Introduction to Organic Laboratory Techniques: A Microscale Approach

by Donald L. Pavia; ngel; Randall G. Engel

• ISBN13: 9780030238482
• ISBN10: 003023848X
• Format: Hardcover
• Copyright: 1999-02-01
• Publisher: Brooks/Cole

Summary

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.

Table of Contents

Introduction
Welcome to Organic Chemistry	2	(2)
Laboratory Safety	4	(16)
Advance Preparation and Laboratory Records	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 Compounds	189	(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 Substances	427	(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 Experiments	469	(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 Experiments	481	(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
Appendices	A1
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
Index	I1