Organic Chemistry

Concepts and Applications

Allan D. Headley

• Publisher: Wiley
• Year: 2019
• ISBN:
  9781119504672
• Edition: 1
• Topic: Physical Sciences
• Subtopic: Organic Chemistry

Provides an in-depth study of organic compounds that bridges the gap between general and organic chemistry

Organic Chemistry: Concepts and Applications presents a comprehensive review of organic compounds that is appropriate for a two-semester sophomore organic chemistry course. The text covers the fundamental concepts needed to understand organic chemistry and clearly shows how to apply the concepts of organic chemistry to problem-solving. In addition, the book highlights the relevance of organic chemistry to the environment, industry, and biological and medical sciences. The author includes multiple-choice questions similar to aptitude exams for professional schools, including the Medical College Admissions Test (MCAT) and Dental Aptitude Test (DAT) to help in the preparation for these important exams.

Rather than categorize content information by functional groups, which often stresses memorization, this textbook instead divides the information into reaction types. This approach bridges the gap between general and organic chemistry and helps students develop a better understanding of the material. A manual of possible solutions for chapter problems for instructors and students is available in the supplementary websites. This important book:

• Provides an in-depth study of organic compounds with division by reaction types that bridges the gap between general and organic chemistry

• Covers the concepts needed to understand organic chemistry and teaches how to apply them for problem-solving

• Puts a focus on the relevance of organic chemistry to the environment, industry, and biological and medical sciences

• Includes multiple choice questions similar to aptitude exams for professional schools

Written for students of organic chemistry, Organic Chemistry: Concepts and Applications is the comprehensive text that presents the material in clear terms and shows how to apply the concepts to problem solving.

1
Bonding and Structure of Organic Compounds

1.1 Introduction

The word “organic” was first used to describe compounds that were derived from plants or animals, but this term was later used to describe compounds that contain mostly carbon and hydrogen atoms. Today, the term organic is loosely used to describe food that is produced without the use of pesticides, hormones, antibiotics, or fertilizers.

In organic chemistry, we will carry out a detailed study of the composition, properties, and reactions of compounds that contain primarily carbon and hydrogen atoms, also known as organic compounds. Even though many organic compounds contain only carbon and hydrogen atoms, a large percentage contains other atoms, such as oxygen, nitrogen, sulfur, as well as halogens; these atoms are referred to as heteroatoms. Atoms other than carbon and hydrogen that are present in organic compounds are called heteroatoms.

Prior to the start of the nineteenth century, chemists were familiar with inorganic compounds; for example, it was known that ammonium cyanate, an inorganic compound, could be easily made by the exchange reaction shown in Reaction (1‐1).

(1‐1)

Even though organic compounds were known, similar reactions that could be used for their synthesis were not known. Instead, organic compounds were obtained primarily from natural sources, such as extraction from plants and other natural sources. As early as 1828, a medical doctor, Friedrich Wöhler, synthesized urea, a known organic compound. The synthesis of urea was accomplished by heating ammonium cyanate (an inorganic compound), as shown by the reaction in Reaction (1‐2).

(1‐2)

This was a major discovery that initiated the era of organic chemistry. For the first time, an organic compound could be synthesized and these types of compounds did not have to be obtained naturally. In the early 1800s, just about all compounds that were used for different reasons, mostly medical, were obtained from natural sources. Today, a large percentage of organic compounds, including urea, which is a major component of fertilizer, adhesives, and resins, are synthesized and are not obtained naturally.

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DID YOU KNOW?

Fruits and vegetables that are produced without the use of pesticides or fertilizers are described as “organic.”

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Organic chemistry is that branch of science that deals with the synthesis and properties of compounds that contain primarily carbon and hydrogen atoms. As mentioned earlier, many other compounds that also contain heteroatoms are also considered organic. It is truly remarkable that the millions of known organic compounds, with new ones being constantly synthesized, all contain only carbons, hydrogens, and just a few heteroatoms! Today, most of the organic compounds that are synthesized are not made from inorganic compounds, but from simpler organic compounds. Some known everyday organic compounds that are made from simple starting organic compounds are shown below.

You may be wondering where are the carbon and hydrogen atoms in these compounds since they are not shown in the structure, except for the first structure, which shows two representations of N,N‐diethyl‐3‐methylbenzamide (DEET). You will learn later in this chapter that at each intersection in the structure, there are carbon and hydrogen atoms or just carbon atoms. DEET contains carbon, hydrogen, oxygen, and nitrogen atoms. Ibuprofen, a painkiller, contains carbon, hydrogen, and oxygen atoms. The artificial sweetener, saccharin, contains carbon, ...

Table of contents

• Cover
• Table of Contents
• Preface
• About the Companion Website
• 1 Bonding and Structure of Organic Compounds
• 2 Carbon Functional Groups and Organic Nomenclature
• 3 Heteroatomic Functional Groups and Organic Nomenclature
• 4 Alkanes, Cycloalkanes, and Alkenes: Isomers, Conformations, and Stabilities
• 5 Stereochemistry
• 6 An Overview of the Reactions of Organic Chemistry
• 7 Acid–Base Reactions in Organic Chemistry
• 8 Addition Reactions Involving Alkenes and Alkynes
• 9 Addition Reactions Involving Carbonyls and Nitriles
• 10 Reduction Reactions in Organic Chemistry
• 11 Oxidation Reactions in Organic Chemistry
• 12 Elimination Reactions of Organic Chemistry
• 13 Spectroscopy Revisited, A More Detailed Examination
• 14 Free Radical Substitution Reactions Involving Alkanes
• 15 Nucleophilic Substitution Reactions at sp3 Carbons
• 16 Nucleophilic Substitution Reactions at Acyl Carbons
• 17 Aromaticity and Aromatic Substitution Reactions
• 18 Conjugated Systems and Pericyclic Reactions
• 19 Catalytic Carbon–Carbon Coupling Reactions
• 20 Synthetic Polymers and Biopolymers
• Index
• End User License Agreement