Covering Cool Organic Discoveries

Covering Cool Organic Discoveries

Chance and wealth played a major role in the great discoveries of organic chemistry (although luck, Pasteur says, favors a ready mind).
Explosives and dynamite!
Alfred Nobel and his family realized the potential of nitroglycerin as a commercial explosive – a substance with more favorable explosive properties than gunpowder. However, in his laboratory, his family found out first-hand how dangerous this substance is. In a massive explosion of nitroglycerin, Alfred’s brother Emil and several of his co-workers were killed. After the accident, Alfred worked to make nitroglycerin safer. Note that when he mixed nitroglycerin syrup with silica powder (diatomaceous earth) he obtained a stable mash which he called dynamite. When he marketed his discovery – along with his explosive hats to safely start the explosion – he became one of the richest men of his time. When he died in 1896, he left his fortune to found the Nobel Foundation. Each year the Nobel Foundation awards the most prestigious Nobel Prizes, and, ironically, the Peace Prize is one of the most famous.

No one knows for sure who discovered fermentation, but fermentation was probably first observed thousands of years ago in crates of rotting fruit. After being bruised and left for several weeks, the fruit is fermented (broken down by the enzymes in yeast) to make alcohol. Although this rotting fruit may not have tasted very good, someone who drank the juice discovered that it had a powerful and pleasant effect on the body. This likely led to the discovery of the wine industry and, soon after, the manufacture of beer, which used grains and honey as a source of sugars and carbohydrates instead of fruit. The Sumerians first began brewing beer about 6000 years ago (although beer-making may have been going on long before this time). In fact, some have suggested that many humans abandoned their nomadic lifestyles and became farmers after the discovery of fermentation, just in order to grow crops to make beer. (This suggestion seems to be consistent with human nature.)

synthesis of urea
The synthesis of the organic compound urea from an inorganic by Friedrich Fuller was a major early breakthrough in organic chemistry. Through this achievement, he showed that organic matter was not held together by a “vital life force”, as was assumed at the time. Wöhler attempted to synthesize ammonium cyanate as a continuation of his studies of inorganic cyanate. Instead, he isolated a substance that appeared to resemble urea, a “substance called an animal substance,” or, in modern terms, an organic compound. By comparing the properties of his compound compound with those of the pure urea he extracted from urine, it was found that the properties of the two are identical.

Tartaric acid brain
Louis Pasteur discovered the penetration of tartaric acid. Why was Pasteur studying tartaric acid? As a French chemist, he was studying wine (of course), of which tartaric acid is one of its components. Note that tartaric acid forms into two different crystal forms. He separated the crystals with tweezers under a microscope, and noticed that crystals of one shape rotated polarized light in one direction, and other crystals rotated light in the opposite direction. He (correctly) believed that these different crystals should be related to the equilibriums (for ease of understanding, just think right or left) of the same molecules.

Dills Alder’s reaction
Two German chemists, Otto Diels and Kurt Alder, discovered the structure of the diene now known as the Diels-Alder reaction. This reaction is absolutely fascinating – it forms two carbon-carbon bonds at once, which is very useful for building strange-looking dicyclic molecules and different six-membered rings. Interestingly, in their classic research paper describing the interaction, Dils and Alder wrote, “We explicitly reserve for ourselves the reaction we have developed to solve such problems [the synthesis of a natural product].” Surprisingly, this “retreat!” The warning of other chemists had the desired effect: other chemists stayed away from this reaction even after the end of World War II, and synthetic chemistry in Germany took a heavy blow. Such statements in the literature usually have the opposite effect to the intended effect. Moses Gomberg discovered it the hard way in 1900 when he reserved the right to study the roots of triphenylmethyl (Ph3Cá) – the first known radical to chemists – and chemists trampled each other to begin their own research on the molecule.

Buckyballs are the newest allotrope of carbon that has been discovered. Allotropes are compounds that contain only one element – in this case, carbon. Other allotropes of carbon include graphite and diamond. Buckyballs, discovered in 1985 by Richard Smalley, Harry Crotto, and Robert Curl, look like molecular soccer balls. Buckyballs were discovered by chance when these chemists blasted a laser on graphite powder, passing the products through a mass spectrometer. They note a peak in their mass spectrum that corresponds exactly to 60 carbon atoms. Using intuition, they believed that the structure corresponding to this peak should be a spherical molecule. They named this molecule Buckminsterfullerene, after Buckminster Fuller, who popularized the geodesic dome; These particles are often called buckyballs because of their spherical shape. Although these molecules have not produced any practical applications yet, they are being studied for use as superconductors, as markers for gasoline (so oil spills can be traced back to a specific oil company), and as drug delivery vehicles.

Legend has it that soap was first discovered by Roman women washing their clothes along the Tiber River. They noticed that in some places of the river their clothes were cleaner than when they washed them in other places. Apparently, beside the river was a sacrificial site, where animal fats from the offerings are supposedly mixed with fire ashes (containing lye, or sodium hydroxide), to make soap. Then the soap went down the hill to the river after it rained.

James Schlatter discovered aspartame by doing something that would make safety experts shiver – he licked his fingers after working in the lab. He found that his fingers tasted very sweet. He credited the sweetness to aspartame, the compound he was working on (and had another taste of synthetic aspartame just to make sure it was just right). Thus one of the most popular sugar substitutes was born. Both Nutrasweet and Equal contain the sugar substitute aspartame, as do many diet sodas.

The story of the discovery of penicillin is perhaps the most famous case of chance in the discovery process. Alexander Fleming was doing research on Staphylococcus bacteria, when he noticed that his culture plates had been contaminated with Penicillium fungi. He disposed of the dishes in a sterile wash, but it did not submerge them properly. When he returned to the lab, he noticed that bacteria had been killed on the dishes in which the mushrooms had grown. He said to himself, “The thing the mushrooms produce must be killing the bacteria.” That thing was penicillin, an antibiotic that would ultimately save countless lives.

Two chemists, James Reebok and Roy Plunkett, working for DuPont, discovered Teflon in 1938. Teflon is the polymeric nonstick surface that prevents eggs, bacon, and pancakes from sticking to pans. When they discovered Teflon, Reebok and Blunkett were working with fluorinated hydrocarbon gases kept in large packages. One day they opened the valve over what they thought was a full gas canister, but no gas came out. At first, they thought the canister had leaked, until they noticed that the supposedly empty canister had the same weight as the full container. Upon opening the container, they found a sticky white substance that had covered the inside of the container – Teflon!