Rent 9780138419172 | Operational Organic Chemistry : A Problem-Solving Approach to the Laboratory Course

Summary Table of Contents

This traditional-scale lab book prepares readers to perform the fundamental operations of organic chemistry in the laboratory and apply the operations intelligently in new situations -- to think and act like an organic chemist. Features traditional-scale laboratory procedures which do not require expensive, special glassware and which provide enough material for visual and physical characterization. Contains 115 experiments -- 12 experiments that teach basic operations, 46 experiments that reinforce concepts, and 47 minilabs (shorter experiment... MORE

Preface

To the Instructor

vii

Introduction

(18)

Laboratory Safety

(10)

Part I Mastering The Operations

(82)

... MORE

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

(7)

2 Extraction and Evaporation. Separating the Components of "Panacetin"

(6)

3 Recrystallization and Melting-Point Measurement. Identifying a Component of "Panacetin"

(5)

4 Heating under Reflux. Synthesis of Salicylic Acid from Wintergreen Oil

(8)

5 Simple Distillation, Gas Chromatography. Preparation of Synthetic Banana Oil

(8)

6 Fractional Distillation. Separation of Petroleum Hydrocarbons

(6)

7 Addition, Mixing, Sublimation. Preparation of Camphor

(7)

8 Boiling Point, Refractive Index. Identification of a Petroleum Hydrocarbon

(7)

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

(7)

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

(7)

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

(7)

12 Vacuum Distillation, Optical Rotation. Optical Activity of Alpha-Pinene

(6)

Part II Correlated Laboratory Experiments

101

(372)

13 Investigation of a Chemical Bond by Infrared Spectrometry

102

(7)

14 Properties of Common Functional Groups

109

(8)

15 Thin-Layer Chromatographic Analysis of Drug Components

117

(6)

16 Separation of an Alkane Clathrate

123

(7)

17 Isomers and Isomerization Reactions

130

(6)

18 Structures and Properties of Stereoisomers

136

(7)

19 Bridgehead Reactivity in an S(N)1 Solvolysis Reaction

143

(7)

20 Reaction of Iodoethane with Sodium Saccharin, an Ambident Nucleophile

150

(6)

21 Dehydration of Methylcyclohexanols

156

(10)

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

166

(9)

23 Stereochemistry of the Addition of Bromine to trans-Cinnamic Acid

175

(7)

24 Hydration of a Difunctional Alkyne

182

(8)

25 Preparation of Bromotriphenylmethane and the Trityl Free Radical

190

(7)

26 Chain-Growth Polymerization of Styrene and Methyl Methacrylate

197

(9)

27 Synthesis of Ethanol by Fermentation

206

(8)

28 The Reaction of Butanols with Hydrobromic Acid

214

(9)

29 Borohydride Reduction of Vanillin to Vanillyl Alcohol

223

(9)

30 Multistep Synthesis of Cyclopentanol from Cyclohexanol

232

(10)

31 Synthesis of Triphenylmethanol and the Trityl Carbocation

242

(10)

32 Identification of a Conjugated Diene from Eucalyptus Oil

252

(7)

33 Spectral Identification of Terpenoids

259

(7)

34 Synthesis and Spectral Analysis of Aspirin

266

(8)

35 Preparation of Nonbenzenoid Aromatic Compounds

274

(10)

36 Mechanism of the Nitration of Arenes by Nitronium Fluoborate

284

(8)

37 Friedel-Crafts Acylation of Anisole

292

(9)

38 Structure of a Natural Product in Anise Oil

301

(7)

39 Identification of an Oxygen-Containing Organic Compound

308

(7)

40 Wittig Synthesis of 1,4-Diphenyl-1,3-Butadiene

315

(8)

41 Effect of Reaction Conditions on the Condensation of Furfural with Cyclopentanone

323

(8)

42 Haloform Oxidation of 4-Methoxyacetophenone

331

(7)

43 Electronic Effect of a para-Iodo Substituent

338

(9)

44 Synthesis and Identification of an Unknown Carboxylic Acid

347

(6)

45 Preparation of the Insect Repellent N,N-Diethyl-m-Toluamide

353

(11)

46 Synthesis of 2-Acetylcyclohexanone by the Stork Enamine Reaction

364

(9)

47 Synthesis of Dimedone and Measurement of Its Tautomeric Equilibrium Constant

373

(8)

48 Preparation of Para Red and Related Azo Dyes

381

(9)

49 Reaction of Phthalimide with Sodium Hypochlorite

390

(9)

50 Identification of an Unknown Amine

399

(8)

51 Preparation and Mass Spectrum of 2-Phenyl-indole

407

(9)

52 Nucleophilic Strength and Reactivity in S(N)Ar Reactions

416

(7)

53 Structure of an Unknown D-Hexose

423

(9)

54 Fatty Acid Content of Commercial Cooking Oils

432

(8)

55 Structure of an Unknown Dipeptide

440

(9)

56 Multistep Synthesis of Benzilic Acid from Benzaldehyde

449

(8)

57 Using the Chemical Literature in an Organic Synthesis

457

(7)

58 A Research Project in Organic Chemistry

464

(9)

Part III Minilabs

473

(56)

1 Making Useful Laboratory Items

474

(1)

2 Extraction of Iodine by Dichloromethane

475

(1)

3 Purification of an Unknown Compound by Recrystallization

476

(1)

4 Developing and Testing a Hypothesis

476

(2)

5 Preparation of Acetate Esters

478

(1)

6 Gas Chromatographic Analysis of Commercial Xylene

479

(1)

7 Isolation of Caffeine from No-Doz Tablets

480

(1)

8 A Missing Label Puzzle

480

(1)

9 Paper Chromatography of Dyes in Commercial Drink Mixes

481

(2)

10 Gas Chromatographic Analysis of an Essential Oil from Orange Peel

483

(1)

11 Identification of an Unknown Felt Tip Pen Ink by TLC

484

(1)

12 Optical Rotation of Turpentine

485

(1)

13 The Structures of Organic Molecules

486

(1)

14 Who Else Has My Compound?

487

(1)

15 Isomers and Molecular Structure

488

(2)

16 Reactivities of Alkyl Halides in Nucleophilic Substitution Reactions

490

(1)

17 An S(N)1 Reaction of Bromotriphenylmethane

491

(1)

18 Preparation and Properties of a Gaseous Alkene

492

(2)

19 The Addition of Iodine to Alpha-Pinene

494

(1)

20 Unsaturation in Commercial Products

495

(2)

21 Free-Radical Bromination of Hydrocarbons

497

(1)

22 The Nylon Rope Trick

498

(1)

23 Nucleophilic Substitution Rates of Alcohols

499

(1)

24 Photoreduction of Benzophenone to Benzopinacol

500

(2)

25 Oxidation of Alcohols by Potassium Perman-ganate

502

(1)

26 Preparation of a Fluorescent Dye

503

(1)

27 Diels-Alder Reaction of Maleic Anhydride and Furan

504

(2)

28 Identification of an Unknown Arene by NMR Spectrometry

506

(1)

29 Interpretation of a Mass Spectrum

507

(1)

30 Nitration of Naphthalene

508

(1)

31 Preparation of Trityl Cations by the Friedel-Crafts Reaction

509

(1)

32 Air Oxidation of Fluorene to 9-Fluorenone

510

(1)

33 A Nucleophilic Addition-Elimination Reaction of Benzil

511

(2)

34 Preparation of Aldol Condensation Products

513

(1)

35 A Spontaneous Reaction of Benzaldehyde

514

(1)

36 Acid/Base Strengths of Organic Compounds

515

(2)

37 Hydrolysis Rates of Esters

517

(1)

38 Preparation of Benzamide

518

(1)

39 Synthesis of Dimedone Derivatives of Benzal-dehyde

519

(1)

40 A Diazonium Salt Reaction of 2-Aminobenzoic Acid

520

(1)

41 Beckmann Rearrangement of Benzophenone Oxime

521

(1)

42 Dyeing with Indigo

522

(1)

43 Reactions of Monosaccharides with Phenols

523

(3)

44 Extraction of Trimyristin from Nutmeg

526

(1)

45 Preparation of a Soap Using a Phase-Transfer Catalyst

526

(1)

46 Isolation of a Protein from Milk

527

(2)

Part IV Qualitative Organic Analysis

529

(44)

An Overview of Qual Organic

530

(1)

Preliminary Work

531

(2)

Purification

531

(1)

Measurement of Physical Constants

531

(1)

Physical Examination

532

(1)

Ignition Test

532

(1)

Classification

533

(19)

Solubility Tests

533

(3)

Classification Tests

536

(16)

Spectral Analysis

552

(1)

Infrared Spectra

552

(1)

NMR Spectra

552

(1)

Identification

553

(18)

List of Possibilities

553

(1)

Additional Tests and Data

554

(1)

Preparation of Derivatives

554

(17)

Exercises

571

(2)

Part V The Operations

573

(189)

A Basic Operations

574

(10)

1 Cleaning and Drying Glassware

574

(1)

2 Using Standard-Taper Glassware

575

(2)

3 Using Glass Rod and Tubing

577

(2)

4 Weighing

579

(2)

5 Measuring Volume

581

(3)

B Operations for Conducting Chemical Reactions

584

(14)

6 Heating

584

(8)

7 Cooling

592

(1)

8 Temperature Monitoring

593

(1)

9 Mixing

594

(1)

10 Addition of Reactants

595

(3)

C Separation Operations

598

(37)

11 Gravity Filtration

598

(2)

12 Vacuum Filtration

600

(2)

13 Extraction

602

(6)

14 Evaporation

608

(3)

15 Steam Distillation

611

(5)

16 Column Chromatography

616

(9)

17 Thin-Layer Chromatography

625

(6)

18 Paper Chromatography

631

(4)

D Washing and Drying Operations

635

(9)

19 Washing Liquids

635

(1)

20 Drying Liquids

636

(4)

21 Drying Solids

640

(2)

22 Drying and Trapping Gases

642

(2)

E Purification Operations

644

(36)

23 Recrystallization

644

(9)

24 Sublimation

653

(3)

25 Simple Distillation

656

(9)

26 Vacuum Distillation

665

(6)

27 Fractional Distillation

671

(9)

F Measuring Physical Constants

680

(17)

28 Melting Point

680

(7)

29 Boiling Point

687

(3)

30 Refractive Index

690

(3)

31 Optical Rotation

693

(4)

G Instrumental Analysis

697

(65)

32 Gas Chromatography

697

(9)

33 High Performance Liquid Chromatography

706

(4)

34 Infrared Spectrometry

710

(23)

35 Nuclear Magnetic Resonance Spectrometry

733

(15)

36 Ultraviolet-Visible Spectrometry

748

(5)

37 Mass Spectrometry

753

(9)

Appendixes and Bibliography

762

(40)

I Laboratory Equipment

763

(2)

II Keeping a Laboratory Notebook

765

(1)

III Writing a Laboratory Report

766

(5)

IV Calculations for Organic Synthesis

771

(2)

V Planning an Experiment

773

(2)

VI Properties of Organic Compounds

775

(10)

VII The Chemical Literature

785

(13)

Bibliography

798

(4)

Index

802

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

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