Bextra -

PROBLEM Compounds called azo dyes are the major source of artificial color in textiles and food. Part of the
15-56 reason for their intense coloring is the conjugation from an electron-donating group through the diazo bridge ( $-\mathrm{N}=\mathrm{N}-$ ) to an electron-withdrawing group on the other side. For the following azo dyes, draw a resonance form that shows how the electron-donating group is related to the electronwithdrawing group on the other side of the diazo bridge. Used curved arrows to show how the electrons are reorganized.
(a)
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Methyl Orange
(b)
C.I. Acid Red 74


CHAPTER 16 -

Chemistry of Benzene: Electrophilic Aromatic Substitution
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0510.jpg?height=779&width=1890&top_left_y=451&top_left_x=231)


CHAPTER 16 -

FIGURE 16.1 In the 19th and early-20th centuries, benzene was used as an aftershave lotion because of its pleasant smell and as a solvent to decaffeinate coffee beans. Neither is a good idea. (credit: modification of work "Ye Old Way (https://loc.getarchive.net/media/ ye-old-way-geo-h-walker-and-co-lith-boston-mass-1)" by Geo. H. Walker \& Co./Library of Congress)


CHAPTER CONTENTS -


CHAPTER CONTENTS - 16.1 Electrophilic Aromatic Substitution Reactions: Bromination

16.2 Other Aromatic Substitutions
16.3 Alkylation and Acylation of Aromatic Rings: The Friedel-Crafts Reaction
16.4 Substituent Effects in Electrophilic Substitutions
16.5 Trisubstituted Benzenes: Additivity of Effects
16.6 Nucleophilic Aromatic Substitution
16.7 Benzyne
16.8 Oxidation of Aromatic Compounds
16.9 Reduction of Aromatic Compounds
16.10 Synthesis of Polysubstituted Benzenes


WHY THIS CHAPTER? This chapter continues the coverage of aromatic molecules begun in the preceding chapter, but we'll shift focus to concentrate on reactions, looking at the relationship between aromatic structure and reactivity. This relationship is critical in understanding how many biological molecules and pharmaceutical agents are synthesized and why they behave as they do.

In the preceding chapter, we looked at aromaticity-the stability associated with benzene and related compounds that contain a cyclic conjugated system of $4 n+2 \pi$ electrons. In this chapter, we'll look at some of the unique reactions that aromatic molecules undergo.


The most common reaction of aromatic compounds is electrophilic aromatic substitution, in which an electrophile ( $E^{+}$) reacts with an aromatic ring and substitutes for one of the hydrogens. The reaction is characteristic of all aromatic rings, not just benzene and substituted benzenes. In fact, the ability of a compound to undergo electrophilic substitution is a good test of aromaticity.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0511.jpg?height=275&width=858&top_left_y=180&top_left_x=628)


Many different substituents can be introduced onto an aromatic ring through electrophilic substitution. To list some possibilities, an aromatic ring can be substituted by a halogen $(-\mathrm{Cl},-\mathrm{Br},-\mathrm{I})$, a nitro group $\left(-\mathrm{NO}_{2}\right)$, a sulfonic acid group $\left(-\mathrm{SO}_{3} \mathrm{H}\right)$, a hydroxyl group $(-\mathrm{OH})$, an alkyl group ( -R ), or an acyl group ( -COR ). Starting from only a few simple materials, it's possible to prepare many thousands of substituted aromatic compounds.
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Halogenation
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0511.jpg?height=205&width=312&top_left_y=926&top_left_x=626)


Before seeing how electrophilic aromatic substitutions occur, let's briefly recall what we said in the chapter on Alkenes: Structure and Reactivity about electrophilic alkene additions. When a reagent such as HCl adds to an alkene, the electrophilic hydrogen ion approaches the $\pi$ electrons of the double bond and forms a bond to one carbon, leaving a positive charge at the other carbon. This carbocation intermediate then reacts with the nucleophilic $\mathrm{Cl}^{-}$ion to yield the addition product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0511.jpg?height=331&width=896&top_left_y=1748&top_left_x=612)

An electrophilic aromatic substitution reaction begins in a similar way, but there are a number of differences. One difference is that aromatic rings are less reactive toward electrophiles than alkenes. For example, $\mathrm{Br}_{2}$ in $\mathrm{CH}_{2} \mathrm{Cl}_{2}$ solution reacts instantly with most alkenes but does not react with benzene at room temperature. For bromination of benzene to take place, a catalyst such as $\mathrm{FeBr}_{3}$ is needed. The catalyst makes the $\mathrm{Br}_{2}$ molecule more electrophilic by polarizing it to give a $\mathrm{FeBr}_{4}{ }^{-} \mathrm{Br}^{+}$species that reacts as if it were $\mathrm{Br}^{+}$. The polarized $\mathrm{Br}_{2}$ molecule then reacts with the nucleophilic benzene ring to yield a nonaromatic carbocation intermediate that is doubly allylic (Section 11.5) and has three resonance forms.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0512.jpg?height=264&width=1183&top_left_y=193&top_left_x=468)

Although more stable than a typical alkyl carbocation because of resonance, the intermediate in electrophilic aromatic substitution is nevertheless much less stable than the starting benzene ring itself, with its $150 \mathrm{~kJ} / \mathrm{mol}$ ( $36 \mathrm{kcal} / \mathrm{mol}$ ) of aromatic stability. Thus, the reaction of an electrophile with a benzene ring is endergonic, has a substantial activation energy, and is rather slow. FIGURE 16.2 shows an energy diagram comparing the reaction of an electrophile with an alkene and with benzene. The benzene reaction is slower (higher $\Delta G^{+}$) because the starting material is more stable.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0512.jpg?height=616&width=807&top_left_y=738&top_left_x=659)

Reaction progress
FIGURE 16.2 A comparison of the reactions of an electrophile ( $E^{+}$) with an alkene and with benzene: $\Delta G^{\ddagger}$ alkene $<\Delta G^{\ddagger}$ benzene. The benzene reaction is slower than the alkene reaction because of the stability of the aromatic ring.
Another difference between alkene addition and aromatic substitution occurs after the carbocation intermediate has formed. Instead of adding $\mathrm{Br}^{-}$to give an addition product, the carbocation intermediate loses $\mathrm{H}^{+}$from the bromine-bearing carbon to give a substitution product. Note that this loss of $\mathrm{H}^{+}$is similar to what occurs in the second step of an E1 reaction (Section 11.10). The net effect of reaction of $\mathrm{Br}_{2}$ with benzene is the substitution of $\mathrm{H}^{+}$by $\mathrm{Br}^{+}$by the overall mechanism shown in FIGURE 16.3.


FIGURE 16.3 MECHANISM -

The mechanism for the electrophilic bromination of benzene. The reaction occurs in two steps and involves a resonance-stabilized carbocation intermediate.


FIGURE 16.3 MECHANISM -

1) An electron pair from the benzene ring attacks the positively polarized bromine, forming a new $\mathrm{C}-\mathrm{Br}$ bond and leaving a nonaromatic carbocation intermediate.
(2) A base removes $\mathrm{H}^{+}$from the carbocation intermediate, and the neutral substitution product forms as two electrons from the $\mathrm{C}-\mathrm{H}$ bond move to re-form the aromatic ring.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0513.jpg?height=142&width=283&top_left_y=425&top_left_x=1187)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0513.jpg?height=132&width=287&top_left_y=598&top_left_x=1125)
(1) Slow
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0513.jpg?height=178&width=318&top_left_y=865&top_left_x=1104)
(2) Fast
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0513.jpg?height=145&width=499&top_left_y=1169&top_left_x=1122)


FIGURE 16.3 MECHANISM -

Why does the reaction of $\mathrm{Br}_{2}$ with benzene take a different course than its reaction with an alkene? The answer is straightforward. If addition occurred, the $150 \mathrm{~kJ} / \mathrm{mol}$ stabilization energy of the aromatic ring would be lost and the overall reaction would be endergonic. When substitution occurs, though, the stability of the aromatic ring is retained and the reaction is exergonic. An energy diagram for the overall process is shown in FIGURE 16.4 .
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0513.jpg?height=714&width=1083&top_left_y=1627&top_left_x=521)

FIGURE 16.4 An energy diagram for the electrophilic bromination of benzene. Because the stability of the aromatic ring is retained, the overall process is exergonic.


FIGURE 16.3 MECHANISM -

PROBLEM Monobromination of toluene gives a mixture of three bromotoluene products. Draw and name 16-1 them.


FIGURE 16.3 MECHANISM - 16.2 Other Aromatic Substitutions

There are many other kinds of electrophilic aromatic substitutions besides bromination, and all occur by the same general mechanism. Let's look at some of these other reactions briefly.


Aromatic Halogenation -

Chlorine and iodine can be introduced into aromatic rings by electrophilic substitution reactions just as bromine can, but fluorine is too reactive and only poor yields of monofluoroaromatic products are obtained by direct fluorination. Instead, other sources of " $\mathrm{F}^{+}$" are used, in which a fluorine atom is bonded to a positively charged nitrogen. One of the most common such reagents goes by the acronym F-TEDA-BF 4 in the presence of trifluoromethanesulfonic acid (TfOH). (You don't need to know the full name of F-TEDA, which is sold under the name Selectfluor.)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0514.jpg?height=392&width=1139&top_left_y=731&top_left_x=493)