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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106
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8answers
62k views

Is a negative pH level physically possible?

A friend of mine was looking over the definition of pH, and wondering if it is possible to have a negative pH level. From the equation below, it certainly seems possible—just have a $1.1$ (or ...
93
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7answers
238k views

Is it actually possible to dispose of a body with hydrofluoric acid?

In the TV show "Breaking Bad", Walter White frequently gets rid of people who get in his way by submerging them in a plastic container full of hydrofluoric acid. This, at least in the TV show, ...
64
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6answers
48k views

Ortho-effect in substituted aromatic acids and bases

When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason ...
56
votes
4answers
208k views

Why add water first then acid?

From school, I remember a very important rule: first you need to pour the water and then the acid (when you need to mix them) not vice-versa. This is because otherwise the aсid becomes very hot and ...
49
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2answers
17k views

Why don't we explode after drinking water?

It is known that acid should be added to water and not the opposite because it results in an exothermic reaction. Our stomach contains HCl, so why don't we explode when we drink water?
41
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4answers
7k views

What is more acidic: D3O+ in D2O or H3O+ in H2O and why?

What is more acidic: $\ce{D3O+}$ in $\ce{D2O}$ or $\ce{H3O+}$ in $\ce{H2O}$ and why? I think it's $\ce{D3O+}$ in $\ce{D2O}$ as I saw somewhere that this property is used in mechanistic studies (...
40
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2answers
15k views

Why does CaCO3 react with HCl, but not with H2SO4?

I have a wonderful reaction of marble chips, $\ce{CaCO3}$, with hydrochloric acid, $\ce{HCl}$, and carbon dioxide was released beautifully (fast, large volume, easy to measure and makes good visual ...
38
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2answers
7k views

Why is arsenous acid denoted H3AsO3?

Inspired by this question, I'm wondering why arsenous acid is frequently denoted $\ce{H3AsO3}$, as opposed to $\ce{As(OH)3}$, which would appear to more accurately reflect its connectivity? [edit] I ...
37
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4answers
43k views

The reason behind the steep rise in pH in the acid base titration curve

Most books refer to a steep rise in pH when a titration reaches the equivalence point. However, I do not understand why … I mean I am adding the same drops of acid to the alkali but just as I near the ...
34
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2answers
14k views

Why is pyrimidine less basic than pyridine?

From Wikipedia's article on pyrimidine: Because of the decreased basicity compared to pyridine, electrophilic substitution of pyrimidine is less facile. But why is pyrimidine less basic than ...
33
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9answers
10k views

Would it be possible to destroy gold?

I'm a writer. I have a scenario in which a sizable amount of gold needs to be rendered unusable, preferably completely destroyed. I know an acid like aqua regia is able to dissolve gold, but would ...
32
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2answers
19k views

Is methanol more acidic than water?

Methanol is slightly more acidic than water. Their $\mathrm{p}K_\mathrm{a}$ values, in water, are $15.5$ and $15.7$, respectively. All other aliphatic alcohols, however, are less acidic than water. ...
31
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1answer
48k views

Acidity of substituted phenols

Phenol has a $\mathrm pK_\mathrm a$ approximately equal to $9.9$. When one studies the acidity of chlorophenols, one notices the following: First of all, chlorophenols are more acidic than phenol, ...
29
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3answers
23k views

What is the strongest acid?

According to Wikipedia, $\ce{HeH+}$ and fluoroantimonic acid are the strongest. According to Nature, Carborane acid is the strongest, but Wikipedia says fluoroantimonic acid is stronger. Links: $\...
29
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2answers
3k views

How to properly store acids at home?

I bought different kinds of acid for experiments and home usage that I stored in secured containers into an IKEA cabinet. I just realized that despite the fact that all the containers are properly ...
28
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5answers
59k views

Acid Accident Treatment

What are the general ways to treat an accident involving highly concentrated or similarly dangerous acids? I have a lab instructor who recently debated with our group about treating an acid spill on ...
28
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4answers
55k views

What's the difference between a nucleophile and a base?

Obviously it depends on the context whether you would call a particular species a nucleophile or a base but are the two terms largely synonymous or is there a difference?
27
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1answer
21k views

What is the pKa of the hydronium, or oxonium, ion (H3O+)?

Although the wikipedia page on Hydronium indicates a $\mathrm{p}K_\text{a}$ of −1.74, I noticed in the discussion of this page that the subject seems debated (cf. http://en.wikipedia.org/wiki/Talk:...
26
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1answer
6k views

Why does lemon juice reduce the “fish” odor of sea food — specifically fish?

In studying about amines, I read that lemon juice is also used to wash fish because it reacts with the amines on and in the fish to convert the amines to its salt, just reducing the "fishy smell". I ...
26
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4answers
6k views

Which molecule is more acidic: CHF3 or CHBr3?

I know that fluorine is more electronegative than bromine. However, because of the size of bromine, it is more stable with a negative charge. In the case of $\ce{HF}$ vs. $\ce{HBr}$, to me, $\ce{HBr}$ ...
24
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4answers
3k views

What software can calculate aqueous solution equilibria?

What software is available out there to calculate the equilibrium in a set of reactions in aqueous solution? In particular, I'm interested in software general enough to simulate things like titration ...
24
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3answers
165k views

How does one tell if a specific molecule is acidic or basic?

Let's take the $\ce{KOH}$ molecule into account. I know it is a base from literature, but how would one go about determining if a molecule is acidic or basic simply based on the structure of the ...
23
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4answers
65k views

Reason for the stronger acidic property of phenol than alcohol

In phenol, pulling the $\mathrm{p}_z$ electrons from the oxygen atom into the ring causes the hydrogen atom to be more partially positive than it is in aliphatic alcohols. This means it is much more ...
23
votes
1answer
5k views

Could milk rust a steel teaspoon?

Recently, while cleaning a neighbour's fridge (turned off for a few weeks), I came across a cup (closed with a lid). Inside the cup was, to my olfactory horror, congealed milk, with a steel (iron) ...
23
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3answers
11k views

The acidity of boric acid

The “real way” boric acid behaves as an acid in water is first by acting as a Lewis acid (bottom reaction, in black). In fairness to the undergrads, I’d bet >25% of graduate students around the ...
22
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2answers
18k views

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

I know there are issues of formulation and industrial processing that make it advantageous to produce many amine containing drugs as their salts rather than as freebases. And if giving the drug ...
22
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3answers
2k views

How was it concluded that the H3O+ rather than H+ is the “acid” ion?

I suspect that initially, scientists believed that the acid ion was $\ce{H^+}$ since $\ce{H2}$ is released through electrolysis, right? But what experiment was done to change the standpoint to assume ...
22
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2answers
27k views

Why are the majority of cleaning solutions basic?

When testing for pH for common household cleaning products, such as dishwasher fluid, I noticed that majority of them tend to be basic? Why is that? Do acid make good cleaning solutions as well?
22
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1answer
2k views

How can I safely handle a concentrated (fuming) nitric acid spill?

I will shortly be using $90~\%$ or higher concentration nitric acid in a home environment for the purpose of decapping ICs. I understand the corrosive dangers of nitric acid, and most of the important ...
21
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5answers
17k views

Is there such a thing as an acid without a hydrogen?

I'm in AP Chemistry and we are learning about the Brønsted-Lowry model and my teacher mentioned that "for the most part" acids have hydrogen, could there be such a thing as an acid that has no ...
21
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4answers
6k views

Why do Organolithium or Grignard reagents act as nucleophiles and not as bases with aldehydes and ketones

I've read entire Chapter 14: Organometallic Compounds of Francis Carey's "Organic Chemistry" but I still didn't get an answer to my question. Quote from the book: Because of their basicity ...
21
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3answers
14k views

Does the number of H+ ions in solution go up on dilution of a weak acid?

In my textbook, a footnote says: In case of weak acids, on dilution the total number of $\ce{H^{+}}$ ions in solution increases because dissociation of the weak acid increases This didn't make ...
21
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2answers
6k views

Chemical compounds responsible for the colors in flowers?

I know that anthocyanins are a class of compounds responsible for the purple colors found in flower petals. Anthocyanins (also anthocyans; from Greek: ἀνθός (anthos) = flower + κυανός (kyanos) = ...
20
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2answers
9k views

Comparing acidities of substituted and aromatic carboxylic acids

When comparing the acidities of carboxylic acids, we primarily see the electropositivity of the carboxylic acid carbons, i.e. we see how effectively the negative charge on the carboxylate ion is ...
20
votes
1answer
35k views

How does adding lemon juice to sugar make better caramel?

It's a common cooking advice: if you want a somewhat softer caramel, add some lemon juice to the sugar: To help prevent the caramel from crystallizing, you can add an acid to the sugar before you ...
20
votes
1answer
11k views

Side reactions of NHS Chemistry

N-Hydroxysuccinimide (NHS) chemistry is commonly used in chemical biology to react with primary amines like lysine and the N-terminus of proteins. I was curious how labile NHS esters are to other ...
19
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2answers
4k views

What are the crystals that have formed around the top of a conc. nitric acid bottle?

I was looking through my chemicals cupboard and found that this decades-old bottle of conc nitric acid had grown a beard. I can't think of any reaction between (presumably) $\ce{NO2}$ and any airborne ...
19
votes
1answer
2k views

Why is proton transfer so fast?

Why is proton transfer always kinetically favored? In other words, why are Brønsted acid-base reactions so quick? Is it because protons are generally unhindered, sterically? This seems plausible; ...
19
votes
4answers
27k views

Why is acetic acid more acidic than phenol?

Acetic acid (ethanoic acid, $\mathrm pK_\mathrm a \approx 5$) is more acidic than phenol ($\mathrm pK_\mathrm a \approx 10$), which is reflected in their reactivity with a weak base such as sodium ...
19
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4answers
70k views

Why is salt needed when using vinegar to clean pennies?

Let's say you have a solution that is vinegar and it has salt (NaCl) dissolved in it. Then you place old dull pennies in it. Then you look at it 5 minutes later and the pennies are clean and looking ...
18
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4answers
48k views

How much can the pH change through dilution?

Consider an acidic solution with Hydrogen ion concentration, $\ce{[H+]}$ of $10^{-5}\:\mathrm{M}$. Since $\:\mathrm{pH} = -\log \ce{[H+]}$ the $\:\mathrm{pH}$ of solution is $5$. Suppose we dilute ...
18
votes
2answers
17k views

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

People say it dissolves, but shouldn't the acid form? $$ \ce{NaCl + H2O ->[?] HCl + ???} $$
18
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2answers
1k views

Mechanism of a dephenylation reaction

I recently came across this reaction in my undergraduate labs. The experiment is taken from this article: J. Chem. Educ., 2008, 85, 413. The condensation of 2-methoxynaphthalene with cinnamoyl ...
18
votes
4answers
4k views

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 ...
18
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2answers
429 views

Lewis Acidity and Bacteria

How does Lewis acidity correlate with bactericidal activity? I read on Wikipedia that the two are positively correlated but no explanation was given. Does it have to do with the movement of ...
17
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4answers
8k views

What's the strongest known organic acid?

What's the strongest known organic acid? Is it maybe trifluoromethanesulfonic acid or tautomer of pentacyanocyclopentadiene? EDIT: Since the question was reactivated I thought about formalising it. I ...
17
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2answers
10k views

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{...
17
votes
4answers
55k views

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 ...
17
votes
3answers
8k views

Why is ammonium a weak acid if ammonia is a weak base?

$\ce{NH3}$ is a weak base so I would have expected $\ce{NH4+}$ to be a strong acid. I can't find a good explanation anywhere and am very confused. Since only a small proportion of $\ce{NH3}$ molecules ...
17
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2answers
6k views

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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