Experimental Organic Chemistry: A Miniscale and Microscale Approach

Contents in Brief
Table of Contents
Ch 1: Introduction, Record Keeping, and Laboratory Safety
	1.1: Introduction
	1.2: Preparing for the Laboratory
	1.3: Working in the Laboratory
	1.4: The Laboratory Notebook
	1.5: General Protocol for the Laboratory Notebook
	1.6: Types of Organic Experiments and Notebook Formats
	1.7: Sample Calculations for Notebook Records
	1.8: Safe Laboratory Practice: Overview
	1.9: Safety: General Discussion
	1.10: Safety: Material Safety Data Sheets (MSDSs)
	1.11: Safety: Disposal of Chemicals
Ch 2: Techniques and Apparatus
	2.1: Glassware: Precautions and Cleaning
	2.2: Standard-Taper Glassware for Miniscale Procedures
	2.3: Standard-Taper Glassware for Microscale Procedures
	2.4: Assembling Apparatus
	2.5: Measuring and Transferring Liquids
	2.6: Weighing Methods
	2.7: Melting-Point Methods and Apparatus
	2.8: Boiling-Point Methods and Apparatus
	2.9: Heating Methods
	2.10: Cooling Techniques
	2.11: Stirring Methods
	2.12: Centrifugation
	2.13: Simple Distillation
	2.14: Fractional Distillation
	2.15: Vacuum Distillation
	2.16: Steam Distillation
	2.17: Filtration Apparatus and Techniques
	2.18: Decolorizing Carbon
	2.19: Decanting Solutions
	2.20: Sublimation
	2.21: Extraction
	2.22: Heating under Reflux
	2.23: Gas Traps
	2.24: Drying Agents
	2.25: Drying Organic Solutions
	2.26: Drying Solids
	2.27: Drying Tubes
	2.28: Drying Apparatus
	2.29: Evaporating Solvents
Ch 3: Solids: Recrystallization and Melting Points
	3.1: Introduction
	3.2: Recrystallization
	3.3: Physical Constants: Melting Points
Ch 4: Liquids: Distillation and Boiling Points
	4.1: Introduction
	4.2: Boiling Points of Pure Liquids
	4.3: Simple Distillation
	4.4: Fractional Distillation
	4.5: Steam Distillation
	4.6: Steam Distillation: Isolation of Citral from Lemon Grass Oil
	4.7: Qualitative Analysis
Ch 5: Extraction
	5.1: Introduction
	5.2: Theory of Extraction
	5.3: Base and Acid Extractions
	5.4: Extraction of a Natural Product: Trimyristin
Ch 6: Chromatography
	6.1: Introduction
	6.2: Thin-Layer Chromatography
	6.3: Column Chromatography
	6.4: Gas-Liquid Chromatography
Ch 7: Stereoisomers
	7.1: Introduction
	7.2: Separation of Diastereomeric 1,2-Cyclohexanediols
	7.3: Isomerization of Dimethyl Maleate to Dimethyl Fumarate
	7.4: Properties of the Enantiomers of Carvone
	7.5: Polarimetry
	7.6: Resolution of Racemic 1-Phenylethanamine
Ch 8: Spectral Methods
	8.1: Introduction
	8.2: Infrared (IR) Spectroscopy
	8.3: Nuclear Magnetic Resonance (NMR) Spectroscopy
	8.4: Ultraviolet and Visible Spectroscopy
	8.5: Mass Spectrometry
Ch 9: Alkanes
	9.1: Introduction
	9.2: Chlorination Using Sulfuryl Chloride
	9.3: Bromination: Selectivity of Hydrogen Atom Abstraction
Ch 10: Alkenes
	10.1: Introduction
	10.2: Dehydrohalogenation of Alkyl Halides
	10.3: Dehydration of Alcohols
	10.4: Addition Reactions of Alkenes: Overview
	10.5: Addition of Hydrobromic Acid to Alkenes
	10.6: Bromination of Alkenes
	10.7: Acid-Catalyzed Hydration of Alkenes
	10.8: Hydroboration-Oxidation of Alkenes
Ch 11: Alkynes
	11.1: Introduction
	11.2: Dehydrohalogenation of 1,2-Dihaloalkanes
	11.3: Addition Reactions of Alkynes
	11.4: Terminal Alkynes as Acids
Ch 12: Dienes: The Diels-Alder Reaction
	12.1: Introduction
	12.2: Mechanistic and Stereochemical Aspects
	12.3: Applications of Diels-Alder Reactions
Ch 13: Kinetic and Thermodynamic Control of a Reaction
	13.1: Introduction
	13.2: Formation of Semicarbazones under Kinetic and Thermodynamic Control
Ch 14: Nucleophilic Aliphatic Substitution: Preparation of Alkyl Halides
	14.1: General Concepts
	14.2: Classification of Nucleophilic Substitution Reactions
	14.3: Competition between Substitution and Elimination
	14.4: Preparation of 1-Bromobutane: An SN2 Reaction
	14.5: Preparation of 2-Chloro-2-Methylbutane: An SN1 Reaction
	14.6: Chemical Kinetics: Evidence for Nucleophilic Substitution Mechanisms
	14.7: Competing Nucleophiles in SN Reactions
	14.8: Competition between Substitution and Elimination
Ch 15: Electrophilic Aromatic Substitution
	15.1: Introduction
	15.2: Friedel-Crafts Alkylation of p-Xylene with 1-Bromopropane
	15.3: Friedel-Crafts Acylation of Anisole
	15.4: Nitration of Bromobenzene
	15.5: Substituent Effects on Electrophilic Aromatic Substitution
	15.6: Azo Dyes and the Chemistry of Dyeing Fabrics
Ch 16: Oxidation of Alcohols and Carbonyl Compounds
	16.1: Introduction
	16.2: Preparation of Aldehydes and Ketones by Oxidation of Alcohols
	16.3: Base-Catalyzed Oxidation-Reduction of Aldehydes: The Cannizzaro Reaction
Ch 17: Reduction Reactions of Double Bonds: Alkenes, Carbonyl Compounds, and Imines
	17.1: Introduction
	17.2: Catalytic Hydrogenation of the Carbon-Carbon Double Bond
	17.3: Reduction of Imines; Preparation of Amines
	17.4: Reduction of Carbonyl Compounds; Preparation of Alcohols
	17.5: Enantioselective Reductions: A Chiral Alcohol from a Ketone
	17.6: Determining Optical Purity
Ch 18: Reactions of Carbonyl Compounds
	18.1: Introduction
	18.2: The Wittig and Related Reactions
	18.3: Reactions of Stabilized Carbanions from Carbonyl Compounds
	18.4: Conjugate Addition to an a,b-Unsaturated Ketone
	18.5: Heterocyclic Compounds: Synthesis of a 1,2,3,4-Tetrahydropyrimidine-2-One
Ch 19: Organometallic Chemistry
	19.1: Introduction
	19.2: Grignard Reagents: Preparation
	19.3: Grignard Reagents: Reactions
	19.4: Special Experimental Techniques
	19.5: Organozinc Reagents: Preparation and Reaction
	19.6: Transition Metal Catalyzed Reactions and Procedure for Suzuki Reaction
Ch 20: Carboxylic Acids and Their Derivatives
	20.1: Introduction
	20.2: Esters and the Fischer Esterification
	20.3: Amides and Insect Repellents
	20.4: Amides and Chemiluminescence
Ch 21: Multistep Organic Synthesis
	21.1: Introduction
	21.2: Sulfanilamide: Discovery and Synthesis of the First Antibiotic
	21.3: Synthesis of 1-Bromo-3-Chloro-5-Iodobenzene
	21.4: Lidocaine: Synthesis of an Anesthetic Agent
Ch 22: Polymers
	22.1: Introduction
	22.2: Chain-Reaction Polymerization
	22.3: Step-Growth Polymerization
Ch 23: Carbohydrates
	23.1: Introduction
	23.2: Monosaccharides: General Principles
	23.3: Disaccharides: Hydrolysis of Sucrose
	23.4: Carbohydrates: Their Characterization and Identification
Ch 24: a-Amino Acids and Peptides
	24.1: Introduction
	24.2: Synthesis of Peptides and Polypeptides
	24.3: Synthesis of the Protected Dipeptide Ala-Phe-OMe
Index