PROBLEM Because of their conjugation, azo dyes are highly colored compounds and the major artificial color
16-45 source for textiles and food. Azo dyes are produced by the reaction of aryl diazonium salts with a second aromatic compound. In the product, the aromatic rings are linked by a diazo bridge ( $-\mathrm{N}=\mathrm{N}-$ ). From the reactants provided, propose a structure for each azo dye and draw the electron-pushing mechanism.
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0554.jpg?height=229&width=1034&top_left_y=208&top_left_x=475)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0554.jpg?height=267&width=1163&top_left_y=460&top_left_x=481)
(c)
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$+$
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0554.jpg?height=215&width=735&top_left_y=744&top_left_x=901)

Reactivity and Orientation of Electrophilic Substitutions
PROBLEM Identify each of the following groups as an activator or deactivator and as an o,p-director or 16-46 m -director:
(a) $\stackrel{\gtrless}{<}\left(\mathrm{CH}_{3}\right)_{2}$
(b)
<img class="imgSvg" id = "m6sn3o8pmqw1dmi1cu" src="data:image/svg+xml;base64,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"/>
(c)
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(d)
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Mechanisms of Electrophilic Substitutions -

PROBLEM Predict the major product(s) of nitration of the following substances. Which react faster than 16-47 benzene, and which slower?
(a) Bromobenzene
(b) Benzonitrile
(c) Benzoic acid
(d) Nitrobenzene
(e) Benzenesulfonic acid (f) ethoxybenzene

PROBLEM Rank the compounds in each group according to their reactivity toward electrophilic substitution.
16-48 (a) Chlorobenzene, o-dichlorobenzene, benzene
(b) $p$-Bromonitrobenzene, nitrobenzene, phenol (c) Fluorobenzene, benzaldehyde, $o$-xylene
(d) Benzonitrile, $p$-methylbenzonitrile, $p$-methoxybenzonitrile


PROBLEM Predict the major monoalkylation products you would expect to obtain from reaction of the
16-49 following substances with chloromethane and $\mathrm{AlCl}_{3}$ :
(a) Bromobenzene
(b) $m$-Bromophenol
(c) $p$-Chloroaniline
(d) 2,4-Dichloronitrobenzene
(e) 2,4-Dichlorophenol (f) Benzoic acid
(g) $p$-Methylbenzenesulfonic acid
(h) 2,5-Dibromotoluene


PROBLEM Name and draw the major product(s) of electrophilic chlorination of the following compounds:
16-50 (a) m-Nitrophenol
(b) o-Xylene
(c) p-Nitrobenzoic acid
(d) $p$-Bromobenzenesulfonic acid


PROBLEM Predict the major product(s) you would obtain from sulfonation of the following compounds:
16-51 (a) Fluorobenzene (b) $m$-Bromophenol (c) $m$-Dichlorobenzene (d) 2,4-Dibromophenol
PROBLEM Rank the following aromatic compounds in the expected order of their reactivity toward
16-52 Friedel-Crafts alkylation. Which compounds are unreactive?
(a) Bromobenzene
(b) Toluene
(c) Phenol
(d) Aniline (e) Nitrobenzene
(f) $p$-Bromotoluene


PROBLEM What product(s) would you expect to obtain from the following reactions:
16-53
(a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=212&width=423&top_left_y=211&top_left_x=477)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=158&width=497&top_left_y=208&top_left_x=993)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=131&width=426&top_left_y=436&top_left_x=481)
(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=153&width=574&top_left_y=433&top_left_x=976)

PROBLEM Predict the major product(s) of the following reactions:
16-54 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=150&width=423&top_left_y=673&top_left_x=477)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=139&width=430&top_left_y=836&top_left_x=479)


Organic Synthesis
PROBLEM How would you synthesize the following substances starting from benzene or phenol? Assume that
16-55 ortho- and para-substitution products can be separated.
(a) o-Bromobenzoic acid
(b) $p$-Methoxytoluene
(c) 2,4,6-Trinitrobenzoic acid
(d) $m$-Bromoaniline

PROBLEM Starting with benzene as your only source of aromatic compounds, how would you synthesize the
16-56 following substances? Assume that you can separate ortho and para isomers if necessary.
(a) p-Chloroacetophenone
(b) $m$-Bromonitrobenzene
(c) $o$-Bromobenzenesulfonic acid
(d) $m$-Chlorobenzenesulfonic acid

PROBLEM Starting with either benzene or toluene, how would you synthesize the following substances:
16-57 Assume that ortho and para isomers can be separated.
(a) 2-Bromo-4-nitrotoluene
(b) 1,3,5-Trinitrobenzene
(c) 2,4,6-Tribromoaniline
(d) m -Fluorobenzoic acid


PROBLEM As written, the following syntheses have flaws. What is wrong with each?
16-58 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=215&width=532&top_left_y=1714&top_left_x=477)
(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=270&width=611&top_left_y=1719&top_left_x=1071)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0555.jpg?height=273&width=613&top_left_y=2005&top_left_x=474)


General Problems -


4-Bromobiphenyl -

PROBLEM Electrophilic substitution on 3-phenylpropanenitrile occurs at the ortho and para positions, but
16-60 reaction with 3 -phenylpropenenitrile occurs at the meta position. Explain, using resonance structures of the intermediates.
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3-Phenylpropanenitrile
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4-Bromobiphenyl -


Benzanilide -

PROBLEM Would you expect the Friedel-Crafts reaction of benzene with ( $R$ )-2-chlorobutane to yield optically
16-63 active or racemic product? Explain.


Benzanilide -

PROBLEM How would you synthesize the following substances starting from benzene?


16-64 (a) -


16-64 (a) -

PROBLEM Phenylboronic acid, $\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{~B}(\mathrm{OH})_{2}$, is nitrated to give $15 \%$ ortho- substitution product and $85 \%$ meta.
16-66 Explain the meta-directing effect of the $-\mathrm{B}(\mathrm{OH})_{2}$ group.


16-64 (a) -

PROBLEM Draw resonance structures of the intermediate carbocations in the bromination of naphthalene,
16-67 and account for the fact that naphthalene undergoes electrophilic substitution at C1 rather than C2.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0557.jpg?height=196&width=584&top_left_y=303&top_left_x=413)


16-64 (a) -

PROBLEM Propose a mechanism for the reaction of 1-chloroanthraquinone with methoxide ion to give the
16-68 substitution product 1-methoxyanthraquinone. Use curved arrows to show the electron flow in each step.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0557.jpg?height=334&width=1037&top_left_y=657&top_left_x=411)


16-64 (a) -

PROBLEM $p$-Bromotoluene reacts with potassium amide to give a mixture of $m$ - and $p$-methylaniline. Explain. 16-69


16-64 (a) -

PROBLEM Propose a mechanism to account for the reaction of benzene with
16-70 2,2,5,5-tetramethyltetrahydrofuran.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0557.jpg?height=226&width=706&top_left_y=1226&top_left_x=411)


16-64 (a) -

PROBLEM Identify the reagents represented by the letters a-e in the following scheme:
16-74
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0558.jpg?height=212&width=1348&top_left_y=252&top_left_x=399)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0558.jpg?height=218&width=869&top_left_y=476&top_left_x=568)


16-64 (a) -

PROBLEM Phenols (ArOH) are relatively acidic, and the presence of a substituent group on the aromatic ring
16-75 has a large effect. The $p K_{\mathrm{a}}$ of unsubstituted phenol, for example, is 9.89 , while that of $p$-nitrophenol is 7.15. Draw resonance structures of the corresponding phenoxide anions and explain the data.


16-64 (a) -

PROBLEM Would you expect $p$-methylphenol to be more acidic or less acidic than unsubstituted phenol?
16-76 Explain. (See Problem 16-75.)
PROBLEM Predict the product(s) for each of the following reactions. In each case, draw the resonance forms of 16-77 the intermediate to explain the observed regiochemistry.
(a)
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(b)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0558.jpg?height=185&width=565&top_left_y=1081&top_left_x=1032)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0558.jpg?height=199&width=390&top_left_y=1291&top_left_x=480)
(d)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0558.jpg?height=139&width=481&top_left_y=1291&top_left_x=936)


CHAPTER 17 -


Alcohols and Phenols -


Alcohols and Phenols -

FIGURE 17.1 The phenol resveratrol, found in the skin of red grapes, continues to be studied for its potential anti-cancer, antiarthritic, and hypoglycemic properties. (credit: modification of work "Weinreben-Ötlingen" by Pierre Likissas/Wikimedia Commons, CC BY 3.0)


CHAPTER CONTENTS -


CHAPTER CONTENTS - 17.1 Naming Alcohols and Phenols

17.2 Properties of Alcohols and Phenols
17.3 Preparation of Alcohols: A Review
17.4 Alcohols from Carbonyl Compounds: Reduction
17.5 Alcohols from Carbonyl Compounds: Grignard Reaction
17.6 Reactions of Alcohols
17.7 Oxidation of Alcohols
17.8 Protection of Alcohols
17.9 Phenols and Their Uses
17.10 Reactions of Phenols
17.11 Spectroscopy of Alcohols and Phenols


WHY THIS CHAPTER? Up to this point, we've focused on developing some general ideas of organic reactivity, looking at the chemistry of hydrocarbons and alkyl halides, and examining some of the tools used in structural studies. With that background, it's now time to begin a study of the oxygen-containing functional groups that lie at the heart of organic and biological chemistry. We'll look at alcohols in this chapter and move on to carbonyl compounds in Chapters 19 through 23.


Alcohols and phenols can be thought of as organic derivatives of water in which one of water's hydrogens is replaced by an organic group: $\mathrm{H}-\mathrm{O}-\mathrm{H}$ versus $\mathrm{R}-\mathrm{O}-\mathrm{H}$ and $\mathrm{Ar}-\mathrm{O}-\mathrm{H}$. In practice, the name alcohol is restricted to
compounds that have their - OH group bonded to a saturated, $s p^{3}$-hybridized carbon atom, while compounds with their -OH group bonded to a vinylic, $s p^{2}$-hybridized carbon are called enols. We'll look at enols in Chapter 22.
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Alcohols occur widely in nature and have many industrial and pharmaceutical applications. Methanol, for instance, is one of the most important of all industrial chemicals. Historically, methanol was prepared by heating wood in the absence of air and thus came to be called wood alcohol. Today, approximately 173 million tons ( 50 billion gallons) of methanol is manufactured worldwide each year, most of it by catalytic reduction of carbon monoxide with hydrogen gas. Methanol is toxic to humans, causing blindness in small doses ( 15 mL ) and death in larger amounts ( $100-250 \mathrm{~mL}$ ). Industrially, it is used both as a solvent and as a starting material for production of formaldehyde $\left(\mathrm{CH}_{2} \mathrm{O}\right)$ and acetic acid $\left(\mathrm{CH}_{3} \mathrm{CO}_{2} \mathrm{H}\right)$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0560.jpg?height=199&width=1036&top_left_y=884&top_left_x=531)


Ethanol was one of the first organic chemicals to be prepared and purified. Its production by fermentation of grains and sugars has been carried out for perhaps 9000 years, and its purification by distillation goes back at least as far as the 12 th century. Today, approximately 88 million tons ( 26 billion gallons) of ethanol are produced worldwide each year, most of it by fermentation of corn, barley, sorghum, and other plant sources. Almost all of this ethanol is used for bus and automobile fuel.


Ethanol for industrial use as a solvent or chemical intermediate is largely obtained by acid-catalyzed hydration of ethylene at high temperature.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0560.jpg?height=207&width=890&top_left_y=1450&top_left_x=607)