Download PDF Organic Chemistry Seventh Edition by William H. Brown

Sinopsis

According to the simplest definition, organic chemistry is the study of the compounds of carbon. Perhaps its most remarkable feature is that most organic compounds consist of carbon and only a few other elements—chiefly, hydrogen, oxygen, and nitrogen. Chemists have discovered or made well over 10 million compounds composed of carbon and these three other elements. Organic compounds are all around us—in our foods, flavors, and fragrances; in our medicines, toiletries, and cosmetics; in our plastics, films, fibers, and resins; in our paints and varnishes; in our glues and adhesives; in our fuels and lubricants; and, of course, in our bodies and the bodies of all living things.
 

Let us review how the elements of C, H, O, and N combine by sharing electron pairs to form bonds, and ultimately molecules. No doubt, you have encountered much of this initial material in previous chemistry courses; however, the chapters that follow require your ability to use this knowledge fluently.

An atom contains a small, dense nucleus made of neutrons and positively charged protons. Most of the mass of an atom is contained in its nucleus. The nucleus is surrounded by an extranuclear space containing negatively charged electrons. The nucleus of an atom has a diameter of 10214 to 10215 meters (m). The electrons occupy a much larger volume with a diameter of approximately 10210 m (Figure 1.1). Shells define the probability of finding an electron in various regions of space relative to the nucleus. The energy of electrons in the shells is quantized. Quantization means that only specific values of energy are possible, rather than a continuum of values. These shells occur only at quantized energies in which three important effects balance each other. The first is the electrostatic attraction that draws the electrons toward the nucleus; the second is the electrostatic repulsion between the electrons; and the third is the wavelike nature of an electron that prefers to be delocalized, thereby spreading the electron density away from the nuclei. Delocalization describes the spreading of electron density over a larger volume of space. Electron shells are identified by the principal quantum numbers 1, 2, 3, and so forth. Each shell can contain up to 2n2 electrons, where n is the number of the shell. Thus, the first shell can contain 2 electrons; the second, 8 electrons; the third, 18 electrons; the fourth, 32 electrons; and so on (Table 1.1). Electrons in the first shell are nearest to the positively charged nucleus and are held most strongly by it; these electrons are lowest in energy. Electrons in higher-numbered shells are farther from the positively charged nucleus and are held less strongly.

Content

1. Covalent Bonding and Shapes of Molecules
2. Alkanes and Cycloalkanes
3. Stereoisomerism and Chirality
4. Acids and Bases
5. Alkenes: Bonding, Nomenclature, and Properties
6. Reactions of Alkenes
7. Alkynes
8. Haloalkanes, Halogenation, and Radical Reactions
9. Nucleophilic Substitution and b-Elimination
10. Alcohols
11. Ethers, Epoxides, and Sulfides
12. Infrared Spectroscopy
13. Nuclear Magnetic Resonance Spectroscopy
14. Mass Spectrometry
15. An Introduction to Organometallic Compounds
16. Aldehydes and Ketones
17. Carboxylic Acids
18. Functional Derivatives of Carboxylic Acids
19. Enolate Anions and Enamines
20. Dienes, Conjugated Systems, and Pericyclic Reactions
21. Benzene and the Concept of Aromaticity
22. Reactions of Benzene and Its Derivatives
23. Amines
24. Catalytic Carbon-Carbon Bond Formation
25. Carbohydrates
26. Lipids
27. Amino Acids and Proteins
28. Nucleic Acids
29. Organic Polymer Chemistry

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