Advanced Practical Organic Chemistry

General introduction

Safety
Safety is your primary responsibility
Safe working practice
Safety risk assessments
Common hazards
Accident and emergency procedures
Bibliography

Keeping records of laboratory work
Introduction
The laboratory notebook
Keeping records of data
Some tips on report and thesis preparation
References

Equipping the laboratory and the bench
Introduction
Setting up the laboratory
General laboratory equipment
The individual bench
Equipment for parallel experiments
Equipment for controlled experimentation

Purification and drying of solvents
Introduction
Purification of solvents
Drying agents
Drying of solvents
References

Reagents: Preparation, purification, and handling
Introduction
Classification of reagents for handling
Techniques for obtaining pure and dry reagents
Techniques for handling and measuring reagents
Preparation and titration of simple organometallic reagents and lithium amide bases
Preparation of diazomethane
References

Gases
Introduction
Use of gas cylinders
Handling gases
Measurement of gases
Inert gases
Reagent gases
References

Vacuum pumps
Introduction
House vacuum systems (low vacuum)
Medium vacuum pumps
High vacuum pumps
Pressure measurement and regulation

Carrying out the reaction
Introduction
Reactions with air-sensitive reagents
Reaction monitoring
Reactions at other than room temperature
Driving equilibria
Agitation
Use of controlled reactor systems
References

Working up the reaction
Introduction
Quenching the reaction
Isolation of the crude product
Data that need to be collected on the crude product prior to purification

Purification
Introduction
Crystallization
Distillation
Sublimation
Flash chromatography
Dry-column flash chromatography
Preparative TLC
Medium pressure and prepacked chromatography systems
Preparative HPLC
References

Small-scale reactions
Introduction
Reactions at or below room temperature
Reactions above room temperature
Reactions in NMR tubes
Purification of materials

Large-scale reactions
Introduction
Carrying out the reaction
Workup and product isolation
Purification of the products

Special procedures
Introduction
Catalytic hydrogenation
Photolysis
Ozonolysis
Flash vacuum pyrolysis (FVP)
Liquid ammonia reactions
Microwave reactions
References

Characterization
Introduction
NMR spectra
IR spectra
UV spectroscopy
Mass spectrometry
Melting point (m.p.) and boiling point (b.p.)
Optical rotation
Microanalysis
Keeping the data

Troubleshooting: What to do when things don’t work

The chemical literature
The structure of the chemical literature
Some important paper-based sources of chemical information
Some important electronic-based sources of chemical information
How to find chemical information
Current awareness
References

Appendices
Properties of common solvents
Properties of common gases
Approximate pKa values for some common reagents versus common bases
Common Bronsted acids
Common Lewis acids
Common reducing reagents
Common oxidizing reagents

Index

Biography

John Leonard is currently a principal scientist at AstraZeneca Pharmaceuticals, where he is primarily involved with synthetic route design and development activities. Prior to this he was a professor of organic chemistry at the University of Salford, UK.Garry Procter is a professor and director of teaching in the School of Chemistry at the University of Manchester, UK. Before this he was director of undergraduate laboratories in the Department of Chemistry and Chemical Biology at Harvard University.Barry Lygo is currently a professor of chemistry at the University of Nottingham, UK, working in the field of asymmetric catalysis and synthesis.

Praise for Previous Editions

"…concise and highly readable … I would recommend this book as an essential purchase for all new research students in the area of organic synthesis"
—Synthesis, June 1995

"This book should be present in every organic chemistry research laboratory…a bargain at the price."
—Chemistry & Industry, July 1995

"Reading this book is like having a thoughtful and smart tutor guiding all your steps in the laboratory…excellent choice.."
—Physical Sciences Educational Reviews