Introduction to Organic Laboratory Techniques : Small-Scale Approach

by Pavia, Donald L.

• ISBN13: 9780030245190
• ISBN10: 0030245192
• Edition: 1st
• Format: Paperback
• Copyright: 1997-07-15
• Publisher: Brooks Cole

Summary

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.

Table of Contents

Welcome to Organic Chemistry!	2	(3)
Laboratory Safety	5	(18)
Advance Preparation and Laboratory Records	23	(8)
Laboratory Glassware	31	(11)
Part One PREPARATIONS AND REACTIONS OF ORGANIC COMPOUNDS	42	(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 TECHNIQUES	588	(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)
APPENDICES	878	(65)
Appendix 1 Tables of Unknowns and Derivatives	878	(10)
Appendix 2 Procedures for Preparing Derivatives	888	(4)
Appendix 3 Infrared Spectroscopy	892	(19)
Appendix 4 Nuclear Magnetic Resonance Spectroscopy	911	(20)
Appendix 5 Carbon-13 Nuclear Magnetic Resonance Spectroscopy	931	(9)
Appendix 6 Index of Spectra	940	(3)
Index	943