Introduction to Organic Laboratory Techniques A Microscale Approach

by Pavia, Donald L.; Lampman, Gary M.; Kriz, George S.; Engel, Randall G.

• ISBN13: 9780495016304
• ISBN10: 0495016306
• Edition: 4th
• Format: Hardcover
• Copyright: 2006-02-01
• Publisher: Brooks Cole

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