Small Scale Approach to Organic Laboratory Techniques

ISBN-10: 1439049327
ISBN-13: 9781439049327
Edition: 3rd 2011
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Book details

List price: $375.95
Edition: 3rd
Copyright year: 2011
Publisher: Brooks/Cole
Publication date: 2/2/2010
Binding: Hardcover
Pages: 1024
Size: 8.50" wide x 11.00" long x 1.50" tall
Weight: 4.488
Language: English

Donald L. Pavia earned his BS degree in chemistry from Reed College and his PhD in organic chemistry from Yale University. In 1970, he joined the faculty at Western Washington University as Assistant Professor and now holds the rank of Professor Emeritus. He is the coauthor of two organic laboratory books that include techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Gary M. Lampman, George S. Kriz and James R. Vyvyan of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY (Cengage Learning). Professor Pavia's research interests center on the synthesis and reactions of valence tautomeric and photochromic compounds, especially pyrylium-3-oxide tautomers. Autoxidations are a special interest. His other interests include the use of computers in teaching organic chemistry, both for lecture presentation and for the simulation of laboratories. He is the author of several computer programs. One such program is SQUALOR (Simulated Qualitative Organic Analysis) for which he won the 1986 EDUCOM/NCRIPTAL award. The program is designed for teaching the methods for solving organic unknowns.

Gary M. Lampman earned his BS degree in chemistry from the University of California, Los Angeles, and his PhD in organic chemistry from the University of Washington. In 1964, he joined the faculty at Western Washington University as Assistant Professor, rising to Professor in 1973. He received the Outstanding Teaching Award for the College of Arts and Sciences in 1976. He now holds the title of Professor Emeritus. Teaching has always been an important part of his life. Contact with students invigorates him. He is the coauthor of two organic laboratory books that include techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE ARPPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning), as well as MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), which highlights techniques to be used with a faculty member's own experiments. He is a co-author, with Donald L. Pavia, George S. Kriz, and James R. Vyvyan of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY, Fourth Edition (Cengage Learning). Professor Lampman also is the author of the computer program for teaching organic nomenclature: ORGANIC NOMENCLATURE: AN INTRODUCTION TO THE IUPAC SYSTEM. His research interests center on synthetic methods involving the reaction of free radicals on unsaturated cobaloximes (vitamin B12 model compounds), synthesis of strained small ring compounds, and chemical education. He is the author of 18 papers in these areas. He is a member of the American Chemical Society (Organic and Chemical Education divisions), and the Washington College Chemistry Teachers Association.

George S. Kriz is Professor of Chemistry at Western Washington University. He earned his B.S. degree in chemistry from the University of California, and his Ph.D. from Indiana University, Bloomington, IN. In 1967 he joined the faculty at Western Washington University and recently served as department chair. He served as the General Chair of the 17th Biennial Conference on Chemical Education for 2001-2002. Professor Kriz was honored with the Peter J. Elich Excellence in Teaching Award (College of Arts and Sciences), Western Washington University, in 2000 and the Distinguised Service Award from the Division of Chemical Education, American Chemical Society (2010). He is the co-author with Donald Pavia, Gary Lampman, and Randall Engel of two organic laboratory books that include both techniques and experiments: INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE APPROACH TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), includes techniques only, and can be used with a faculty member's own experiments. He is a co-author, with Donald Pavia, Gary Lampman, and James Vyvyan, of an organic spectroscopy book, INTRODUCTION TO SPECTROSCOPY (Cengage Learning). Professor Kriz's research interests include: developing new experiments for the organic chemistry laboratory; chemical education and the teaching of chemistry courses for general-understanding audiences; and determination of the structures of natural products using spectroscopic methods.

Randall G. Engel has taught chemistry for almost 35 years. He has co-authored with Donald Pavia, Gary Lampman, and George Kriz INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES: A MICROSCALE APPROACH (Cengage Learning), and A SMALL SCALE INTRODUCTION TO ORGANIC LABORATORY TECHNIQUES (Cengage Learning). Their book, MICROSCALE AND MACROSCALE TECHNIQUES IN THE ORGANIC LABORATORY (Cengage Learning), includes techniques only, and can be used with a faculty member's own experiments. Engel received his B.A. degree in chemistry from Cornell College and his M.S. degree in chemistry from Western Washington University. He began his teaching career at Wenatchee Valley College in 1975 and continued at Green River Community College and Edmonds Community College. Presently he teaches organic chemistry on a part-time basis at North Seattle Community College.

Introduction
Welcome to Organic Chemistry
Laboratory Safety
Organization of the Textbook
Advance Preparation
Budgeting Time
Purpose
Introduction to Basic Laboratory Techniques
Solubility
Crystallization
Extraction
A Separation and Purification Scheme
Extractions with a Separatory Funnel
Extractions with a Screw-Cap Centrifuge Tube
Chromatography
Thin-Layer Chromatography
Selecting the Correct Solvent for Thin-Layer Chromatography
Monitoring a Reaction with Thin Layer Chromatography
Column Chromatography
Simple and Fractional Distillation
Infrared Spectroscopy and Boiling-Point Determination Essay
Aspirin
Acetylsalicylic Acid
Essay
Analgesics
Acetaminophen
Essay
Identification of Drugs
TLC Analysis of Analgesic Drugs
Essay
Caffeine
Isolation of Caffeine
Extraction of Caffeine from Tea
Isolation of Caffeine from a Tea Bag
Essay
Esters--Flavors and Fragrances
Isopentyl Acetate (Banana Oil)
Essay, Terpenes and Phenylpropanoids
Isolation of Eugenol from Cloves
Essay
Stereochemical Theory of Odor
Spearmint and Caraway Oil: (+)- and (-)- Carvones
Essay
The Chemistry of Vision
Isolation of Chlorophyll and Carotenoid Pigments from Spinach
Essay: Ethanol and Fermentation Chemistry
Ethanol from Sucrose
Introduction to Molecular Modeling
Essay: Molecular Modeling and Molecular Mechanics
An Introduction to Molecular Modeling
The Conformations of n-Butane: Local Minima
Cyclohexane Chair and Boat Conformations
Substituted Cyclohexane Rings (Critical Thinking Exercise)
cis- and trans-2-Butene
Essay: Computational Chemistry - Ab initio and Semiempirical Methods
Computational Chemistry
Heats of Formation: Isomerism, Tautomerism, and Regioselectivity
Heats of Reactions: SN1 Reaction Rates
Density-Electrostatic Potential
Maps: Acidities of Carboxylic Acids
Density -Electrostatic Potential Maps: Carbocations
Density -LUMO Maps: Reactivities of Carbonyl Groups
Preparations and Reactions of Organic Compounds
Reactivities of Some Alkyl Halides
Nucleophilic Substitution Reactions: Competing Nucleophiles
Competing Nucleophiles with 1-Butanol or 2-Butanol
Competing Nucleophiles with 2-Methyl-2-Propanol
Analysis
Synthesis of n-Butyl Bromide and t-Pentyl Chloride
n-Butyl Bromide
t-Pentyl Chloride
4-Methylcyclohexene Essay
Fats and Oils
Methyl Stearate from Methyl Oleate
Essay: Petroleum and Fossil Fuels
Gas Chromatographic Analysis of Gasolines
Essay: Biofuels
Biodiesel
Biodiesel from Coconut Oil
Biodiesel from Other Oils
Analysis of Biodiesel
Ethanol from Corn
Essay: Green Chemistry
Chiral Reduction of Ethyl Acetoacetate; Optical Purity Determination
Chiral Reduction of Ethyl Acetoacetate
NMR Determination of the Optical Purity of Ethyl (S)-3-Hydroxybutanoate
Nitration of Aromatic Compounds Using a Recyclable Catalyst
Reduction of Ketones Using Carrots as Biological Reducing Agents
Resolution of (+/-)-alpha-Phenylethylamine and Determination of Optical Purity
Resolution of (+/-)-alpha-Phenylethylamine
Determination of Optical Purity Using NMR and a Chiral Resolving Agent
An Oxidation-Reduction Scheme: Borneol, Camphor, Isoborneol
Multistep Reaction Sequences: The Conversion of Benzaldehyde to Benzilic Acid
Preparation of Benzoin by Thiamine Catalysis
Preparation of Benzil
Preparation of Benzilic Acid
Triphenylmethanol and Benzoic Acid
Triphenylmethanol
Benzoic Acid
Aqueous-Based Organozinc Reactions
Sonogashira Coupling of Iodosubstituted Aromatic Compounds with Alkynes Using a Palladium Catalyst
Grubbs Catalyzed Metathesis of Eugenol with 1,4-Butenediol to Prepare a Natural Product
The Aldol Condensation Reaction: Preparation of Benzalacetophenones (Chalcones)
A Green Enantioselective Aldol Condensation Reaction
Preparation of an ?,?-Unsaturated Ketone via Michael and Aldol Condensation Reactions
Preparation of Triphenylpyridine
1,4-Diphenyl-1,3-Butadiene
Relative Reactivities of Several Aromatic Compounds
Nitration of Methyl Benzoate
Essay
Local Anesthetics
Benzocaine
Essay
Pheromones: Insect Attractants and Repellants
N,N-Diethyl-m-toluamide: The Insect Repellent "OFF."
Essay: Sulfa Drugs
Sulfa Drugs: Preparation of Sulfanilamide
Essay: Polymers and Plastics
Preparation and Properties of Polymers: Polyester, Nylon, and Polystyrene
Polyesters
Polyamide (Nylon)
Polystyrene
Infrared Spectra of Polymer Samples
Ring-Opening Metathesis Polymerization (ROMP)
Using a Grubbs Catalyst: A Three Step Synthesis of a Polymer
Diels-Alder Reaction of Furan and Maleic Anhydride
Ring Opening of Anhydride in Methanol
Ring-Opening Metathesis Polymerization (ROMP)
Diels-Adler Reaction
Conversion of the Diels-Adler Adduct to the Diester
Synthesizing the Polymer by Ring-Opening Metathesis Polymerization (ROMP) Essay
Diels-Alder Reaction and Insecticides
The Diels-Alder Reaction of Cyclopentadiene with Maleic Anhydride
Diels-Adler Reaction with Anthracine-9-Methanol
Photoreduction of Benzophenone and Rearrangement of Benzpinacol to Benzopinacolone
Photoreduction of Benzophenone
Synthesis of ?-Benzopinacolone: The Acid-Catalyzed Rearrangement of Benzpinacol
Essay
Fireflies and Photochemistry
Luminol
Essay
The Chemistry of Sweeteners
Carbohydrates
Analysis of a Diet Soft Drink by HPLC
Identification of Organic Substances
Identification of Unknowns
Solubility Tests
Tests for the Elements (N, S, X)
Tests for Unsaturation
Aldehydes and Ketones
Carboxylic Acids
Phenols
Amines
Alcohols
Esters
Project-Based Experiments
Preparation of a C-4 or C-5 Acetate Ester
Isolation of Essential Oils from Allspice, Caraway, Cinnamon, Cloves, Cumin, Fennel, or Star Anise
Isolation of Essential Oils by Steam Distillation
Identification of the Constituents of Essential Oils by Gas Chromatography-Mass Spectrometry
Investigation of the Essential Oils of Herbs and Spices-Mini-Research Project
Competing Nucleophiles in SN1 and SN2
Reactions: Investigations Using 2-Pentanol and 3-Pentanol
Friedel-Crafts Acylation
The Analysis of Antihistamine Drugs by Gas Chromatography-Mass Spectrometry
Carbonation of an Unknown Aromatic Halide
The Aldehyde Enigma
Synthesis of Substituted Chalcones: A Guided-Inquiry Experience
Green Epoxidation of Chalcones
Cyclopropanation Reactions of Chalcones
Michael and Aldol Condensation Reactions
Esterification Reactions of Vanillin: The Use of NMR to Solve a Structure Proof Problem
An Oxidation Puzzle
The Techniques
Laboratory Safety
The Laboratory Notebook, Calculations, and Laboratory Records
Laboratory Glassware: Care and Cleaning
How to Find Data for Compounds: Handbooks and Catalogues
Measurement of Volume and Weight
Heating and Cooling Methods
Reaction Methods
Filtration
Physical Constants of Solids: The Melting Point
Solubility
Crystallization: Purification of Solids
Extractions, Separations, and Drying Agents
Physical Constants of Liquids: The Boiling Point and Density
Simple Distillation
Fractional Distillation, Azeotropes
Vacuum Distillation, Manometers
Sublimation
Steam Distillation
Column Chromatography
Thin-Layer Chromatography
High-Performance Liquid Chromatography (HPLC)
Gas Chromatography
Polarimetry
Refractometry
Infrared Spectroscopy
Nuclear Magnetic Resonance Spectroscopy (Proton NMR)
Carbon-13 Nuclear Magnetic Resonance Spectroscopy
6 Mass Spectrometry
Guide to the Chemical Literature
Tables of Unknowns and Derivatives
Procedure for Preparing Derivatives
Index of Spectra

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