Organic Chemistry - How it works
I NTRODUCTION TO C ARBON
As the element essential to all of life, and hence the basis for a vast field of study, carbon is addressed in its own essay. The Carbon essay, in addition to examining the chemical properties of carbon (discussed below), approaches a number of subjects, such as the allotropes of carbon. These include three crystalline forms (graphite, diamond, and buckminsterfullerene), as well as amorphous carbon. In addition, two oxides of carbon—carbon dioxide and carbon monoxide—are important, in the case of the former, to the natural carbon cycle, and in the case of the latter, to industry. Both also pose environmental dangers.
The purpose of this summary of the carbon essay is to provide a hint of the complexities involved with this sixth element on the periodic table, the 14th most abundant element on Earth. In the human body, carbon is second only to oxygen in abundance, and accounts for 18% of the body's mass. Capable of combining in seemingly endless ways, carbon, along with hydrogen, is at the center of huge families of compounds. These are the hydrocarbons, present in deposits of fossil fuels: natural gas, petroleum, and coal.
A PROPENSITY FOR LIMITLESS BONDING.
Carbon has a valence electron configuration of 2s 2 2p 2 . Likewise all the members of Group 4 on the periodic table (Group 14 in the IUPAC version of the table)—sometimes known as the "carbon family"—have configurations of ns 2 np 2 , where n is the number of the period or row the element occupies on the table. There are two elements noted for their ability to form long strings of atoms and seemingly endless varieties of molecules: one is carbon, and the other is silicon, directly below it on the periodic table.
Just as carbon is at the center of a vast network of organic compounds, silicon holds the same function in the inorganic realm. It is found in virtually all types of rocks, except the calcium carbonates—which, as their name implies, contain carbon. In terms of known elemental mass, silicon is second only to oxygen in abundance on Earth. Silicon atoms are about one and a half times as large as those of carbon; thus not even silicon can compete with carbon's ability to form
Carbon is further distinguished by its high value of electronegativity, the relative ability of an atom to attract valence electrons. To mention a few basic aspects of chemical bonding, developed at considerably greater length in the Chemical Bonding essay, if two atoms have an electric charge and thus are ions, they form strong ionic bonds. Ionic bonding occurs when a metal bonds with a nonmetal. The other principal type of bond is a covalent bond, in which two uncharged atoms share eight valence electrons. If the electronegativity values of the two elements involved are equal, then they share the electrons equally; but if one element has a higher electronegativity value, the electrons will be more drawn to that element.
The electronegativity of carbon is certainly not the highest on the periodic table. That distinction belongs to fluorine, with an electronegativity value of 4.0, which makes it the most reactive of all elements. Fluorine is at the head of Group 7, the halogens, all of which are highly reactive and most of which have high electronegativity values. If one ignores the noble gases, which are virtually unreactive and occupy the extreme right-hand side of the periodic table, electronegativity values are highest in the upper right-hand side of the table—the location of fluorine—and lowest in the lower left. In other words, the value increases with group or column number (again, leaving out the noble gases in Group 8), and decreases with period or row number.
With an electronegativity of 2.5, carbon ties with sulfur and iodine (a halogen) for sixth place, behind only fluorine; oxygen (3.5); nitrogen and chlorine (3.0); and bromine (2.8). Thus its electronegativity is high, without being too high. Fluorine is not likely to form the long chains for which is carbon is known, simply because its electronegativity is so high, it overpowers other elements with which it comes into contact. In addition, with four valence electrons, carbon is ideally suited to find other elements (or other carbon atoms) for forming covalent bonds according to the octet rule, whereby most elements bond so that they have eight valence electrons.
C ARBON'S M ULTIPLE B ONDS
Carbon—with its four valence electrons—happens to be tetravalent, or capable of bonding to four other atoms at once. It is not necessarily the case that an element has the ability to bond with as many other elements as it has valence electrons; in fact, this is rarely the case. Additionally, carbon is capable of forming not only a single bond, with one pair of shared valence electrons, but a double bond (two pairs) or even a triple bond (three pairs.)
Another special property of carbon is its ability to bond in long chains that constitute strings of carbons and other atoms. Furthermore, though sometimes carbon forms a typical molecule (for example, carbon dioxide, or CO 2, is just one carbon atom with two oxygens), it is also capable of forming "molecules" that are really not molecules in the way that the word is typically used in chemistry. Graphite, for instance, is just a series of "sheets" of carbon atoms bonded tightly in a hexagonal, or six-sided, pattern, while a diamond is simply a huge "molecule" composed of carbon atoms strung together by covalent bonds.
O RGANIC C HEMISTRY
Organic chemistry is the study of carbon, its compounds, and their properties. The only major carbon compounds considered inorganic are carbonates (for instance, calcium carbonate, alluded to above, which is one of the major forms of mineral on Earth) and oxides, such as carbon dioxide and carbon monoxide. This leaves a huge array of compounds to be studied, as we shall see.
The term "organic" in everyday language connotes "living," but organic chemistry is involved with plenty of compounds not part of living organisms: petroleum, for instance, is an organic compound that ultimately comes from the decayed bodies of organisms that once were alive. It should be stressed that organic compounds do not have to be produced by living things, or even by things that once were alive; they can be produced artificially in a laboratory.
The breakthrough event in organic chemistry came in 1828, when German chemist Friedrich Wöhler (1800-1882) heated a sample of ammonium cyanate (NH 4 OCN) and converted it to urea (H 2 N-CO-NH 2 ). Ammonium cyanite is an inorganic material, whereas urea, a waste product in the urine of mammals, is an organic one. "Without benefit of a kidney, a bladder, or a
Ammonium cyanate and urea are isomers: substances having the same formula, but possessing different chemical properties. Thus they have exactly the same numbers and proportions of atoms, yet these atoms are arranged in different ways. In urea, the carbon forms an organic chain, and in ammonium cyanate, it does not. Thus, to reduce the specifics of organic chemistry even further, this discipline can be said to constitute the study of carbon chains, and ways to rearrange them to create new substances.