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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55
votes
6answers
44k 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 ...
4
votes
2answers
6k views

How to set up equation for buffer reaction?

For buffer equations, how can you tell what to react with water? For example, if I have a 1 M acetic acid solution and 1 M sodium acetate solution (a conjugate acid-base pair) mixed together and am ...
98
votes
8answers
55k 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 ...
36
votes
4answers
40k 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 ...
26
votes
4answers
43k 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?
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 ...
14
votes
1answer
5k views

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 ...
38
votes
2answers
5k 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 ...
28
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2answers
14k 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. ...
23
votes
3answers
154k 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 ...
15
votes
2answers
9k 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{...
11
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1answer
9k views

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} ...
9
votes
3answers
4k views

The pH of a neutralized solution

If pH is defined as the concentration of hydrogen ions in solution, then how can a ‘neutralized’ solution (defined as having an equal amount of hydrogen and hydroxide ions) have a pH other than 7? ...
17
votes
4answers
21k 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 ...
27
votes
1answer
16k 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:...
9
votes
4answers
3k views

Strong and Weak Acids/Bases

I'm so confused... $\ce{HClO}$ is a weak acid. then why is its conjugate base, $\ce{ClO-}$, a weak base in water? shouldn't they be inversely proportional? shouldn't $\ce{ClO-}$, be a strong base? ...
9
votes
1answer
1k views

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 ...
6
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2answers
14k views

Why is water not part of the equilibrium constant?

In the acid base reaction $$\ce{NH4+ + H2O <-> NH3 + H3O+}$$ the acidity constant, which is a relation between concentrations is given by $$K_{\mathrm{a}}=\frac {\ce{[NH3]} \cdot \ce{[H3O+]}}{...
-1
votes
2answers
323 views

Calculate pH of a mixture of a strong base and acid. Knowing only the pH, wt/v%, and volume of both solution. [closed]

Title explains all. I have been stuck on this for an hour and for some reason cannot understand it. I have tried to do an ICE table but get stuck halfway as I do not know whether I would use the w/v ...
21
votes
3answers
13k 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 ...
15
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2answers
10k views

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?
18
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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 ...
9
votes
3answers
7k views

How can the equilibrium shift, while Kc remains constant?

Consider the following reversible reaction. $$\ce{Cr2O7^2-(aq) + H2O(l) <=> 2 CrO4^2-(aq) + 2 H+(aq)}$$ What will happen to the position of equilibrium and the value of $K_c$ when more ...
5
votes
1answer
5k views

Why do sodium halides react so differently with sulfuric acid?

Why do sodium halides react so differently with sulfuric acid? \begin{align} \ce{NaF + H2SO4 &-> NaHSO4 + HF} \tag{1a}\label{NaF}\\ \ce{NaCl + H2SO4 &-> NaHSO4 + HCl} \tag{...
2
votes
1answer
698 views

How to determine the strongest oxyacid of chlorine?

Which is the strongest acid here? $\ce{HClO}$ $\ce{HClO2}$ $\ce{HClO3}$ $\ce{HClO4}$ I found this question, didn't really get the first answer, but this one in particular seemed ...
88
votes
7answers
212k 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, ...
7
votes
1answer
1k views

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 ...
12
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3answers
2k views

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. ...
3
votes
2answers
1k views

Are aromatic amines or amides less basic?

When the lone pair of an amino group $\ce{R-NH2}$ is involved in resonance, its basicity decreases. But, between conjugation with carbonyl group $\ce{R}=\ce{R'CO}$ or resonance with benzene $\ce{R} = \...
28
votes
3answers
22k 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: $\...
11
votes
4answers
51k views

Shouldn't the pH at the equivalence point always be 7?

I learned in class that the equivalence point in an acid-base titration is reached when the solution contains an equal amount of substance of $\ce{OH-}$ and $\ce{H+}$ ions. However, in a weak acid and ...
16
votes
3answers
6k 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 ...
12
votes
2answers
1k views

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 ...
10
votes
2answers
5k views

How can bromine water be called a solution?

Bromine water is a reagent which is used to test for unsaturation in organic compound. It is $2.8~\%$ bromine in water according to Wikipedia. But how is it made? This link describes the procedure ...
21
votes
4answers
5k 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 ...
11
votes
2answers
141k views

What are the products of the dissociation of sodium bicarbonate in water? What is the relative pH of the solution?

I had a recent question on a test that asked what the products would be if sodium hydrogen carbonate were dissolved in water. I had a few candidate answers $\displaystyle\ce{NaHCO3 -> Na+ + HCO3-}$...
4
votes
2answers
28k views

Why is a buffer solution best when pH = pKa i.e. when A-/HA=1

Buffers work best when $\mathrm{pH}$=$\mathrm{p}K_\mathrm{a}$ From the Henderson-Hasselbalch equation, $\mathrm{pH}= \mathrm{p}K_\mathrm{a} + \log_{10}\left(\frac{[\ce{A-}]}{[\ce{HA}]}\right)$ If $...
3
votes
3answers
10k views

Protonation of Guanidine

Why is the $\ce{sp^2}$ hybridized nitrogen atom in guanidine the most basic? I know that as a general guideline, $\ce{sp^3}$ hybridized atoms are more basic than $\ce{sp^2}$. Bases are electron pair ...
14
votes
1answer
14k views

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 ...
9
votes
1answer
2k views

Is methanol really more acidic than water?

The question Why is methanol more acidic than water? deals with the reasoning of why methanol is more acidic than water. However, as mentioned in the comments of that question, the acidity constant of ...
2
votes
2answers
1k views

How concentrated can an acid be?

How concentrated can an acid be without it being supersaturated? Is there a certain limit to how concentrated an acid or base can be? When I mean concentration, I mean molarity; so how concentrated ...
29
votes
1answer
41k 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, ...
6
votes
3answers
1k views

Relative acidity of p-chlorobenzoic acid and p-flurobenzoic acid

I want to compare the relative acidity of p-chlorobenzoic acid and p-flurobenzoic acid. Both of the facts below point to p-chlorobenzoic acid being more acidic: The carboxylic acid group is too far ...
12
votes
1answer
1k views

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 ...
10
votes
1answer
8k views

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

When salicylic acid deprotonates (losing the proton from the carboxyl group) it forms a hydrogen bond with between the oxygen in the carboxylate anion and the hydrogen in the alcohol group. However, ...
8
votes
2answers
45k views

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?
14
votes
1answer
5k views

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 ...
5
votes
3answers
36k views

pH range outside conventional 0-14 [duplicate]

Is a pH value outside 0 - 14 possible? I asked my teacher who said: yes, it is, but very difficult to achieve. Then on the internet, I found multiple answers, one saying it is but because of a fault ...
5
votes
1answer
150 views

Is there any notion of pH out of solution?

For example, could one define a $\mathrm{pH}$ for pure acetic acid? It's a weak acid in water, but if someone handed you $1~\mathrm L$ of pure acetic acid, what would its $\mathrm{pH}$ be?
2
votes
1answer
616 views

Chalcogens' hydrides as acids?

I've noticed that chalcogens never form binary acids, and instead end up like water, with very little acidity. Why is this? Or am I wrong and there's a counterexample, if so please give it.