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Introduction to Organic Laboratory Techniques: A Microscale Approach

ISBN: 9780030238482 | 003023848X
Edition: 3rd
Format: Hardcover
Publisher: Brooks/Cole
Pub. Date: 2/1/1999

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SummaryTable of Contents
This edition features the successful format that has characterized the previous editions. It includes essays that add relevance and interest to the experiments, and emphasis on the development of the important laboratory techniques, the use of spectroscopy and instrumental methods of analysis, a section featuring conventional-scale experiments and methods, and a wide selection of well-tested and well-written experiments.
Introduction
Welcome to Organic Chemistry
2(2)
Laboratory Safety
4(16)
Advance Pre... MORE
20(7)
Laboratory Glassware
27(11)
Part One Basic Laboratory Concepts
Introduction to Microscale Laboratory
38(11)
Solubility
49(11)
Crystallization
60(11)
Extraction
71(9)
Chromatography
80(7)
Simple and Fractional Distillation
87(9)
Simple and Fractional Distillation (Semi-Microscale Procedure)
89(3)
Simple and Fractional Distillation (Microscale Procedure)
92(4)
Part Two Introduction to Microscale Methods
Isolation of the Active Ingredient in an Analgesic Drug
96(6)
Essay Aspirin
100(2)
Acetylsalicylic Acid
102(7)
Essay Analgesics
105(4)
Acetaminophen
109(6)
Acetaminophen (Microscale Procedure)
110(2)
Acetaminophen (Semi-Microscale Procedure)
112(3)
Essay Identification of Drugs
114(1)
TLC Analysis of Analgesic Drugs
115(8)
Essay Caffeine
119(4)
Isolation of Caffeine from Tea
123(8)
Essay Esters---Flavors and Fragrances
128(3)
Isopentyl Acetate (Banana Oil)
131(8)
Isopentyl Acetate (Microscale Procedure)
132(1)
Isopentyl Acetate (Semi-Microscale Procedure)
133(6)
Essay Terpenes and Phenylpropanoids
135(4)
Essential Oils from Spices: Oil of Cloves
139(7)
Oil of Cloves (Microscale Procedure)
140(1)
Oil of Cloves (Semi-Microscale Procedure)
141(5)
Essay Stereochemical Theory of Odor
143(3)
Spearmint and Caraway Oil: (+)- and (-)-Carvones
146(12)
Essay The Chemistry of Vision
154(4)
Isolation of Chlorophyll and Carotenoid Pigments from Spinach
158(12)
Part Three Introduction to Molecular Modeling
Essay Molecular Modeling and Molecular Mechanics
166(4)
An Introduction to Molecular Modeling
170(12)
The Conformations of n-Butane: Local Minima
171(1)
Cyclohexane Chair and Boat Conformations
172(1)
Substituted Cyclohexane Rings
173(1)
cis- and trans-2-Butene
173(9)
Essay Computational Chemistry-Ab Initio and Semiempirical Methods
174(8)
Computational Chemistry
182(7)
Heats of Formation: Isomerism, Tautomerism, and Regioselectivity
183(2)
Heats of Reaction: SN1 Reaction Rates
185(1)
Density-Electrostatic Potential Maps---Acidities of Carboxylic Acids
186(1)
Density-Electrostatic Potential Maps: Carbocations
186(1)
Density-LUMO Maps: Reactivities of Carbonyl Groups
187(2)
Part Four Preparations and Reactions of Organic Compounds189(238)
Reactivities of Some Alkyl Halides
190(4)
Nucleophilic Substitution Reactions: Competing Nucleophiles
194(9)
Competitive Nucleophiles with 1-Butanol or 2-Butanol
196(2)
Competitive Nucleophiles with 2-Methyl-2-propanol
198(1)
Analysis
199(4)
Hydrolysis of Some Alkyl Chlorides
203(5)
Synthesis of n-Butyl Bromide and t-Pentyl Chloride
208(7)
n-Butyl Bromide (Microscale Procedure)
210(1)
n-Butyl Bromide (Semimicroscale Procedure)
211(2)
t-Pentyl Chloride (Microscale Procedure)
213(1)
t-Pentyl Chloride (Semimicroscale Procedure)
214(1)
Elimination Reactions: Dehydration and Dehydrohalogenation
215(7)
Dehydration of 1-Butanol and 2-Butanol
219(1)
Dehydrobromination of 1-Bromobutane and 2-Bromobutane
220(2)
4-Methylcyclohexene
222(12)
4-Methylcyclohexene (Microscale Procedure)
224(1)
4-Methylcyclohexene (Semi-Microscale Procedure)
225(9)
Essay Petroleum and Fossil Fuels
227(7)
Gas-Chromatographic Analysis of Gasolines
234(10)
Essay Fats and Oils
239(5)
Methyl Stearate from Methyl Oleate
244(4)
Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene
248(10)
Essay Ethanol and Fermentation Chemistry
256(2)
Ethanol from Sucrose
258(8)
Essay Detection of Alcohol: The Breathalyzer
263(3)
An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol
266(12)
Chiral Reduction of Ethyl Acetoacetate: Optical Purity Determination Using a Chiral Shift Reagent
278(7)
Chiral Reduction of Ethyl Acetoacetate
279(3)
NMR Determination of the Optical Purity of (S)-(+)-Ethyl 3-Hydroxybutanoate
282(3)
Resolution of (±)-α-Phenylethylamine and Determination of Optical Purity
285(7)
Resolution of (±)-α-Phenylethylamine
288(2)
Determination of Optical Purity Using NMR and a Chiral Resolving Agent
290(2)
Triphenylmethanol and Benzoic Acid
292(15)
Triphenylmethanol
297(2)
Benzoic Acid
299(8)
Essay Thiamine as a Coenzyme
302(5)
Coenzyme Synthesis of Benzoin
307(3)
Benzil
310(2)
Benzilic Acid
312(4)
The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones)
316(4)
Preparation of an α,β-Unsaturated Ketone via Michael and Aldol Condensation Reactions
320(3)
Enamine Reactions: 2-Acetylcyclohexanone
323(10)
1,4-Diphenyl-1,3-butadiene
333(5)
Relative Reactivities of Several Aromatic Compounds
338(4)
Nitration of Methyl Benzoate
342(8)
Essay Local Anesthetics
346(4)
Benzocaine
350(3)
Methyl Salicylate (Oil of Wintergreen)
353(8)
Essay Soaps and Detergents
356(5)
Preparation of a Soap
361(2)
Preparation of a Detergent
363(10)
Essay Pheromones: Insect Attractants and Repellants
366(7)
N,N-Diethyl-m-toluamide: The Insect Repellent ``OFF''
373(8)
Essay Sulfa Drugs
378(3)
Sulfa Drugs: Preparation of Sulfanilamide
381(14)
Essay Polymers and Plastics
385(10)
Preparation of Properties of Polymers: Polyester, Nylon, and Polystyrene
395(11)
Polyesters
395(2)
Polyamide (Nylon)
397(1)
Polystyrene
398(2)
Infrared Spectra of Polymer Samples
400(6)
Essay Diels-Alder Reaction and Insecticides
402(4)
The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride
406(5)
Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone
411(11)
Photoreduction of Benzophenone
412(6)
Synthesis of β-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol
418(4)
Essay Fireflies and Photochemistry
419(3)
Luminol
422(5)
Part Five Identification of Organic Substances427(42)
Identification of Unknowns
428(41)
Solubility Tests
433(5)
Tests of the Elements (N, S, X)
438(6)
Tests for Unsaturation
444(4)
Aldehydes and Ketones
448(5)
Carboxylic Acids
453(2)
Phenols
455(3)
Amines
458(3)
Alcohols
461(4)
Esters
465(4)
Part Six Macroscale Experiments469(12)
Essay How to Scale Up a Reaction: Macroscale Methods
470(2)
Preparation of a C-4 or C-5 Acetate Ester
472(3)
Synthesis of n-Butyl Bromide and t-Pentyl Chloride
475(4)
n-Butyl Bromide
476(2)
t-Pentyl Chloride
478(1)
Nitration of Methyl Benzoate
479(2)
Part Seven Project-Based Experiments481(1)
A Separation and Purification Scheme
482(3)
Essay How to Scale Down an Experiment
483(2)
Conversion of Cyclohexanol to Bromocyclohexane
485(2)
Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel
487(6)
Isolation of Essential Oils by Steam Distillation
489(3)
Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry
492(1)
Investigation of the Essential Oils of Herbs and Spices---A Mini-Research Project
492(1)
Friedel-Crafts Acylation
493(7)
The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry
500(2)
The Aldehyde Enigma
502(2)
Michael and Aldol Condensation Reactions
504(3)
Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem
507(5)
Part Eight The Techniques
Measurement of Volume and Weight
512(9)
Heating and Cooling Methods
521(8)
Reaction Methods
529(16)
Filtration
545(13)
Crystallization: Purification of Solids
558(18)
Physical Constants: Melting Points, Boiling Points, Density
576(19)
Extractions, Separations, and Drying Agents
595(22)
Simple Distillation
617(12)
Vacuum Distillation, Manometers
629(15)
Fractional Distillation, Azeotropes
644(18)
Steam Distillation
662(7)
Column Chromatography
669(24)
High-Performance Liquid Chromatography (HPLC)
693(4)
Thin-Layer Chromatography
697(14)
Gas Chromatography
711(15)
Sublimation
726(5)
Polarimetry
731(6)
Refractometry
737(5)
Preparation of Samples for Spectroscopy
742(18)
Guide to the Chemical Literature
760
AppendicesA1
Appendix 1 Tables of Unknowns and Derivatives
A2
Appendix 2 Procedures for Preparing Derivatives
A11
Appendix 3 Infrared Spectroscopy
A14
Appendix 4 Nuclear Magnetic Resonance Spectroscopy
A32
Appendix 5 Carbon-13 Nuclear Magnetic Resonance Spectroscopy
A50
Appendix 6 Mass Spectrometry
A58
Appendix 7 Index of Spectra
A76
IndexI1

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