Creative Chemistry: Descriptive of Recent Achievements in the Chemical Industries - Edwin E. Slosson

There! I had to introduce you to the whole receiving line, but now that that ceremony is over we are at liberty to do as we do at a reception, meet our old friends, get acquainted with one or two more and turn our backs on the rest. Two of them, I am sure, you've met before, phenol, which is common carbolic acid, and naphthalene, which we use for mothballs. But notice one thing in passing, that not one of them is a dye. They are all colorless liquids or white solids. Also they all have an indescribable odor—all odors that you don't know are indescribable—which gives them and their progeny, even when odorless, the name of "aromatic compounds."

Fig. 8. Diagram of the products obtained from coal and some of their uses.

The most important of the ten because he is the father of the family is benzene, otherwise called benzol, but must not be confused with "benzine" spelled with an i which we used to burn and clean our clothes with. "Benzine" is a kind of gasoline, but benzene alias benzol has quite another constitution, although it looks and burns the same. Now the search for the constitution of benzene is one of the most exciting chapters in chemistry; also one of the most intricate chapters, but, in spite of that, I believe I can make the main point of it clear even to those who have never studied chemistry—provided they retain their childish liking for puzzles. It is really much like putting together the old six-block Chinese puzzle. The chemist can work better if he has a picture of what he is working with. Now his unit is the molecule, which is too small even to analyze with the microscope, no matter how high powered. So he makes up a sort of diagram of the molecule, and since he knows the number of atoms and that they are somehow attached to one another, he represents each atom by the first letter of its name and the points of attachment or bonds by straight lines connecting the atoms of the different elements. Now it is one of the rules of the game that all the bonds must be connected or hooked up with atoms at both ends, that there shall be no free hands reaching out into empty space. Carbon, for instance, has four bonds and hydrogen only one. They unite, therefore, in the proportion of one atom of carbon to four of hydrogen, or CH₄, which is methane or marsh gas and obviously the simplest of the hydrocarbons. But we have more complex hydrocarbons such as C₆H₁₄, known as hexane. Now if you try to draw the diagrams or structural formulas of these two compounds you will easily get

Each carbon atom, you see, has its four hands outstretched and duly grasped by one-handed hydrogen atoms or by neighboring carbon atoms in the chain. We can have such chains as long as you please, thirty or more in a chain; they are all contained in kerosene and paraffin.

So far the chemist found it east to construct diagrams that would satisfy his sense of the fitness of things, but when he found that benzene had the compostion C₆H₆ he was puzzled. If you try to draw the picture of C₆H₆ you will get something like this:

which is an absurdity because more than half of the carbon hands are waving wildly around asking to be held by something. Benzene, C₆H₆, evidently is like hexane, C₆H₁₄, in having a chain of six carbon atoms, but it has dropped its H's like an Englishman. Eight of the H's are missing.

Now one of the men who was worried over this benzene puzzle was the German chemist, Kekulé. One evening after working over the problem all day he was sitting by the fire trying to rest, but he could not throw it off his mind. The carbon and the hydrogen atoms danced like imps on the carpet and as he watched them through his half-closed eyes he suddenly saw that the chain of six carbon atoms had joined at the ends and formed a ring while the six hydrogen atoms were holding on to the outside hands, in this fashion: