有機化學實驗

本書根據我國高校有機化學實驗項目特點，結合國外有機化學實驗內容，圍繞實驗安全、正確操作實驗相關技術、實驗基本技能、波譜方法在有機化學實驗中的應用以及有機化學實驗項目等內容展開，其中本教材率先引入了英國《危險健康控制》(Control of Substances Hazardous to Health(COSHH))系統，詳細介紹了評估化學品安全性的方法，強調了實驗安全的重要性；在正確操作實驗相關技術部分，對有機化學實驗中常用到的稱量法、藥品轉移法、加熱冷卻法、玻璃儀器清洗法等均做了詳細介紹；在實驗基本技能部分，對迴流、過濾、熔沸點測定、重結晶、乾燥、萃取、旋轉蒸發等重要有機合成操作技能進行了詳細的講解，並對原理進行了簡介；波譜方法在有機化學實驗中的應用部分，對常用的四大波譜方法的機理和操作進行了簡單的介紹；實驗部分，則包括了《環己烷的純化》等共35個有機化學實驗，其中《由Robinson關環反應制備雙甲酮》等近8個實驗引進自雷丁大學有機化學實驗項目，並進行了相應的改編。

1 Introduction

1.1 Safety in the Laboratory

1.2 Chemical Hazards

1.3 Use of a COSHH Form

1.4 Pre-lab Reports or Notebooks Used in the Laboratory

1.5 Lab Reports

1.6 Samples of Reports and COSHH Form

1.7 Commonly Used Laboratory Glassware

2 Carrying out an Experiment

2.1 Measurements in a Laboratory

2.2 Transferring Reagents

2.3 Heating and Cooling Methods

2.4 Setting up a Reaction

2.5 Methods for Glassware Cleaning

2.6 Literature Investigation for the Experiment

3 Basic Techniques in Organic Laboratory

3.1 Assembling Glassware

3.2 Refluxing

3.3 Simple Inert Gas Protection

3.4 Smelling a Chemical

3.5 Boiling Point and Distillation

3.6 Melting Points

3.7 Sublimation

3.8 Filtration

3.9 Recrystallization

3.10 Drying Organic Solvents

3.11 Drying Organic Solutions

3.12 Drying Solid Organic Compounds

3.13 Extraction

3.14 Rota-evaporation

3.15 Chromatography

3.15.1 Thin-Layer Chromatography

3.15.2 Flash Chromatography

3.15.3 High Performance Liquid Chromatography

3.15.4 Gas Chromatography

4 Application of Spectroscopy in Organic Laboratory

4. 1 Introduction

4. 2 Ultraviolet-Visible Spectroscopy

4. 3 Fourier Transform Infrared Spectroscopy

4. 4 Mass Spectrometry

4. 5 Nuclear Magnetic Resonance Spectroscopy

5 Organic Experiments

5.1 Purification of Liquids by Distillation

5.2 Purification of Organic Compounds by Extraction

5.3 Purification of Solids by Recrystallization

5.4 Purification of Cyclohexane

5.5 Preparation of Bromoethane

5.6 Synthesis of Ethyl Acetate

5.7 Synthesis of Benzoin

5.8 Synthesis of Cinnamic Acid by the Perkin Reaction

5.9 Synthesis of Cinnamic Acid by the Knoevenagel Condensation

5.10 Synthesis of Methyl Orange

5.11 Synthesis of Ethyl Benzoate

5.12 The Diels-Alder Reaction

5.13 Synthesis of Acetanilide

5.14 Bromination of Acetanilide

5.15 Deprotection of the Acetyl Protecting Group from p-Bromoacetanilide

5.16 Synthesis of Aspirin

5.17 Synthesis of Ferrocene via the Phase Transfer Catalysis

5.18 Synthesis of 2-Nitro-l,3-benzenediol

5.19 Preparation of the Urea-Formaldehyde Resin

5.20 Preparation of Cyclohexene

5.21 Synthesis of 2-Chloro-2-methylpropane

5.22 Synthesis of Dibutyl Ether

5.23 Synthesis of Butyl Phenyl Ether

5.24 Synthesis of Hexane-1,6-dionic Acid

5.25 Preparation of Furfuryl Alcohol and 2-Furoic Acid by the Cannizzaro Reaction

5.26 A Solvent Free Cannizzaro Reaction

5.27 Reduction of 3-Nitroacetophenone Using Sodium Borohydride

5.28 Reduction of 3-Nitroacetophenone Using Sn/HCl

5.29 Synthesis of 4-Vinylbenzoic Acid via the Wittig Reaction

5.30 Preparation of 1,5-Diphenylpenta-l,4-dien-3-one Using the Aldol Condensation

5.31 Preparation of 2-Methylbutan-2-ol via the Grignard Reagent

5.32 Preparation of Dimedone via the Robinson Annulation

5.33 Preparation of Phenacetin from p-Aminophenol via a Two-Step Synthesis

5.34 Extraction of Alkaloids from Chinese Herbs--Coptis Chinensis

5.35 Extraction of Caffeine from Teas

6 Appendices

6.1 List of Equipment and Glassware for Each Experiment

6.2 List of Chemicals for Each Experiment

6.3 Appendix Tables

6.4 Abbreviations ^[1]