Questions tagged [acid-base]

This tag should be applied to questions concerning acid and base reactions. An acid is capable of donating a hydron/ proton (Brønsted acid) or capable of forming a covalent bond with an electron pair (Lewis acid). A base on the other hand is a chemical species/ molecular entity having an available pair of electrons capable of forming a covalent bond with a hydron/ proton (Brønsted base) or with the vacant orbital of some other species (Lewis base).

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16
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2answers
4k views

Why is HF the least acidic hydrogen halide?

Fluorine is the most electronegative halogen and therefore, there is larger difference in electronegativity between the atoms of $\ce{HF}$ than any other hydrogen halide, which means the positive ...
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643 views

What is the oxidation state of Mn in HMn(CO)5?

What is the oxidation state of $\ce{Mn}$ in $\ce{HMn(CO)5}$? If $\ce{H}$ has an oxidation state of $+1$, then $\ce{Mn}$ should have oxidation state of $-1$, which I'm not sure is possible. On the ...
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Why would 1kW power supplies fail around Nitric acid (HNO3) gas?

I experienced a situation where some electrical power supplies (rated over 1kW) were exposed to nitric acid ($\mathrm{HNO_3}$) fumes at roughly 9ppm for half a day; these power supplies intermittently ...
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Does nitrogen inversion affect the basicity of amines?

If I were to compare the basic strength of 1-azabicyclo[2.2.1]heptane and triethylamine: Can I say that 1-azabicyclo[2.2.1]heptane is more basic than triethylamine because the lone pair of electrons ...
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Why is nitric acid such a strong oxidizing agent?

In my teaching-lab experiments I've seen that nitric acid solutions are able to facilitate the dissolution of metals such as silver, even though they are more active than hydrogen. Does anyone know ...
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Experimental verification of the field effect

March's Advanced Organic Chemistry has the following paragraph The other effect operates not through bonds, but directly through space or solvent molecules, and is called the field effect. It ...
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Why concentrated sulfuric acid for dehydration and dilute for hydration?

To dehydrate ethanol one uses concentrated sulfuric acid: $$\ce{C2H5OH ->[\text{conc.} H2SO4] C2H4 + H2O}$$ but to go in the reverse direction, dilute sulfuric acid is used: $$\ce{C2H4 + H2O -&...
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Difference between Sildenafil and Sildenafil citrate

The data I found seems to show no difference between Sildenafil and Sildenafil citrate. But if they are the same things, why Pfizer use Sildenafil citrate instead of Sildenafil as their product Viagra?...
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How should the hydrated proton be represented in chemical equations?

I learned the equation $$\ce{H2O + H+ -> H3O+}$$ And I know $\ce{H+}$ and $\ce{H3O+}$ really mean the same thing. But I am confused as to when I should use $\ce{H+}$ and when I should use $\ce{...
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Why is formic acid a stronger acid than acetic acid?

I am told that because the methyl group is electron donating in the conjugate base of acetic acid, this destabilizes the conjugate base by exacerbating the existing negative formal charge on the ...
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What is the Ka of OH- and Kb of H3O+?

What is the $K_\mathrm{a}$ of $\ce{OH^-}$ and $K_\mathrm{b}$ of $\ce{H_3O^+}$? Have these constants been determined?
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Is cyclopentadiene or cycloheptatriene more acidic?

Which of the following cyclic compounds are more acidic? The most acidic proton is positioned on the carbon that is at the top of the above drawings (the methylene hydrogens) on each of the two ...
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Determining the pH of an organic solvent

Our work is faced with the issue of determining the charge of compounds that are dissolved in chloroform. One could realistically determine the charge of the relevant moieties knowing the $\mathrm{p}...
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983 views

Alkane deprotonation by organolithiums

Butyllithium isomers are all stored in alkane solvents. Theoretically, equilibrium should (given enough time) lead to formation of mostly n-hexyllithium in the case of n-BuLi stored in (mostly) n-...
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290 views

By how many pKa units will the pKa value of a ketone be minimized by addition of a Lewis acid

I want to enolize a ketone, for instance acetone with a $\mathrm{p}K_\mathrm{a}$ value of about 20 (in $\ce{H2O}$). I'd like to know if there exists a rule of thumb to predict how the $\mathrm{p}K_\...
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Why is it considered acid rain with pH <5.6?

I recently read in a book that rain is considered acid rain if the pH falls below 5.6. However a substance is acidic when the pH is below 7; so why is the boundary for acid rain 5.6? I was thinking ...
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Why is magic acid a superacid?

The above is a representation of magic acid. The left part is the acid; the right part is the solvent. Why would this combination make for a particularly good acid? The left part looks like a ...
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If caffeine is an alkaloid, why is coffee acidic?

I have just put together on my mind these two facts: caffeine is an alkaloid and brewed coffee is slightly acidic (pH = 5). My Biology teacher and my Chemistry teacher could not elaborate satisfying ...
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1answer
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Calculating the pH of a highly dilute solution of HCl

For relatively high concentrations of $\ce{HCl}$, I usually just assume that $[\ce{H+}] = [\ce{HCl}]$, because $\ce{HCl}$ is a strong acid and is completely ionized in solution. By taking the negative ...
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Does hydrogen bonding strength correspond to Brønsted basicity in a given medium?

It does seem that there is a correlation. Both are measures of proton affinity. Heck, isn't hydrogen bonding present in the transition states of most acid base reactions (excluding those involving ...
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Why does acetylene, having an acidic proton, not react with strong bases like NaOH and KOH?

In acetylene (ethyne, HC≡CH), the carbons are sp-hybridised, which make the attached protons more acidic than those in alkenes or alkanes. (See also: Relative acidities of alkanes, alkenes, and ...
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Does bleach (without rinsing) leave residues and can vinegar, baking soda neutralize them?

It's very difficult to get accurate information concerning household bleach residues. Imagine, for instance, that you pour pure (or diluted) bleach onto fabric or synthetic foam and let it dry without ...
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Why are weak acids weak?

What are weak acids? My chemistry and biology classes skimmed over them briefly but nothing in depth. I understand that an acid is weak if it partially dissociates and breaks down into ionic compounds,...
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How does the litmus pH indicator work?

I'm wondering about how does the litmus solution work as a pH indicator. And another question: When you put drops of litmus solution into an colorless acid (e.g. $\ce{HCl}$), it turns red. But then ...
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665 views

How can benzaldehyde have a pKa of 14.9?

There are numerous websites out there which claim that the pKa of benzaldehyde – C6H5CHO – is 14.90. (Just do a Google search for benzaldehyde pka to see what I ...
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Why isn't water acidic?

The definition of an acid is a compound with a hydrogen cation and a non-metal anion. Water is a hydroxide bonded to a hydrogen atom. This hydroxide has a net negative charge, too, since the negative ...
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Does latex protect against acids?

I heard somewhere that some plastics are pretty good at resisting decently strong acids. To what degree is this true? Does latex protect against corrosives? Are plastics good at "resisting" bases or ...
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Clear definition of a 'non-oxidizing acid'?

From the Beryllium article in Wikipedia: Beryllium dissolves readily in non-oxidizing acids, such as $\ce{HCl}$ and diluted $\ce{H2SO4}$, but not in nitric acid or water as this forms the oxide. I ...
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Why stepwise dissociation for acids but not hydroxide bases?

My son asked this over the weekend and I didn't have a good answer: how come with polyprotic acids we assume that the release of each $\ce{H+}$ is progressively harder, but with bases like $\ce{Ca(OH)...
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What makes Coke acidic?

What makes Coke and other soft drinks acidic? These drinks are carbonated, so a freshly-opened can should have a lot of dissolved carbonic acid, but the ingredients also lists phosphoric acid. Would ...
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1answer
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Can H4O 2+ form?

Like $\ce{NH4+}$ ,Is there any possibility of formation of $\ce{H4O^{2+}}$ (of tetrahedral structure)? My theory is: it can be formed by osmosis setup where heavy acids like $\ce{H3PO4}$ or $\ce{...
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Why isn't dry CaCl₂ used to dry HCl gas instead of concentrated sulfuric acid?

In our chemistry books, it is said that concentrated sulphuric acid is used to dry $\ce{HCl}$ gas. But, concentrated sulphuric acid is a strong oxidising agent so, why isn't $\ce{HCl}$ gas oxidised ...
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How can aluminium oxide be called an acid?

Aluminium oxide is amphoteric. It is easy to see that it is a Brønsted-Lowry base through the following reaction: $$\ce{Al_2O_3 + 6HCl \rightarrow 2AlCl_3 + 3H_2O}$$ The aluminum oxide splits and ...
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How to remove stain from pavement after having dropped sulfuric acid on it?

I had this car battery that flipped in my car trunk. When I got it out of there it spilled some acid on the pavement. It's a sulfuric acid battery. I added some baking soda on it and poured some more ...
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Is LiOH a weaker base than NaOH?

Is LiOH a weaker base than NaOH? Note: I'm not interested in "why," but rather what the "real" pKb values are. $$ \begin{array}{lcc} \text{Data for Alkali Metal Hydroxides} \\ \hline \text{Cation} &...
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Chilling water in copper vessel

Does chilling drinking water in copper bottle result in any chemical reaction that turns it dangerous for consumption in any way? Few days back, in summer, I carried kokum juice in copper bottle. I ...
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Why are acids usually depicted in fiction as green?

In cartoons, etc., acid is generally shown as vividly green, as in this scene from the Simpsons: We even have the colour "acid green". But when I used to use acids in chemistry class, they weren't ...
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How to separate HCl and NaOH from salt and water solution?

I mean, how can we reverse the neutralization reaction of $\ce{HCl}$ and $\ce{NaOH}$ to get back $\ce{HCl}$ and $\ce{NaOH}$. I want to extract $\ce{HCl}$ and $\ce{NaOH}$ from a mixture of common salt ...
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Dissolving Organic Tissues [duplicate]

Watching some movie/TV this question came to mind, purely theoretical of course, if one wanted to dissolve a human corpse, like getting rid of a body after killing someone, is it better to use an acid ...
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931 views

Why are synthetic pH indicators used over natural indicators?

Synthetic indicators seem to be exclusively used when determining the pH of a substance with an indicator (with the exception of that school experiment where you boil cabbage to demonstrate natural pH ...
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1answer
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Relative acidities of alkanes, alkenes, and alkynes

How does one explain the trend in bond lengths and acidity of the following hydrocarbons? $$\begin{array}{ccc} \hline \text{Species} & \ce{C-H}\text{ bond length / Å} & \mathrm{p}K_\mathrm{a} ...
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Is the equation pH + pOH = 14 valid at different temperatures?

$\mathrm{pH} + \mathrm{pOH} = 14$ For water at 60 degrees Celsius, $K_\mathrm{w} = 1 \times 10^{-13} = [\ce{H+}] \times [\ce{OH-}]$ Hence, $[\ce{H+}] = 1 \times 10^{-6.5} = [\ce{OH-}]$ So $\...
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How is volatility useful in the production of acids?

Sulfuric acid because of its low volatility can be used to manufacture more volatile acids from their corresponding salts. How does volatility affect the production of acids? Isn't it that sulfuric ...
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Why is boric acid soapy to touch?

Bases are soapy to touch because of soap formation on contact with lipids present on our skin. If this is the case then why and how is boric acid soapy to touch?
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Explanation of Lemon Juice-Invisible Ink

A cute homegrown spy-trick we all know: lemon juice invisible ink. But there is no scholary article available in the internet about this phenomenon. A rough explanation I found in Scientific American:...
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pKa differences and reactivity

I know a lot of chemists like to quote $\mathrm{p}K_\mathrm{a}$ values and subtract them to reinforce some notion about some acid-base reaction being highly favorable or highly unfavorable or whatnot. ...
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How do I calculate the degree of dissociation in equilibrium?

In my textbook, for calculating the percentage dissociation of $\ce{HF}$ for the given equation: $$\ce{HF + H2O <=> H3O+ + F-}$$ The solution is: Initial Concentrations $$[\ce{HF}] = 0.08~\...
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Basicity Alteration Due To Ortho Effect In Methoxy Aniline System

I wanted to ask something more in reference to this question Ortho-effect in substituted aromatic acids and bases Suppose instead of toluidine, 2-methoxyaniline and 3-methoxyaniline are present. Now ...
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Why would sulfuric acid turn gray/black?

About 2 years ago I purchased 2 liters of 98% concentrated sulfuric acid. It's in a standard poly bottle with leakproof lids, and originally was clear. Recently I noticed the acids have turned a dark ...
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How to analyze a acid and salt mixture using titrimetry?

Given a mixture of $\ce{HCl}$ and $\ce{MCl3}$ and the following dissociation constants for $\ce{M(OH)3}$, how can the concentrations of $\ce{HCl}$ and $\ce{MCl3}$ be determined separately by titrating ...