| Structure | $K_{\text {a }}$ | $\mathrm{p} K_{\mathrm{a}}$ |  |
| :---: | :---: | :---: | :---: |
| $\mathrm{CF}_{3} \mathrm{CO}_{2} \mathrm{H}$ | 0.59 | 0.23 | Stronger acid |
| $\mathrm{HCO}_{2} \mathrm{H}$ | $1.77 \times 10^{-4}$ | 3.75 |  |
| $\mathrm{HOCH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | $1.5 \times 10^{-4}$ | 3.84 |  |
| $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CO}_{2} \mathrm{H}$ | $6.46 \times 10^{-5}$ | 4.19 |  |
| $\mathrm{H}_{2} \mathrm{C}=\mathrm{CHCO}_{2} \mathrm{H}$ | $5.6 \times 10^{-5}$ | 4.25 |  |
| $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ | $1.75 \times 10^{-5}$ | 4.76 | ![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0704.jpg?height=30&width=66&top_left_y=1274&top_left_x=1374) |
| $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CO}_{2} \mathrm{H}$ | $1.34 \times 10^{-5}$ | 4.87 | acid |
| $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$ (ethanol) | $\left(1 \times 10^{-16}\right)$ | (16) |  |


Methyl 4-cyanopentanoate - 20.2 Structure and Properties of Carboxylic Acids

Although much weaker than mineral acids, carboxylic acids are nevertheless much stronger acids than alcohols and phenols. The $K_{\mathrm{a}}$ of ethanol, for example, is approximately $10^{-16}$, making it a weaker acid than acetic acid by a factor of $10^{11}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0704.jpg?height=318&width=906&top_left_y=1668&top_left_x=607)


Why are carboxylic acids so much more acidic than alcohols, even though both contain - OH groups? An alcohol dissociates to give an alkoxide ion, in which the negative charge is localized on a single electronegative atom. A carboxylic acid, however, gives a carboxylate ion, in which the negative charge is delocalized over two equivalent oxygen atoms (FIGURE 20.2). In resonance terms (Section 2.4), a carboxylate ion is a stabilized resonance hybrid of two equivalent structures. Since a carboxylate ion is more stable than an alkoxide ion, it is lower in energy and more favored in the dissociation equilibrium.
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Acetate ion
(delocalized charge)


FIGURE 20.2 An alkoxide ion has its charge localized on one oxygen atom and is less stable, while a carboxylate ion has the charge spread equally over both oxygens and is therefore more stable.


Experimental evidence for the equivalence of the two carboxylate oxygens comes from X-ray crystallographic studies on sodium formate. Both carbon-oxygen bonds are 127 pm in length, midway between the $\mathrm{C}=\mathrm{O}$ double bond ( 120 pm ) and the $\mathrm{C}-\mathrm{O}$ single bond ( 134 pm ) of formic acid. An electrostatic potential map of the formate ion also shows how the negative charge (red) is spread equally over both oxygens.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0705.jpg?height=373&width=1077&top_left_y=1559&top_left_x=528)


PROBLEM Assume you have a mixture of naphthalene and benzoic acid that you want to separate. How might 20-3 you take advantage of the acidity of one component in the mixture to effect a separation?


PROBLEM The $K_{\mathrm{a}}$ for dichloroacetic acid is $3.32 \times 10^{-2}$. Approximately what percentage of the acid is 20-4 dissociated in a 0.10 M aqueous solution?


Methyl 4-cyanopentanoate - 20.3 Biological Acids and the Henderson-Hasselbalch Equation

In acidic solution, at low pH , a carboxylic acid is completely undissociated and exists entirely as RCOH. In basic solution, at high pH , a carboxylic acid is completely dissociated and exists entirely as $\mathrm{RCO}_{2}{ }^{-}$. Inside living cells, however, the pH is neither acidic nor basic but is instead buffered to a nearly neutral pH of $3.5-4.5$ in humans, a value often referred to as physiological $p H$. In what form, then, do carboxylic acids exist inside cells? The question is an important one for understanding the acid catalysts so often found in biological reactions.


If the $\mathrm{p} K_{\mathrm{a}}$ value of a given acid and the pH of the medium are known, the percentages of dissociated and
undissociated forms can be calculated using the Henderson-Hasselbalch equation.
For any acid HA, we have


$$
\begin{aligned}
\mathrm{p} K_{\mathrm{a}} & =-\log \frac{\left[\mathrm{H}_{3} \mathrm{O}^{+}\right]\left[\mathrm{A}^{-}\right]}{[\mathrm{HA}]}=-\log \left[\mathrm{H}_{3} \mathrm{O}^{+}\right]-\log \frac{\left[\mathrm{A}^{-}\right]}{[\mathrm{HA}]} \\
& =\mathrm{pH}-\log \frac{\left[\mathrm{A}^{-}\right]}{[\mathrm{HA}]}
\end{aligned}
$$


which can be rearranged to give


$$
\mathrm{pH}=\mathrm{p} K_{\mathrm{a}}+\log \frac{\left[\mathrm{A}^{-}\right]}{[\mathrm{HA}]} \quad \text { Henderson-Hasselbalch equation }
$$


so


$$
\log \frac{\left[\mathrm{A}^{-}\right]}{[\mathrm{HA}]}=\mathrm{pH}-\mathrm{p} K_{\mathrm{a}}
$$

This equation says that the logarithm of the concentration of dissociated acid [ $\mathrm{A}^{-}$] divided by the concentration of undissociated acid [HA] is equal to the pH of the solution minus the $\mathrm{p} K_{\mathrm{a}}$ of the acid. Thus, if we know both the pH of the solution and the $\mathrm{p} K_{\mathrm{a}}$ of the acid, we can calculate the ratio of [ $\mathrm{A}^{-}$] to [HA]. Furthermore, when $\mathrm{pH}=\mathrm{p} K_{\mathrm{a}}$, then HA and $\mathrm{A}^{-}$are present in equal amounts because $\log 1=0$.


As an example of how to use the Henderson-Hasselbalch equation, let's find out what species are present in a 0.0010 M solution of acetic acid at $\mathrm{pH}=7.3$. According to Table $20-3$, the $\mathrm{p} K_{\mathrm{a}}$ of acetic acid is 4.76 . From the Henderson-Hasselbalch equation, we have


$$
\begin{aligned}
\log \frac{\left[\mathrm{A}^{-}\right]}{\mathrm{HA}} & =\mathrm{pH}-\mathrm{p} K_{\mathrm{a}}=7.3-4.76=2.54 \\
\frac{\left[\mathrm{~A}^{-}\right]}{\mathrm{HA}} & =\operatorname{antilog}(2.54)=3.5 \times 10^{2} \quad \text { so }\left[\mathrm{A}^{-}\right]=\left(3.5 \times 10^{2}\right)[\mathrm{HA}]
\end{aligned}
$$


In addition, we know that


$$
\left[\mathrm{A}^{-}\right]+[\mathrm{HA}]=0.0010 \mathrm{M}
$$


Solving the two simultaneous equations gives $\left[\mathrm{A}^{-}\right]=0.0010 \mathrm{M}$ and $[\mathrm{HA}]=3 \times 10^{-6} \mathrm{M}$. In other words, at a physiological pH of 7.3 , essentially $100 \%$ of acetic acid molecules in a 0.0010 M solution are dissociated to the acetate ion.


What is true for acetic acid is also true for other carboxylic acids: At the physiological pH that occurs inside cells, carboxylic acids are almost entirely dissociated. To reflect this fact, we always refer to cellular carboxylic acids by the name of their anion-acetate, lactate, citrate, and so forth, rather than acetic acid, lactic acid, and citric acid.


PROBLEM Calculate the percentages of dissociated and undissociated forms present in the following 20-5 solutions:
(a) 0.0010 M glycolic acid $\left(\mathrm{HOCH}_{2} \mathrm{CO}_{2} \mathrm{H} ; \mathrm{p} K_{\mathrm{a}}=3.83\right)$ at $\mathrm{pH}=4.50$
(b) 0.0020 M propanoic $\operatorname{acid}\left(\mathrm{p} K_{\mathrm{a}}=4.87\right)$ at $\mathrm{pH}=5.30$


Methyl 4-cyanopentanoate - 20.4 Substituent Effects on Acidity

The listing of $\mathrm{p} K_{\mathrm{a}}$ values shown previously in TABLE 20.3 indicates that there are substantial differences in acidity from one carboxylic acid to another. For example, trifluoroacetic acid ( $K_{\mathrm{a}}=0.59$ ) is 33,000 times as strong as acetic acid $\left(K_{\mathrm{a}}=1.75 \times 10^{-5}\right)$. How can we account for such differences?


Because the dissociation of a carboxylic acid is an equilibrium process, any factor that stabilizes the carboxylate anion relative to undissociated carboxylic acid will drive the equilibrium toward increased dissociation and result in increased acidity. For instance, three electron-withdrawing fluorine atoms delocalize the negative charge in the trifluoroacetate anion, thereby stabilizing the ion and increasing the acidity of $\mathrm{CF}_{3} \mathrm{CO}_{2} \mathrm{H}$. In the same way, glycolic acid $\left(\mathrm{HOCH}_{2} \mathrm{CO}_{2} \mathrm{H} ; \mathrm{p} K_{\mathrm{a}}=3.83\right)$ is stronger than acetic acid because of the electronwithdrawing effect of the electronegative oxygen atom.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0707.jpg?height=354&width=746&top_left_y=189&top_left_x=684)


Because inductive effects operate through $\sigma$ bonds and are dependent on distance, the effect of halogen substitution decreases as the substituent moves farther from the carboxyl. Thus, 2-chlorobutanoic acid has $\mathrm{p} K_{\mathrm{a}}=2.86,3$-chlorobutanoic acid has $\mathrm{p} K_{\mathrm{a}}=4.05$, and 4-chlorobutanoic acid has $\mathrm{p} K_{\mathrm{a}}=4.52$, similar to that of butanoic acid itself.
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$\mathrm{p} K_{\mathrm{a}}=4.52$
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$\mathrm{p} K_{\mathrm{a}}=4.05$
Acidity


Substituent effects on acidity are also found in substituted benzoic acids. We said during the discussion of electrophilic aromatic substitution in Section 16.4 that substituents on the aromatic ring strongly affect reactivity. Aromatic rings with electron-donating groups are activated toward further electrophilic substitution, and aromatic rings with electron-withdrawing groups are deactivated. Exactly the same effects can be observed on the acidity of substituted benzoic acids (TABLE 20.4).


|  | Y | <smiles>[Y]c1ccc(C(=O)O)cc1</smiles> |  |  |
| :---: | :---: | :---: | :---: | :---: |
|  |  | $K_{\mathrm{a}} \times 1$ | $\mathrm{p} K_{\mathrm{a}}$ |  |
| Stronger acid | $-\mathrm{NO}_{2}$ | 39 | 3.41 | Deactivating groups |
|  | -CN | 28 | 3.55 |  |
|  | - CHO | 18 | 3.75 |  |
|  | -Br | 11 | 3.96 |  |
|  | -Cl | 10 | 4.0 |  |
|  | -H | 6.46 | 4.19 |  |
| Weaker | $-\mathrm{CH}_{3}$ | 4.3 | 4.34 | Activating groups |
|  | $-\mathrm{OCH}_{3}$ | 3.5 | 4.46 |  |
|  | -OH | 3.3 | 4.48 |  |


As TABLE 20.4 shows, an electron-donating (activating) group such as methoxy decreases acidity by destabilizing the carboxylate anion, and an electron-withdrawing (deactivating) group such as nitro increases acidity by stabilizing the carboxylate anion.
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$p$-Methoxybenzoic acid ( $\mathrm{p} K_{\mathrm{a}}=4.46$ )
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Benzoic acid
( $\mathrm{p} K_{\mathrm{a}}=4.19$ )
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$p$-Nitrobenzoic acid $\left(\mathrm{p} K_{\mathrm{a}}=3.41\right)$


Acidity -

Because it's much easier to measure the acidity of a substituted benzoic acid than it is to determine the relative reactivity of an aromatic ring toward electrophilic substitution, the correlation between the two effects is useful for predicting reactivity. If we want to know the effect of a certain substituent on electrophilic reactivity, we can simply find the acidity of the corresponding benzoic acid. Worked Example 20.1 gives an illustration.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0708.jpg?height=285&width=380&top_left_y=779&top_left_x=626)
... lets us predict the reactivity of this substituted benzene to electrophilic attack.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0708.jpg?height=126&width=234&top_left_y=937&top_left_x=1257)


WORKED EXAMPLE 20.1 -


Predicting the Effect of a Substituent on the Reactivity of an Aromatic Ring toward Electrophilic Substitution -

The $\mathrm{p} K_{\mathrm{a}}$ of $p$-(trifluoromethyl)benzoic acid is 3.6 . Is the trifluoromethyl substituent an activating or deactivating group in electrophilic aromatic substitution?


Strategy -

Decide whether $p$-(trifluoromethyl)benzoic acid is stronger or weaker than benzoic acid. A substituent that strengthens the acid is a deactivating group because it withdraws electrons, and a substituent that weakens the acid is an activating group because it donates electrons.


Solution -

A p $K_{\mathrm{a}}$ of 3.6 means that $p$-(trifluoromethyl)benzoic acid is stronger than benzoic acid, whose $\mathrm{p} K_{\mathrm{a}}$ is 4.19. Thus, the trifluoromethyl substituent favors dissociation by helping stabilize the negative charge. Trifluoromethyl must therefore be an electron-withdrawing, deactivating group.


Solution -


Solution -

Lactic acid


Solution -

PROBLEM Dicarboxylic acids have two dissociation constants, one for the initial dissociation into a monoanion 20-7 and one for the second dissociation into a dianion. For oxalic acid, $\mathrm{HO}_{2} \mathrm{C}-\mathrm{CO}_{2} \mathrm{H}$, the first ionization constant is $\mathrm{p} K_{\mathrm{a} 1}=1.2$ and the second ionization constant is $\mathrm{p} K_{\mathrm{a} 2}=4.2$. Why is the second carboxyl group far less acidic than the first?


Solution -

PROBLEM The $\mathrm{p} K_{\mathrm{a}}$ of $p$-cyclopropylbenzoic acid is 4.45. Is cyclopropylbenzene likely to be more reactive or 20-8 less reactive than benzene toward electrophilic bromination? Explain.


Solution -

PROBLEM Rank the following compounds in order of increasing acidity. Don't look at a table of $\mathrm{p} K_{\mathrm{a}}$ data to help 20-9 with your answer.
(a) Benzoic acid, $p$-methylbenzoic acid, $p$-chlorobenzoic acid
(b) $p$-Nitrobenzoic acid, acetic acid, benzoic acid


Solution - 20.5 Preparing Carboxylic Acids

Let's review briefly some of the methods for preparing carboxylic acids that we've seen in previous chapters.


- Oxidation of a substituted alkylbenzene with $\mathrm{KMnO}_{4}$ gives a substituted benzoic acid (Section 16.8). Both primary and secondary alkyl groups can be oxidized, but tertiary groups are not affected.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0709.jpg?height=144&width=857&top_left_y=481&top_left_x=653)
$p-$ Nitrotoluene
$p$-Nitrobenzoic acid (88\%)
- Oxidation of a primary alcohol or an aldehyde yields a carboxylic acid (Section 17.7 and Section 19.3). Primary alcohols are often oxidized with the Dess Martin periodinane, and aldehydes are similarly oxidized with alkaline $\mathrm{KMnO}_{4}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0709.jpg?height=115&width=819&top_left_y=802&top_left_x=653)


4-Methyl-1-pentanol
4-Methylpentanoic acid
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0709.jpg?height=115&width=882&top_left_y=1013&top_left_x=649)


Hexanal
Hexanoic acid