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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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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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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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 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 does aqua regia dissolve gold?

I recently learned that aqua regia can dissolve less reactive or noble metals like gold. Aqua regia is a mixture of $\ce{HCl}$ and $\ce{HNO3}$, but separately, neither of these acids dissolve gold. ...
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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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How does H2SO4 dissociate?

Apologies for this extremely basic question, I'm just beginning with Chemistry so please don't be too harsh on me. My book says that sulfuric acid, $\ce{H2SO4}$, dissociates in its ions following ...
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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 do strong acids have weak conjugate bases?

This question is based on the Brønsted-Lowry model. I saw many answers to similar questions online. However none of them have given a detailed answer that is based on molecular structure (the answers ...
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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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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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Comparing basicity of imidazole and 2-imidazoline

I recently sat for an exam in which I was asked to compare the basicity of the above compounds. I thought imidazole would be more basic because it is aromatic but according to the answer key 2-...
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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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Comparing pKa of hydrocarbons

We have to compare their acidic strength, and we know acidic strength is directly proportional to stability of the anion. So the first compound is more acidic due to its being aromatic after ...
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What bases are fit for human consumption and can be used in foods?

I know that are several acids that can be found in the kitchen, such as citric acid and vinegar. However, I never heard of a base that can be used in the kitchen to raise the pH levels of any food. ...
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Is the Henderson–Hasselbalch equation volume independent?

Looking at this equation $\mathrm{pH} = \mathrm{p}K_\text{a} +\log\frac{[\ce{CB}]}{[\ce{A}]}$ makes me think that it is concentration independent. What I mean is, when we look at $\frac{[\ce{CB}]}{[\...
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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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Can I make a buffer from two different weak acids or bases?

Can I make a buffer using two different acids/bases? For example, adding 1 mole of acetic acid and 1 mole of ammonia? The only information I can ever find is that I can make a buffer using only an ...
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What is the acid dissociation constant of cacodylic acid?

What is the $\mathrm pK_\mathrm a$ of cacodylic acid? I cann't seem to find one answer on the internet. I have read 1.67, 6.37, and 4.8 in my $\mathrm pK_\mathrm a$ table. What is the reason for this? ...
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Which is more basic: 1,2‐dihydropyridine or 1,4‐dihydropyridine?

Which compound is more basic of the two? My thinking: In compound A, the lone pair of nitrogen are in resonance with two other double bonds. The resonance chain here seems to be longer as compared to ...
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Basicities of nitrogen atoms in purine

Arrange the sites in purine in order of basicity. I feel that 9 is the least basic as nitrogen's lone pair is delocalised. However, I am unable to rank 1, 3, and 7 in a particular order. Is there a ...
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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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Why will CuSO4 solution be acidic?

An end-chapter problem posed in an 11-grade texbook asks to analyse whether a water solution of CuSO4 will be acidic. The standard answer is yes, because "$\ce{H2SO4}$ is a strong acid, hence $\ce{...
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Do enolates get protonated at the carbon or oxygen atom?

An enolate has two resonance structures. When it gets protonated, where is the $\ce{H+}$ more likely to go? On the oxygen to produce an enol, which tautomerizes to the keto, or on directly onto the ...
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Comparing acidity of anilinium ion and para-fluoro anilium ion

Which of these compounds - anilinium ion and para-fluoro anilium ion - is more acidic? I thought the answer would the be first one since $\ce{-F}$ is an ortho-para activating group, so the electron ...
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Comparing the Lewis acidity of carbon tetrafluoride and silicon tetrafluoride

I've been asked to compare the relative acidity of $\ce{CF4}$ and $\ce{SiF4}$. As both atoms have noble gas configurations, neither can act as a lewis acid and so I assume the question is inferring ...
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Volume required to dilute solution for a pH change

A $\pu{100 mL}$ solution of $\ce{NaOH}$ has a $\mathrm{pH}$ of $13$. What volume of water in $\pu{mL}$ must be added to change the $\mathrm{pH}$ to $11$? My steps: Begin by calculating conc. of $[\...
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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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Why is 4-hydroxypyridine more acidic than benzoic acid?

4-hydroxypyridine (or 4-pyridone) has a $\mathrm{p}K_\mathrm{a}$ in the ballpark of $3$ to $3.33\:^1$ (in the pdf linked below, the $\mathrm{p}K_\mathrm{a}$ of 1-methyl-4-pyridone has been given to be ...
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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:
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Is steric inhibition of resonance or steric inhibition of protonation dominant in o-toluidine?

I wish to know which effect out of steric inhibition of resonance (SIR) or steric inhibition of protonation (SIP) is dominant over the other when comparing basicities of o-toluidine and aniline: ...
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Why is o-toluic acid (2-methylbenzoic acid) more acidic than benzoic acid? [duplicate]

Why does the methyl group at the ortho-position stabilize the carboxylate ion? I recognize that there will be a steric clash between the carboxyl group and the methyl group but I don't understand why ...
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How to calculate the pH of an acetic acid/ calcium acetate buffer?

Problem: A buffer was made by mixing $\pu{500 mL}$ of $\pu{1 M}$ acetic acid and $\pu{500 mL}$ of $\pu{0.5 M}$ calcium acetate. What are the resulting concentrations of acetic acid (henceforth ...
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Fitting titration curve

To simulate the action of gastric $\ce{HCl}$, we have titrated 100 ml of a meal with 0.1 N $\ce{HCl}$. To plot the data, use (R-code) ...
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Why does nitric acid have a different molecular structure from phosphoric and arsenic acids?

I remember that this really bugged me as an undergrad, and upon revisiting some inorganic chemistry notes I realized I still don't have a satisfactory answer for it. The structure of nitric acid, $\ce{...
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Is there a terminology contradiction about whether the conjugate of a strong acid is a “weak base”?

(Please note, I am not simply asking, "Is the conjugate of a strong acid a weak base?" I'm asking about the contradictory ways those terms seem to be used.) I was revisiting strong/weak acids/bases ...
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Why do these two calculations give me different answers for the same acid-base titration?

In class, I performed an weak acid-strong base titration using commercial white vinegar and sodium hydroxide with the aim of finding the concentration of of ethanoic acid in the vinegar, and I used ...
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Why would the loss of H₂ to space mean that the Earth's geochemistry would be based on acid/base reactions?

I am reading a paper[1] that contains the line: Most of the $\ce{H2}$ in the Earth's mantle escaped to space early in the Earth's history; consequently, the overwhelming majority of the abiotic ...
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Why is acetone less acidic than cyclohexanol?

The $\mathrm{p}K_\mathrm{a}$ of acetone is 19, whereas the $\mathrm{p}K_\mathrm{a}$ of cyclohexanol is 16. However, acetone is resonance stabilized and its major resonance structure displays the ...
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Reaction of aluminium trichloride with water

Since $\ce{Al^3+}$ is an acidic cation, shouldn't it react with water like this? \begin{align} \ce{AlCl3 + 6H2O &<=> [Al(H2O)6]^3+ + 3Cl^-} \tag1\\ \ce{[Al(H2O)6]^3+ +H2O &<=> ...
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Is the behavior of a dilute strong acid the same as the behavior of a weak acid?

My assumption is yes, as the $\mathrm{pH}$ levels of each will be similar and thus they have the same acidity. Is this correct or am I missing something?
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Why are acetic acid and sodium bicarbonate mixed to unblock a drain?

I have always wondered about the rationale behind combining white vinegar and sodium bicarbonate to perform household cleaning jobs, and to unblock drains. I would have expected white vinegar to act ...
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Why is CF3COOH exceptionally acidic?

The pKa values of almost all carboxylic acids lie much above 0. But this is violated by trifluoroacetic acid(-0.25). How can this be justified?

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