Principles of Organic Chemistry

Robert J. Ouellette, J. David Rawn

• Publisher: Elsevier
• Year: 2015
• eBook ISBN: 9780128026342
• Topic: Physical Sciences
• Subtopic: Organic Chemistry

Class-tested and thoughtfully designed for student engagement, Principles of Organic Chemistry provides the tools and foundations needed by students in a short course or one-semester class on the subject. This book does not dilute the material or rely on rote memorization. Rather, it focuses on the underlying principles in order to make accessible the science that underpins so much of our day-to-day lives, as well as present further study and practice in medical and scientific fields. This book provides context and structure for learning the fundamental principles of organic chemistry, enabling the reader to proceed from simple to complex examples in a systematic and logical way.Utilizing clear and consistently colored figures, Principles of Organic Chemistry begins by exploring the step-by-step processes (or mechanisms) by which reactions occur to create molecular structures. It then describes some of the many ways these reactions make new compounds, examined by functional groups and corresponding common reaction mechanisms. Throughout, this book includes biochemical and pharmaceutical examples with varying degrees of difficulty, with worked answers and without, as well as advanced topics in later chapters for optional coverage.- Incorporates valuable and engaging applications of the content to biological and industrial uses- Includes a wealth of useful figures and problems to support reader comprehension and study- Provides a high quality chapter on stereochemistry as well as advanced topics such as synthetic polymers and spectroscopy for class customization

1

Structure of Organic Compounds

1.1 Organic and Inorganic Compounds

Organic chemistry began to emerge as a science about 200 years ago. By the late eighteenth century, substances were divided into two classes called inorganic and organic compounds. Inorganic compounds were derived from mineral sources, whereas organic compounds were obtained only from plants or animals. Organic compounds were more difficult to work with in the laboratory, and decomposed more easily, than inorganic compounds. The differences between inorganic and organic compounds were attributed to a “vital force” associated with organic compounds. This unusual attribute was thought to exist only in living matter. It was believed that without the vital force, organic compounds could not be synthesized in the laboratory. However, by the mid-nineteenth century, chemists had learned both how to work with organic compounds and how to synthesize them.

Organic compounds always contain carbon and a limited number of other elements, such as hydrogen, oxygen, and nitrogen. Compounds containing sulfur, phosphorus, and halogens are known but are less prevalent. Most organic compounds contain many more atoms per structural unit than inorganic compounds and have more complex structures. Common examples of organic compounds include the sugar sucrose (C₁₂H₂₂O₁₁), vitamin B2 (C₁₁₇H₁₂₀N₄O₆), cholesterol (C₂₇H₄₆O), and the fat glycerol tripalmitate (C₅₁H₉₈O₆). Some organic molecules are gigantic. DNA, which stores genetic information, has molecular weights that range from 3 million in Escherichia coli to 2 billion for mammals.

Based on the physical characteristics of compounds, such as solubility, melting point, and boiling point, chemists have proposed that the atoms of the elements are bonded in compounds in two principal ways—ionic bonds and covalent bonds. Both types of bonds result from a change in the electronic structure of atoms as they associate with each other. Thus, the number and type of bonds formed and the resultant shape of the molecule depend on the electron configuration of the atoms. Therefore, we will review some of the electronic features of atoms and the periodic properties of the elements before describing the structures of organic compounds.

1.2 Atomic Structure

Each atom has a central, small, dense nucleus that contains protons and neutrons; electrons are located outside the nucleus. Protons have a + 1 charge; electrons have a − 1 charge. The number of protons, which determines the identity of an atom, is given as its atomic number. Since atoms have an equal number of protons and electrons and are electrically neutral, the atomic number also indicates the number of electrons in the atom. The number of electrons in the hydrogen, carbon, nitrogen, and oxygen atoms are one, six, seven, and eight, respectively.

The periodic table of the elements is arranged by atomic number. The elements are arrayed in horizontal rows called periods and vertical columns called groups. In this text, we will emphasize hydrogen in the first period and the elements carbon, nitrogen, and oxygen in the second period. The electronic structure of these atoms is the basis for their chemical reactivity.

Atomic Orbitals

Electrons around the nucleus of an atom a...

Table of contents

• Cover image
• Title page
• Table of Contents
• Copyright
• 1: Structure of Organic Compounds
• 2: Properties of Organic Compounds
• 3: Alkanes and Cycloalkanes
• 4: Alkenes and Alkynes
• 5: Aromatic Compounds
• 6: Stereochemistry
• 7: Nucleophilic Substitution and Elimination Reactions
• 8: Alcohols and Phenols
• 9: Ethers and Epoxides
• 10: Aldehydes and Ketones
• 11: Carboxylic Acids and Esters
• 12: Amines and Amides
• 13: Carbohydrates
• 14: Amino Acids, Peptides, and Proteins
• 15: Synthetic Polymers
• 16: Spectroscopy
• Solutions to In-Chapter Problems
• Index