Aspirin, NSAIDs, and COX-2 Inhibitors -

Medicinal chemists have therefore devised a number of drugs that act as selective inhibitors of only the COX-2 enzyme. Inflammation is thereby controlled without blocking protective functions. Originally heralded as a breakthrough in arthritis treatment, the first generation of COX-2 inhibitors, including rofecoxib, (marketed as Vioxx), celecoxib, (marketed as Celebrex), and Valdecoxib (marketed as Bextra), turned out to cause potentially serious heart problems, particularly in elderly or compromised patients. As a result, all three Cox-2 inhibitors were removed from the U.S. and other markets. Further studies, however, concluded that in proper doses the Cox-2 inhibitors were little different from other NSAIDs, and Vioxx returned to the market in 2017 for topical treatment of osteoarthritis.
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Aspirin, NSAIDs, and COX-2 Inhibitors -

Rofecoxib
(Vioxx)


Key Terms -

- antiaromatic
- Hückel $4 n+2$ rule
- arene
- meta (m)
- aromatic
- ortho (o)
- benzyl group
- para (p)
- degenerate orbitals
- phenyl group
- heterocycle
- ring-current


Key Terms -


Summary -

Aromatic rings are a common part of many biological structures and are particularly important in nucleic acid chemistry and in the chemistry of several amino acids. In this chapter, we've seen how and why aromatic compounds are different from such apparently related compounds as cycloalkenes.


Summary -

The word aromatic is used for historical reasons to refer to the class of compounds related structurally to benzene. Aromatic compounds are systematically named according to IUPAC rules, but many common names
are also used. Disubstituted benzenes are referred to as ortho ( 1,2 disubstituted), meta ( 1,3 disubstituted), or para (1,4 disubstituted) derivatives. The $\mathrm{C}_{6} \mathrm{H}_{5}$ - unit itself is referred to as a phenyl group, and the $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2}-$ unit is a benzyl group.


Summary -

Benzene is described by valence-bond theory as a resonance hybrid of two equivalent structures and is described by molecular orbital theory as a planar, cyclic, conjugated molecule with six $\pi$ electrons. According to the Hückel rule, a molecule must have $4 \boldsymbol{n}+2 \boldsymbol{\pi}$ electrons, where $n=0,1,2,3$, and so on, to be aromatic. Planar, cyclic, conjugated molecules with other numbers of $\pi$ electrons are antiaromatic.


Summary -

Other substances besides benzene-like compounds are also aromatic. The cyclopentadienyl anion and the cycloheptatrienyl cation, for instance, are aromatic ions. Pyridine and pyrimidine are six-membered, nitrogencontaining, aromatic heterocycles. Pyrrole and imidazole are five-membered, nitrogen-containing heterocycles. Naphthalene, quinoline, indole, and many others are polycyclic aromatic compounds.


Summary -

Aromatic compounds have the following characteristics:


Summary -

- Aromatic compounds are cyclic, planar, and conjugated.
- Aromatic compounds are unusually stable. Benzene, for instance, has a heat of hydrogenation $150 \mathrm{~kJ} / \mathrm{mol}$ less than we might expect for a cyclic triene.
- Aromatic compounds react with electrophiles to give substitution products, in which cyclic conjugation is retained, rather than addition products, in which conjugation is destroyed.
- Aromatic compounds have $4 n+2 \pi$ electrons, which are delocalized over the ring.


Summary -


Additional Problems -


Visualizing Chemistry -

PROBLEM Give IUPAC names for the following substances (red $=0$, blue $=\mathrm{N}$ ):


15-13 (a) -


15-13 (a) -

PROBLEM All-cis cyclodecapentaene is a stable molecule that shows a single absorption in its ${ }^{1} \mathrm{H}$ NMR 15-14 spectrum at $5.67 \delta$. Tell whether it is aromatic, and explain its NMR spectrum.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0500.jpg?height=391&width=421&top_left_y=1840&top_left_x=424)

PROBLEM 1,6-Methanonaphthalene has an interesting ${ }^{1} \mathrm{H}$ NMR spectrum in which the eight hydrogens
15-15 around the perimeter absorb at 6.9 to $7.3 \delta$, while the two $\mathrm{CH}_{2}$ protons absorb at $-0.5 \delta$. Tell whether it is aromatic, and explain its NMR spectrum.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0501.jpg?height=402&width=495&top_left_y=184&top_left_x=430)


1,6-Methanonaphthalene -

PROBLEM The following molecular model is that of a carbocation. Draw two resonance structures for the
15-16 carbocation, indicating the positions of the double bonds.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0501.jpg?height=394&width=484&top_left_y=730&top_left_x=425)


1,6-Methanonaphthalene -

PROBLEM Azulene, an isomer of naphthalene, has a remarkably large dipole moment for a hydrocarbon ( $\mu=$
15-17 1.0 D). Explain, using resonance structures.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0501.jpg?height=396&width=646&top_left_y=1252&top_left_x=428)


Naming Aromatic Compounds -

PROBLEM Give IUPAC names for the following compounds:


15-18 (a) -


15-18 (a) -

PROBLEM Draw structures corresponding to the following names:
15-19 (a) 3-Methyl-1,2-benzenediamine (b) 1,3,5-Benzenetriol (c) 3-Methyl-2-phenylhexane
(d) $o$-Aminobenzoic acid (e) $m$-Bromophenol (f) 2,4,6-Trinitrophenol (picric acid)

PROBLEM Draw and name all possible isomers of the following:
15-20 (a) Dinitrobenzene (b) Bromodimethylbenzene
(c) Trinitrophenol


15-18 (a) -

PROBLEM Draw and name all possible aromatic compounds with the formula $\mathrm{C}_{7} \mathrm{H}_{7} \mathrm{Cl}$.
15-21
PROBLEM Draw and name all possible aromatic compounds with the formula $\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{Br}$. (There are 14.) 15-22


Structure of Aromatic Compounds -

PROBLEM Propose structures for aromatic hydrocarbons that meet the following descriptions:
15-23 (a) $\mathrm{C}_{9} \mathrm{H}_{12}$; gives only one $\mathrm{C}_{9} \mathrm{H}_{11} \mathrm{Br}$ product on substitution of a hydrogen on the aromatic ring with bromine
(b) $\mathrm{C}_{10} \mathrm{H}_{14}$; gives only one $\mathrm{C}_{10} \mathrm{H}_{13} \mathrm{Cl}$ product on substitution of a hydrogen on the aromatic ring with chlorine
(c) $\mathrm{C}_{8} \mathrm{H}_{10}$; gives three $\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{Br}$ products on substitution of a hydrogen on the aromatic ring with bromine
(d) $\mathrm{C}_{10} \mathrm{H}_{14}$; gives two $\mathrm{C}_{10} \mathrm{H}_{13} \mathrm{Cl}$ products on substitution of a hydrogen on the aromatic ring with chlorine


Structure of Aromatic Compounds -

PROBLEM Look at the three resonance structures of naphthalene shown in Section 15.6, and account for the
15-24 fact that not all carbon-carbon bonds have the same length. The C1-C2 bond is 136 pm long, whereas the $\mathrm{C} 2-\mathrm{C} 3$ bond is 139 pm long.


Structure of Aromatic Compounds -


Structure of Aromatic Compounds -

Anthracene


Structure of Aromatic Compounds -

Phenanthrene


Structure of Aromatic Compounds -

PROBLEM Look at the five resonance structures for phenanthrene (Problem 26), and predict which of its
15-27 carbon-carbon bonds is shortest.
PROBLEM In 1932, A. A. Levine and A. G. Cole studied the ozonolysis of $o$-xylene and isolated three products:
15-28 glyoxal, 2,3-butanedione, and pyruvaldehyde:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0502.jpg?height=218&width=1174&top_left_y=1883&top_left_x=416)


Structure of Aromatic Compounds -

In what ratio would you expect the three products to be formed if $o$-xylene is a resonance hybrid of two structures? The actual ratio found was 3 parts glyoxal, 1 part 2,3-butanedione, and 2 parts pyruvaldehyde. What conclusions can you draw about the structure of $o$-xylene?


Aromaticity and Hückel's Rule -

PROBLEM 3-Chlorocyclopropene, on treatment with $\mathrm{AgBF}_{4}$, gives a precipitate of AgCl and a stable solution
15-29 of a product that shows a single ${ }^{1} \mathrm{H}$ NMR absorption at $11.04 \delta$. What is a likely structure for the product, and what is its relation to Hückel's rule?
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3-Chlorocyclopropene -

PROBLEM Draw an energy diagram for the three molecular orbitals of the cyclopropenyl system $\left(\mathrm{C}_{3} \mathrm{H}_{3}\right)$. How
15-30 are these three molecular orbitals occupied in the cyclopropenyl anion, cation, and radical? Which of the three substances is aromatic according to Hückel's rule?


3-Chlorocyclopropene -

PROBLEM Cyclopropanone is highly reactive because of its large amount of angle strain.
15-31 Methylcyclopropenone, although even more strained than cyclopropanone, is nevertheless quite stable and can even be distilled. Explain, taking the polarity of the carbonyl group into account.
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3-Chlorocyclopropene -

Cyclopropanone


Methylcyclopropenone -


Methylcyclopropenone -

Cyclopentadienone


Methylcyclopropenone -

PROBLEM Which would you expect to be most stable, cyclononatetraenyl radical, cation, or anion? 15-33 (Cyclononatetraene has a ring of nine carbons and four double bonds.)


Methylcyclopropenone -

PROBLEM How might you convert 1,3,5,7-cyclononatetraene to an aromatic substance?
15-34
PROBLEM Calicene, like azulene (Problem 17), has an unusually large dipole moment for a hydrocarbon.
15-35 Explain, using resonance structures.
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Calicene -


Calicene -

Pentalene dianion


Calicene -

PROBLEM Indole is an aromatic heterocycle that has a benzene ring fused to a pyrrole ring. Draw an orbital 15-37 picture of indole.
(a) How many $\pi$ electrons does indole have?
(b) What is the electronic relationship of indole to naphthalene?
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Calicene -

Indole


Ribavirin -


Spectroscopy -

PROBLEM Compound $\mathbf{A}, \mathrm{C}_{8} \mathrm{H}_{10}$, yields three substitution products, $\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{Br}$, on reaction with $\mathrm{Br}_{2}$. Propose two
15-39 possible structures for $\mathbf{A}$. The ${ }^{1} \mathrm{H}$ NMR spectrum of $\mathbf{A}$ shows a complex four-proton multiplet at 7.0 $\delta$ and a six-proton singlet at $2.30 \delta$. What is the structure of $\mathbf{A}$ ?


Spectroscopy -

PROBLEM What is the structure of a hydrocarbon that has $\mathrm{M}^{+}=120$ in its mass spectrum and has the following 15-40 ${ }^{1}$ H NMR spectrum?
$7.25 \delta(5 \mathrm{H}$, broad singlet); $2.90 \delta(1 \mathrm{H}$, septet, $J=7 \mathrm{~Hz}) ; 1.22 \delta(6 \mathrm{H}$, doublet, $J=7 \mathrm{~Hz})$


Spectroscopy -

PROBLEM Propose structures for compounds that fit the following descriptions:
15-41 (a) $\mathrm{C}_{10} \mathrm{H}_{14}$
${ }^{1} \mathrm{H}$ NMR: $7.18 \delta(4 \mathrm{H}$, broad singlet); $2.70 \delta(4 \mathrm{H}$, quartet, $J=7 \mathrm{~Hz}) ; 1.20 \delta(6 \mathrm{H}$, triplet, $J=7 \mathrm{~Hz})$ IR absorption at $745 \mathrm{~cm}^{-1}$
(b) $\mathrm{C}_{10} \mathrm{H}_{14}$
${ }^{1}$ H NMR: $7.0 \delta(4 \mathrm{H}$, broad singlet); $2.85 \delta(1 \mathrm{H}$, septet, $J=8 \mathrm{~Hz}) ; 2.28 \delta(3 \mathrm{H}$, singlet $) ; 1.20 \delta(6$ H , doublet, $J=8 \mathrm{~Hz}$ )


Spectroscopy -

IR absorption at $825 \mathrm{~cm}^{-1}$


General Problems -

PROBLEM On reaction with acid, 4-pyrone is protonated on the carbonyl-group oxygen to give a stable cationic 15-42 product. Using resonance structures and the Hückel $4 n+2$ rule, explain why the protonated product is so stable.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0504.jpg?height=242&width=381&top_left_y=1841&top_left_x=422)


General Problems -


Bextra -

PROBLEM $N$-Phenylsydnone, so-named because it was first studied at the University of Sydney, Australia, 15-44 behaves like a typical aromatic molecule. Explain, using the Hückel $4 n+2$ rule.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0505.jpg?height=196&width=800&top_left_y=672&top_left_x=413)
$N$-Phenylsydnone
PROBLEM Show the relative energy levels of the seven $\pi$ molecular orbitals of the cycloheptatrienyl system.
15-45 Tell which of the seven orbitals are filled in the cation, radical, and anion, and account for the aromaticity of the cycloheptatrienyl cation.


Bextra -

PROBLEM 1-Phenyl-2-butene has an ultraviolet absorption at $\lambda_{\max }=208 \mathrm{~nm}(\varepsilon=8000)$. On treatment with a
15-46 small amount of strong acid, isomerization occurs and a new substance with $\lambda_{\max }=250 \mathrm{~nm}(\varepsilon=$ 15,800 ) is formed. Propose a structure for this isomer, and suggest a mechanism for its formation.


Bextra -

PROBLEM Propose structures for aromatic compounds that have the following ${ }^{1} \mathrm{H}$ NMR spectra:
15-47 (a) $\mathrm{C}_{8} \mathrm{H}_{9} \mathrm{Br}$
IR absorption at $820 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0505.jpg?height=502&width=1402&top_left_y=1424&top_left_x=475)
(b) $\mathrm{C}_{9} \mathrm{H}_{12}$


Bextra -

IR absorption at $750 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0506.jpg?height=502&width=1397&top_left_y=321&top_left_x=478)
(c) $\mathrm{C}_{11} \mathrm{H}_{16}$

IR absorption at $820 \mathrm{~cm}^{-1}$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0506.jpg?height=518&width=1402&top_left_y=950&top_left_x=475)


Bextra -

PROBLEM Propose a structure for a molecule $\mathrm{C}_{14} \mathrm{H}_{12}$ that has the following ${ }^{1} \mathrm{H}$ NMR spectrum and has IR 15-48 absorptions at 700, 740 , and $890 \mathrm{~cm}^{-1}$ :
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0506.jpg?height=507&width=1400&top_left_y=1595&top_left_x=414)


Bextra -

PROBLEM The proton NMR spectrum for a compound with formula $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{O}_{2}$ is shown. The infrared spectrum
15-49 has a strong band at $1711 \mathrm{~cm}^{-1}$. The normal carbon-13 NMR spectral results are tabulated along with the DEPT-135 and DEPT-90 information. Draw the structure of this compound.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0507.jpg?height=1540&width=1489&top_left_y=192&top_left_x=410)


Bextra -

PROBLEM The proton NMR spectrum of a compound with formula $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NCl}_{2}$ is shown. The normal carbon-13 15-50 and DEPT experimental results are tabulated. The infrared spectrum shows peaks at 3432 and 3313 $\mathrm{cm}^{-1}$ and a series of medium-sized peaks between 1618 and $1466 \mathrm{~cm}^{-1}$. Draw the structure of this compound.


Bextra -

| Normal Carbon | DEPT-135 | DEPT-90 |
| :--- | :--- | :--- |
| 118.0 ppm | Positive | Positive |
| 119.5 | No peak | No peak |
| 128.0 | Positive | Positive |
| 140.0 | No peak | No peak |


Bextra -


Bextra -

PROBLEM Aromatic substitution reactions occur by addition of an electrophile such as $\mathrm{Br}^{+}$to an aromatic
15-51 ring to yield an allylic carbocation intermediate, followed by loss of $\mathrm{H}^{+}$. Show the structure of the intermediate formed by reaction of benzene with $\mathrm{Br}^{+}$.


Bextra -

PROBLEM The substitution reaction of toluene with $\mathrm{Br}_{2}$ can, in principle, lead to the formation of three
15-52 isomeric bromotoluene products. In practice, however, only $o$ - and $p$-bromotoluene are formed in substantial amounts. The meta isomer is not formed. Draw the structures of the three possible carbocation intermediates (Problem 51), and explain why ortho and para products predominate over meta products.


Bextra -

PROBLEM After the following reaction, the chemical shift of $\mathrm{H}_{\mathrm{a}}$ moves downfield from 6.98 ppm to 7.30 ppm .
15-54 Explain.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0508.jpg?height=421&width=1162&top_left_y=1822&top_left_x=411)


Bextra -

PROBLEM The following compound is the product initially formed in a Claisen rearrangement, which we'll see
15-55 in Section 18.4. This product is not isolated, but tautomerizes to its enol form. Give the structure of the enol and provide an explanation as to why the enol tautomer is favored.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0509.jpg?height=199&width=497&top_left_y=188&top_left_x=413)