Dissenter
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  • fluorine's 3d orbital
Why are tertiary carbocations the most reactive, if they're already stable?
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28 votes

This is an excellent question. Please correct me if I'm wrong, but I think this is what you are grasping at: First, it is true that tertiary carbocations are generally more stable than primary ...

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Why doesn't HCl form when you dissolve NaCl in water?
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22 votes

If you dissolve NaCl in water you will get some HCl molecules but there's definitely not going to be a significant concentration of HCl formed. The reaction that you propose - $\ce{Cl- + H2O -> ...

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Can you make napalm out of gasoline and orange juice concentrate?
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17 votes

Here's an excerpt from an interview with the author of Fight Club, Chuck Palhniuk. How to make Napalm with Frozen Orange Juice and Gasoline? Well, Ed Norton changed one ingredient in every one ...

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Does sulfur and phosphorus expand their octet?
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16 votes

Whether sulfur or phosphorous actually expand their octet is contested within the chemistry community. Another term for this octet expansion is "hypervalency." You can find many works of research ...

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Why is the iodide anion a good nucleophile but a poor base?
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16 votes

You should clarify whether the iodide anion is a good nucleophile in a polar protic or polar aprotic solvent. Also let's note that nucleophilicity is a kinetic property, while acidity/basicity are ...

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Why does hydrogen fluoride have a boiling point so much lower than that of water?
15 votes

I think there are a variety of qualitative ways of looking at this: Perhaps the most obvious is that $\ce{H2O}$ can form a greater number of hydrogen bonds due to having an equal numbers of hydrogen ...

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Why formulate drugs as HCl salts when HCl is in stomach acid?
15 votes

Another reason is that many drugs which are conjugated to hydrochloride salts is they are amines, and amines by themselves often stink. So people might be turned off from taking drugs that smell ...

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Thermodynamics adding salt to water changes the temperature
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14 votes

The keyword is that the salt dissolves. Dissolution entails at least two steps: 1) Overcoming solvent-solvent interactions and bonds. An extreme example: your dinner plate doesn't dissolve in your ...

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Why doesn't calcium carbonate dissolve in water even though it is an ionic compound?
13 votes

Teacher stated that the ionic compounds dissolve in water except some carbonates. That is, at best, an oversimplification. Other ionic compounds such as silver sulfide are sparingly soluble in water. ...

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Why are weak acids weak?
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12 votes

What are weak acids? Examples of weak acids in water solution would be acetic acid (main component of vinegar) and ammonium ion (conjugate acid of ammonia). I understand that an acid is weak if ...

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Why do strong acids have weak conjugate bases?
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12 votes

All chemical processes are reversible at least to some extent. Keeping this in mind, a strong acid must have a weak conjugate base (I think you mean strong acids have weak conjugate bases). Why? ...

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Why is arsenous acid denoted H3AsO3?
12 votes

You can write it however you want. Check this out: Note the presence of formulas such as $\ce{(HO)_2SO_2}$ for sulfuric acid. This information sheet is the same formula sheet I used when I was taught....

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What is the difference between "bromine" and "bromine water" in their reaction with an alkene?
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11 votes

From ChemGuide: Using bromine water as a test for alkenes If you shake an alkene with bromine water (or bubble a gaseous alkene through bromine water), the solution becomes colourless. ...

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Why is a strong base needed for an E2 reaction and not a an E1 reaction?
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11 votes

E2 is a concerted mechanism. The alpha proton in an E2 reaction substrate is also only weakly acidic because the bond between the alpha proton and the alpha carbon is relatively strong; there is only ...

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Why is electronegativity increasing with oxidation state increase?
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10 votes

Yes absolutely, electronegativities are hardly static values when you start combining elements and forming ions or molecules. Electronegativity is simply a measure of an ability of an atom to ...

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Why do esters actually smell?
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9 votes

The term aromaticity originated with the discovery of unusually stable hydrocarbons that also happened to have strong smells. Many hydrocarbons smell, but not all are aromatic. Nowadays, a compound ...

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What is the proper Lewis structure for HCOOH?
9 votes

With familiarity you will recognize that $\ce{COOH}$ in a formula generally refers to a carboxylic acid group. Sometimes you will also see $\ce{CO_2H}$. Either is acceptable. Vinegar, or acetic acid, ...

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What is the reason for the different solubility of silver halides in ammonia?
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8 votes

Silver chloride is very thermodynamically stable in ammonia solution. The $K$ for the dissolution of silver chloride in ammonia solution is only $\pu{2.9E-3}.$ suggesting that the product — silver ...

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Why is tetramethylammonium hydroxide a stronger base than tri- or dimethyl amine?
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8 votes

Between 1 and 2, 2 is more basic as the 3 methyl groups would produce a +I effect resulting in better availability of the lone pair than in option 2. I agree that more methyl groups would result in a ...

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Bonding in the phosphate ion
8 votes

Phosphorus ($\ce{_{15}P}$) - being the fifteenth element - has fifteen electrons, five valence electrons and the following electron configuration: $\ce{1s^2,~2s^2,~2p^6,~3s^2,~3p^3}$ ...

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Comparing formula for enthalpy change with bond dissociation energy and formation enthalpy
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8 votes

Yes. The two methods are equivalent. You can try this with the dimerization of $\ce{NO_2}$ into $\ce{N_2O_4}$. In this reaction we form one $\ce{N-N}$ bond. Every other bond stays the same. $\ce{...

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What is the difference between a reaction of Lewis acids with Lewis bases and a redox reaction?
8 votes

It's indeed redox - Lewis theory doesn't account for redox, but on grounds of Usanovich's theory ... A Lewis acid is an electron pair acceptor; a Lewis base is an electron pair donor. The simplest ...

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Why 6.023x10^23 is not written as 6023x10^20?
8 votes

You could write it as either. But the former is scientific notation while the latter is not considered scientific notation. In scientific notation, you move the decimal place until you have a ...

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Effect of temperature on Hydrogen Bonding?
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8 votes

Yes. Temperature disrupts bond of all kinds. Heat up a protein hot enough and you can even disrupt its primary structure - the linear sequence of amino acids, and amino acids are held together through ...

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What is the difference between enthalpy of formation and Gibbs free energy of formation?
8 votes

Gibbs free energy is not more "precise." The two are different but complementary. Enthalpy and Gibbs Free Energy indicate different things. Enthalpy can tell you about the relative stabilities of the ...

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Why exception is noted in the solubility of lead salts?
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7 votes

Lead sulfate is insoluble in cold water whereas most of the sulfates are soluble in cold water. Lead chloride is also insoluble in cold water but is soluble in hot water. Why? Lead ion is a ...

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Why are inert gas (especially Xenon) compounds powerful oxidizing agents?
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7 votes

Let's be clear here. Xenon by itself is not an oxidizing agent. Instead, certain compounds of xenon tend to be strong oxidizing agents. First, let's consider an analogous case - the nitro group. ...

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Is ozone an electrophile in the ozonolysis reaction?
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7 votes

Electrons are concentrated on the two terminal oxygens in ozone but remember, ozone exhibits resonance. The electrons can be delocalized across each oxygen through p-orbitals. So yes, at first if ...

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Why does hydrogen bonding in salicylic acid make it more acidic?
7 votes

If the COO(-) group on salicylic acid's conjugate base didn't hydrogen bond, then wouldn't the COO(-) therefore be more inclined to pick up a proton and return the entire molecule to salicylic acid? ...

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Causes of reversible reaction
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7 votes

First, let's tackle what an irreversible reaction is. Baking a cake, for example, is commonly considered "irreversible." The eggs, flour, milk, etc. which you started with are no longer present in ...

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