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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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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 ...
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7answers
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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 ...
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4answers
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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 ...
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4answers
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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?
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2answers
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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 ...
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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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2answers
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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 ...
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2answers
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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. ...
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3answers
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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 ...
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2answers
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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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3answers
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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? ...
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7answers
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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, ...
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4answers
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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 ...
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1answer
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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:...
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2answers
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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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1answer
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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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3answers
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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? ...
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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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1answer
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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{...
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1answer
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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 ...
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3answers
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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 ...
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2answers
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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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3answers
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Why are acetals stable to bases and nucleophiles?

Why are acetals stable to bases and nucleophiles? Could it be due to electronic effects? Lone pairs on the two oxygen atoms create an unfavorable environment for the approaching nucleophiles and ...
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2answers
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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+]}}{...
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2answers
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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} = \...
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3answers
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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: $\...
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4answers
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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 ...
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2answers
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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 ...
16
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3answers
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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 ...
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2answers
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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 ...
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2answers
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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 ...
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1answer
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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, ...
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3answers
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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 ...
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2answers
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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 $\displaystyle\ce{NaHCO3 -> Na+ + HCO3-}$...
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1answer
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Can someone please explain buffers to me?

This is what I understand so far: The concept of a buffer is to minimize any swings in pH. In order to do this you need to create a solution with both acidic and basic compounds. To create one, you ...
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2answers
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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 $...
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4answers
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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 ...
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1answer
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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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3answers
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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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2answers
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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 ...
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1answer
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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, ...
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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 ...
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1answer
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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 ...
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Why does polonium form acidic oxides?

All metals form basic oxides. Metallic oxides are basic in character. Polonium is a metal, so it should form basic oxides but it forms acidic oxides. Why are its oxides acidic in character?
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Why are metal oxides basic and non-metals' acidic or neutral

Recently I came across the fact: Metal oxides basic and non-metals' acidic or neutral. Searching for it, partly my query is solved, as I found: Metal oxides or $\ce{O2-}$ forms $\ce{OH-}$ after ...
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2answers
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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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1answer
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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 ...
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1answer
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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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2answers
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Do hydrogen halides (HX) form strong or weak acids?

I know that when dissolved in water, hydrogen halides ($\ce{H-X}$), become acids. I know that $\ce{HF}$ forms a weak acid, but can it be generalized that all $\ce{HX}$ acids do so?
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1answer
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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?