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Multiscale Operational Organic Chemistry : A Problem-Solving Approach to the Laboratory Course,9780130154958
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Multiscale Operational Organic Chemistry : A Problem-Solving Approach to the Laboratory Course

by
Edition:
2nd
ISBN13:

9780130154958

ISBN10:
0130154954
Format:
Hardcover
Pub. Date:
1/1/2009
Publisher(s):
Prentice Hall
List Price: $140.20
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Summary

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.

Table of Contents

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

Excerpts

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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