If you want to continue arguing, well, then I might have to bonk you on the head with my thesis rather than my degree...
Please please please! Bonk him! Bonk him!

If you want to continue arguing, well, then I might have to bonk you on the head with my thesis rather than my degree...

Well, then, let's hear how the acidity of carbonic acid is so much different from, say, sulphurous acid.
I already told you how. In carboxylic acids, the ionized molecule forms a tautomer and is thereby stabilized. Your turn. You tell us about sulphurous acid and the mechanism for stabilizing the anion.
Some chemists will consider hydrocyanic acid to be organic, others won't. Nobody considers sodium cyanide to be an organic compound.
Now, you are arguing that HCN is not "slightly" organic but that it's up for a vote. Although I am nobody, I am puzzled by the second sentence. What is your source for yet another blanket statement?
Actually, no- by this definition, an ionic compound such as sodium carbonate or potassium benzoate would not be organic, since ions are not molecules.
Well, now you're contradicting yourself. You are correct that molecules, in chemistry lexicon, are not considered molecules but they can be organic. You are dead wrong that sodium carbonate or potassium benzoate are ions. These are molecules, namely salts. Salts are molecules as they are not charged. See here.
Why specify the hybridization as sp1,2,3? Do you know any examples where carbon is covalently bonded, but not in one of these arrangements?
No. Just wanted to reemphasize the covalent nature of carbon in organic molecules.
If you want to continue arguing, well, then I might have to bonk you on the head with my thesis rather than my degree...
Bonk away. And I agree that a thesis would be more effective as it weighs more.![]()
The Russian papers and evidence are pretty solid stuff.
I remember when they first went back and checked old wells that had gone dry, and found they had filled up again. Who knew?
Thus, if the oil/coal's too far down, it takes more energy to pump it up than you can gain from burning it.
At the same time, as it becomes scarcer the price goes up and and up, so even though it costs more to extract, it will probably be worth it economically.Yup. This is a real problem. Since most of the easy-to-get oil has been found, extraction is becoming more difficult, expensive and energy intensive. Eventually you could reach a point where the amount of energy you get from the oil you recover is less than the energy you expended in recovering it. I don't get the impression that this is going to happen any time soon, but that's only an impression.
No, there is no tautomerization in the carbonate ion. Tautomers don't stabilize things anyway- you may be thinking of resonance, in which the negative charge is delocalized over two or three oxygens (which does stabilize the anion). You get the same resonance in nitrate, sulphate, phosphate, nitrite, sulphite, phosphite, chlorite, chlorate, perchlorate....I already told you how. In carboxylic acids, the ionized molecule forms a tautomer and is thereby stabilized. Your turn. You tell us about sulphurous acid and the mechanism for stabilizing the anion.
Cyanide is more often considered a pseudohalide than an organic ion- that's well-known enough that it doesn't need a cite.Although I am nobody, I am puzzled by the second sentence. What is your source for yet another blanket statement?
(Cotton, Wilkinson, Murillo, Bochmann, Advanced Inorganic Chemistry, 6th Ed., p. 228) The same book has a list of the important inorganic compounds of carbon, including the oxides, sulphides, halides, and HCN.An important area of "inorganic" carbon chemistry is that of compounds with C-N bonds. The most important species are the cyanide, cyanate, and thiocyanate ions and their derivatives. We can regard many of these compounds as being pseudohalogens or pseudohalides, but the analogies, although reasonably apt for cyanogen, (CN)2, are not especially valid in other cases.
Molecules are not considered molecules....who did you say was being contradictory?Well, now you're contradicting yourself. You are correct that molecules, in chemistry lexicon, are not considered molecules but they can be organic.
There is no such thing as a potassium carbonate molecule.You are dead wrong that sodium carbonate or potassium benzoate are ions. These are molecules, namely salts. Salts are molecules as they are not charged.
No, there is no tautomerization in the carbonate ion. Tautomers don't stabilize things anyway- you may be thinking of resonance, in which the negative charge is delocalized over two or three oxygens (which does stabilize the anion). You get the same resonance in nitrate, sulphate, phosphate, nitrite, sulphite, phosphite, chlorite, chlorate, perchlorate....
Resonance is not unique to organic chemistry.
Cyanide is more often considered a pseudohalide than an organic ion- that's well-known enough that it doesn't need a cite.
Here's one:
(Cotton, Wilkinson, Murillo, Bochmann, Advanced Inorganic Chemistry, 6th Ed., p. 228) The same book has a list of the important inorganic compounds of carbon, including the oxides, sulphides, halides, and HCN.
Complex ions which contain cyanide as ligands (such as ferricyanide, [Fe(CN)6]3-) are always considered to be simple coordination compounds, and not organometallic compounds (which would include iron pentacarbonyl, Fe(CO)5).
Molecules are not considered molecules....who did you say was being contradictory?
There is no such thing as a potassium carbonate molecule.
Potassium carbonate contains potassium ions and carbonate ions in a 2:1 ratio in an alternating lattice. No one potassium ion is bonded to or affiliated with any particular carbonate ion. There are no bonds between the potassium and carbonate (forget anything you may have read about "ionic bonds"- there's an attraction, but it's not a bond).
Salts are electrically neutral because they contain enough anions to balance the cations, and vice versa, but they are not, and do not contain, molecules.
Still trying to figure out what your case is...You're right. Resonance was the word I wanted. Does this help your case?
Don't quote wikipedia at me. Particularly when there's nothing there that backs you up.Read
No, it makes a pair of ions, or a very small crystal of potassium carbonate.You're being pedantic and avoiding the issue. Suppose you had two ions of potassium and one carbonate ion. Would that make a molecule?
Because I'm still trying to figure out how you think sulphurous acid is so very different from carbonic acid.You should take your own advice regarding ionic "bonds" regarding your question about sulfurous acid. (Why haven't you addressed that one, by the way?).
So do a lot of other acids.Whether it's resonance or magic, carbonic acid behaves like a carboxylic acid.
Mineral acids, strong or not, are not, repeat, NOT ionic. They ionize in water, but when pure, they are covalent.Although I believe you're wrong, let's pretend for a minute that the anions of strong mineral acids also resonate. One critical difference is that their "bonds" with hydrogen are ionic, not covalent. These anions don't need to have the hydrogens dissociate to resonate whereas the the carbonate anion does. Please address this.
I say it isn't because it acts like a typical inorganic anion.Madalch, with all due respect, stick to the issue. That being whether or not the carbonate ion is organic or not. I say it is because it acts like an organic acid. You say it isn't because there's no direct carbon-hydrogen bond.
Cases where you've defined the molecule to be organic simply because it fits your definition, rather than what chemists consider to be organic.I've posted structures where that is true but the molecules are still organic. So, I reject your defintion because it doesn't hold in too many cases.
You're very welcome.Thank you plenty, Tricky. I think I never realized how much the earth's surface has been plowed over within the past 500 or so million years. Thank you for fixing that. Still, a few gaps remain.
Originally? Well, the sun. Before that, the Big Bang. Most of the CO2 and Methane in the atmosphere of the earth (prior to life on earth) were released through volcanic degassing, I assume through processes involved as the earth cooled. I honestly don't know enough to say what form the carbon, hydrogen and oxygen atoms were in before they formed CO2 and CH4, the two most stable of small carbon-containing molecules.Where did the carbon, hydrocarbons originally come from? Just atmospheric CO2 and maybe a small amount dissolved in water?
That is true. (BTW, oil is in the crust. The mantle is far too hot to preserve oil or probably much methane.) The question of how much there is has been around for ages. Technology has vastly increased the definition of "close enough to the surface", as well as the areas where we can search for oil. Previously unthinkable areas for drilling, like Antarctica are now coming within reach. The short answer is: There will always be oil, if you are willing to pay enough. At some point, though, even the most inefficient solar collectors become more cost-effective.Then two more things: Whether oil/coal are biogenic or abiogenic in origin doesn't really say much about peak oil or other theories about the end of the age of oil. The problem of oil isn't so much one about how much oil there really is, totally, in the mantle. The problem of oil is how much is there close enough to the surface.
No, I won't correct you. In fact, you are exactly right, although the cost is in much more than energy. There are a myriad of problems associated with deep drilling, most of them associated with the tremendous temperatures you get at great depth. Drill pipe that can withstand this temperature and the corrosive fluids associated with it, has to be made of alloys that are incredibly expensive (and some are still theoretical). Instruments fail at these temperatures and pressures.Pumping oil up consumes energy, the more the deeper it is. Thus, if the oil/coal's too far down, it takes more energy to pump it up than you can gain from burning it. I guess (hope?) Tricky will correct the living hell out of me now and tell me about pumping water down for great justice.
Still trying to figure out what your case is...
Don't quote wikipedia at me. Particularly when there's nothing there that backs you up.
No, it makes a pair of ions, or a very small crystal of potassium carbonate.
Because I'm still trying to figure out how you think sulphurous acid is so very different from carbonic acid.
So do a lot of other acids.
Mineral acids, strong or not, are not, repeat, NOT ionic. They ionize in water, but when pure, they are covalent.
Hydrogen chloride has a covalent bond between the hydrogen and the chlorine. That's why it's a gas at room temperature, has a very low boiling and melting point, and can be dissolved in solvents of low polarity.
Sulphuric acid is also covalent. There is some auto-ionization of the pure acid, but only about 1% of the acid is in the form of [H3SO4][HSO4] or other products. Note that there is no [H+][HSO4-], as a bare proton cannot exist for any length of time in any solvent without finding some source of electron density- some lone pair or bond to protonate. It's charge-to-radius ratio is far too large.
Weak inorganic acids such as sulphurous, phosphoric, or nitrous are clearly not ionic, since that would make them strong acids. But they're not.
Why are you so insistent that carbonates be considered organic? Other than the fact that they contain carbon, how are they similar to organic compounds?
I say it isn't because it acts like a typical inorganic anion.
Cases where you've defined the molecule to be organic simply because it fits your definition, rather than what chemists consider to be organic.
Humor me. No mention of pseudohalide here.
Really? Where does it say that resonance only occurs in organic compounds? Where does it say that carbonic acid ionizes according to a completely different mechanism than do inorganic acids?Well, if it doesn't back me up, it certainly does completely contradict a couple of your "just so" statements. Where's the easily-found citation on pseudohalides?
That's correct- molecules are neutral, not charged.So, not a molecule? No ionic molecules in your world? So, only uncharged groups of atoms can be called molecules?
Tell you what- how carbonic acid ionizes in a completely different fashion from acids such as sulphurous and nitric? It doesn't.Why not just tell me?
No, they don't.Yes, and they happen to be organic.
What I was responding to was this gem: "One critical difference is that their "bonds" with hydrogen are ionic, not covalent."Maybe you haven't noticed that, in a previous post, I noted that there is no such thing as a purely ionic or purely covalent bond. No?
Yes, they do.Because they act like the rest of the series of carboxylic anions. They don't ionize in the same manner as inorganic acids.
Since the distinction between organic compounds and inorganic ones is simply a convention, one must go with the convention that most chemists use. And chemists don't consider carbonates to be organic. (Apart from covalent ones like ethylene carbonate, of course.)Why are you so insistent that it's inorganic? My approach makes infinitely more sense than your indefinite, wishy-washy, "everyone else thinks so" approach.
Really? Where does it say that resonance only occurs in organic compounds?
Where does it say that carbonic acid ionizes according to a completely different mechanism than do inorganic acids?
Oh, here's your reference on pseudohalides:http://en.wikipedia.org/wiki/Pseudohalide Happy?
That's correct- molecules are neutral, not charged.
Tell you what- how carbonic acid ionizes in a completely different fashion from acids such as sulphurous and nitric? It doesn't.
No, they don't.
What I was responding to was this gem: "One critical difference is that their "bonds" with hydrogen are ionic, not covalent."
This is absolutely wrong. While some bonds are more ionic than others, bonds with hydrogen have very little ionic character (unless in a metal hydride). The hydrogen-oxygen bonds in inorganic acids are not significantly different from those in organic acids.
Yes, they do.
Since the distinction between organic compounds and inorganic ones is simply a convention, one must go with the convention that most chemists use. And chemists don't consider carbonates to be organic. (Apart from covalent ones like ethylene carbonate, of course.)


Nominated, because it is a great example of how skeptics should be. They should be convincible with proper evidence. They should be honest. They should be honorable. Slimething shows us how it is done.Well, thanks to Madalch, I've gone and done some research and it turns out that he is correct and I am wrong.
***
So, I hereby apologize* for the needless argumentation, confusion and cussedness I visited upon everyone in the Forum. I should have checked my facts before I foisted my personal views on one-carbon organicity, especially given that scientific convention had already decided otherwise.
All I can say is that I won't soon make that mistake again.
Sorry,
Slimey
*Especially to Madalch, geni, Hokulele, hell too many people to list. Madalch, let the bashing begin!![]()
No worries. After all, didn't we all come here for a good argument?So, I hereby apologize for the needless argumentation, confusion and cussedness I visited upon everyone in the Forum.
Madalch, let the bashing begin!
We're quibbling over carbonates. Slimeyis arguing that they're organic due to their electronic characteristics while the evil guys
think it's inorganic because it's found in rocks. Carbonates, by the way, have cabon and oxygen and, at one time, had hydrogen. However, even poor bicarbonate, with its lone hydrogen, can't catch a break as it's been labeled inorganic by the truly evil.
I would like to point out that while a few have proposed rules, and one "generally" rule, on what is organic and what isn't, all have fallen except mine. If you missed it, organic is a molecule that contains carbon bound covalentely to any other atom and is in sp1, sp2 or sp3 arrangement. Anybody have an exception to that one? If not, carbonates are organic.![]()
As far as "peak oil" goes, there is no doubt that we will eventually have to switch from a hydrocarbon-based fuel source, but technology keeps pushing that date further into the future. At present, there are numerous technologies in development for shale oil, enhanced recovery, refining of previously unusable hydrocarbons et. al. that we probably have more than a half century left before the real crunch hits. I'm hoping the transition will be gradual. I'm scared it won't.