The Systematic Identification of Organic Compounds

by Hermann, Christine K. F.; Morrill, Terence C.; Shriner, Ralph L.; Fuson, Reynold C.

• ISBN13: 9781119799665
• ISBN10: 111979966X
• Edition: 9th
• Format: Paperback
• Copyright: 2023-03-28
• Publisher: Wiley

Summary

The Systematic Identification of Organic Compounds

A comprehensive introduction to the identification of unknown organic compounds

Identifying unknown compounds is one of the most important parts of the study of chemistry. From basic characteristics such as melting and/or boiling point to more complex data generated through cutting-edge techniques, the range of possible methods for identifying unknown organic compounds is substantial. The utility of a research reference which compiles known techniques and characteristics of possible compounds is clear.

The Systematic Identification of Organic Compounds provides such a reference, designed to teach a hands-on approach in the chemistry lab. It takes readers step-by-step through the process of identifying an unknown compound and elucidating its structure from infrared, nuclear magnetic resonance, and mass spectra in addition to solubility characteristics, melting point, boiling point, and classification tests. The result is an essential overview for advanced chemistry students looking to understand this exciting area of laboratory work.

Readers of the ninth edition of The Systematic Identification of Organic Compounds will also find:

• A detailed chapter on safety, personal protection equipment, chemical storage, safety data sheets, and other safety concerns
• New NMR, IR, and mass spectra with detailed explanations on interpretation
• Questions at the end of each chapter designed to facilitate and reinforce progression, keyed to a companion website for instructors
• Tables of known compounds including data relevant for identification
• Companion website with structural problems from experimental data for students to practice how to reason and solve

The Systematic Identification of Organic Compounds is a useful reference for advanced undergraduates and graduate students studying organic chemistry, organic spectroscopy, and related subjects.

Author Biography

Christine K. F. Hermann, PhD is Professor and Chair of the Department of Chemistry, Radford University, Radford, Virginia, USA.

Table of Contents

Preface

Chapter 1 Introduction

1.1 The Systematic Identification of Organic Compounds:

1.2 Suggestions to Students and Instructors

Chapter 2 Laboratory Safety

2.1 Working Safely in the Laboratory

2.2 Training

2.3 Personal Protection Equipment

2.4 Safety Data Sheets

2.5 Storage of Chemicals

2.6 Disposal of Chemicals

2.7 Safely Using Equipment in the Laboratory

Chapter 3 Identification of Unknowns

3.1 Discussion of Report Form

3.2 Preliminary Examination

3.3 Physical Properties

3.4 Molecular Weight Determination

3.5 Molecular Formula Determination

3.6 Solubility Tests

3.7 Infrared, Nuclear Magnetic Resonance, and Mass Spectra Analyses

3.8 Classification Tests

3.9 Preparation of a Satisfactory Derivative

3.10 Mixtures

3.11 Report Forms

Chapter 4 Preliminary Examination, Physical Properties, and Elemental Analysis

4.1 Preliminary Examination

4.2 Determination of Physical Properties

4.3 Optical Rotation

4.4 Recrystallization

4.5 Qualitative Elemental Analysis

4.6 Quantitative Elemental Analysis

Chapter 5 Classification of Organic Compounds by Solubility

5.1 Solubility in Water, Aqueous Acids and Bases, and Ether

5.2 Solubility in Organic Solvents

Chapter 6 Separation of Mixtures

6.1 Preliminary Examination of Mixtures

6.2 Distillation and Sublimation

6.3 Extractions: Separation Based Upon Salt Formation

6.4 Chromatography

Chapter 7 Nuclear Magnetic Resonance Spectrometry

7.1 Theory of Nuclear Magnetic Resonance

7.2 Preparation of the Sample

7.3 Proton Spectra

7.4 Carbon-13 Spectra

7.5 DEPT

7.6 COSY

7.7 HSQC

Chapter 8 Infrared Spectrometry

8.1 Theory of Infrared Spectrometry

8.2 Preparation of the Sample

8.3 Functional Group Identification

Chapter 9 Mass Spectrometry

9.1 Theory of Mass Spectrometry

9.2 Cleavage Reactions

Chapter 10 Chemical Tests for Functional Groups

10.1 Acid Anhydrides

10.2 Acyl Halides

10.3 Alcohols

10.4 Aldehydes

10.5 Amides

10.6 Amines and Amine Salts

10.7 Amino Acids

10.8 Carbohydrates

10.9 Carboxylic Acids

10.10 Esters

10.11 Ethers

10.12 Halides

10.13 Hydrocarbons -- Alkanes

10.14 Hydrocarbons -- Alkenes

10.15 Hydrocarbons -- Alkynes

10.16 Hydrocarbons -- Aromatic

10.17 Ketones

10.18 Nitriles

10.19 Nitro Compounds

10.20 Phenols

10.21 Sulfonamides, Sulfonic Acids, and Sulfonyl Chlorides

Chapter 11 The Preparation of Derivatives

11.1 Carboxylic Acids, Acid Anhydrides, and Acid Halides

11.2 Alcohols

11.3 Aldehydes and Ketones

11.4 Amides

11.5 Amines

11.6 Amino Acids

11.7 Carbohydrates

11.8 Esters

11.9 Ethers -- Aliphatic

11.10 Ethers -- Aromatic

11.11 Halides -- Alkyl

11.12 Halides -- Aromatic

11.13 Hydrocarbons -- Aromatic

11.14 Nitriles

11.15 Nitro Compounds

11.16 Phenols

11.17 Sulfonic Acids, Sulfonyl Chlorides, and Sulfonamides

Chapter 12 Structural Problems

12.1 Compounds with Structures Previously Described in the Literature

12.2 Determination of the Structure of New Compounds Not Described in the Chemical Literature

12.3 Problems

Chapter 13 Chemical Literature

13.1 Handbooks

13.2 Compendia

13.3 Spectral Collections

13.4 Journals

13.5 Abstracts and Indexes

13.6 Monographs

Appendix I Handy Tables for the Organic Lab

Appendix II Tables of Derivatives

Appendix III Equipment and Chemicals for the Laboratory

Index