Introduction to Organic Laboratory Techniques A Microscale Approach

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

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ISBN: 9780495016304 | 0495016306
Cover: Hardcover
Copyright: 2/1/2006

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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.

PART 1 Introduction to Basic Laboratory Techniques

(150)

Introduction to Microscale Laboratory

(11)

Solubility

(8)

Crystallization

(11)

Semimicroscale Crystallization---Erlenmeyer Flask and Hirsch Funnel

(3)

Microscale Crystallization---Craig Tube

(2)

Selecting a Solvent to Crystallize a Substance

(1)

Mixture Melting Points

(1)

Critical Thinking Application

(3)

Extraction

(10)

Extraction of Caffeine

(3)

Distribution of a Solute between Two Immiscible Solvents

(1)

How Do You Determine Which One Is the Organic Layer?

(1)

Use of Extraction to Isolate a Neutral Compound from a Mixture Containing an Acid or Base Impurity

(2)

Critical Thinking Application

(2)

Chromatography

(9)

Thin-Layer Chromatography

(2)

Selecting the Correct Solvent for Thin-Layer Chromatography

(1)

Monitoring a Reaction with Thin-Layer Chromatography

(2)

Column Chromatography

(3)

Simple and Fractional Distillation

(6)

Simple and Fractional Distillation (Semimicroscale Procedure)

(3)

Simple and Fractional Distillation (Microscale Procedure)

(1)

Infrared Spectroscopy and Boiling-Point Determination

(6)

Aspirin

(2)

Acetylsalicylic Acid

(8)

Analgesics

(4)

Isolation of the Active Ingredient in an Analgesic Drug

(4)

Acetaminophen

(7)

Acetaminophen (Microscale Procedure)

(2)

Acetaminophen (Semimicroscale Procedure)

(2)

Identification of Drugs

(2)

TLC Analysis of Analgesic Drugs

(8)

Caffeine

(3)

Isolation of Caffeine from Tea or Coffee

(13)

Extraction of Caffeine from Tea with Methylene Chloride

(2)

Extraction of Caffeine from Tea or Coffee Using Solid Phase Extraction (SPE)

(4)

Esters---Flavors and Fragrances

(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

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Introduction to Organic Laboratory Techniques A Microscale Approach

Summary

Table of Contents

Supplemental Materials