9780130154958

This practical laboratory book provides both microscale and multiscale experiments. It encourages readers to think in the laboratory by solving a scientific problem in the process of carrying out an experiment. An "operational" approach is featured, equipping readers to master the major lab operations as they carry out problem solving experiments. Over 400 problems and exercises are provided. A valuable reference for organic chemists and chemical technicians.

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Preface

viii

To the Instructor

viii

Introduction

1

(8)

Laboratory Safety

9

(10)

Part I Mastering the Operations

19

(88)

Learning Basic Operations. The Effect of pH on a Food Preservative

20

(8)

Extraction and Evaporation. Separating the Components of ``Panacetin''

28

(7)

Recrystallization and Melting-Point Measurement. Identifying a Constituent of ``Panacetin''

35

(5)

Heating Under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil

40

(9)

Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil

49

(9)

Fractional Distillation. Separation of Petroleum Hydrocarbons

58

(7)

Addition, Mixing, Sublimation, Preparation of Camphor

65

(7)

Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon

72

(6)

Column Chromatography, UV-VIS Spectrometry. Isolation and Isomerization of Lycopene from Tomato Paste

78

(9)

Steam Distillation, Infrared Spectrometry. Isolation and Identification of the Major Constituent of Clove Oil

87

(7)

Thin-Layer Chromatography, NMR Spectrometry. Identification of Unknown Ketones

94

(7)

Vacuum Distillation, Optical Rotation. Optical Activity of α-Pinene

101

(6)

Part II Correlated Laboratory Experiments

107

(352)

Investigation of a Chemical Bond by Infrared Spectrometry

108

(7)

Properties of Common Functional Groups

115

(8)

Thin-Layer Chromatographic Analysis of Drug Components

123

(5)

Separation of an Alkane Clathrate

128

(7)

Isomers and Isomerization Reactions

135

(6)

Structures and Properties of Stereoisomers

141

(8)

Bridgehead Reactivity in an SN1 Solvolysis Reaction

149

(7)

Reaction of Iodoethane with Saccharin, an Ambident Nucleophile

156

(6)

Dehydration of Methylcyclohexanols

162

(10)

Synthesis of 7,7-Dichloronorcarane Using a Phase-Transfer Catalyst

172

(9)

Stereochemistry of the Addition of Bromine to trans-Cinnamic Acid

181

(7)

Preparation of Bromotriphenylmethane and the Trityl Free Radical

188

(8)

Chain-growth Polymerization of Styrene and Methyl Methacrylate

196

(9)

Synthesis of Ethanol by Fermentation

205

(8)

Reaction of Butanols with Hydrobromic Acid

213

(10)

Borohydride Reduction of Vanillin to Vanillyl Alcohol

223

(9)

Synthesis of Triphenylmethanol and the Trityl Carbocation

232

(11)

Identification of a Conjugated Diene from Eucalyptus Oil

243

(7)

Spectral Identification of Terpenoids

250

(7)

Synthesis and Spectral Analysis of Aspirin

257

(8)

Preparation of Nonbenzenoid Aromatic Compounds

265

(10)

Mechanism of the Nitration of Arenes by Nitronium Fluoborate

275

(7)

Friedel-Crafts Acylation of Anisole

282

(9)

Structure of a Natural Product in Anise Oil

291

(7)

Identification of an Oxygen-containing Organic Compound

298

(7)

Wittig Synthesis of 1,4-Diphenyl-1,3-butadiene

305

(8)

Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone

313

(9)

Haloform Oxidation of 4'-Methoxyacetophenone

322

(7)

Electronic Effect of a para-Iodo Substituent

329

(9)

Synthesis and Identification of an Unknown Carboxylic Acid

338

(6)

Preparation of the Insect Repellent N, N-Diethyl-meta-toluamide

344

(11)

Synthesis of Dimedone and Measurement of its Tautomeric Equilibrium Constant

355

(8)

Preparation of Para Red and Related Azo Dyes

363

(9)

Reaction of Phthalimide with Sodium Hypochlorite

372

(9)

Identification of an Unknown Amine

381

(7)

Preparation and Mass Spectrum of 2-Phenylindole

388

(10)

Nucleophilic Strength and Reactivity in SNAr Reactions

398

(7)

Structure of an Unknown D-Hexose

405

(9)

Fatty Acid Content of Commerical Cooking Oils

414

(8)

Structure of an Unknown Dipeptide

422

(10)

Multistep Synthesis of Benzilic Acid from Benzaldehyde

432

(10)

Using the Chemical Literature in an Organic Synthesis

442

(7)

A Research Project in Organic Chemistry

449

(10)

Part III Minilabs

459

(54)

Making Useful Laboratory Items

460

(1)

Extraction of Iodine by Dichloromethane

461

(1)

Purification of an Unknown Compound by Recrystallization

462

(1)

Developing and Testing a Hypothesis

462

(2)

Preparation of Acetate Esters

464

(1)

Gas Chromatographic Analysis of Commercial Xylene

465

(1)

Isolation of Caffeine from No-Doz Tablets

466

(1)

A Missing-Label Puzzle

466

(1)

Paper Chromatography of Dyes in Commercial Drink Mixes

467

(2)

Gas Chromatographic Analysis of an Essential Oil from Orange Peel

469

(1)

Identification of an Unknown Felt-Tip-Pen Ink by TLC

470

(1)

Optical Rotation of Turpentine

471

(1)

The Structures of Organic Molecules

472

(1)

Who Else Has My Compound?

473

(1)

Isomers and Molecular Structure

474

(1)

Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions

475

(2)

An SN1 Reaction of Bromotriphenylmethane

477

(1)

Preparation and Properties of a Gaseous Alkene

478

(2)

The Addition of Iodine to α-Pinene

480

(1)

Unsaturation in Commercial Products

481

(1)

Free-Radical Bromination of Hydrocarbons

482

(1)

The Nylon Rope Trick

483

(2)

Nucleophilic Substitution Rates of Alcohols

485

(1)

Photoreduction of Benzophenone to Benzopinacol

486

(1)

Oxidation of Alcohols by Potassium Permanganate

487

(1)

Preparation of a Fluorescent Dye

488

(1)

Diels--Alder Reaction of Maleic Anhydride and Furan

489

(2)

Identification of an Unknown Arene by NMR Spectrometry

491

(1)

Interpretation of a Mass Spectrum

492

(1)

Nitration of Naphthalene

493

(1)

Preparation of Trityl Cations by the Friedel-Crafts Reaction

494

(1)

Air Oxidation of Fluorene to 9-Fluorenone

495

(1)

A Nucleophilic Addition-Elimination Reaction of Benzil

496

(2)

Preparation of Aldol Condensation Products

498

(1)

A Spontaneous Reaction of Benzaldehyde

499

(1)

Acid--Base Strengths of Organic Compounds

500

(2)

Hydrolysis Rates of Esters

502

(1)

Preparation of Benzamide

503

(1)

Synthesis of Dimedone Derivatives of Benzaldehyde

504

(1)

A Diazonium Salt Reaction of 2-Aminobenzoic Acid

505

(1)

Beckmann Rearrangement of Benzophenone Oxime

506

(1)

Dyeing with Indigo

507

(1)

Reaction of Monosaccharides with Phenols

508

(2)

Extraction of Trimyristin from Nutmeg

510

(1)

Preparation of a Soap Using a Phase-Transfer Catalyst

511

(1)

Isolation of a Protein from Milk

512

(1)

Part IV Qualitative Organic Analysis

513

(46)

An Overview of Qual Organic

514

(1)

Preliminary Work

515

(2)

Purification

515

(1)

Measurement of Physical Constants

515

(1)

Physical Examination

516

(1)

Ignition Test

516

(1)

Classification

517

(20)

Solubility Tests

517

(3)

Classification Tests

520

(17)

Spectral Analysis

537

(1)

Infrared Spectra

537

(1)

NMR Spectra

537

(1)

Identification

538

(19)

List of Possibilities

538

(1)

Additional Tests and Data

539

(1)

Preparation of Derivatives

540

(17)

Exercises

557

(2)

Part V The Operations

559

(238)

Basic Operations

560

(1)

Cleaning and Drying Glassware

560

(1)

Using Specialized Glassware

561

(4)

Using Glass Rod and Tubing

565

(3)

Weighing

568

(2)

Measuring Volume

570

(3)

Making Transfers

573

(4)

Operations for Conducting Chemical Reactions

577

(1)

Heating

577

(13)

Cooling

590

(1)

Temperature Monitoring

591

(1)

Mixing

592

(2)

Addition of Reactants

594

(3)

Separation Operations

597

(1)

Gravity Filtration

597

(3)

Vacuum Filtration

600

(3)

Centrifugation

603

(2)

Extraction

605

(10)

Evaporation

615

(5)

Steam Distillation

620

(6)

Column Chromatography

626

(11)

Thin-Layer Chromatography

637

(7)

Paper Chromatography

644

(4)

Washing and Drying Operations

648

(1)

Washing Liquids

648

(2)

Drying Liquids

650

(5)

Drying Solids

655

(2)

Drying and Trapping Gases

657

(4)

Purification Operations

661

(1)

Recrystallization

661

(15)

Sublimation

676

(3)

Simple Distillation

679

(13)

Vacuum Distillation

692

(11)

Fractional Distillation

703

(11)

Measuring Physical Constants

714

(1)

Melting Point

714

(6)

Boiling Point

720

(5)

Refractive Index

725

(3)

Optical Rotation

728

(4)

Instrumental Analysis

732

(1)

Gas Chromatography

732

(9)

High-Performance Liquid Chromatography

741

(4)

Infrared Spectrometry

745

(24)

Nuclear Magnetic Resonance Spectrometry

769

(14)

Ultraviolet-Visible Spectrometry

783

(5)

Mass Spectrometry

788

(9)

Appendixes and Bibliography

797

(38)

I Laboratory Equipment

798

(4)

II Keeping a Laboratory Notebook

802

(1)

III Writing a Laboratory Report

803

(5)

IV Calculations for Organic Synthesis

808

(2)

V Planning an Experiment

810

(2)

VI Properties of Organic Compounds

812

(10)

VII The Chemical Literature

822

(13)

Bibliography

835

(6)

Index

841

What is included with this book?

The New copy of this book will include any supplemental materials advertised. Please check the title of the book to determine if it should include any access cards, study guides, lab manuals, CDs, etc.

The Used, Rental and eBook copies of this book are not guaranteed to include any supplemental materials. Typically, only the book itself is included. This is true even if the title states it includes any access cards, study guides, lab manuals, CDs, etc.

To the Instructor This book is a multiscale laboratory textbook based on the third edition of Operational Organic Chemistry. -A Problem-Solving Approach to the Laboratory Course. Every experiment and minilab can be performed by students using either standard scale glassware, such as that available in an organic chemistry lab kit with 19/22 standard-taper joints, or microscale glassware, such as that in a microscale lab kit with 14hO standard-taper joints and threaded connectors. Most of the microscale experiments could be performed successfully with alternative microscale glassware, such as that provided in a Williamson lab kit (described in Microscale and Macroscale Organic Experiments, D.C. Heath and Co.). However, some might need to be scaled down further, and the instructor would have to provide additional instructions regarding the use of the glassware. Some organic chemists regard a microscale experiment as one involving approximately 0.1 g of the limiting reactant. Dealing with such small quantities can be discouraging to students with standard scale fingers, who tend to end up with a drop or a few grains of product, if any. I have adopted a more flexible definition of a microscale experiment as one that can be performed with the glassware available in a typical microscale lab. In writing this textbook, I have been guided by my convictions that students (1) perform better in the organic laboratory course if they master the major lab operations early and apply them throughout, (2) learn organic chemistry better if they keep their minds engaged by approaching each experiment as a problem-solving exercise, and (3) perform any task better if they are sufficiently motivated. Part I of this book is devoted to experiments designed to teach the basic laboratory operations, where an operation, as used here, is a process that uses one or more basic lab techniques-such as heating, cooling, or vacuum filtration-to accomplish some end, such as the purification of a solid. Once students have mastered the major operations by completing the appropriate experiments in Part I, they should be ready to apply those operations in Part II, which contains a large selection of experiments that are correlated with topics found in most organic chemistry lecture textbooks. This operational approach helps students understand that an organic synthesis, for example, is not a unique phenomenon that can be experienced only by mechanically following a detailed "recipe." Rather, it is the outcome of a logical sequence of interrelated operations adapted to the requirements of the synthesis. In addition to teaching lab skills, the experiments in this book are designed to help students develop the observational and critical thinking skills that are essential prerequisites for a successful career in science and in virtually every other profession. From the student's viewpoint, the purpose of each major experiment is the solution of a problem through the application of scientific methodology. Before each experiment, the student must first define the problem based on information provided in a hypothetical Scenario. After a preliminary reading of the experiment, the student should be able to develop a working hypothesis regarding its outcome. During the experiment, the student gathers and evaluates evidence bearing on the problem and, as necessary, reevaluates and revises the hypothesis based on experimental observations and data. Finally, the student tests the hypothesis by obtaining a melting point, a spectrum, a gas chromatogram, or by some other means, and arrives at a conclusion. Because of the level at which most undergraduate organic chemistry are taught, the problems must, of necessity, be kept relatively simple and (with a few exceptions) should not be compared to "real" research problems tackled by professional chemists. It is not the intent of this book to make every student a research chemist; most students who tak

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Multiscale Operational Organic Chemistry : A Problem-Solving Approach to the Laboratory Course

Multiscale Operational Organic Chemistry : A Problem-Solving Approach to the Laboratory Course

0130154954

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