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Experimental Organic Chemistry

by: Palleros, Daniel R.

Experimental Organic Chemistry

by: Palleros, Daniel R.

ISBN 13:
9780471282501
ISBN 10:
0471282502
Edition: 1st
Format: Hardcover
Copyright: 02/04/2000
Publisher: Wiley

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Summary

This cutting-edge lab manual takes a multiscale approach, presenting both micro, semi-micro, and macroscale techniques. The manual is easy to navigate with all relevant techniques found as they are needed. Cutting-edge subjects such as HPLC, bioorganic chemistry, multistep synthesis, and more are presented in a clear and engaging fashion.

SECTION 1 THE BASICS

(58)

Laboratory Safety

(16)

General Safety Guidelines

(3)

Chemical Toxicity

(1)

Dealing with Chemicals and Waste Disposal

(8)

Online Safety Resources

(4)

Basic Concepts

(26)

Polarity and H-Bonds

(4)

Physical Data

(1)

Solvents

(2)

Balancing Chemical Equations

(2)

Concentration Units

(1)

Moles and Millimoles

(2)

Mineral Acids

(1)

Calculation of Yields

(2)

Scaling Up, Scaling Down

(1)

Keeping Lab Books and Writing Lab Reports

(1)

Chemical Literature

(10)

Basic Operations

(14)

Handling Liquids

(1)

Heating

(1)

Filtration

(4)

Refluxing

(2)

Evaporation

(2)

Centrifugation

(1)

Caring for Glassware

(2)

Measuring Pressure

(2)

SECTION 2 THE EXPERIMENTS

(608)

Recrystallization and Melting Point

(25)

Overview

(1)

Recrystallization

(7)

Decolorizing Charcoal

(1)

Recrystallization from Mixed Solvents

(1)

Microscale Recrystallization

(1)

Melting Point

(4)

Sublimation

(11)

Recrystallization of Acetanilide and Urea

(1)

Recrystallization of Acetanilide

(2)

Microscale Recrystallization of Urea

(1)

Determination of Melting Points

(4)

Extraction

(27)

Introduction

(1)

Solvent-Solvent Partitioning

(6)

Macroscale Liquid-Liquid Extraction

(1)

Microscale Liquid-Liquid Extraction

(1)

Drying the Organic Layer

(1)

Solid-Liquid Extraction

(2)

Countercurrent Distribution

(16)

Isolation of Caffeine from Tea

103

(1)

Tea, Coffee, and Caffeine

103

(2)

Caffeine from Tea: Overview of the Experiment

105

(4)

Isolation of Caffeine

109

(1)

Purification of Caffeine by Sublimation

110

(1)

Purification of Caffeine by Recrystallization (Alternative Procedure)

111

(2)

Distillation---Separation and Purification of Organic Liquids

113

(31)

Boiling Point

113

(1)

Boiling Point and Molecular Structure

114

(1)

Simple Distillation

115

(5)

Fractional Distillation

120

(3)

Ideal and Nonideal Solutions

123

(1)

Azeotropic Mixtures

124

(1)

Fractionating Columns

125

(1)

Microscale Distillation

126

(2)

Boiling Point Determination

128

(1)

Vacuum Distillation

129

(1)

Steam Distillation

130

(14)

Distillation of Alcohols

136

(1)

Distillation of Methanol from a Mixture with Ferric Chloride

136

(1)

Separation of Methanol-Water by Simple Distillation

137

(1)

Separation of Methanol-Water by Fractional Distillation

138

(1)

Analysis of the Distillation Fractions by Density

139

(3)

Isolation of Anise Oil

142

(1)

Overview

142

(1)

Isolation of Anise Oil

142

(2)

Gas Chromatography

144

(28)

Introduction

144

(1)

The Chromatographic Methods

144

(2)

Partition Chromatography

146

(3)

Gas Chromatography

149

(2)

The Gas Chromatograph

151

(4)

Measuring the Retention Time

155

(1)

Integration

156

(1)

Quantitative Analysis

157

(1)

Quantitative Analysis: A Closer Look (Advanced Level)

158

(3)

Qualitative Analysis

161

(1)

Running GC: Step by Step

162

(1)

Gas Chromatography Do's and Don'ts

163

(9)

Gas Chromatography of Alcohols

167

(1)

Analysis of Alcohols

167

(1)

Separation of Methanol and Water

168

(2)

Analysis of Anise Oil

170

(1)

Analysis of Anise Oil

170

(2)

Thin-Layer Chromatography

172

(25)

Overview

172

(1)

The Adsorption Process

173

(2)

Selection of TLC Conditions

175

(3)

Running TLC Plates

178

(4)

Adsorption Isotherms (Advanced Level)

182

(2)

Applications of TLC

184

(2)

Other Stationary Phases

186

(1)

TLC Do's and Don'ts

186

(11)

TLC Analysis of Vegetable Extracts

190

(1)

Plant Pigments

190

(2)

Isolation and Analysis of Plant Pigments

192

(5)

Column Chromatography

197

(17)

Overview

197

(1)

Practical Aspects

197

(5)

Applications

202

(1)

Column Chromatography Do's and Don'ts

203

(11)

Isolation of C60 from Fullerene Soot

206

(1)

Fullerenes

206

(1)

Isolation of Fullerenes

207

(1)

A Chemical Test for Fullerenes

208

(1)

Overview of the Experiment

209

(1)

Isolation of C60 from Fullerene Soot

209

(5)

High-Performance Liquid Chromatography

214

(24)

Overview

214

(1)

HPLC Systems

214

(1)

HPLC Versus GC

215

(1)

Solvents

216

(1)

Pumps

217

(1)

Injection Port

217

(1)

Columns

218

(1)

Detectors

219

(1)

Why is HPLC High Performance?

220

(1)

Reversed-Phase Chromatography

221

(1)

Other Chemically Bonded Stationary Phases

222

(1)

Size-Exclusion Chromatography

223

(1)

Quantitative Determinations: Standard Curve Method

224

(1)

HPLC Do's and Don'ts

224

(14)

Vitamin Analysis---A Quantitative Study

227

(1)

Water-Soluble and Fat-Soluble Vitamins

227

(2)

Vitamin Stability

229

(1)

International Units

230

(1)

Characterization of Vitamin A

230

(1)

Overview of the Experiment

231

(7)

Refractometry and Polarimetry

238

(23)

Refractive Index

238

(1)

The Refractometer

239

(1)

Measuring the Refractive Index

240

(2)

Polarimetry

242

(3)

The Polarimeter

245

(1)

Measuring the Optical Rotation

246

(1)

Optical Rotation of Mixtures

247

(14)

Analysis of Essential Oils

250

(1)

Terpenoids

250

(2)

Essential Oils

252

(1)

Specific Rotation

253

(1)

Refractive Index

253

(1)

Composition of Essential Oils

253

(2)

Separation of Carvone and Limonene

255

(1)

Carvone and Limonene

255

(1)

Analysis of the Crude Oils

256

(1)

Separation of Carvone and Limonene

257

(4)

Alcohols and Alkenes

261

(12)

Alkenes from Alcohols

261

(1)

Dehydration Mechanisms

262

(2)

Characterization of Alkenes

264

(9)

The Dehydration of Methylcyclohexanols

268

(1)

Overview

268

(1)

Dehydration of Methylcyclohexanols

269

(1)

Analysis of the Product Mixture

270

(3)

Alkyl Halides

273

(19)

Preparation

273

(1)

Reactions

274

(1)

Alkyl Halides from Alcohols

274

(2)

Characterization Tests

276

(16)

Synthesis of n-Butyl Bromide and 2-Chloro-2-Methylbutane

280

(1)

Synthesis of n-Butyl Bromide

280

(4)

Synthesis of 2-Chloro-2-Methylbutane

284

(1)

Characterization Tests

285

(7)

Acid-Base Extraction

292

(31)

Introduction

292

(1)

Acids and Bases

292

(2)

Structural Effects on Acid-Base Properties

294

(4)

Acid-Base Extraction

298

(5)

Overview

303

(20)

Isolation of Eugenol from Cloves

307

(1)

Ancient Medicine

307

(1)

Eugenol from Cloves: Overview of the Experiment

307

(1)

Isolation of Eugenol

308

(2)

GC and IR Analyses

310

(5)

Isolation of the Active Ingredients in an Analgesic Tablet

315

(1)

Overview

315

(2)

Separation of the Active Ingredients in Excedrin

317

(1)

Analysis

317

(6)

Phenols and Ethers

323

(13)

Phenols and Ethers

323

(1)

Williamson Ether Synthesis

323

(1)

Characterization of Phenols: Ferric Chloride Test

324

(1)

IR and NMR of Phenols and Ethers

325

(11)

Medicinal Chemistry: From Tylenol to a Banned Chemical

327

(1)

Analgesics

327

(2)

The Experiment: Overview

329

(1)

Conversion of Acetaminophen into Phenacetin

330

(2)

Ferric Chloride Test

332

(1)

Analysis of Analgesics by TLC

332

(4)

Electrophilic Aromatic Substitution

336

(19)

Mechanism of Electrophilic Aromatic Substitution

336

(1)

Nitration and Halogenation

337

(1)

Effects of Substituents

338

(17)

Iodination of Tyrosine

342

(1)

Synthesis of 3,5-Diiodotyrosine

342

(8)

Two Substitution Puzzles

350

(1)

Overview

350

(1)

NMR Analysis

351

(1)

Nitration of Phenacetin

352

(1)

Bromination of Phenacetin

353

(2)

Nucleophilic Aromatic Substitution

355

(13)

Nucleophilic Aromatic Substitution

355

(1)

Dinitroanilines

356

(12)

Dinitrocompounds-Herbicides

360

(1)

Synthesis of Trifluralin

360

(1)

Synthesis of N-(n-Butyl)-2,4-Dinitroaniline

361

(1)

Herbicide Effects of Trifluralin and N-(n-Butyl)-2,4-Dinitroaniline

362

(6)

Chemical Kinetics

368

(23)

Mechanistic Studies

368

(1)

Chemical Kinetics

368

(2)

Experimental Aspects

370

(1)

Integrated Rate Equations

370

(2)

Reaction Half-Life

372

(1)

Transition States

372

(3)

Dependence of the Rate Constant with Temperature: Arrhenius Equation

375

(1)

Following the Kinetics

375

(2)

Best Fit

377

(14)

Nucleophilic Aromatic Substitution Kinetics

381

(1)

The Problem

381

(2)

To Follow the Kinetics

383

(1)

Overview of the Experiment

383

(1)

Synthesis of 2,4-Dinitroanisole

384

(1)

Visible Spectrum of N-(n-Butyl)-2,4-Dinitroaniline

384

(1)

Beer's Law of N-(n-Butyl)-2,4-Dinitroaniline

385

(1)

Kinetics of the Reaction of 2,4-Dinitroanisole with n-Butylamine in Methanol

385

(6)

Diels-Alder Reaction

391

(24)

Diels-Alder Reaction

391

(1)

Endo versus Exo

392

(1)

Solvent Effects

393

(2)

Experimental Considerations: Following the Reaction

395

(20)

Diels-Alder Reactions in Toluene

398

(1)

Reaction of 9-Anthraldehyde with Maleic Anhydride

398

(2)

Reaction of Phencyclone with Norbornadiene

400

(8)

Diels-Alder Reaction in Water

408

(1)

Reaction of 9-Anthracenemethanol with N-Ethylmaleimide

408

(1)

Kinetics of the Reaction of 9-Anthracenemethanol with NEM

409

(6)

Aldehydes and Ketones

415

(23)

Introduction

415

(1)

Preparation

416

(1)

Reactions of Aldehydes and Ketones

416

(7)

IR and NMR of Aldehydes and Ketones

423

(15)

Identification of Aldehydes and Ketones

427

(1)

Characterization Tests

428

(2)

Preparation of Derivatives

430

(1)

The Unknown

430

(3)

Synthesis of trans-Cinnamic Acid

433

(1)

Synthesis of trans-Cinnamic Acid:Perkin Condensation

433

(5)

Oxidation-Reduction

438

(35)

Overview

438

(1)

Selectivity

439

(1)

Oxidations

440

(4)

Phase Transfer Catalysis

444

(1)

Reductions

445

(28)

Oxidation-Reduction

451

(1)

Reduction of Benzophenone

451

(1)

Oxidation of Benzhydrol

452

(1)

Reduction of trans-Cinnamaldehyde

453

(1)

Oxidation of trans-Cinnamyl Alcohol

454

(1)

Reduction of Camphor

455

(1)

Oxidation of Isoborneol

456

(1)

Synthesis of Terephthalic Acid

456

(2)

Monoreduction of m-Dinitrobenzene

458

(15)

Esters

473

(26)

Esters in Nature and Society

473

(1)

Preparation of Esters

474

(2)

Acetylation

476

(1)

Ester Hydrolysis

476

(1)

Characterization of Esters

477

(1)

IR and NMR of Esters and Carboxylic Acids

477

(22)

Preparation of Fruity Fragrances

480

(1)

Preparation of Methyl trans-Cinnamate: A Component of Strawberry Aroma

480

(2)

Preparation of n-Propyl Acetate and Isoamyl Acetate

482

(2)

Hydroxamic Acid Test

484

(7)

Transforming Bengay into Aspirin

491

(1)

Overview

491

(2)

Separation of Methyl Salicylate

493

(1)

Hydrolysis of Methyl Salicylate

493

(1)

Synthesis of Aspirin

494

(1)

Analysis

494

(5)

Multistep Synthesis

499

(33)

Overview

499

(1)

Multistep Synthesis

500

(2)

Retrosynthetic Analysis

502

(5)

Planning a Multistep Synthesis

507

(1)

Linear versus Convergent Synthesis

508

(24)

Synthesis of an Ant Alarm Pheromone: 2-Methyl-4-Heptanone

511

(1)

Overview

511

(1)

Synthetic Route

511

(1)

Grignard Reactions

512

(2)

Oxidation of Secondary Alcohols

514

(1)

Synthesis of 2-Methyl-4-Heptanol

514

(2)

Synthesis of 2-Methyl-4-Heptanone

516

(1)

Vacuum Distillation

516

(4)

Synthesis of Ionones: An Open-Ended Experiment

520

(1)

Ionones

520

(1)

Synthetic Pathway

520

(2)

Characterization of Ionones

522

(1)

Preparation of Pseudoionones

523

(1)

Cyclization with Sulfuric Acid-Acetic Acid

524

(1)

Cyclization with Phosphoric Acid

525

(7)

Molecules of Life

532

(24)

Proteins

532

(7)

Carbohydrates

539

(17)

Chemistry of Milk

546

(1)

Composition of Milk

546

(3)

Isolation and Characterization of Casein

549

(3)

Isolation and Characterization of Lactose

552

(4)

Lipids

556

(21)

Fats and Oils

556

(2)

Characterization of Oils

558

(1)

Uncommon Fatty Acids and Related Compounds

559

(1)

Saponification

560

(1)

Steroids

560

(2)

Bile Acids

562

(1)

Inclusion Compounds

562

(15)

Lipids

566

(1)

Analysis of Oils

566

(1)

Trimyristin From Nutmeg

567

(2)

Preparation of Azelaic Acid from Castor Oil

569

(1)

Urea Complexes of Fatty Acids

570

(1)

Solubility of Cholesterol

570

(1)

Bile Acids

571

(6)

Polymers

577

(34)

Introduction

577

(2)

Chain-Reaction Polymerization

579

(2)

Step-Reaction Polymerization

581

(2)

Polymer Structure

583

(1)

Some Typical Polymers

584

(4)

Plasticizers

588

(1)

Applications and Recycling

589

(1)

Identification of Plastics

590

(21)

Synthesis and Analysis of Polymers

595

(1)

Overview

595

(1)

Emulsion Polymerization of Styrene with Persulfate

596

(1)

Emulsion Polymerization of Methyl Methacrylate

597

(1)

Bulk Copolymerization of Styrene and Divinylbenzene: Effect of a Plasticizer

598

(1)

Bulk Polymerization of Methyl Methacrylate

599

(1)

Cellulose Triacetate

599

(2)

Phenolic Resins

601

(1)

Preparation of Nylon 6.6: The Nylon Rope Trick

601

(1)

Analysis of Polymers

602

(9)

Dyes and Pigments

611

(24)

Dyes, Pigments, and Colors

611

(1)

Azo Dyes

612

(1)

Synthesis of Azo Dyes

613

(2)

Cationic Dyes

615

(1)

Anthraquinone Dyes

616

(1)

Indigo Dyes

617

(1)

Other Dyes

618

(1)

Mode of Application

619

(1)

Dyeing

620

(15)

Colored Chemistry

626

(1)

Direct Dyes

627

(3)

Mordant Dyeing

630

(1)

Ingrain Dyes

630

(2)

Vat Dyes

632

(1)

Dye Fastness

633

(2)

Bioorganic Chemistry

635

(18)

Enzymes: Biological Catalysts

635

(1)

How Enzymes Work

635

(2)

Using Enzymes

637

(2)

Prochiral Molecules

639

(1)

Reduction of Ketones

640

(2)

Enantiomeric Excess

642

(11)

Asymmetric Synthesis with Baker's Yeast: An Open-Ended Experiment

645

(1)

Overview

645

(1)

Investigating the Course of the Reaction

646

(1)

Conformational Analysis: Determining Whether the Diol is Threo or Erythro (Advanced Level)

647

(2)

Reduction of 1-Phenyl-1,2-Propanedione with Baker's Yeast

649

(1)

Analysis

650

(3)

Molecules of Heredity

653

(14)

Nucleosides and Nucleotides

653

(3)

Base Pairing

656

(1)

Purine and Pyrimidine Bases

657

(1)

Chemical Transformations

658

(9)

Analysis of Nucleosides

662

(1)

Overview of the Experiment

662

(1)

Analysis of an RNA Digest

662

(2)

Deamination of Cytidine to Uridine

664

(3)

SECTION 3 SPECTROSCOPY

667

(136)

Absorption Spectroscopy

669

(6)

The Nature of Light

669

(1)

Interaction between Electromagnetic Radiation and Matter

670

(2)

Absorption Spectroscopy

672

(3)

Infrared Spectroscopy

675

(32)

Molecular Vibrations

675

(2)

Stretching and Bending Vibrations

677

(2)

IR and Dipole Moment

679

(1)

Regions of the IR Spectrum

680

(1)

Experimental Aspects

681

(4)

Interpreting IR Spectra

685

(8)

Case Studies

693

(2)

Concentration and Solvent Effects on IR

695

(2)

Instrumentation

697

(10)

Ultraviolet-Visible Spectroscopy

707

(12)

Electronic Transitions

707

(2)

Chromophores and Auxochromes

709

(1)

Structural Effects on UV-Visible Spectra: Woodward-Fieser Rules

710

(1)

Applications of UV-Visible Spectroscopy

711

(3)

Spectrophotometers

714

(5)

Nuclear Magnetic Resonance

719

(64)

Nuclear Spin

719

(2)

The Resonance Phenomenon: A Closer Look

721

(3)

Obtaining the NMR Spectrum

724

(2)

1H-NMR

726

(1)

Electronic Shielding

727

(2)

The Chemical Shift

729

(1)

Effect of Pi Electrons

730

(2)

Hydrogen Equivalence: A Closer Look

732

(1)

Integrals

732

(2)

Spin-Spin Splitting

734

(5)

Typical Coupling Patterns

739

(1)

The Coupling Constant

739

(3)

Coupling: A Closer Look

742

(8)

Chemical Shift Correlations

750

(6)

Coupling of Hydrogens Attached to Heteroatoms

756

(2)

13C-NMR

758

(2)

13C-NMR Chemical Shifts

760

(5)

Aromatic Systems

765

(3)

Effect of Chirality on the NMR

768

(3)

Running the Spectrum

771

(1)

Two-Dimensional NMR

772

(2)

Interpreting 1H-NMR Spectra

774

(9)

Mass Spectrometry

783

(20)

Overview

783

(1)

Instrumentation

784

(1)

The Molecular Ion

785

(4)

Charge Localization

789

(1)

Fragmentations

790

(6)

MS Case Studies

796

(2)

Interpreting Mass Spectra

798

(2)

High-Resolution Mass Spectra

800

(3)

Answers to Odd-Numbered Exercises

803

(18)

Credits

821

(2)

Index

823

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Experimental Organic Chemistry

Experimental Organic Chemistry

9780471282501

0471282502

Summary

Author Biography

Table of Contents

Supplemental Materials

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