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Introduction to Organic Laboratory Techniques : A Microscale Approach,9780495016304
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Introduction to Organic Laboratory Techniques : A Microscale Approach

by ; ; ;
Edition:
4th
ISBN13:

9780495016304

ISBN10:
0495016306
Format:
Hardcover
Pub. Date:
2/1/2006
Publisher(s):
Cengage Learning
List Price: $371.32
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Summary

In this laboratory textbook for students of organic chemistry, experiments are designed to utilize microscale glassware and equipment. The textbook features a large number of traditional organic reactions and syntheses, as well as the isolation of natural products and experiments with a biological or health sciences focus. The organization of the text is based on essays and topics of current interest. The lab manual contains a comprehensive treatment of laboratory techniques.

Table of Contents

PART 1 Introduction to Basic Laboratory Techniques
1(150)
Introduction to Microscale Laboratory
2(11)
Solubility
13(8)
Crystallization
21(11)
Semimicroscale Crystallization---Erlenmeyer Flask and Hirsch Funnel
22(3)
Microscale Crystallization---Craig Tube
25(2)
Selecting a Solvent to Crystallize a Substance
27(1)
Mixture Melting Points
28(1)
Critical Thinking Application
29(3)
Extraction
32(10)
Extraction of Caffeine
33(3)
Distribution of a Solute between Two Immiscible Solvents
36(1)
How Do You Determine Which One Is the Organic Layer?
37(1)
Use of Extraction to Isolate a Neutral Compound from a Mixture Containing an Acid or Base Impurity
38(2)
Critical Thinking Application
40(2)
Chromatography
42(9)
Thin-Layer Chromatography
43(2)
Selecting the Correct Solvent for Thin-Layer Chromatography
45(1)
Monitoring a Reaction with Thin-Layer Chromatography
46(2)
Column Chromatography
48(3)
Simple and Fractional Distillation
51(6)
Simple and Fractional Distillation (Semimicroscale Procedure)
53(3)
Simple and Fractional Distillation (Microscale Procedure)
56(1)
Infrared Spectroscopy and Boiling-Point Determination
57(6)
Aspirin
61(2)
Acetylsalicylic Acid
63(8)
Analgesics
67(4)
Isolation of the Active Ingredient in an Analgesic Drug
71(4)
Acetaminophen
75(7)
Acetaminophen (Microscale Procedure)
76(2)
Acetaminophen (Semimicroscale Procedure)
78(2)
Identification of Drugs
80(2)
TLC Analysis of Analgesic Drugs
82(8)
Caffeine
87(3)
Isolation of Caffeine from Tea or Coffee
90(13)
Extraction of Caffeine from Tea with Methylene Chloride
93(2)
Extraction of Caffeine from Tea or Coffee Using Solid Phase Extraction (SPE)
95(4)
Esters---Flavors and Fragrances
99(4)
Isopentyl Acetate (Banana Oil)
103(9)
Isopentyl Acetate (Microscale Procedure)
104(2)
Isopentyl Acetate (Semimicroscale Procedure)
106(2)
Terpenes and Phenylpropanoids
108(4)
Essential Oils: Extraction of Oil of Cloves by Steam Distillation and Liquid Carbon Dioxide
112(12)
Oil of Cloves (Microscale Procedure)
113(2)
Oil of Cloves (Semimicroscale Procedure)
115(1)
Extraction of Oil of Cloves with Liquid Carbon Dioxide---A Demonstration
116(3)
Stereochemical Theory of Odor
119(5)
Spearmint and Caraway Oil: (+)-and (--)-Carvones
124(12)
The Chemistry of Vision
132(4)
Isolation of Chlorophyll and Carotenoid Pigments from Spinach
136(9)
Ethanol and Fermentation Chemistry
142(3)
Ethanol from Sucrose
145(6)
PART 2 Introduction to Molecular Modeling
151(24)
Molecular Modeling and Molecular Mechanics
152(4)
An Introduction to Molecular Modeling
156(12)
The Conformations of n-Butane: Local Minima
157(1)
Cyclohexane Chair and Boat Conformations
158(1)
Substituted Cyclohexane Rings
159(1)
cis- And trans-2-Butene
159(1)
Computational Chemistry---ab Initio and Semiempirical Methods
160(8)
Computational Chemistry
168(7)
Heats of Formation: Isomerism, Tautomerism, and Regioselectivity
169(2)
Heats of Reaction: SN1 Reaction Rates
171(1)
Density--Electrostatic Potential Maps---Acidities of Carboxylic Acids
172(1)
Density--Electrostatic Potential Maps: Carbocations
173(1)
Density--LUMO Maps: Reactivities of Carbonyl Groups
173(2)
PART 3 Properties and Reactions of Organic Compounds
175(272)
Reactivities of Some Alkyl Halides
176(4)
Nucleophilic Substitution Reactions: Competing Nucleophiles
180(10)
Competitive Nucleophiles with 1-Butanol or 2-Butanol
183(3)
Competitive Nucleophiles with 2-Methyl-2-Propanol
186(1)
Analysis
187(3)
Hydrolysis of Some Alkyl Chlorides
190(5)
Synthesis of n-Butyl Bromide and t-Pentyl Chloride
195(9)
n-Butyl Bromide
197(2)
n-Butyl Bromide (Semimicroscale Procedure)
199(1)
t-Pentyl Chloride (Microscale Procedure)
200(1)
t-Pentyl Chloride (Semimicroscale Procedure)
201(1)
t-Pentyl Chloride (Macroscale Procedure)
202(2)
Elimination Reactions: Dehydration and Dehydrohalogenation
204(7)
Dehydration of 1-Butanol and 2-Butanol
207(1)
Dehydrobromination of 1-Bromobutane and 2-Bromobutane
208(3)
4-Methylcyclohexene
211(6)
4-Methylcyclohexene (Microscale Procedure)
213(1)
4-Methylcyclohexene (Semimicroscale Procedure)
214(3)
Phase-Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene
217(7)
Relative Reactivities of Several Aromatic Compounds
224(4)
Nitration of Methyl Benzoate
228(11)
Fats and Oils
233(6)
Methyl Stearate from Methyl Oleate
239(10)
Soaps and Detergents
243(6)
Preparation of a Soap
249(2)
Preparation of a Detergent
251(13)
Petroleum and Fossil Fuels
255(9)
Gas-Chromatographic Analysis of Gasolines
264(10)
Green Chemistry
268(6)
Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination
274(10)
Chiral Reduction of Ethyl Acetoacetate
275(4)
NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate
279(5)
Nitration of Aromatic Compounds Using a Recyclable Catalyst
284(4)
An Oxidation--Reduction Scheme: Borneol, Camphor, Isoborneol
288(14)
Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid
302(12)
Preparation of Benzoin by Thiamine Catalysis
303(6)
Preparation of Benzil
309(2)
Preparation of Benzilic Acid
311(3)
Tetraphenylcyclopentadienone
314(3)
Triphenylmethanol and Benzoic Acid
317(11)
Triphenylmethanol
322(3)
Benzoic Acid
325(3)
Aqueous-Based Organozinc Reactions
328(3)
Resolution of (±)-α-Phenylethylamine and Determination of Optical Purity
331(8)
Resolution of (±)-α-Phenylethylamine
334(3)
Determination of Optical Purity Using NMR and a Chiral Resolving Agent
337(2)
The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones)
339(5)
Preparation of an α,β-Unsaturated Ketone via Michael and Aldol Condensation Reactions
344(4)
Enamine Reactions: 2-Acetylcyclohexanone
348(11)
1,4-Diphenyl-1,3-butadiene
359(11)
Benzyltriphenylphosphonium Chloride (Wittig Salt)
362(1)
Preparation of 1,4-Diphenyl-1,3-Butadiene Using Sodium Ethoxide to Generate the Ylide
362(2)
Preparation of 1,4-Diphenyl-1,3-Butadiene Using Potassium Phosphate to Generate the Ylide
364(3)
Local Anesthetics
367(3)
Benzocaine
370(3)
Methyl Salicylate (Oil of Wintergreen)
373(10)
Pheromones: Insect Attractants and Repellents
377(6)
N,N-Diethyl-m-Toluamide: The Insect Repellent ``OFF''
383(9)
Sulfa Drugs
388(4)
Sulfa Drugs: Preparation of Sulfanilamide
392(14)
Polymers and Plastics
397(9)
Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene
406(13)
Polyesters
407(2)
Polyamide (Nylon)
409(1)
Polystyrene
410(2)
Infrared Spectra of Polymer Samples
412(2)
Diels--Alder Reaction and Insecticides
414(5)
The Diels--Alder Reaction of Cyclopentadiene with Maleic Anhydride
419(5)
Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone
424(13)
Photoreduction of Benzophenone
425(6)
Synthesis of β-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol
431(2)
Fireflies and Photochemistry
433(4)
Luminol
437(7)
The Chemistry of Sweeteners
441(3)
Analysis of a Diet Soft Drink by HPLC
444(3)
PART 4 Identification of Organic Substances
447(48)
Identification of Unknowns
448(47)
Solubility Tests
454(6)
Tests for the Elements (N, S, X)
460(6)
Tests for Unsaturation
466(4)
Aldehydes and Ketones
470(7)
Carboxylic Acids
477(2)
Phenols
479(3)
Amines
482(4)
Alcohols
486(5)
Esters
491(4)
PART 5 Project-Based Experiments
495(46)
A Separation and Purification Scheme
496(2)
Preparation of a C-4 or C-5 Acetate Ester
498(4)
Extraction of Essential Oils from Caraway, Cinnamon, Cloves, Cumin, or Fennel by Steam Distillation
502(8)
Isolation of Essential Oils by Steam Distillation
504(3)
Identification of the Constituents of Essential Oils by Gas Chromatography--Mass Spectrometry
507(1)
Investigation of the Essential Oils of Herbs and Spices---A Mini--Research Project
508(2)
Competing Nucleophiles in SN1 and SN2 Reactions: Investigations Using 2-Pentanol and 3-Pentanol
510(5)
Friedel--Crafts Acylation
515(7)
The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry
522(2)
The Use of Organozinc Reagents in Synthesis: An Exercise in Synthesis and Structure Proof by Spectroscopy
524(3)
The Aldehyde Enigma
527(2)
Synthesis of Substituted Chalcones: A Guided-Inquiry Experience
529(4)
Michael and Aldol Condensation Reactions
533(3)
Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem
536(2)
An Oxidation Puzzle
538(3)
PART 6 The Techniques
541(416)
Laboratory Safety
542(16)
The Laboratory Notebook, Calculations, and Laboratory Records
558(8)
Laboratory Glassware: Care and Cleaning
566(8)
How to Find Data for Compounds: Handbooks and Catalogs
574(7)
Measurement of Volume and Weight
581(8)
Heating and Cooling Methods
589(9)
Reaction Methods
598(18)
Filtration
616(11)
Physical Constants of Solids: The Melting Point
627(10)
Solubility
637(10)
Crystallization: Purification of Solids
647(22)
Extractions, Separations, and Drying Agents
669(25)
Physical Constants of Liquids: The Boiling Point and Density
694(9)
Simple Distillation
703(12)
Fractional Distillation, Azeotropes
715(17)
Vacuum Distillation, Manometers
732(13)
Sublimation
745(5)
Steam Distillation
750(6)
Column Chromatography
756(21)
Thin-Layer Chromatography
777(15)
High-Performance Liquid Chromatography (HPLC)
792(5)
Gas Chromatography
797(21)
Polarimetry
818(9)
Refractometry
827(6)
Infrared Spectroscopy
833(35)
Nuclear Magnetic Resonance Spectroscopy (Proton NMR)
868(38)
Carbon-13 Nuclear Magnetic Resonance Spectroscopy
906(18)
Mass Spectrometry
924(18)
Guide to the Chemical Literature
942(15)
Appendices
957(22)
Tables of Unknowns and Derivatives
958(13)
Procedures for Preparing Derivatives
971(5)
Index of Spectra
976(3)
Index 979


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