Alkaloids: From Cocaine to Dental Anesthetics -

Prilocaine
(Citanest)
An estimate from the U.S. National Academy of Sciences is that less than $1 \%$ of all living species have been characterized. Thus, alkaloid chemistry remains an active area of research, and innumerable substances with potentially useful properties have yet to be discovered. Undoubtedly even the caine anesthetics will become obsolete at some point, perhaps supplanted by newly discovered alkaloids.


Key Terms -

- acidity constant $\left(K_{\mathrm{a}}\right)$
- alkaloid
- Brønsted-Lowry acid
- Brønsted-Lowry base
- conjugate acid
- conjugate base
- dipole moment ( $\mu$ )
- dispersion force
- electronegativity (EN)
- electrostatic potential map
- formal charge
- hydrogen bond
- hydrophilic
- hydrophobic
- inductive effect
- intermolecular force
- Lewis acid
- Lewis base
- noncovalent interaction
- $\mathrm{p} K_{\mathrm{a}}$
- polar covalent bond
- resonance form
- resonance hybrid
- van der Waals force


Key Terms -


Summary -

Understanding organic chemistry means knowing not just what happens but also why and how it happens at the molecular level. In this chapter, we've reviewed some of the ways that chemists describe and account for chemical reactivity, thereby providing a foundation for understanding the specific reactions that will be discussed in subsequent chapters.


Summary -

Organic molecules often have polar covalent bonds as a result of unsymmetrical electron sharing caused by differences in the electronegativity of atoms. A carbon-oxygen bond is polar, for example, because oxygen attracts the shared electrons more strongly than carbon does. Carbon-hydrogen bonds are relatively nonpolar. Many molecules as a whole are also polar, owing to the presence of individual polar bonds and electron lone pairs. The polarity of a molecule is measured by its dipole moment, $\boldsymbol{\mu}$.


Summary -

Plus (+) and minus (-) signs are often used to indicate the presence of formal charges on atoms in molecules. Assigning formal charges to specific atoms is a bookkeeping technique that makes it possible to keep track of the valence electrons around an atom and offers some clues about chemical reactivity.


Summary -

Some substances, such as acetate ion and benzene, can't be represented by a single line-bond structure and must be considered as a resonance hybrid of two or more structures, none of which would be correct by themselves. The only difference between two resonance forms is in the location of their $\pi$ and nonbonding electrons. The nuclei remain in the same places in both structures, and the hybridization of the atoms remains
the same.
Acidity and basicity are closely related to the ideas of polarity and electronegativity. A Brønsted-Lowry acid is a compound that can donate a proton (hydrogen ion, $\mathrm{H}^{+}$), and a Brønsted-Lowry base is a compound that can accept a proton. The strength of a Brønsted-Lowry acid or base is expressed by its acidity constant, $\boldsymbol{K}_{\mathbf{a}}$, or by the negative logarithm of the acidity constant, $\mathbf{p} \boldsymbol{K}_{\mathbf{a}}$. The larger the $\mathrm{p} K_{\mathrm{a}}$, the weaker the acid. More useful is the Lewis definition of acids and bases. A Lewis acid is a compound that has a low-energy empty orbital that can accept an electron pair; $\mathrm{Mg}^{2+}, \mathrm{BF}_{3}, \mathrm{AlCl}_{3}$, and $\mathrm{H}^{+}$are examples. A Lewis base is a compound that can donate an unshared electron pair; $\mathrm{NH}_{3}$ and $\mathrm{H}_{2} \mathrm{O}$ are examples. Most organic molecules that contain oxygen and nitrogen can act as Lewis bases toward sufficiently strong acids.


Summary -

A variety of noncovalent interactions have a significant effect on the properties of large biomolecules. Hydrogen bonding-the attractive interaction between a positively polarized hydrogen atom bonded to an oxygen or nitrogen atom with an unshared electron pair on another O or N atom, is particularly important in giving proteins and nucleic acids their shapes.


Additional Problems -


Visualizing Chemistry -

PROBLEM Fill in the multiple bonds in the following model of naphthalene, $\mathrm{C}_{10} \mathrm{H}_{8}$ (black $=\mathrm{C}$, gray $=\mathrm{H}$ ). How 2-20 many resonance structures does naphthalene have? Draw them.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0057.jpg?height=400&width=508&top_left_y=1074&top_left_x=424)


Visualizing Chemistry -

PROBLEM The following model is a representation of ibuprofen, a common over-the-counter pain reliever.
2-21 Indicate the positions of the multiple bonds, and draw a skeletal structure (black $=\mathrm{C}$, red = O, gray $=\mathrm{H})$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0057.jpg?height=324&width=654&top_left_y=1654&top_left_x=416)


Visualizing Chemistry -

PROBLEM cis-1,2-Dichloroethylene and trans-1,2-dichloroethylene are isomers, compounds with the same
$\mathbf{2 - 2 2}$ formula but different chemical structures. Look at the following electrostatic potential maps, and tell whether either compound has a dipole moment.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=373&width=581&top_left_y=193&top_left_x=417)
cis-1,2-Dichloroethylene
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=392&width=551&top_left_y=189&top_left_x=1058)
trans-1,2-Dichloroethylene


Visualizing Chemistry -

PROBLEM The following molecular models are representations of (a) adenine and (b) cytosine, constituents of
2-23 DNA (deoxyribonucleic acid). Indicate the positions of multiple bonds and lone pairs for both, and draw skeletal structures (black = C, red = O, blue = N, gray = H).
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=451&width=475&top_left_y=794&top_left_x=478)


Visualizing Chemistry -

Adenine
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=481&width=372&top_left_y=795&top_left_x=1034)


Visualizing Chemistry -

Cytosine


Mechanism Problems -


Mechanism Problems -

PROBLEM Use the curved-arrow formalism to show how the electrons flow in the resonance form on the left to 2-26 give the one on the right.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=354&width=562&top_left_y=2051&top_left_x=407)
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=126&width=633&top_left_y=2065&top_left_x=479)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0058.jpg?height=128&width=467&top_left_y=2072&top_left_x=1181)
c)
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PROBLEM Double bonds can also act like Lewis bases, sharing their electrons with Lewis acids. Use curved
2-27 arrows to show how each of the following double bonds will react with HCl and draw the resulting
carbocation.
(a) $\mathrm{H}_{2} \mathrm{C}=\mathrm{CH}_{2}$
(b)
<img class="imgSvg" id = "m6sn3m4dhyxfiqkf4va" src="data:image/svg+xml;base64,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"/>
(c)
<img class="imgSvg" id = "m6sn3m4eftf3q4pnxor" src="data:image/svg+xml;base64,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Electronegativity and Dipole Moments -

PROBLEM Identify the most electronegative element in each of the following molecules:
2-28 (a) $\mathrm{CH}_{2} \mathrm{FCl}$
(b) $\mathrm{FCH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$
(c) $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}$
(d) $\mathrm{CH}_{3} \mathrm{OCH}_{2} \mathrm{Li}$


Electronegativity and Dipole Moments -

PROBLEM Use the electronegativity table given in Figure 2.3 to predict which bond in each of the following
2-29 pairs is more polar, and indicate the direction of bond polarity for each compound.
(a) $\mathrm{H}_{3} \mathrm{C}-\mathrm{Cl}$ or $\mathrm{Cl}-\mathrm{Cl}$
(b) $\mathrm{H}_{3} \mathrm{C}-\mathrm{H}$ or $\mathrm{H}-\mathrm{Cl}$
(c) $\mathrm{HO}-\mathrm{CH}_{3}$ or $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{Si}-\mathrm{CH}_{3}$
(d) $\mathrm{H}_{3} \mathrm{C}-\mathrm{Li}$ or $\mathrm{Li}-\mathrm{OH}$


Electronegativity and Dipole Moments -


Electronegativity and Dipole Moments -

PROBLEM (a) The $\mathrm{H}-\mathrm{Cl}$ bond length is 136 pm . What would the dipole moment of HCl be if the molecule
2-31 were $100 \%$ ionic, $\mathrm{H}^{+} \mathrm{Cl}^{-}$?
(b) The actual dipole moment of HCl is 1.08 D . What is the percent ionic character of the $\mathrm{H}-\mathrm{Cl}$ bond?


Electronegativity and Dipole Moments -

PROBLEM Phosgene, $\mathrm{Cl}_{2} \mathrm{C}=\mathrm{O}$, has a smaller dipole moment than formaldehyde, $\mathrm{H}_{2} \mathrm{C}=\mathrm{O}$, even though it
2-32 contains electronegative chlorine atoms in place of hydrogen. Explain.
PROBLEM Fluoromethane $\left(\mathrm{CH}_{3} \mathrm{~F}, \mu=1.81 \mathrm{D}\right)$ has a smaller dipole moment than chloromethane $\left(\mathrm{CH}_{3} \mathrm{Cl}, \mu=\right.$
2-33 1.87 D ) even though fluorine is more electronegative than chlorine. Explain.
PROBLEM Methanethiol, $\mathrm{CH}_{3} \mathrm{SH}$, has a substantial dipole moment ( $\mu=1.52$ ) even though carbon and sulfur
2-34 have identical electronegativities. Explain.


Formal Charges -

PROBLEM Calculate the formal charges on the atoms shown in red.
2-35 (a) ${ }_{\left(\mathrm{CH}_{3}\right)_{2}} \mathrm{OO}_{\mathrm{BF}}^{3}$
(b) $\mathrm{H}_{2} \ddot{\mathrm{C}}-\mathrm{N} \equiv \mathrm{N}$ :
(c) $\mathrm{H}_{2} \mathrm{C}=\mathrm{N}=\ddot{\mathrm{N}}$ :
(d) $: \ddot{0}=\ddot{0}-\ddot{0}:$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0059.jpg?height=163&width=259&top_left_y=1637&top_left_x=1394)
(f)


Formal Charges -


Resonance -


Resonance -

(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0060.jpg?height=224&width=329&top_left_y=224&top_left_x=464)


Resonance -

PROBLEM 1,3-Cyclobutadiene is a rectangular molecule with two shorter double bonds and two longer single 2-39 bonds. Why do the following structures not represent resonance forms?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0060.jpg?height=104&width=302&top_left_y=935&top_left_x=418)


Resonance -

Acids and Bases
PROBLEM Alcohols can act either as weak acids or as weak bases, just as water can. Show the reaction of
2-40 methanol, $\mathrm{CH}_{3} \mathrm{OH}$, with a strong acid such as HCl and with a strong base such as $\mathrm{Na}^{+}{ }^{-} \mathrm{NH}_{2}$
PROBLEM The $\mathrm{O}-\mathrm{H}$ hydrogen in acetic acid is more acidic than any of the $\mathrm{C}-\mathrm{H}$ hydrogens. Explain this result
2-41 using resonance structures.
<img class="imgSvg" id = "m6sn3m5aam9f4n1ijag" 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Resonance -

Acetic acid


Resonance -

PROBLEM Draw electron-dot structures for the following molecules, indicating any unshared electron pairs.
2-42 Which of the compounds are likely to act as Lewis acids and which as Lewis bases?
(a) $\mathrm{AlBr}_{3}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{NH}_{2}$
(c) $\mathrm{BH}_{3}$
(d) HF
(e) $\mathrm{CH}_{3} \mathrm{SCH}_{3}$
(f) $\mathrm{TiCl}_{4}$


Resonance -

PROBLEM Write the products of the following acid-base reactions:
2-43 (a) $\mathrm{CH}_{3} \mathrm{OH}+\mathrm{H}_{2} \mathrm{SO}_{4} \rightleftarrows$ ? (b) $\mathrm{CH}_{3} \mathrm{OH}+\mathrm{NaNH}_{2} \rightleftarrows$ ?
(c) $\mathrm{CH}_{3} \mathrm{NH}_{3}^{+} \mathrm{Cl}^{-}+\mathrm{NaOH} \rightleftarrows$ ?


Resonance -

Acetic acid
$\left(p K_{a}=4.76\right)$


Resonance -

PROBLEM Which, if any, of the substances in Problem 2-44 is a strong enough acid to react almost completely
2-45 with NaOH ? (The $\mathrm{p} K_{\mathrm{a}}$ of $\mathrm{H}_{2} \mathrm{O}$ is 15.74.)
PROBLEM The ammonium ion $\left(\mathrm{NH}_{4}{ }^{+}, \mathrm{p} K_{\mathrm{a}}=9.25\right)$ has a lower $\mathrm{p} K_{\mathrm{a}}$ than the methylammonium ion $\left(\mathrm{CH}_{3} \mathrm{NH}_{3}{ }^{+}\right.$,
2-46 $\mathrm{p} K_{\mathrm{a}}=10.66$ ). Which is the stronger base, ammonia $\left(\mathrm{NH}_{3}\right)$ or methylamine $\left(\mathrm{CH}_{3} \mathrm{NH}_{2}\right)$ ? Explain.
PROBLEM Is tert-butoxide anion a strong enough base to react significantly with water? In other words,
2-47 can a solution of potassium tert-butoxide be prepared in water? The $\mathrm{p} K_{\mathrm{a}}$ of tert-butyl alcohol is approximately 18.
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Potassium tert-butoxide -

PROBLEM Predict the structure of the product formed in the reaction of the organic base pyridine with the
2-48 organic acid acetic acid, and use curved arrows to indicate the direction of electron flow.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0061.jpg?height=167&width=554&top_left_y=475&top_left_x=417)


Potassium tert-butoxide -

Pyridine Acetic acid
PROBLEM Calculate $K_{\mathrm{a}}$ values from the following $\mathrm{p} K_{\mathrm{a}}$ 's:
2-49 (a) Acetone, $\mathrm{p} K_{\mathrm{a}}=19.3$ (b) Formic acid, $\mathrm{p} K_{\mathrm{a}}=3.75$
PROBLEM Calculate $\mathrm{p} K_{\mathrm{a}}$ values from the following $K_{\mathrm{a}}$ 's:
2-50 (a) Nitromethane, $K_{\mathrm{a}}=5.0 \times 10^{-11}$
(b) Acrylic acid, $K_{\mathrm{a}}=5.6 \times 10^{-5}$


Potassium tert-butoxide -

PROBLEM What is the pH of a 0.050 M solution of formic acid, $\mathrm{p} K_{\mathrm{a}}=3.75$ ?
2-51
PROBLEM Sodium bicarbonate, $\mathrm{NaHCO}_{3}$, is the sodium salt of carbonic acid $\left(\mathrm{H}_{2} \mathrm{CO}_{3}\right), \mathrm{p} K_{\mathrm{a}}=6.37$. Which of the
2-52 substances shown in Problem 2-44 will react significantly with sodium bicarbonate?


General Problems -

PROBLEM Maleic acid has a dipole moment, but the closely related fumaric acid, a substance involved in the
2-53 citric acid cycle by which food molecules are metabolized, does not. Explain.
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Maleic acid
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General Problems -

Fumaric acid


General Problems -

PROBLEM Assume that you have two unlabeled bottles, one of which contains phenol ( $\mathrm{p} K_{\mathrm{a}}=9.9$ ) and one of
2-54 which contains acetic acid ( $\mathrm{p} K_{\mathrm{a}}=4.76$ ). In light of your answer to Problem 2-52, suggest a simple way to determine what is in each bottle.


General Problems -

PROBLEM Identify the acids and bases in the following reactions:
2-55 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0061.jpg?height=77&width=494&top_left_y=1864&top_left_x=477)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0061.jpg?height=185&width=762&top_left_y=1862&top_left_x=985)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0061.jpg?height=210&width=938&top_left_y=2050&top_left_x=477)
(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0061.jpg?height=223&width=546&top_left_y=2268&top_left_x=475)


General Problems -


General Problems -

PROBLEM Draw as many resonance structures as you can for the following species, adding appropriate formal
2-57 charges to each:
(a) Nitromethane,


General Problems -

PROBLEM Carbocations, which contain a trivalent, positively charged carbon atom, react with water to give
2-58 alcohols:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0062.jpg?height=196&width=673&top_left_y=1038&top_left_x=414)

How can you account for the fact that the following carbocation gives a mixture of two alcohols on reaction with water?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0062.jpg?height=180&width=1001&top_left_y=1341&top_left_x=413)


General Problems -

PROBLEM We'll see in the next chapter that organic molecules can be classified according to the functional
2-59 groups they contain, where a functional group is a collection of atoms with a characteristic chemical reactivity. Use the electronegativity values given in Figure 2.3 to predict the direction of polarization of the following functional groups.
<img class="imgSvg" id = "m6sn3m604brhfwgx4en" 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y1zZXJpZjsKICAgICAgICAgICAgIj48L3RleHQ+PC9nPjwvc3ZnPg=="/>
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Ketone
(b)
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src="data:image/svg+xml;base64,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Alcohol
(c)
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General Problems -

Amide
(d) $-\mathrm{C} \equiv \mathrm{N}$


General Problems -

Nitrile


General Problems -

PROBLEM The azide functional group, which occurs in azidobenzene, contains three adjacent nitrogen atoms.
2-60 One resonance structure for azidobenzene is shown. Draw three additional resonance structures, and assign appropriate formal charges to the atoms in all four.


General Problems -

Azidobenzene