Thiols -

Thiols, also called mercaptans, are sulfur analogs of alcohols. They are named by the same system used for alcohols, with the suffix -thiol used in place of -ol. The -SH group itself is referred to as a mercapto group. Like alcohols, thiols are weakly acidic; the $\mathrm{p}_{\mathrm{a}}$ of $\mathrm{CH}_{3} \mathrm{SH}$, for instance, is 10.3 . Unlike alcohols, however, thiols don't typically form hydrogen bonds because the sulfur atom is not sufficiently electronegative.
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Ethanethiol
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$m$-Mercaptobenzoic acid


Thiols -

The most striking characteristic of thiols is their appalling odor. Skunk scent, for instance, is caused primarily by the simple thiols 3-methyl-1-butanethiol and 2-butene-1-thiol. Volatile thiols such as ethanethiol are also added to natural gas and liquefied propane to serve as an easily detectable warning in case of leaks.


Thiols -

Thiols are usually prepared from alkyl halides by $\mathrm{S}_{\mathrm{N}} 2$ displacement with a sulfur nucleophile such as hydrosulfide anion, ${ }^{-}$SH.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0618.jpg?height=158&width=1432&top_left_y=1943&top_left_x=344)

The reaction often works poorly unless an excess of the nucleophile is used because the product thiol can undergo a second $S_{N} 2$ reaction with alkyl halide to give a sulfide ( $\mathbf{R}-\mathbf{S}-\mathbf{R}$ ') as by-product. To circumvent this problem, thiourea, $\left(\mathrm{NH}_{2}\right)_{2} \mathrm{C}=\mathrm{S}$, is often used as the nucleophile in the preparation of a thiol from an alkyl halide. The reaction occurs by displacement of the halide ion to yield an intermediate alkyl isothiourea salt, which is hydrolyzed by subsequent reaction with aqueous base.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0619.jpg?height=489&width=1605&top_left_y=189&top_left_x=260)


Thiols -

Thiols can be oxidized by $\mathrm{Br}_{2}$ or $\mathrm{I}_{2}$ to yield disulfides ( $\mathbf{R}-\mathbf{S}-\mathbf{S}-\mathbf{R}^{\prime}$ ). The reaction is easily reversed, and a disulfide can be reduced back to a thiol by treatment with zinc and acid.


Thiols -

$$
2 \mathrm{R}-\mathrm{SH} \underset{\mathrm{Zn}, \mathrm{H}^{+}}{\stackrel{\mathrm{I}_{2}}{\rightleftarrows}} \mathrm{R}-\mathrm{S}-\mathrm{S}-\mathrm{R}+2 \mathrm{HI}
$$


Thiols -

A thiol
A disulfide
This thiol-disulfide interconversion is a key part of numerous biological processes. We'll see in Chapter 26, for instance, that disulfide formation is involved in defining the structure and three-dimensional conformations of proteins, where disulfide "bridges" often form cross-links between cysteine amino-acid units in the protein chains. Disulfide formation is also involved in the process by which cells protect themselves from oxidative degradation. A cellular component called glutathione removes potentially harmful oxidants and is itself oxidized to glutathione disulfide in the process. Reduction back to the thiol requires the coenzyme reduced flavin adenine dinucleotide, abbreviated $\mathrm{FADH}_{2}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0619.jpg?height=538&width=1429&top_left_y=1249&top_left_x=348)


Sulfides -

Sulfides are the sulfur analogs of ethers just as thiols are the sulfur analogs of alcohols. Sulfides are named by following the same rules used for ethers, with sulfide used in place of ether for simple compounds and alkylthio used in place of alkoxy for more complex substances.
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Dimethyl sulfide -


Dimethyl sulfide -

Treatment of a thiol with a base, such as NaH , gives the corresponding thiolate ion ( $\mathrm{RS}^{-}$), which undergoes reaction with a primary or secondary alkyl halide to give a sulfide. The reaction occurs by an $S_{N} 2$ mechanism, analogous to the Williamson synthesis of ethers (Section 18.2).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0620.jpg?height=294&width=1031&top_left_y=184&top_left_x=547)


Dimethyl sulfide -

Despite their close structural similarity, sulfides and ethers differ substantially in their chemistry. Because the valence electrons on sulfur are farther from the nucleus and are less tightly held than those on oxygen ( $3 p$ electrons versus $2 p$ electrons), sulfur compounds are more nucleophilic than their oxygen analogs. Unlike dialkyl ethers, dialkyl sulfides react rapidly with primary alkyl halides by an $\mathrm{S}_{\mathrm{N}} 2$ mechanism to give sulfonium ions $\left(\mathrm{R}_{3} \mathrm{~S}^{+}\right)$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0620.jpg?height=107&width=779&top_left_y=716&top_left_x=646)


Dimethyl sulfide -

Dimethyl sulfide Iodomethane Trimethylsulfonium iodide
The most common example of this process in living organisms is the reaction of the amino acid methionine with adenosine triphosphate (ATP; Section 6.8) to give $S$-adenosylmethionine. The reaction is somewhat unusual in that the biological leaving group in this $\mathrm{S}_{\mathrm{N}} 2$ process is the triphosphate ion rather than the more frequently seen diphosphate ion (Section 11.6).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0620.jpg?height=589&width=1397&top_left_y=1077&top_left_x=359)

Adenosine triphosphate (ATP)
$S$-Adenosylmethionine
Sulfonium ions are themselves useful alkylating agents because a nucleophile can attack one of the groups bonded to the positively charged sulfur, displacing a neutral sulfide as leaving group. We saw an example of this in Section 11.6 (FIGURE 11.17), in which $S$-adenosylmethionine transferred a methyl group to norepinephrine to give adrenaline.


Dimethyl sulfide -

Another difference between sulfides and ethers is that sulfides are easily oxidized. Treatment of a sulfide with hydrogen peroxide, $\mathrm{H}_{2} \mathrm{O}_{2}$, at room temperature yields the corresponding sulfoxide ( $\mathbf{R}_{\mathbf{2}} \mathbf{S O}$ ), and further oxidation of the sulfoxide with a peroxyacid yields a sulfone ( $\mathbf{R}_{\mathbf{2}} \mathbf{S O}_{\mathbf{2}} \mathbf{)}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0620.jpg?height=264&width=1223&top_left_y=2053&top_left_x=451)


Dimethyl sulfide -

Dimethyl sulfoxide (DMSO) is a particularly well-known sulfoxide that is often used as a polar aprotic solvent. It must be handled with care, however, because it has a remarkable ability to penetrate the skin, carrying along whatever is dissolved in it.
<img class="imgSvg" id = "m6sn3oj4zfb32g3vj9" src="data:image/svg+xml;base64,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"/>


Dimethyl sulfide -

Dimethyl sulfoxide (a polar aprotic solvent)


Dimethyl sulfide -

PROBLEM 2-Butene-1-thiol is one component of skunk spray. How would you synthesize this substance 18-17 (either cis or trans) from methyl 2-butenoate? From 1,3-butadiene?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0621.jpg?height=98&width=397&top_left_y=935&top_left_x=425)
$\mathrm{CH}_{3} \mathrm{CH}=\mathrm{CHCH}_{2} \mathrm{SH}$
Methyl 2-butenoate
2-Butene-1-thiol


Dimethyl sulfide - 18.8 Spectroscopy of Ethers


Infrared Spectroscopy -

Ethers are difficult to identify by IR spectroscopy. Although they show an absorption due to C-O single-bond stretching in the range 1050 to $1150 \mathrm{~cm}^{-1}$, many other kinds of absorptions occur in the same range. FIGURE 18.3 shows the IR spectrum of diethyl ether and identifies the $\mathrm{C}-\mathrm{O}$ stretch. Phenyl alkyl ethers show two strong absorbances for $\mathrm{C}-\mathrm{O}$ stretching at 1050 and $1250 \mathrm{~cm}^{-1}$. FIGURE 18.4 shows the IR spectrum of anisole.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0621.jpg?height=457&width=1389&top_left_y=1452&top_left_x=365)

FIGURE 18.3 The infrared spectrum of diethyl ether, $\mathrm{CH}_{3} \mathbf{C H}_{2} \mathbf{O C H}_{2} \mathbf{C H}_{3}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0621.jpg?height=505&width=1429&top_left_y=1967&top_left_x=348)


Infrared Spectroscopy -

FIGURE 18.4 The infrared spectrum of anisole.


Nuclear Magnetic Resonance Spectroscopy -

Hydrogens on carbon next to an ether oxygen are shifted downfield from the normal alkane resonance and show ${ }^{1}$ H NMR absorptions in the region 3.4 to $4.5 \delta$. This downfield shift is clearly seen in the spectrum of dipropyl ether shown in FIGURE 18.5.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0622.jpg?height=508&width=1392&top_left_y=407&top_left_x=361)

FIGURE 18.5 The ${ }^{\mathbf{1}} \mathbf{H}$ NMR spectrum of dipropyl ether. Protons on carbon next to oxygen are shifted downfield to $3.4 \delta$.
Epoxides absorb at a slightly higher field than other ethers and show characteristic resonances at 2.5 to 3.5 $\delta$ in their ${ }^{1}$ H NMR spectra, as indicated for 1,2-epoxypropane in FIGURE 18.6. The methylene protons of this epoxide are diastereotopic, and display complex splitting (see Section 13.7 and Section 13.8).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0622.jpg?height=545&width=1392&top_left_y=1126&top_left_x=364)


Ether carbon atoms also exhibit a downfield shift in the ${ }^{13}$ C NMR spectrum, where they usually absorb in the 50 to $80 \delta$ range. For example, the carbon atoms next to oxygen in methyl propyl ether absorb at 58.5 and $74.8 \delta$. Similarly, the methyl carbon in anisole absorbs at $54.8 \delta$.


PROBLEM The ${ }^{1} \mathrm{H}$ NMR spectrum shown is that of a cyclic ether with the formula $\mathrm{C}_{4} \mathrm{H}_{8} \mathrm{O}$. Propose a structure. 18-18
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0623.jpg?height=503&width=1397&top_left_y=193&top_left_x=418)


(30) CHEMISTRY MATTERS -

Epoxy Resins and Adhesives
Few nonchemists know exactly what an epoxide is, but practically everyone has used an "epoxy glue" for household repairs or an epoxy resin for a protective coating. Worldwide, approximately 14 billion dollars' worth of epoxy resins and adhesives are used annually for a vast number of applications, including many in the aerospace industry. Much of the Boeing 787 Dreamliner, for instance, is held together with epoxy-based adhesives.


(30) CHEMISTRY MATTERS -

Epoxy resins and adhesives generally consist of two components that are mixed just prior to use. One component is a liquid "prepolymer," and the second is a "curing agent" that reacts with the prepolymer and causes it to solidify.


(30) CHEMISTRY MATTERS -

The most widely used epoxy resins and adhesives are based on a prepolymer made from bisphenol A and epichlorohydrin. On treatment with base, bisphenol A is converted into its anion, which acts as a nucleophile in an $\mathrm{S}_{\mathrm{N}} 2$ reaction with epichlorohydrin. Each epichlorohydrin molecule can react with two molecules of bisphenol $A$, once by $S_{N} 2$ displacement of chloride ion and once by nucleophilic opening of the epoxide ring. At the same time, each bisphenol A molecule can react with two epichlorohydrins, leading to a long polymer chain. Each end of a prepolymer chain has an unreacted epoxy group, and each chain has numerous secondary alcohol groups spaced regularly along its midsection.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0624.jpg?height=526&width=890&top_left_y=1160&top_left_x=615)


(30) CHEMISTRY MATTERS -

FIGURE 18.7 Kayaks are often made of a high-strength polymer coated with epoxy resin. (credit: "Potomac River Festival Virginia 2017 Great Falls Kayak Race" by Watts/Flickr, CC BY 2.0)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0624.jpg?height=194&width=727&top_left_y=1768&top_left_x=691)


(30) CHEMISTRY MATTERS -

Bisphenol A
Epichlorohydrin
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0624.jpg?height=440&width=1291&top_left_y=2051&top_left_x=414)


(30) CHEMISTRY MATTERS -

When an epoxide is to be used, a basic curing agent such as a tertiary amine, $\mathrm{R}_{3} \mathrm{~N}$, is added to cause the individual prepolymer chains to link together. This cross-linking of chains is simply a base-catalyzed, $\mathrm{S}_{\mathrm{N}} 2$ epoxide ring-opening of an -OH group in the middle of one chain with an epoxide group on the end of another chain. The result of such cross-linking is formation of a vast, three-dimensional tangle that has enormous strength and chemical resistance.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0625.jpg?height=416&width=901&top_left_y=426&top_left_x=612)


Key Terms -

```
• alkoxymercuration • sulfone
- crown ether
- sulfonium ion
• disulfide (R-S-S-R') . sulfoxide
- ether (R-0-R')
- thiol
- mercapto group
- thiolate ion (RS`)
- sulfide (R-S-R')
- Williamson ether synthesis
```


Key Terms -


Summary -

This chapter has finished the coverage of functional groups with $\mathrm{C}-\mathrm{O}$ and $\mathrm{C}-\mathrm{S}$ single bonds, focusing primarily on ethers, epoxides, thiols, and sulfides. Ethers are compounds that have two organic groups bonded to the same oxygen atom, ROR'. The organic groups can be alkyl, vinylic, or aryl, and the oxygen atom can be in a ring or in an open chain. Ethers are prepared by either Williamson ether synthesis, which involves $\mathrm{S}_{\mathrm{N}} 2$ reaction of an alkoxide ion with a primary alkyl halide, or the alkoxymercuration reaction, which involves Markovnikov addition of an alcohol to an alkene.


Summary -

Ethers are inert to most reagents but react with strong acids to give cleavage products. Both HI and HBr are often used. The cleavage reaction takes place by an $\mathrm{S}_{\mathrm{N}} 2$ mechanism at the less highly substituted site if only primary and secondary alkyl groups are bonded to the ether oxygen, but by an $\mathrm{S}_{\mathrm{N}} 1$ or E1 mechanism if one of the alkyl groups bonded to oxygen is tertiary.


Summary -

Epoxides are cyclic ethers with a three-membered, oxygen-containing ring. Because of the strain in the ring, epoxides undergo a cleavage reaction with both acids and bases. Acid-catalyzed ring-opening occurs with a regiochemistry that depends on the structure of the epoxide. Cleavage of the $\mathrm{C}-\mathrm{O}$ bond at the less highly substituted site occurs if both epoxide carbons are primary or secondary, but cleavage of the $\mathrm{C}-\mathrm{O}$ bond to the more highly substituted site occurs if one of the epoxide carbons is tertiary. Base-catalyzed epoxide ringopening occurs by $\mathrm{S}_{\mathrm{N}} 2$ reaction of a nucleophile at the less hindered epoxide carbon.


Summary -

Thiols, the sulfur analogs of alcohols, are usually prepared by $S_{N} 2$ reaction of an alkyl halide with thiourea. Mild oxidation of a thiol yields a disulfide, and mild reduction of a disulfide returns the thiol. Sulfides, the sulfur analogs of ethers, are prepared by an $\mathrm{S}_{\mathrm{N}} 2$ reaction between a thiolate anion and a primary or secondary alkyl halide. Sulfides are more nucleophilic than ethers and can be alkylated by reaction with a primary alkyl halide to yield a sulfonium ion. Sulfides can also be oxidized to sulfoxides and to sulfones.


Summary of Reactions -

1. Synthesis of ethers (Section 18.2)
a. Williamson ether synthesis


Summary of Reactions -

$$
\mathrm{RO}^{-}+\mathrm{R}^{\prime} \mathrm{CH}_{2} \mathrm{X} \longrightarrow \mathrm{ROCH}_{2} \mathrm{R}^{\prime}+\mathrm{X}^{-}
$$


Summary of Reactions -

b. Alkoxymercuration/demercuration
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0626.jpg?height=132&width=626&top_left_y=235&top_left_x=801)
2. Reactions of ethers
a. Cleavage by HBr or HI (Section 18.3)


Summary of Reactions -

$$
\mathrm{R}-\mathrm{O}-\mathrm{R}^{\prime} \xrightarrow[\mathrm{H}_{2} \mathrm{O}]{\mathrm{HX}} \mathrm{RX}+\mathrm{R}^{\prime} \mathrm{OH}
$$


Summary of Reactions -

b. Acid-catalyzed epoxide opening (Section 18.5)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0626.jpg?height=280&width=519&top_left_y=586&top_left_x=857)
c. Base-catalyzed epoxide opening (Section 18.5)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0626.jpg?height=139&width=556&top_left_y=906&top_left_x=836)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0626.jpg?height=107&width=760&top_left_y=1047&top_left_x=731)
3. Synthesis of thiols (Section 18.7)


Summary of Reactions -

$$
\mathrm{RCH}_{2} \mathrm{Br} \xrightarrow[\text { 2. } \mathrm{H}_{2} \mathrm{O}, \mathrm{NaOH}]{\text { 1. } \left.\mathrm{H}_{2} \mathrm{~N}\right)_{2} \mathrm{C}=\mathrm{S}} \quad \mathrm{RCH}_{2} \mathrm{SH}
$$


Summary of Reactions -

4. Oxidation of thiols to disulfides (Section 18.7)


Summary of Reactions -

$$
2 \mathrm{RSH} \xrightarrow{\mathrm{I}_{2}, \mathrm{H}_{2} \mathrm{O}} \quad \mathrm{RS}-\mathrm{SR}
$$


Summary of Reactions -

5. Synthesis of sulfides (Section 18.7)


Summary of Reactions -

$$
\mathrm{RS}^{-}+\mathrm{R}^{\prime} \mathrm{CH}_{2} \mathrm{Br} \longrightarrow \mathrm{RSCH}_{2} \mathrm{R}^{\prime}+\mathrm{Br}^{-}
$$


Summary of Reactions -

6. Oxidation of sulfides to sulfoxides and sulfones (Section 18.7)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0626.jpg?height=123&width=424&top_left_y=1570&top_left_x=875)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0626.jpg?height=118&width=445&top_left_y=1703&top_left_x=870)


Additional Problems -


Visualizing Chemistry -

PROBLEM Give IUPAC names for the following compounds (red = O; reddish brown = Br; yellow $=\mathrm{S}$ ):


Visualizing Chemistry -


Visualizing Chemistry -

PROBLEM Show the product, including stereochemistry, that would result from reaction of the following
18-20 epoxide with HBr :
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0627.jpg?height=367&width=553&top_left_y=627&top_left_x=423)

PROBLEM Show the product, including stereochemistry, of the following reaction:
18-21
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0627.jpg?height=364&width=804&top_left_y=1076&top_left_x=422)


Visualizing Chemistry -

PROBLEM Treatment of the following alkene with a peroxyacid yields an epoxide different from that obtained
18-22 by reaction with aqueous $\mathrm{Br}_{2}$ followed by base treatment. Propose structures for the two epoxides, and explain the result.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0627.jpg?height=430&width=418&top_left_y=1628&top_left_x=428)


Mechanism Problems -

PROBLEM Predict the product(s) and provide the mechanism for each of the following reactions.


Mechanism Problems -


Mechanism Problems -

PROBLEM Predict the product(s) and provide the mechanism for each of the following two-step processes.


Mechanism Problems -

PROBLEM The alkoxymercuration of alkenes involves the formation of an organomercury intermediate (I),
18-26 which is reduced with $\mathrm{NaBH}_{4}$ to give an ether product. Predict the ether product and provide the mechanism for the following reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0628.jpg?height=112&width=741&top_left_y=725&top_left_x=421)


Mechanism Problems -

PROBLEM Predict the product(s) and provide the mechanism for the following reactions:


Mechanism Problems -

PROBLEM In the formation of the prepolymer used to make epoxy resins, a bisphenol reacts with
18-29 epichlorohydrin in the presence of a base. Show the product and mechanism when two moles of phenol react with epichlorohydrin.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0628.jpg?height=193&width=657&top_left_y=1516&top_left_x=414)


Epichlorohydrin -

PROBLEM Ethers undergo an acid-catalyzed cleavage reaction when treated with the Lewis acid $\mathrm{BBr}_{3}$ at room 18-30 temperature. Propose a mechanism for the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0628.jpg?height=147&width=804&top_left_y=1905&top_left_x=411)


Epichlorohydrin -

PROBLEM Treatment of 1,1-diphenyl-1,2-epoxyethane with aqueous acid yields diphenyl acetaldehyde as the
18-31 major product. Propose a mechanism for the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0628.jpg?height=155&width=432&top_left_y=2172&top_left_x=413)


Epichlorohydrin -

PROBLEM Fluoxetine, a heavily prescribed antidepressant marketed under the name Prozac, can be prepared
18-32 by a route that begins with reaction between a phenol and an alkyl chloride.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0629.jpg?height=527&width=1489&top_left_y=181&top_left_x=416)
(a) The rate of the reaction depends on both phenol and alkyl halide. Is this an $\mathrm{S}_{\mathrm{N}} 1$ or an $\mathrm{S}_{\mathrm{N}} 2$ reaction? Show the mechanism.
(b) The physiologically active enantiomer of fluoxetine has $(S)$ stereochemistry. Based on your answer in part (a), draw the structure of the alkyl chloride you would need, showing the correct stereochemistry.


Epichlorohydrin -

PROBLEM When 2-methyl-2,5-pentanediol is treated with sulfuric acid, dehydration occurs and
18-33 2,2-dimethyltetrahydrofuran is formed. Suggest a mechanism for this reaction. Which of the two oxygen atoms is most likely to be eliminated, and why?
<img class="imgSvg" id = "m6sn3ojrj6wd62mo0u" src="data:image/svg+xml;base64,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"/>


2,2-Dimethyltetrahydrofuran -

PROBLEM Methyl aryl ethers, such as anisole, are cleaved to iodomethane and a phenoxide ion by treatment 18-34 with LiI in hot DMF. Propose a mechanism for this reaction.


2,2-Dimethyltetrahydrofuran -

PROBLEM The herbicide acifluorfen can be prepared by a route that begins with reaction between a phenol 18-35 and an aryl fluoride. Propose a mechanism.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0629.jpg?height=502&width=1486&top_left_y=1446&top_left_x=406)


2,2-Dimethyltetrahydrofuran -

PROBLEM Aldehydes and ketones undergo acid-catalyzed reaction with alcohols to yield hemiacetals, from 18-36 aldehydes or ketals with ketones compounds that have one alcohol-like oxygen and one ether-like oxygen bonded to the same carbon. Further reaction of a hemiacetal with alcohol then yields an acetal, a compound that has two ether-like oxygens bonded to the same carbon.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0629.jpg?height=221&width=1045&top_left_y=2161&top_left_x=410)
(a) Show the structures of the hemiketal and ketal you would obtain by reaction of cyclohexanone with ethanol.
(b) Propose a mechanism for the conversion of a hemiacetal into a ketal.


2,2-Dimethyltetrahydrofuran -

PROBLEM Propose a mechanism to account for the following transformation. What two kinds of reactions are 18-37 occurring?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0630.jpg?height=364&width=944&top_left_y=295&top_left_x=409)


Naming Ethers -

PROBLEM Draw structures corresponding to the following IUPAC names:
18-38 (a) Ethyl 1-ethylpropyl ether (b) Di(p-chlorophenyl) ether (c) 3,4-Dimethoxybenzoic acid
(d) Cyclopentyloxycyclohexane (e) 4-Allyl-2-methoxyphenol (eugenol; from oil of cloves)


Naming Ethers -

PROBLEM Give IUPAC names for the following structures:
18-39
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0630.jpg?height=771&width=1239&top_left_y=948&top_left_x=405)


Naming Ethers -


Naming Ethers -

PROBLEM How would you prepare the following compounds from 1-phenylethanol?
18-41
(a) Methyl 1-phenylethyl ether
(b) Phenylepoxyethane
(c) tert-Butyl 1-phenylethyl ether
(d) 1-Phenylethanethiol


Naming Ethers -

PROBLEM tert-Butyl ethers can be prepared by the reaction of an alcohol with 2 -methylpropene in the 18-42 presence of an acid catalyst. Propose a mechanism for this reaction.