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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Why is carbonic acid a weaker acid than acetic acid?

Is it because the $\ce{OH}$ group next to $\ce{COOH}$ in carbonic acid donates electron density to the $\ce{COO-}$ by resonance, making it a stronger base, compared to a weaker electron donating ...
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Weird Wikipedia Section on Oxidizing Behavior of Nitric and Sulfuric Acids

It has been my understanding that when nitric, perchloric, or sulfuric acids act as oxidizing agents, they must exist as whole $\ce{HNO_3}$ or $\ce{HClO_4}$ or $\ce{H_2SO_4}$ molecules that are still ...
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Why does the ionic product of water remain constant after addition of non-neutral solute?

In my textbook, it is given that the ionic product of water $K_\mathrm{w}$ remains constant even when a non-neutral solute such as an acid is added to it. $$K_\mathrm{w} = \ce{[H3O+][OH-]}$$ When a ...
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What is the reason that tertiary alcohol pKa is higher than primary alcohol pKa?

A tertiary alcohol has a $\mathrm{p}K_\mathrm{a}$ of 18 while a primary alcohol has a $\mathrm{p}K_\mathrm{a}$ of 16. Shouldn't the tertiary alcohol be more acidic since its conjugate base is more ...
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Is Saliva an acid or base?

I have a debate with some friends who believe that saliva is just basic, but with the enzymes which make them reactive with objects in our mouth, shouldn't it be an acid in this case?
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Inductive vs resonance effects and the acidity of phenol

A lot of people rationalize the acidity of phenol by saying that resonance is responsible for much of phenol's acidity as opposed to aliphatic alcohols. However, this image suggests that in fact the ...
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Find the initial volume of the weak acid given a titration graph

Question: Below is a picture of a titration between a weak acid, $\ce{HA}$, and a 0.150 M $\ce{NaOH}$ solution. Find the initial volume of the weak acid in milliliters in this titration. My ...
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Can water be a Lewis acid?

I asked this question to my teacher a few days ago. In a reaction such as $$\ce{NH3 + H2O -> NH4+ + OH-},$$ $\ce{NH3}$ is a Lewis base, but is $\ce{H2O}$ a Lewis acid? He said that it isn't. Now ...
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Why is the pKa (COOH) of alanine and glycine similar but the pKa (NH3) different?

Alanine is heavier with a ($\ce{-CH3}$) than glycine which has an ($\ce{-H}$). What makes them have different $\mathrm{p}K_\text{a}(\ce{-NH3+})$ $(\mathrm{p}K_\text{a}: \text{Ala}=9.69, \text{Gly}=9....
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Hydrogen halide acidity

Why is it that $pK_{\ce{a-HF}} \lt pK_{\ce{a-HCl}}\lt pK_{\ce{a-HBr}}\lt pK_{\ce{a-HI}}$, although the electronegativity decreases? The more electronegative the atom accompanying hydrogen, the lower ...
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Why does ammonia act as an acid in only the first of these two reactions?

$$\ce{2Na(l) +2NH3 (g) ->2NaNH2(s) + H2(g)}$$ $$\ce{CH3Cl (alc) +NH3 (alc) -> CH3NH2 (alc) +HCl(alc)}$$ Doesn't ammonia donate a proton in both cases?
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Why is benzoic acid a stronger acid than 3-aminobenzoic acid?

Why is benzoic acid a stronger acid than 3-aminobenzoic acid? Obviously at meta position, only negative inductive effect will operate. But, how does that make it a weaker acid than benzoic acid?
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Identifying a glass frosting chemical

I have purchased an "unknown" white coloured powder from the market which can frost glass objects. Here are some properties of this powder White in colour When mixed with HCL or water, it results in ...
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Most basic nitrogen in Adenine

I need to find the most basic site of Adenine: The $\ce{NH2}$ group and $\ce{NH}$ cant be strong base as electrons are delocalised. This leaves us with $1,7,3$. I thought that electron density on $1,...
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Why isn't the side chain of arginine totally protonated at low pH?

I was wondering why arginine cannot be protonated at $\mathrm{pH\ 0}$ on all the $\ce{N}$ atoms in the side chain, as they all have a free electron pair. As this image shows, it can only be protonated ...
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Questions about Buffer System (Lab)

I will be doing a lab on Hydrogen Phosphate buffer system tomorrow and I have a few questions about the buffer system. I am not sure if my assumptions are correct. (1) What would happen to the rate ...
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Why does the pH of soft drinks get lower as they go flat?

I am doing an investigation about the chemistry of soft drinks and as part of this I observed the effect of time on the pH of soft drinks fully expecting the pH to increase as the carbonic acid, a ...
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How to prove that chloroform is more acidic than fluoroform? [duplicate]

How to prove that chloroform is more acidic than fluoroform? Using the concept that the inductive effect is dominant over the resonance (mesomeric effect) in the case of halide substituents: $\...
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How sure can we be about the structure of purine?

While answering the question Basicities of nitrogen atoms in purine, I noticed, that there might be a rapid interchange of the hydrogen bonded to the nitrogen atoms. I have found a crystal structure ...
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What is the relationship between the two definitions of the difference between basicity and nucleophilicity?

(Clarification: this is a question about terminology, not so much about when to use different concepts. I think I do understand which characteristics of a species to use when trying to determine ...
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Why do strong acid-weak base reactions “essentially go to completion”?

This is what my textbook says. I understand that the strong acid would readily donate a hydrogen ion, but I can't see how all the weak base will readily accept it (at least not to "essential ...
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How is aqua regia stored?

How is aqua regia stored as it dissolves all metals?
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Should the 'a' in the acid dissociation constant (Ka or pKa) be capitalised?

In science, the negative logarithm of the acid dissociation constant is denoted $\mathrm{p}K_\mathrm{a}$ or $\mathrm{p}K_\mathrm{A}$ depending on the source (lowercase "a" or uppercase "A"). Since it ...
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Calculating charge on amino acid from pKa

I have been given $\mathrm pK_\mathrm a$ values of an amino group, a carboxyl group and a side chain of cysteine. How can I find the ionic charge on it at different $\mathrm{pH}$ values?
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Calculating Buffer Capacity

I completed a titration of Ammonium Acetate buffer solution and to it I added $\pu{2M}$ Hydrochloric Acid. I measured the initial $\ce{pH}$ of the buffer solution before any acid was added and I ...
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Clogged drain, commercial products are ineffective

I have a clogged drain from my shower. Commercial products like Savo or WC Net totally don't work. Is there any chemical substance which can be bought without permission or which can be made easily to ...
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Activity of hydrogen ion

I am not from chemistry background. Could you tell me in simple words what the activity of hydrogen $a_{\ce{H+}}$ is? It arises in the context that the negative logarithm of the activity of hydrogen ...
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Why is carbon dioxide considered a Lewis acid?

$\ce{CO2}$ is considered a Lewis acid. How it is an acid? According to Lewis: “species that accept an electron pair are acids”. But $\ce{CO2}$ can't accept electron pairs because oxygen and carbon ...
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Why is hydrochloric acid often sold as 33% concentration?

What is the historical perspective for the choice of 33% concentration that is often found in commercial sales of Hydrochloric acid? Is this the same reason we find sulfuric acid sold at 37% and ...
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Can sodium bicarbonate be considered an acid?

I was reading about acids and bases today and finally decided to question the statement that "baking soda is a base." Let's start with the dissolving of baking soda, $\ce{NaHCO3}$. The equation to ...
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How do cloves break down plastic?

When my family buys powdered cloves in bulk, we put them in plastic until we get home - which takes at very most an hour. As soon as we get home, we transfer them into glass because we have had issues ...
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Acetic acid freezing distilation

How can acetic acid be distilled by freezing when its freezing point is above the freezing point of water. Examples on the web show the water portion of the vinegar as ice and the acid as a liquid ...
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Why are strong acids and bases not suitable as primary standards?

This is one of the questions with which I have puzzled over, and can arrive at no definite conclusion. Why are strong acids or bases, such as $\ce{H2SO4}$,$\ce{ HNO3}$, $\ce{HCl}$, and $\ce{NaOH}$ not ...
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Is oxalic acid dihydrate considered a primary acid standard in analytical chemistry?

Using oxalic acid dihydrate as a primary standard just seems really odd to me. I'd expect a primary standard to be oven dried. It just seems weird that a hydrate would be used. Granted, I saw ...
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Can “Common Ion Effect” suppress the dissociation of water molecules in acidulated water?

$$\begin{align} \ce{H2O &<=> H+ + OH-} \\ K &= \frac{[\ce{H+}][\ce{OH-}]}{[\ce{H2O}]} \\ \ce{H2SO4 &<=> 2H+ + SO4^2-} \end{align}$$ In acidulated water water dissociates into ...
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Why is methoxy group an electron donating group?

I am studying acidity of carboxylic acids and I found that benzoic Acid is more acidic than p-methoxybenzoic acid. It is written in my book that this happens because methoxy group is an electron ...
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Why is ammonia more basic than acetonitrile

Why is $\ce{NH_3}$ more basic than $\ce{CH3CN}$? I tried to reason it out with the hybridization of nitrogen in both the molecules. In $\ce{NH_3}$ nitrogen is $\mathrm{sp^3}$ hybridized while in ...
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How is it possible to quantify the strength of a Lewis acid/base?

When the $pK_a$ scale is not applicable - when there is no proton/charged species transfer - what should be used to quantify the strength of an acid?
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Calculating the pH of a dilluted aqueous KOH solution

Calculate $\mathrm{p}\ce{H}$ of an aqueous solution of $0.01\:\mathrm{nM}~\ce{KOH}$ in water. I think that water also has $\ce{OH-}$ ions in concentration of $10^{-7}\:\mathrm{M}$ (since $\mathrm{p}\...
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Which of mono-, di-, triphenylmethane is the most acidic?

Question How would you compare the acidity of the most acidic proton in each of the following molecules? diphenylmethane toluene triphenylmethane The answer says 3 is the most ...
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What is the meaning of cmmol in chemistry?

I came across a unit called $\text{cmmol dm}^{-3}$ in buffer solutions. What does this unit mean?
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Why does ammonia accept a hydrogen to form ammonium when its octet is already complete?

Why does ammonia accept a hydrogen to form ammonium when its octet is already complete as $\ce{NH3}$ and it should be, seemingly, stable as $\ce{NH3}$?
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What exactly is basicity?

In my textbook, it’s given that the trend of the basicity of the elements of group 15 is $$\ce{NH3 > PH3 > AsH3 > SbH3 \ge BiH3}$$ Also, it’s said that the reducing character decreases down ...
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Is metallic sodium a strong base?

Chemical properties: Sodium metal and sodium amide ($\ce{NaNH2}$ ) are strong bases. They react with ethyne to form sodium acetylide with the liberation of hydrogen gas. How can a metal considered a ...
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Why is HCl a stronger acid than Acetic Acid?

Drawing the conjugate bases, Oxygen is more electronegative than Chlorine so negative charge on Oxygen is more stable than Chlorine, Thus My argument that Acetic Acid is more acidic. Also the O¯ ...
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Which species dissociate completely in ionic equations?

I am tasked with writing a molecular equation, an overall ionic equation, and a net ionic equation for the reaction between an aqueous solution of phosphoric acid, $\ce{H3PO4{(aq)}}$ and an aqueous ...
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Acidity order of 4-halophenols

How do I theoretically predict the acidity order of the following para-halophenols? (experimental $\mathrm{p}K\mathrm{a}$ values beside each) parafluorophenol (9.92) parachlorophenol (9.41) ...
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Why is it that weak bases usually contain nitrogen?

Why do weak bases usually contain nitrogen? I know there are two electrons on top for a bond of $\ce{H}$ but why is it mostly nitrogen? I know there are other elemental bases too but why do I keep ...
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Rate and mechanism of the reaction of Mg and HCl

In the reaction between hydrochloric acid and Magnesium the overall reaction is: $$\ce{Mg + 2HCl -> MgCl2 + H2}$$ My proposed mechanism of reaction is that $\ce{HCl}$ dissociates in $\ce{H2O}$ ...
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Acidity of cyclopentadiene when fused to benzene rings

Why does fusion to a benzene ring reduce the acidity of a cyclopentadiene ring? For example, acidity decreases going from cyclopenta-1,3-diene to indene and to fluorene: