Solution - 2.8 Acid and Base Strength

Notice also in TABLE 2.3 that there is an inverse relationship between the acid strength of an acid and the base strength of its conjugate base. A strong acid has a weak conjugate base, and a weak acid has a strong conjugate base. To understand this inverse relationship, think about what is happening to the acidic hydrogen in an acid-base reaction. A strong acid is one that loses $\mathrm{H}^{+}$easily, meaning that its conjugate base holds the $\mathrm{H}^{+}$ weakly and is therefore a weak base. A weak acid is one that loses $\mathrm{H}^{+}$with difficulty, meaning that its conjugate base holds the proton tightly and is therefore a strong base. The fact that HCl is a strong acid, for example, means that $\mathrm{Cl}^{-}$does not hold $\mathrm{H}^{+}$tightly and is thus a weak base. Water, on the other hand, is a weak acid, meaning that $\mathrm{OH}^{-}$holds $\mathrm{H}^{+}$tightly and is a strong base.


Solution - 2.8 Acid and Base Strength

|  | Acid | Name | $\mathrm{p} K_{\mathrm{a}}$ | Conjugate base | Name |  |
| :---: | :---: | :---: | :---: | :---: | :---: | :---: |
| Weaker acid | $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$ | Ethanol | 16.00 | $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{O}^{-}$ | Ethoxide ion | Stronger base |
|  | $\mathrm{H}_{2} \mathrm{O}$ | Water | 15.74 | $\mathrm{HO}^{-}$ | Hydroxide ion |  |
|  | HCN | Hydrocyanic acid | 9.31 | $\mathrm{CN}^{-}$ | Cyanide ion |  |
|  | $\mathrm{H}_{2} \mathrm{PO}_{4}{ }^{-}$ | Dihydrogen phosphate ion | 7.21 | $\mathrm{HPO}_{4}{ }^{2-}$ | Hydrogen phosphate ion |  |
|  | $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$ | Acetic acid | 4.76 | $\mathrm{CH}_{3} \mathrm{CO}_{2}{ }^{-}$ | Acetate ion |  |
|  | $\mathrm{H}_{3} \mathrm{PO}_{4}$ | Phosphoric acid | 2.16 | $\mathrm{H}_{2} \mathrm{PO}_{4}{ }^{-}$ | Dihydrogen phosphate ion |  |
|  | $\mathrm{HNO}_{3}$ | Nitric acid | -1.3 | $\mathrm{NO}_{3}{ }^{-}$ | Nitrate ion |  |
| acid | HCl | Hydrochloric acid | -7.0 | $\mathrm{Cl}^{-}$ | Chloride ion | base |


Solution - 2.8 Acid and Base Strength


Solution - 2.8 Acid and Base Strength

Phenylalanine
( $\mathrm{p} K_{\mathrm{a}}=1.83$ )
Tryptophan
$\left(\mathrm{p} K_{\mathrm{a}}=2.83\right)$
PROBLEM Amide ion, $\mathrm{H}_{2} \mathrm{~N}^{-}$, is a much stronger base than hydroxide ion, $\mathrm{HO}^{-}$. Which is the stronger acid, $\mathrm{NH}_{3}$
2-13 or $\mathrm{H}_{2} \mathrm{O}$ ? Explain.


Solution - 2.9 Predicting Acid-Base Reactions from $\mathrm{p} K_{\mathrm{a}}$ Values

Compilations of $\mathrm{p} K_{\mathrm{a}}$ values like those in TABLE 2.3 and Appendix B are useful for predicting whether a given acid-base reaction will take place, because $\mathrm{H}^{+}$will always go from the stronger acid to the stronger base. That is, an acid will donate a proton to the conjugate base of a weaker acid, and the conjugate base of a weaker acid will remove a proton from a stronger acid. Since water ( $\mathrm{p} K_{\mathrm{a}}=15.74$ ) is a weaker acid than acetic acid ( $\mathrm{p} K_{\mathrm{a}}=4.76$ ), for example, hydroxide ion holds a proton more tightly than acetate ion does. Hydroxide ion will therefore react to a large extent with acetic acid, $\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}$, to yield acetate ion and $\mathrm{H}_{2} \mathrm{O}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0046.jpg?height=254&width=1259&top_left_y=203&top_left_x=418)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0046.jpg?height=282&width=1245&top_left_y=496&top_left_x=429)


Another way to predict acid-base reactivity is to remember that the product conjugate acid in an acid-base reaction must be weaker and less reactive than the starting acid and the product conjugate base must be weaker and less reactive than the starting base. In the reaction of acetic acid with hydroxide ion, for example, the product conjugate acid $\left(\mathrm{H}_{2} \mathrm{O}\right)$ is weaker than the starting acid $\left(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\right)$, and the product conjugate base $\left(\mathrm{CH}_{3} \mathrm{CO}_{2}{ }^{-}\right)$is weaker than the starting base $\left(\mathrm{OH}^{-}\right)$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0046.jpg?height=210&width=716&top_left_y=1012&top_left_x=702)


WORKED EXAMPLE 2.4 -


Predicting Acid Strengths from $\mathbf{p} K_{\mathbf{a}}$ Values -

Water has $\mathrm{p} K_{\mathrm{a}}=15.74$, and acetylene has $\mathrm{p} K_{\mathrm{a}}=25$. Which is the stronger acid? Does hydroxide ion react to a significant extent with acetylene?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0046.jpg?height=82&width=798&top_left_y=1493&top_left_x=666)


Acetylene


Strategy -

In comparing two acids, the one with the lower $\mathrm{p} K_{\mathrm{a}}$ is stronger. Thus, water is a stronger acid than acetylene and gives up $\mathrm{H}^{+}$more easily.


Solution -

Because water is a stronger acid and gives up $\mathrm{H}^{+}$more easily than acetylene, the $\mathrm{HO}^{-}$ion must have less affinity for $\mathrm{H}^{+}$than the $\mathrm{HC} \equiv \mathrm{C}$ : $^{-}$ion. In other words, the anion of acetylene is a stronger base than hydroxide ion, and the reaction will not proceed significantly as written.


WORKED EXAMPLE 2.5 -


Calculating $K_{\mathrm{a}}$ from $\mathrm{p} K_{\mathrm{a}}$ -

According to the data in TABLE 2.3, acetic acid has $\mathrm{p} K_{\mathrm{a}}=4.76$. What is its $K_{\mathrm{a}}$ ?


Strategy -

Since $\mathrm{p} K_{\mathrm{a}}$ is the negative logarithm of $K_{\mathrm{a}}$, it's necessary to use a calculator with an ANTILOG or INV LOG function. Enter the value of the $\mathrm{p} K_{\mathrm{a}}(4.76)$, change the sign $(-4.76)$, and then find the antilog $\left(1.74 \times 10^{-5}\right)$.


Solution -

$K_{\mathrm{a}}=1.74 \times 10^{-5}$.


Solution -

PROBLEM Will either of the following reactions take place to a significant extent as written, according to the 2-14 data in Table 2.3?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0047.jpg?height=191&width=947&top_left_y=468&top_left_x=410)


Solution -

PROBLEM Ammonia, $\mathrm{NH}_{3}$, has $\mathrm{p} K_{\mathrm{a}} \approx 36$, and acetone has $\mathrm{p} K_{\mathrm{a}} \approx 19$. Will the following reaction take place to a 2-15 significant extent?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0047.jpg?height=150&width=1053&top_left_y=787&top_left_x=411)


Solution -

Acetone
PROBLEM What is the $K_{\mathrm{a}}$ of HCN if its $\mathrm{p} K_{\mathrm{a}}=9.31$ ?
2-16


Solution - 2.10 Organic Acids and Organic Bases

Many of the reactions we'll be seeing in future chapters, including practically all biological reactions, involve organic acids and organic bases. Although it's too early to go into the details of these processes now, you might keep the following generalities in mind:


Organic Acids -

Organic acids are characterized by the presence of a positively polarized hydrogen atom (blue in electrostatic potential maps) and are of two main kinds: acids such as methanol and acetic acid that contain a hydrogen atom bonded to an electronegative oxygen atom $(\mathrm{O}-\mathrm{H})$ and those such as acetone (Section 2.5) that contain a hydrogen atom bonded to a carbon atom next to a $\mathrm{C}=\mathrm{O}$ bond $(\mathrm{O}=\mathrm{C}-\mathrm{C}-\mathrm{H})$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0047.jpg?height=427&width=1193&top_left_y=1630&top_left_x=453)
<img class="imgSvg" id = "m6sn3m1c28wexp2y415" src="data:image/svg+xml;base64,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"/>

Methanol
$\left(\mathrm{p} K_{a}=15.54\right)$
<img class="imgSvg" id = "m6sn3m1dw0nyzj2bq8a" src="data:image/svg+xml;base64,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"/>

Acetic acid
$\left(\mathrm{p} K_{\mathrm{a}}=4.76\right)$
<img class="imgSvg" id = "m6sn3m1dka1styaqrf" src="data:image/svg+xml;base64,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"/>


Organic Acids -

Acetone
$\left(p K_{a}=19.3\right)$


Organic Acids -

Methanol contains an $\mathrm{O}-\mathrm{H}$ bond and is a weak acid, while acetic acid also contains an $\mathrm{O}-\mathrm{H}$ bond and is a somewhat stronger acid. In both cases, acidity is due to the fact that the conjugate base resulting from loss of $\mathrm{H}^{+}$ is stabilized by having its negative charge on a strongly electronegative oxygen atom. In addition, the conjugate base of acetic acid is stabilized by resonance (Section 2.4 and Section 2.5).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0048.jpg?height=354&width=906&top_left_y=189&top_left_x=311)


Organic Acids -

Anion is stabilized both by having negative charge on a highly electronegative atom and by resonance.


Organic Acids -

The acidity of acetone and other compounds with $\mathrm{C}=\mathrm{O}$ bonds is due to the fact that the conjugate base resulting from loss of $\mathrm{H}^{+}$is stabilized by resonance. In addition, one of the resonance forms stabilizes the negative charge by placing it on an electronegative oxygen atom.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0048.jpg?height=186&width=969&top_left_y=704&top_left_x=383)


Organic Acids -

Anion is stabilized both by resonance and by having negative charge on a highly electronegative atom.


Organic Acids -

Electrostatic potential maps of the conjugate bases from methanol, acetic acid, and acetone are shown in FIGURE 2.5. As you might expect, all three show a substantial amount of negative charge (red) on oxygen.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0048.jpg?height=321&width=269&top_left_y=1043&top_left_x=489)
$\mathrm{CH}_{3} \mathrm{O}^{-}$
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0048.jpg?height=326&width=354&top_left_y=1038&top_left_x=842)
<img class="imgSvg" id = "m6sn3m1e4xquh8nvzui" src="data:image/svg+xml;base64,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"/>
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0048.jpg?height=324&width=364&top_left_y=1039&top_left_x=1287)
<img class="imgSvg" id = "m6sn3m1fj6mxdba17l" src="data:image/svg+xml;base64,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"/>


Organic Acids -

FIGURE 2.5 Electrostatic potential maps of the conjugate bases of (a) methanol, (b) acetic acid, and (c) acetone. The electronegative oxygen atoms stabilize the negative charge in all three.


Organic Acids -

Compounds called carboxylic acids, which contain the $-\mathrm{CO}_{2} \mathrm{H}$ grouping, occur abundantly in all living organisms and are involved in almost all metabolic pathways. Acetic acid, pyruvic acid, and citric acid are examples. You might note that at the typical pH of 7.3 found within cells, carboxylic acids are usually dissociated and exist as their carboxylate anions, $-\mathrm{CO}_{2}{ }^{-}$.
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Acetic acid
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Pyruvic acid
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Organic Acids -

Citric acid


Organic Bases -

Organic bases are characterized by the presence of an atom (reddish in electrostatic potential maps) with a lone pair of electrons that can bond to $\mathrm{H}^{+}$. Nitrogen-containing compounds such as methylamine are the most common organic bases and are involved in almost all metabolic pathways, but oxygen-containing compounds can also act as bases when reacting with a sufficiently strong acid. Note that some oxygen-containing compounds can act both as acids and as bases depending on the circumstances, just as water can. Methanol and acetone, for instance, act as acids when they donate a proton but as bases when their oxygen atom accepts a proton.
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Methylamine
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0049.jpg?height=204&width=259&top_left_y=256&top_left_x=1036)
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Methanol
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0049.jpg?height=256&width=299&top_left_y=200&top_left_x=1328)
<img class="imgSvg" id = "m6sn3m1tcff5oxh9ia" src="data:image/svg+xml;base64,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"/>


Organic Bases -

Acetone


Organic Bases -

We'll see in Chapter 26 that substances called amino acids, so-named because they are both amines $\left(-\mathrm{NH}_{2}\right)$ and carboxylic acids $\left(-\mathrm{CO}_{2} \mathrm{H}\right)$, are the building blocks from which the proteins in all living organisms are made. Twenty different amino acids go into making up proteins-alanine is an example. Interestingly, alanine and other amino acids exist primarily in a doubly charged form called a zwitterion rather than in the uncharged form. The zwitterion form arises because amino acids have both acidic and basic sites within the same molecule and therefore undergo an internal acid-base reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0049.jpg?height=174&width=369&top_left_y=1016&top_left_x=756)


Organic Bases -


Organic Bases -

Alanine
(zwitterion form)


Organic Bases - 2.11 Acids and Bases: The Lewis Definition

The Lewis definition of acids and bases is more encompassing than the Brønsted-Lowry definition because it's not limited to substances that donate or accept just protons. A Lewis acid is a substance that accepts an electron pair, and a Lewis base is a substance that donates an electron pair. The donated electron pair is shared between the acid and the base in a covalent bond.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0049.jpg?height=253&width=657&top_left_y=1581&top_left_x=731)


Lewis Acids and the Curved Arrow Formalism -

The fact that a Lewis acid is able to accept an electron pair means that it must have either a vacant, low-energy orbital or a polar bond to hydrogen so that it can donate $\mathrm{H}^{+}$(which has an empty $1 s$ orbital). Thus, the Lewis definition of acidity includes many species in addition to $\mathrm{H}^{+}$. For example, various metal cations, such as $\mathrm{Mg}^{2+}$, are Lewis acids because they accept a pair of electrons when they form a bond to a base. We'll also see in later chapters that certain metabolic reactions begin with an acid-base reaction between $\mathrm{Mg}^{2+}$ as a Lewis acid and an organic diphosphate or triphosphate ion as the Lewis base.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0049.jpg?height=199&width=969&top_left_y=2188&top_left_x=589)

Lewis acid
Lewis base
Acid-base complex (an organodiphosphate ion)
In the same way, compounds of group 3A elements, such as $\mathrm{BF}_{3}$ and $\mathrm{AlCl}_{3}$, are Lewis acids because they have
unfilled valence orbitals and can accept electron pairs from Lewis bases, as shown in FIGURE 2.6. Similarly, many transition-metal compounds, such as $\mathrm{TiCl}_{4}, \mathrm{FeCl}_{3}, \mathrm{ZnCl}_{2}$, and $\mathrm{SnCl}_{4}$, are Lewis acids.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0050.jpg?height=440&width=1031&top_left_y=344&top_left_x=544)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0050.jpg?height=245&width=873&top_left_y=818&top_left_x=607)


| Boron
 trifluoride
 (Lewis acid) | Dimethyl
 ether
 (Lewis base) |
| :---: | :---: |


Acid-base complex


FIGURE 2.6 The reaction of boron trifluoride, a Lewis acid, with dimethyl ether, a Lewis base. The Lewis acid accepts a pair of electrons, and the Lewis base donates a pair of nonbonding electrons. Note how the movement of electrons from the Lewis base to the Lewis acid is indicated by a curved arrow. Note also how, in electrostatic potential maps, the boron becomes more negative (red) after reaction because it has gained electrons and the oxygen atom becomes more positive (blue) because it has donated electrons.

Look closely at the acid-base reaction in FIGURE 2.6, and notice how it's shown. Dimethyl ether, the Lewis base, donates an electron pair to a vacant valence orbital of the boron atom in $\mathrm{BF}_{3}$, a Lewis acid. The direction of electron-pair flow from base to acid is shown using a curved arrow, just as the direction of electron flow from one resonance structure to another was shown using curved arrows in Section 2.5. We'll use this curved-arrow notation throughout the remainder of this text to indicate electron flow during reactions, so get used to seeing it.


Some further examples of Lewis acids follow:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0050.jpg?height=660&width=874&top_left_y=1681&top_left_x=620)


Lewis Bases -

The Lewis definition of a base-a compound with a pair of nonbonding electrons that it can use to bond to a Lewis acid-is similar to the Brønsted-Lowry definition. Thus, $\mathrm{H}_{2} \mathrm{O}$, with its two pairs of nonbonding electrons
on oxygen, acts as a Lewis base by donating an electron pair to an $\mathrm{H}^{+}$in forming the hydronium ion, $\mathrm{H}_{3} \mathrm{O}^{+}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0051.jpg?height=240&width=648&top_left_y=257&top_left_x=733)

In a more general sense, most oxygen- and nitrogen-containing organic compounds can act as Lewis bases because they have lone pairs of electrons. A divalent oxygen compound has two lone pairs of electrons, and a trivalent nitrogen compound has one lone pair. Note in the following examples that some compounds can act as both acids and bases, just as water can. Alcohols and carboxylic acids, for instance, act as acids when they donate an $\mathrm{H}^{+}$but as bases when their oxygen atom accepts an $\mathrm{H}^{+}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0051.jpg?height=706&width=1094&top_left_y=734&top_left_x=510)


Lewis Bases -

Note also that some Lewis bases, such as carboxylic acids, esters, and amides, have more than one atom with a lone pair of electrons and can therefore react at more than one site. Acetic acid, for example, can be protonated either on the doubly bonded oxygen atom or on the singly bonded oxygen atom. Reaction normally occurs only once in such instances, and the more stable of the two possible protonation products is formed. For acetic acid, protonation by reaction with sulfuric acid occurs on the doubly bonded oxygen because that product is stabilized by two resonance forms.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0051.jpg?height=169&width=953&top_left_y=1721&top_left_x=586)


Lewis Bases -

Acetic acid (base)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0051.jpg?height=207&width=472&top_left_y=1921&top_left_x=973)


WORKED EXAMPLE 2.6 -


Using Curved Arrows to Show Electron Flow -

Using curved arrows, show how acetaldehyde, $\mathrm{CH}_{3} \mathrm{CHO}$, can act as a Lewis base.


Strategy -

A Lewis base donates an electron pair to a Lewis acid. We therefore need to locate the electron lone pairs on acetaldehyde and use a curved arrow to show the movement of a pair toward the H atom of the acid.


Solution -


Solution -

Acetaldehyde


Solution -

PROBLEM Using curved arrows, show how the species in part (a) can act as Lewis bases in their reactions with 2-17 HCl , and show how the species in part (b) can act as Lewis acids in their reaction with $\mathrm{OH}^{-}$.
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}, \mathrm{HN}\left(\mathrm{CH}_{3}\right)_{2}, \mathrm{P}\left(\mathrm{CH}_{3}\right)_{3}$
(b) $\mathrm{H}_{3} \mathrm{C}^{+}, \mathrm{B}\left(\mathrm{CH}_{3}\right)_{3}, \mathrm{MgBr}_{2}$


Solution -

Histidine
(a) Look at the electrostatic potential map of imidazole, and identify the most acidic hydrogen atom and the most basic nitrogen atom.
(b) Draw structures for the resonance forms of the products that result when imidazole is protonated by an acid and deprotonated by a base.


Solution - 2.12 Noncovalent Interactions between Molecules

When thinking about chemical reactivity, chemists usually focus their attention on bonds, the covalent interactions between atoms within molecules. Also important, however, particularly in large biomolecules like proteins and nucleic acids, are a variety of interactions between molecules that strongly affect molecular properties. Collectively called either intermolecular forces, van der Waals forces, or noncovalent interactions, they are of several different types: dipole-dipole forces, dispersion forces, and hydrogen bonds.


Dipole-dipole forces occur between polar molecules as a result of electrostatic interactions among dipoles. The forces can be either attractive or repulsive depending on the orientation of the molecules-attractive when unlike charges are together and repulsive when like charges are together. The attractive geometry is lower in energy and therefore predominates (FIGURE 2.7).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0052.jpg?height=324&width=1216&top_left_y=1777&top_left_x=454)

FIGURE 2.7 Dipole-dipole forces cause polar molecules (a) to attract one another when they orient with unlike charges together, but (b) to repel one another when they orient with like charges together.


Dispersion forces occur between all neighboring molecules and arise because the electron distribution within molecules is constantly changing. Although uniform on a time-averaged basis, the electron distribution even in nonpolar molecules is likely to be nonuniform at any given instant. One side of a molecule may, by chance, have a slight excess of electrons relative to the opposite side, giving the molecule a temporary dipole. This temporary dipole in one molecule causes a nearby molecule to adopt a temporarily opposite dipole, resulting in a tiny attraction between the two (FIGURE 2.8). Temporary molecular dipoles have only a fleeting existence and are constantly changing, but their cumulative effect is often strong enough to hold molecules close together so that a substance is a liquid or solid rather than a gas.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0053.jpg?height=316&width=936&top_left_y=191&top_left_x=599)


FIGURE 2.8 Attractive dispersion forces in nonpolar molecules are caused by temporary dipoles, as shown in these models of pentane, $\mathrm{C}_{5} \mathrm{H}_{12}$.


Perhaps the most important noncovalent interaction in biological molecules is the hydrogen bond, an attractive interaction between a hydrogen atom bonded to an electronegative O or N atom and an unshared electron pair on another O or N atom. In essence, a hydrogen bond is a very strong dipole-dipole interaction involving polarized $\mathrm{O}-\mathrm{H}$ or $\mathrm{N}-\mathrm{H}$ bonds. Electrostatic potential maps of water and ammonia clearly show the positively polarized hydrogens (blue) and the negatively polarized oxygens and nitrogens (red).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0053.jpg?height=182&width=354&top_left_y=836&top_left_x=666)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0053.jpg?height=188&width=358&top_left_y=833&top_left_x=1179)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0053.jpg?height=259&width=994&top_left_y=1063&top_left_x=562)


Hydrogen bonding has enormous consequences for living organisms. Hydrogen bonds cause water to be a liquid rather than a gas at ordinary temperatures, they hold enzymes in the shapes necessary for catalyzing biological reactions, and they cause strands of deoxyribonucleic acid (DNA) to pair up and coil into the double helix that stores genetic information.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0053.jpg?height=792&width=1076&top_left_y=1530&top_left_x=522)


A deoxyribonucleic acid segment -

One further point before leaving the subject of noncovalent interactions: biochemists frequently use the term hydrophilic, meaning "water-loving," to describe a substance that is attracted to water and the term hydrophobic, meaning "water-fearing," to describe a substance that is not strongly attracted to water.


A deoxyribonucleic acid segment -

Hydrophilic substances, such as table sugar, often have a number of -OH groups in their structure so they can form hydrogen bonds and dissolve in water, whereas hydrophobic substances, such as vegetable oil, do not have groups that form hydrogen bonds and do not dissolve in water.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0054.jpg?height=397&width=909&top_left_y=341&top_left_x=605)


A deoxyribonucleic acid segment -


A deoxyribonucleic acid segment -

Vitamin C (ascorbic acid)


Alkaloids: From Cocaine to Dental Anesthetics -

Just as ammonia $\left(\mathrm{NH}_{3}\right)$ is a weak base, there are a large number of nitrogen-containing organic compounds called amines that are also weak bases. In the early days of organic chemistry, basic amines derived from natural sources were known as vegetable alkali, but they are now called alkaloids. More than 20,000 alkaloids are known. Their study provided much of the impetus for the growth of organic chemistry in the nineteenth century and remains today an active and fascinating area of research.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0055.jpg?height=597&width=896&top_left_y=677&top_left_x=612)


FIGURE 2.9 The coca bush Erythroxylon coca, native to upland rain forest areas of Colombia, Ecuador, Peru, Bolivia, and western Brazil, is the source of the alkaloid cocaine. (credit: "Erythroxylum coca" by Danna Guevara/Wikimedia Commons, CC BY 4.0)