A Small Scale Approach to Organic Laboratory Techniques

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  • Edition: 3rd
  • Format: Hardcover
  • Copyright: 2010-02-02
  • Publisher: Cengage Learning
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Supplemental Materials

What is included with this book?


Featuring new experiments, a new essay, and new coverage of nanotechnology, this organic chemistry laboratory book offers a comprehensive treatment of laboratory techniques including small-scale and some microscale methods that use standard-scale ("macroscale") glassware and equipment. The book is organized based on essays and topics of current interest and covers a large number of traditional organic reactions and syntheses, as well as experiments with a biological or health science focus. Seven introductory technique-based experiments, thirteen project-based experiments, and sections on green chemistry and biofuels, spark reader interest.

Table of Contents

Welcome to Organic Chemistry
Laboratory Safety
Organization of the Textbook
Advance Preparation
Budgeting Time
Introduction to Basic Laboratory Techniques
A Separation and Purification Scheme
Extractions with a Separatory Funnel
Extractions with a Screw-Cap Centrifuge Tube
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
Acetylsalicylic Acid
Identification of Drugs
TLC Analysis of Analgesic Drugs
Isolation of Caffeine
Extraction of Caffeine from Tea
Isolation of Caffeine from a Tea Bag
Esters--Flavors and Fragrances
Isopentyl Acetate (Banana Oil)
Essay, Terpenes and Phenylpropanoids
Isolation of Eugenol from Cloves
Stereochemical Theory of Odor
Spearmint and Caraway Oil: (+)- and (-)- Carvones
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
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 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
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
Relative Reactivities of Several Aromatic Compounds
Nitration of Methyl Benzoate
Local Anesthetics
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
Polyamide (Nylon)
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
Fireflies and Photochemistry
The Chemistry of Sweeteners
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
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
Physical Constants of Solids: The Melting Point
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
Steam Distillation
Column Chromatography
Thin-Layer Chromatography
High-Performance Liquid Chromatography (HPLC)
Gas Chromatography
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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