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Introduction to Organic Laboratory Techniques : Small-Scale Approach

ISBN: 9780030245190 | 0030245192
Edition: 1st
Format: Paperback
Publisher: Brooks Cole
Pub. Date: 7/15/1997

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SummaryTable of Contents
In this laboratory textbook for students of organic chemistry, experiments are designed to utilize standard-scale ("macroscale") glassware and equipment but with smaller amounts of chemicals and reagents. 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. Contains a comprehensive treatment of laboratory techniques including both small-scale and some microscale methods.
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Welcome to Organic Chemistry!2(3)
Laboratory Safety5(18)
Advance Preparation and Laboratory Records23(8)
Laboratory Glassware31(11)
Part One PREPARATIONS AND REACTIONS OF ORGANIC COMPOUNDS42(546)
Experiment 1 Isolation of the Active Ingredient in an Analgesic Drug
42(4)
Essay Aspirin
46(7)
Experiment 2 Acetylsalicylic Acid
49(4)
Essay Analgesics
53(10)
Experiment 3 Acetanilide
57(3)
Experiment 4 Acetaminophen
60(3)
Essay Caffeine
63(14)
Experiment 5 Isolation of Caffeine
68(9)
Experiment 5A Isolation of Caffeine from Tea Leaves
71(3)
Experiment 5B Isolation of Caffeine from a Tea Bag
74(2)
Experiment 5C Isolation of Caffeine from "Mountain Dew" Syrup
76(1)
Essay Identification of Drugs
77(8)
Experiment 6 TLC Analysis of Analgesic Drugs
79(6)
Essay Ethanol and Fermentation Chemistry
85(8)
Experiment 7 Ethanol from Sucrose
88(5)
Essay Esters--Flavors and Fragrances
93(17)
Experiment 8 Isopentyl Acetate (Banana Oil)
96(4)
Experiment 9 Preparation of a C-4 or C-5 Acetate Ester
100(3)
Experiment 10 Methyl Salicylate (Oil of Wintergreen)
103(5)
Experiment 11 Hydrolysis of Methyl Salicylate
108(2)
Essay Fats and Oils
110(17)
Experiment 12 Analysis of Fats and Oils by Gas Chromatography
116(5)
Experiment 13 Methyl Stearate from Methyl Oleate
121(6)
Essay Soaps and Detergents
127(12)
Experiment 14 Preparation of Soap
133(2)
Experiment 15 Preparation of a Detergent
135(4)
Essay Pheromones: Insect Attractants and Repellents
139(12)
Experiment 16 N,N-Diethyl-m-Toluamide: The Insect Repellent "OFF"
145(6)
Essay Petroleum and Fossil Fuels
151(14)
Experiment 17 Gas Chromatographic Analysis of Gasolines
159(6)
Essay Terpenes and Phenylpropanoids
165(24)
Experiment 18 Isolation of Essential Oils from Allspice, Cloves, Cumin, Caraway, Cinnamon, or Fennel
169(4)
Experiment 19 Thin-Layer Chromatography from Monitoring the Oxidation of Borneol to Camphor
173(3)
Experiment 20 An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol
176(13)
Essay Stereochemical Theory of Odor
189(41)
Experiment 21 Spearmint and Caraway Oil: (+) and (-) Carvones
192(8)
Experiment 22 Reactivities of Some Alkyl Halides
200(4)
Experiment 23 Synthesis of n-Butyl Bromide and t-Pentyl Chloride
204(7)
Experiment 23A n-Butyl Bromide
207(2)
Experiment 23B t-Penyl Chloride
209(2)
Experiment 24 Nucleophilic Substitution Reactions: Competing Nucleophiles
211(10)
Experiment 24A Competitive Nucleophiles with 1-Butanol or 2-Butanol
214(2)
Experiment 24B Competitive Nucleophiles with 2-Methyl-2-Propanol
216(2)
Experiment 24C Analysis
218(3)
Experiment 25 Hydrolysis of Some Alkyl Chlorides
221(9)
Experiment 25A Hydrolysis of Some Alkyl Chlorides (Titration Method)
225(2)
Experiment 25B Hydrolysis of Alkyl Chlorides (Computer-Interfaced Method)
227(3)
Essay Detection of Alcohol: The Breathalyzer
230(83)
Experiment 26 Chromic Acid Oxidation of Alcohols
234(14)
Experiment 26A Chromic Acid Oxidation of Alcohols--Visible Spectrophotometer Method
241(1)
Experiment 26B Chromic Acid Oxidation of Alcohols--UV-VIS Spectrophotometer Method
242(2)
Experiment 26C Chromic Acid Oxidation of Alcohols--Computer-Interfaced Method
244(4)
Experiment 27 4-Methylcyclohexene
248(5)
Experiment 28 Phase Transfer Catalysis: Addition of Dichlorocarbene to Cyclohexene
253(8)
Experiment 29 Markovnikov and Anti-Markovnikov Hydration of 1-Methylcyclohexene
261(15)
Experiment 29A Hydroboration-Oxidation of 1-Methylcyclohexene
266(4)
Experiment 29B Oxymercuration of 1-Methylcyclohexene
270(3)
Experiment 29C Analysis Procedures
273(3)
Experiment 30 Triphenylmethanol and Benzoic Acid
276(12)
Experiment 30A Triphenylmethanol
283(2)
Experiment 30B Benzoic Acid
285(3)
Experiment 31 Carbonation of an Unknown Aromatic Halide
288(31)
Experiment 32 The Preparation of Pinacol and the Pinacol Rearrangement
291(6)
Experiment 32A Preparation of Pinacol Hexahydrate
293(2)
Experiment 32B Preparation of Pinacolone
295(2)
Experiment 33 Nitration of Methyl Benzoate
297(4)
Experiment 34 Relative Reactivities of Several Aromatic Compounds
301(5)
Experiment 35 Friedel-Crafts Acylation
306(7)
Essay Synthetic Dyes
313(10)
Experiment 36 Methyl Orange
318(5)
Essay Dyes and Fabrics
323(14)
Experiment 37 Dyes, Fabrics, and Dyeing
330(7)
Essay Food Colors
337(10)
Experiment 38 Chromatography of Some Dye Mixtures
342(5)
Essay The Chemistry of Vision
347(13)
Experiment 39 Isolation of Chlorophyll and Carotenoid Pigments from Spinach
352(8)
Essay Thiamine as a Coenzyme
360(15)
Experiment 40 Coenzyme Synthesis of Benzoin
365(4)
Experiment 41 Benzil
369(2)
Experiment 42 Benzilic Acid
371(4)
Essay Sulfa Drugs
375(13)
Experiment 43 Sulfa Drugs: Preparation of Sulfanilamide
378(5)
Experiment 44 p-Aminobenzioc Acid
383(5)
Essay Local Anesthetics
388(29)
Experiment 45 Benzocaine
392(3)
Experiment 46 Tetraphenylcyclopentadienone
395(3)
Experiment 47 Enamine Reactions: 2-Acetylcyclohexanone
398(11)
Experiment 48 The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones)
409(4)
Experiment 49 Preparation of an XXX, B-Unsaturated Ketone via Michael and Aldol Condensation Reactions
413(4)
Essay Molecular Modeling and Molecular Mechanics
417(10)
Experiment 50 An Introduction to Molecular Modeling
423(4)
Experiment 50A The Conformations of n-Butane: Local Minima
423(2)
Experiment 50B Cyclohexane Chair and Boat Conformations
425(1)
Experiment 50C Substituted Cyclohexane Rings
426(1)
Experiment 50D cis- and trans-2-Butane
426(1)
Essay Diels-Alder Reaction and Insecticides
427(25)
Experiment 51 The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride
432(4)
Experiment 52 Benzyne Formation and the Diels-Alder Reaction: Preparation of 1, 2, 3, 4-Tetraphenylnaphthalene
436(6)
Experiment 53 Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone
442(10)
Experiment 53A Photoreduction of Benzophenone
443(7)
Experiment 53B Synthesis of B-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol
450(2)
Essay Fireflies and Photochemistry
452(15)
Experiment 54 Luminol
455(5)
Experiment 55 1, 4-Diphenyl-1, 3-butadiene
460(7)
Essay Polymers and Plastics
467(66)
Experiment 56 Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene
477(8)
Experiment 56A Polyesters
478(1)
Experiment 56B Polyamide (Nylon)
478(3)
Experiment 56C Polystyrene
481(2)
Experiment 56D Infrared Spectra of Polymer Samples
483(2)
Experiment 57 Identification of Unknowns
485(48)
Experiment 57A Solubility Tests
491(5)
Experiment 57B Tests for the Elements (N, S, X)
496(7)
Experiment 57C Tests for Unsaturation
503(5)
Experiment 57D Aldehydes and Ketones
508(6)
Experiment 57E Carboxylic Acids
514(3)
Experiment 57F Phenols
517(3)
Experiment 57G Amines
520(4)
Experiment 57H Alcohols
524(5)
Experiment 57I Esters
529(4)
Essay The Chemistry of Sweeteners
533(16)
Experiment 58 Carbohydrates
536(10)
Experiment 59 Analysis of a Diet Soft Drink by HPLC
546(3)
Essay Chemistry of Milk
549(39)
Experiment 60 Isolation of Casein and Lactose from Milk
554(6)
Experiment 60A Isolation of Casein from Milk
557(1)
Experiment 60B Isolation of Lactose from Milk
558(2)
Experiment 61 Mutarotation of Lactose
560(3)
Experiment 62 Resolution of (+ -)-XXX-Phenylethylamine and Determination of Optical Purity
563(7)
Experiment 62A Resolution of (+)-XXX-Phenylethylamine
566(2)
Experiment 62B Determination of Optical Purity Using NMR and a Chiral Resolving Agent
568(2)
Experiment 63 Chiral Reduction of Ethyl Acetoacetate: Optical Purity Determination Using a Chiral Shift Reagent
570(9)
Experiment 63A Chiral Reduction of Ethyl Acetoacetate
571(3)
Experiment 63B NMR Determination of the Optical Purity of (S)-(+) Ethyl 3-Hydroxybutanoate
574(5)
Experiment 64 Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem
579(2)
Experiment 65 The Fatty Acids: An Exercise in Molecular Modeling
581(7)
Part Two THE TECHNIQUES588(290)
Technique 1 Measurement of Volume and Weight
588(12)
Technique 2 Heating and Cooling Methods
600(12)
Technique 3 Reaction Methods
612(22)
Technique 4 Filtration
634(14)
Technique 5 Crystallization: Purification of Solids
648(17)
Technique 6 Physical Constants: Melting Points, Boiling Points, Density
665(20)
Technique 7 Extractions, Separations, and Drying Agents
685(21)
Technique 8 Simple Distillation
706(11)
Technique 9 Vacuum Distillation, Manometers
717(15)
Technique 10 Fractional Distillation, Azeotropes
732(21)
Technique 11 Steam Distillation
753(8)
Technique 12 Column Chromatography
761(26)
Technique 13 High-Performance Liquid Chromatography (HPLC)
787(5)
Technique 14 Thin-Layer Chromatography
792(16)
Technique 15 Gas Chromatography
808(16)
Technique 16 Sublimation
824(5)
Technique 17 Polarimetry
829(7)
Technique 18 Refractometry
836(6)
Technique 19 Preparation of Samples for Spectroscopy
842(19)
Technique 20 Guide to the Chemical Literature
861(17)
APPENDICES878(65)
Appendix 1 Tables of Unknowns and Derivatives878(10)
Appendix 2 Procedures for Preparing Derivatives888(4)
Appendix 3 Infrared Spectroscopy892(19)
Appendix 4 Nuclear Magnetic Resonance Spectroscopy911(20)
Appendix 5 Carbon-13 Nuclear Magnetic Resonance Spectroscopy931(9)
Appendix 6 Index of Spectra940(3)
Index943

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