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Any research that uses new organic chemicals, or ones that are not commercially available, will at some time require the synthesis of such compounds. Therefore, organic synthesis is important in many areas of both applied and academic research, from chemistry to biology, biochemistry, and materials science. The third edition of a bestseller, Advanced Practical Organic Chemistry is a guide that explains the basic techniques of organic chemistry, presenting the necessary information for readers to carry out widely used modern organic synthesis reactions. This book is written for advanced undergraduate and graduate students as well as industrial organic chemists, particularly those involved in pharmaceutical, agrochemical, and other areas of fine chemical research. It provides the novice or nonspecialist with the often difficult-to-find information on reagent properties needed to perform general techniques. With over 80 years combined experience training and developing organic research chemists in industry and academia, the authors offer sufficient guidance for researchers to perform reactions under conditions that give the highest chance of success, including the appropriate precautions to take and proper experimental protocols. The text also covers the following topics:











Record keeping and equipment
Solvent purification and reagent preparation
Using gases and working with vacuum pumps
Purification, including crystallization and distillation
Small-scale and large-scale reactions
Characterization, including NMR spectra, melting point and boiling point, and microanalysis
Efficient ways to find information in the chemical literature








With fully updated text and all newly drawn figures, the third edition provides a powerful tool for building the knowledge on the most up-to-date techniques commonly used in organic 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

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