caraway Oil (Macro- and Microscale)

(1)

Clove Oil (Macroscale)

(1)

Cumin Oil (Macroscale)

(2)

Infrared Absorption Spectroscopy

(14)

Spectroscopic Structure Determination: A Lifelong Quest

107

(18)

H- Nuclear Magnetic Resonance

125

(18)

Proton Spectrum of Ethylbenzene

132

(1)

Proton Spectra of Alcohols

132

(1)

Carbon-13 Spectrum of Ethylbenzene

133

(1)

Acquire the Spectra of an Unknown Compound Supplied by Your Instructor, and Determine the Structure

133

(10)

Advanced Structure Determination

143

(28)

The Literature of Organic Chemistry

171

(12)

Properties of Hydrocarbons

183

(4)

Solubility

184

(1)

Relative Density

184

(1)

Flammability

184

(1)

Addition of Bromine

184

(1)

Reaction with Potassium Permanganate

184

(1)

Reaction with Sulfuric Acid

184

(3)

Nucleophilic Substitution of Alkyl Halides

187

(6)

Structural Effects on SN1 and SN2 Reactivity

188

(1)

Effects of Solvent on SN1 Reactivity

189

(1)

Effect of Temperature on Reaction Rates

190

(1)

Reaction of Ethyl Bromide with Hydroxide Ion, an SN2 Reaction

191

(2)

Properties of Alcohols

193

(4)

Reaction with Sodium (Demonstation)

193

(1)

Solubility in Water

194

(1)

Lucas Test

194

(1)

Oxidation Using Chromic Acid

195

(1)

Ester Formation

195

(2)

The Grignard Reaction

197

(8)

Triphenylmethanol and Benzoic Acid (Macro- and Microscale)

198

(2)

Preparation of Triphenylmethanol (Macro- and Microscale)

200

(2)

Preparation of Benzoic Acid (Macro- and Microscale)

202

(1)

Preparation of Malachite Green

203

(2)

Dehydration of Alcohols

205

(6)

Preparation of Cyclohexene (Macroscale)

206

(1)

Dehydration of 2-Methylcyclohexanol (Macroscale)

207

(1)

Dehydration of 2-Methylcyclohexanol (Microscale)

208

(3)

Oxidation and Reduction

211

(8)

Preparation of Cyclohexanone (Macroscale)

213

(1)

Preparation of Adipic Acid (Microscale)

214

(1)

Oxidation of para-Nitrobenzyl alcohol (Microscale)

214

(1)

Haloform Reaction (Microscale)

215

(1)

Reduction of Benzophenone (Microscale)

216

(1)

Reduction of para-Nitrobenzyaldehyde (Microscale)

216

(3)

Aldehydes and Ketones

219

(6)

Reactions with Nitrogen Compounds

220

(1)

Oxidation Reactions

221

(1)

Iodoform Test

222

(1)

Infrared Spectra

222

(1)

Crossed Aldol Condensation (Microscale)

222

(3)

Determination of pKa: Effects of Substituents on Acidity

225

(4)

Determination of the pKa of Unknown Substituted Benzoic Acid (Microscale)

226

(3)

Carboxylic Acid Mini-Unknown

229

(4)

Esterification and Saponification: Effects of Substituents on Reactivity

233

(4)

Preparation of Methyl Benzoates (Microscale)

233

(1)

Rate Measurements

234

(1)

Calculation of the Rate Constant for Hydrolysis

235

(2)

Friedel-Crafts Alkylation and Acylation

237

(6)

Preparation of BHT (Macroscale)

238

(2)

Preparation of p-di-t-Butylbenzene (Microscale)

240

(1)

Friedel-Crafts Synthesis of an Unsymmetrical Diaryl Ketone

241

(2)

Aromatic Nitration

243

(6)

Preparation and Separation of o- and p-Nitroaniline (Macroscale)

244

(2)

Nitration of Toluene and Analysis of Products (Microscale)

246

(3)

Aromatic Nucleophilic Substitution

249

(6)

Preparation of 2,4-Dinitrophenol (Microscale)

251

(1)

Reaction of 2,4-Dinitrohalobenzenes with Ammonia and Hydrazine (Microscale)

251

(4)

Properties of Amines

255

(4)

Solubility in Water

255

(1)

Basicity

256

(1)

Hinsberg Test

256

(1)

Reactions of Diazonium Salts (Microscale)

256

(3)

Chemiluminescence

259

(6)

Bis-(2,4-Dinitrophenyl) Oxalate (Microscale)

261

(1)

Chemiluminescence (Microscale)

262

(3)

Photodimerization of Benzophenone

265

(4)

Photochemical Preparation of Benzopinacol (Microscale)

266

(1)

Preparation of Benzopinacolone (Microscale)

266

(3)

The Diels-Alder Reaction

269

(6)

Endo-Norbornene-5,6-cis-Dicarboxylic Anhydride (Macroscale)

271

(1)

Endo-Norbornene-5,6-cis-Dicarboxylic Anhydride (Microscale)

271

(4)

Phase Transfer Catalysis

275

(4)

Preparation of Nerolin (Macroscale)

276

(3)

Derivatives of Carboxylic Acids: Synthesis of a Plant Hormone

279

(4)

Acid Chloride Method (Microscale)

281

(1)

Nitrile Method (Microscale)

281

(2)

Synthesis of Coumarin

283

(6)

Ethyl Coumarin-3-carboxylate (Macroscale)

284

(1)

Coumarin-3-carboxylic Acid

285

(1)

Coumarin

285

(4)

Benzyne

289

(4)

1,4-Dihydronaphthalene- 1,4-endoxide (Microscale)

290

(1)

1-Naphthol (Microscale)

290

(3)

Heterocyclic Syntheses: Pyrimidines, Pyridones, Isoxazoles, Quinolines, and Indoles

293

(8)

Reactions of Acetylacetone with Nucleophiles

294

(2)

Reaction with Cyanoacetamide

295

(1)

Reaction with Guanidine

295

(1)

Reaction with Hydrazine

295

(1)

Reaction with Hydroxylamine

295

(1)

4-(p-Toluidino)-3-penten-2-one (Microscale)

296

(1)

2,4,6-Trimethylquinoline (Microscale)

296

(1)

3-Acetyl-2-methyl-4-phenylpyrrole (Macroscale)

297

(1)

3-Acetyl-2,4,6-trimethylpyridine (Macroscale)

298

(1)

3,5-Diacetyl-2,4,6-trimethyl-1,4-dihydropyridine (Macroscale)

298

(3)

Heterocyclic Synthesis: Phenytoin

301

(4)

Preparation of Phenytoin (Microscale)

302

(3)

Synthesis of Sulfanilamide

305

(4)

Synthesis of para-Acetamidobenzenesulfonyl Chloride

307

(1)

Amination of p-Acetamidobenzenesulfonyl Chloride

307

(1)

Sulfanilamide

307

(2)

Resolution of α-Phenylethylamine

309

(6)

Chemistry of Sugars

315

(8)

Thin-Layer Chromatography of Sugars

318

(1)

Characterization Reactions

319

(1)

Isomerization of Glucose

319

(1)

N-p-Tolyl-D-glucosylamine and N-p-Tolyl-1-amino-1-deoxy-D-fructose

320

(3)

Acid-Catalyzed and Enzyme-Catalyzed Hydrolysis of Polysaccharides

323

(4)

Enzymatic Hydrolysis of Starch

324

(1)

Acid Hydrolysis of Starch

324

(3)

Analysis of Fats and Oils

327

(4)

Transesterification of Triglycerides (Microscale)

329

(1)

GC Analysis of Methyl Esters

329

(1)

Isolation of Trimyristin (Microscale)

329

(1)

Hydrolysis of Trimyristin

329

(2)

Synthetic Organic Polymers

331

(8)

Polystyrene (Microscale)

332

(2)

Nylon (Microscale)

334

(1)

Polyurethanes (Microscale)

335

(4)

Dyes and Dyeing

339

(8)

Dyeing the Fiber (Microscale)

343

(1)

Comparison of Mono- and Dis-Azo Dyes in Neutral and Acid Solution (Microscale)

344

(1)

Disperse and Cross-Dyeing (Microscale)

344

(1)

Cationic Dyes (Microscale)

344

(3)

Qualitative Organic Analysis

347

(34)

Physical Properties

348

(3)

Solubility Classification

351

(2)

Analytical Data

353

(1)

Detection of Other Elements

354

(2)

Equivalent Weights

356

(1)

Miscellaneous Chemical Tests

357

(1)

Derivatives

358

(23)

Appendix A Selected Atomic Weights

381

(1)

Appendix B Common Acids and Bases

382

(1)

Appendix C Common Organic Liquids

383

(1)

Appendix D Representative Calculations

384

(3)

Index

387

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Organic Chemistry Laboratory Standard and Microscale Experiments

Summary

Table of Contents

Supplemental Materials