The Fascinating Acetylacetone Molecule and Its Acetylacetonate Salts

Chemistry, Technology
[caption id="attachment_20255" align="alignright" width="400"] Cobalt III Acetylacetonate[/caption] Acetylacetone is the simplest of the β-diketones and supports the phenomenon we call keto-enol tautomerism (see the illustration). Notice that the third carbon atom in the 5-carbon keto chain loans one of its hydrogen atoms in forming the enol tautomer. The freedom to move of this hydrogen atom suggests acetylacetone is a weak acid.1 In effect, the saturated di-ketone becomes an unsaturated di-alcohol. Only instead of two hydrogen atoms, one to each oxygen atom, there is just the one hydrogen atom that must be shared. Preparation Commercially, acetylacetone or H(acac) can be prepared from isopropenyl acetate by heating it in the presence of an appropriate metal catalyst. Dissociation and Reaction Since it is an acid, it can ionize or "disassociate", giving a positive…
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Our Planet and Atmosphere: Ozone – the “Other” Oxygen

Health, Technology
[caption id="attachment_20184" align="alignright" width="440"] The Blue Ridge Mountains of Virginia[/caption] Oxygen atoms are very reactive chemically. We call them electrophilic or "electron loving" because the oxygen atom seeks to bind to other electron-rich sources, especially itself. Thus oxygen is present in our atmosphere primarily as the molecular O₂. Another Form A small percentage of atmospheric oxygen exists in another form, ozone, O₃. This less stable form of oxygen is produced by ultraviolet light or high voltage electrical discharge. It's garlicky odor may be discerned after a heavy thunderstorm. Geometry The O₂ molecule consists of only two atoms, and two points make a line, right? So what shape is the O₃ molecule? Unlike its more abundant companion, ozone is non-linear. As a result, it carries partial charges on its constituent atoms.…
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Goiter, Seafood and Table Salt – What’s the Connection?

Food, Health
Times change. Travel is now common. Cross-country shipping is common. How does all of this fit in with our discussion concerning seafood, goiter, and iodized salt? Not long ago, I met a woman, a lovely older lady, who had a very large goiter encircling her neck. It was shocking and I felt so sorry for her. A month later I saw her following surgery and she looked perfectly normal! Many surgeries have come a long way. Nevertheless, what is the cause of goiter, and how do seafood and iodized salt come into the picture? What Causes Goiter This is not a medical article, per se, but touches upon the food chemistry behind the common, endemic variety of hypothyroidism.¹ In time, insufficient thyroid hormone secretion produces a goiter. The hormone lacking…
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Tylenol, Its Structure, Nomenclature, and a Lab Synthesis

Chemistry, Medicine
Tylenol® is a trade name for acetaminophen.1 Does the latter word sound foreign to you? Let's find out what it means. This compound contraction combines acetyl with amino with phenol. What's in a Name? Does acetyl remind you of acetic acid or vinegar? Acetic acid is CH3COOH. The acetyl group is written CH3CO–. Amino is familiar too, as in amino acid? The basic amino group is written NH2–, though at times one or both of the hydrogen atoms are replaced by something else, as it is for Tylenol. Finally, "phen" stands for phenyl. Remove one atom from a benzene ring and you have phenyl. C₆H₅– is the simplest phenyl ring. Again, hydrogen atoms may be replaced with something else. The end result of putting these together to form acetaminophen is…
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Slip ’em a Mickey: Chloral Hydrate, a Stabilized Geminal Diol

Health, Medicine
Among the endless thousands of organic compounds that are familiar to the public, one is associated with foul bars, booze, and foul play. It is chloral hydrate (Cl₃C-CH(OH)₂). Combined with an alcoholic beverage, the result, an infamous "Mickey Finn" causes the victim to pass out as quickly as if he had been knocked out. Mickey (Not Steamboat Mickey) In the Movies In old-movie and TV shows, the bad guy (often in a saloon) wants to capture his victim by rendering him unconscious. Maybe he even wants to sell the man to a ship's captain who needs to complete his crew. The poor guy is Shanghaied! An interesting example is this old Bonanza western TV show episode: Was There an Actual Mickey Finn? It appears there was! In the latter part…
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How the Tear Ingredient Lysozyme Fights Bacteria

Biology, Chemistry
[caption id="attachment_19802" align="alignright" width="460"] 1,4-beta glycosidic bond[/caption] Human tears largely consist of water, sodium, and potassium electrolytes. However, these are not the only important substances found in tears. There are a number of complex organic substances essential in maintaining the eye. One ingredient is lysozyme, prominent among a group of chemicals which exhibit antibacterial behavior [see the PubChem reference for an image of lysozyme]. Lysozyme Modus Operandum The University of Colorado reference (cited) makes the following statement: "The enzyme lysozyme breaks down bacterial cell walls, which are made of a unique compound called peptidoglycan." Molecular Structure of the Contenders [caption id="attachment_19810" align="alignright" width="330"] cyclohexane chair conformer[/caption] The fifty-cent name for lysozyme is N-acetylmuramide glycanhydrolase. The suffix at the end of the name, -ase, indicates this compound is an enzyme. An…
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Why is My Potato Salad Mushy? Heat Capacity

Food, Physics
If you have a curious mind, you look at everyday matters differently. You ask yourself questions others do not care about. What is spider silk made of? What happens when water boils? Why do canned whole tomatoes look so perfect? Why are buttercups so bright? Are there dust storms on Mars? But now we ask: Since others make delicious potato salad, why is my potato salad mushy? The Challenge Potato salad is one of the most satisfying foods out there. It is low-cost and complements even simple meals. But it can detract from a meal if the potatoes are too hard, or if the potato salad is better called mashed potato salad. Such results obviously involve potato variety, size, and uniformity of the cut pieces. But more is involved. Temperature…
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Cooking Onions: Flavor Chemistry Changes

Chemistry, Food
[caption id="attachment_21597" align="alignright" width="480"] M-m-m, Sweet![/caption] An onion, particularly a yellow or Bermuda onion possesses a strong, perhaps acrid flavor. And its aroma? You are likely to weep when you chop one! Yet, if you take that same onion and fry it, it can be just as fragrant and sweet as ever you could wish. What happened? It's a matter of chemistry. From Wild to Tame The flavor of a raw onion is the product of a number of complex organic substances. The ingredient primarily responsible for tear-ing, is (Z)-propanethial-S-oxide. This compound, a lachrymator (tear-producing gas), is produced when onion cell walls are broken by slicing and chopping. Does frying result in a decrease of this chemical, resulting in sweetness? Does this compound decompose on frying to producing the sweetness?1…
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Some Prospered from the Stock Market Crash of 1929 and the Great Depression

History, People
[caption id="attachment_19683" align="alignright" width="440"] Soup kitchen opened in Chicago by Al Capone.[/caption] The Great Depression is the term applied to a serious and long-lasting financial depression that began in the United States in 1929 and lasted through approximately 1941. Naturally, it affected the world in general. Curiously, but when you think about it, not too surprisingly, not all U.S. citizens suffered from the Great Depression. In fact, some even prospered as a result of it. Who? How? The Masses Probably contrary to what you might suppose, life expectancy actually rose. It's natural to think suicide would have lowered life expectancy; yet suicide represents only a tiny fraction of total deaths. Even though suicides increased, longevity improved. The CNN reference offers some suggestions why. Individual Success Charles Darrow: Some prospered not…
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Initiating a Fission Chain Reaction: What is Critical Mass?

Physics, Technology
[caption id="attachment_19651" align="alignright" width="600"] One basic fission reaction[/caption] What is critical mass? Before we answer that question, we want to discuss the topic of fission, itself. When we speak of atomic bombs, we do not usually mean hydrogen bombs or fusion bombs in which the nuclei of hydrogen atoms fuse together.¹ Rather, we mean fission bombs, in which large atoms of radioactive (unstable) elements are torn apart to produce smaller atoms with the release tremendous energy. One simple atomic explosion reaction is written, 1 n + 235U → [236U] → 92Kr + 141Ba + 3 n The above equation informs us that one energetic neutron properly striking an atom of uranium, isotope 235, produces, first and temporarily, an ordinarily stable atom of uranium, isotope 236. [caption id="attachment_19652" align="alignleft" width="300"] Uraninite…
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