Phenols occur widely throughout nature and also serve as intermediates in the industrial synthesis of products as diverse as adhesives and antiseptics. Phenol itself is a general disinfectant found in coal tar; methyl salicylate is a flavoring agent found in oil of wintergreen; and urushiols are the allergenic constituents of poison oak and poison ivy. Note that the word phenol is the name both of the specific compound (hydroxybenzene) and of the class of compounds.
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Phenol (also known as carbolic acid)
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Methyl salicylate
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CHAPTER CONTENTS - 17.1 Naming Alcohols and Phenols

Urushiols ( $\mathrm{R}=$ different $\mathrm{C}_{15}$ alkyl and alkenyl chains)


A primary $\left(\mathbf{1}^{\circ}\right)$ alcohol A secondary (2 ${ }^{\circ}$ ) alcohol A tertiary ( $\mathbf{3}^{\circ}$ ) alcohol -

Simple alcohols are named in the IUPAC system as derivatives of the parent alkane, using the suffix -ol.


RULE 1 -

Select the longest carbon chain containing the hydroxyl group, and derive the parent name by replacing the $-e$ ending of the corresponding alkane with $-o l$. The $-e$ is deleted to prevent the occurrence of two adjacent vowels: propanol rather than propaneol, for example.


RULE 1 -

RULE 2
Number the alkane chain beginning at the end nearer the hydroxyl group.
RULE 3
Number the substituents according to their position on the chain, and write the name, listing the substituents in alphabetical order and identifying the position to which the -OH is bonded. Note that in naming cis-1,4-cyclohexanediol, the final -e of cyclohexane is not deleted because the next letter, $d$, is not a vowel; that is, cyclohexanediol rather than cyclohexandiol. Also, as with alkenes (Section 7.3), newer IUPAC naming recommendations place the locant immediately before the suffix rather than before the parent.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0561.jpg?height=172&width=240&top_left_y=1063&top_left_x=517)


RULE 1 -


RULE 1 -

Some simple and widely occurring alcohols have common names that are accepted by IUPAC. For example:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0561.jpg?height=175&width=809&top_left_y=1471&top_left_x=295)


Benzyl alcohol (phenylmethanol) -


Allyl alcohol (2-propen-1-ol) -

tert-Butyl alcohol (2-methyl-2-propanol)


Allyl alcohol (2-propen-1-ol) -

$$
\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}
$$


Allyl alcohol (2-propen-1-ol) -


Allyl alcohol (2-propen-1-ol) -

Glycerol (1,2,3-propanetriol)


Allyl alcohol (2-propen-1-ol) -

Phenols are named as described previously for aromatic compounds according to the rules discussed in Section 15.1, with -phenol used as the parent name rather than -benzene.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0561.jpg?height=261&width=706&top_left_y=1843&top_left_x=707)


Allyl alcohol (2-propen-1-ol) -

PROBLEM Draw structures corresponding to the following IUPAC names:
17-2 (a) (Z)-2-Ethyl-2-buten-1-ol
(b) 3-Cyclohexen-1-ol
(c) trans-3-Chlorocycloheptanol
(d) 1,4-Pentanediol
(e) 2,6-Dimethylphenol
(f)
-(2-Hydroxyethyl)phenol


Allyl alcohol (2-propen-1-ol) - 17.2 Properties of Alcohols and Phenols

Alcohols and phenols have nearly the same geometry around the oxygen atom as water. The $\mathrm{R}-\mathrm{O}-\mathrm{H}$ bond angle has an approximately tetrahedral value ( $108.5^{\circ}$ in methanol, for instance), and the oxygen atom is $s p^{3}$-hybridized.


Also like water, alcohols and phenols have higher boiling points than might be expected, because of hydrogenbonding (Section 2.12). A positively polarized -OH hydrogen atom from one molecule is attracted to a lone pair of electrons on the electronegative oxygen atom of another molecule, resulting in a weak force that holds the molecules together (FIGURE 17.2). These intermolecular attractions must be overcome for a molecule to break free from the liquid and enter the vapor state, so the boiling temperature is raised. For example, 1-propanol ( $\mathrm{MW}=60$ ), butane $(\mathrm{MW}=58)$, and chloroethane $(\mathrm{MW}=65)$ have similar molecular weights, yet 1-propanol boils at $97^{\circ} \mathrm{C}$, compared with $-0.5^{\circ} \mathrm{C}$ for the alkane and $12.5^{\circ} \mathrm{C}$ for the chloroalkane.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0562.jpg?height=535&width=1245&top_left_y=898&top_left_x=435)


FIGURE 17.2 Hydrogen-bonding in alcohols and phenols. Attraction between a positively polarized -OH hydrogen and a negatively polarized oxygen holds molecules together. The electrostatic potential map of methanol shows the positively polarized -OH hydrogen and the negatively polarized oxygen.


Another similarity with water is that alcohols and phenols are both weakly basic and weakly acidic. As weak bases, they are reversibly protonated by strong acids to yield oxonium ions, $\mathrm{ROH}_{2}{ }^{+}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0562.jpg?height=123&width=611&top_left_y=1662&top_left_x=757)


An alcohol
An oxonium ion


$$
\left[\text { or } \mathrm{ArOH}+\mathrm{HX} \rightleftarrows \stackrel{+}{\mathrm{H}}_{2} \mathrm{ArO}^{-}\right]
$$


As weak acids, they dissociate slightly in dilute aqueous solution by donating a proton to water, generating $\mathrm{H}_{3} \mathrm{O}^{+}$ and an alkoxide ion, $\mathrm{RO}^{-}$, or a phenoxide ion, $\mathrm{ArO}^{-}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0563.jpg?height=145&width=771&top_left_y=185&top_left_x=677)


An alcohol
An alkoxide ion
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0563.jpg?height=245&width=1049&top_left_y=425&top_left_x=538)


Recall from the earlier discussion of acidity in Section 2.7 to Section 2.11 that the strength of any acid HA in water can be expressed by an acidity constant, $K_{\mathrm{a}}$.


$$
K_{\mathrm{a}}=\frac{\left[\mathrm{A}^{-}\right]\left[\mathrm{H}_{3} \mathrm{O}^{+}\right]}{[\mathrm{HA}]} \quad \mathrm{p} K_{\mathrm{a}}=-\log K_{\mathrm{a}}
$$


Compounds with a smaller $K_{\mathrm{a}}$ and larger $\mathrm{p} K_{\mathrm{a}}$ are less acidic, whereas compounds with a larger $K_{\mathrm{a}}$ and smaller $\mathrm{p} K_{\mathrm{a}}$ are more acidic. As shown in TABLE 17.1, simple alcohols like methanol and ethanol are about as acidic as water, but the more highly substituted tert-butyl alcohol is somewhat weaker. Substituent groups also have a significant effect: 2,2,2-trifluoroethanol is approximately 3700 times stronger than ethanol, for instance. Phenols and thiols, the sulfur analogs of alcohols, are substantially more acidic than water.


| Compound | $\mathrm{p} K_{\mathrm{a}}$ |  |
| :---: | :---: | :---: |
| $\left(\mathrm{CH}_{3}\right)_{3} \mathrm{COH}$ | 18 | Weaker acid |
| $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OH}$ | 16 |  |
| $\mathrm{H}_{2} \mathrm{O}$ | 15.74 |  |
| $\mathrm{CH}_{3} \mathrm{OH}$ | 15.54 |  |
| $\mathrm{CF}_{3} \mathrm{CH}_{2} \mathrm{OH}$ | 12.43 |  |
| p-Aminophenol | 10.46 |  |
| $\mathrm{CH}_{3} \mathrm{SH}$ | 10.3 |  |
| $p$-Methylphenol | 10.17 |  |
| Phenol | 9.89 |  |
| $p$-Chlorophenol | 9.38 | acid |
| p-Nitrophenol | 7.15 |  |


The effect of alkyl substitution on alcohol acidity is due primarily to solvation of the alkoxide ion formed on acid dissociation. The more readily the alkoxide ion is solvated by water, the more stable it is, the more its formation is energetically favored, and the greater the acidity of the parent alcohol. For example, the oxygen atom of an unhindered alkoxide ion, such as that from methanol, is sterically accessible and is easily solvated by water. The oxygen atom of a hindered alkoxide ion, however, such as that from tert-butyl alcohol, is less easily solvated and is therefore less stable.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0564.jpg?height=530&width=1221&top_left_y=185&top_left_x=449)

Inductive effects (Section 16.4) are also important in determining alcohol acidities. Electron-withdrawing halogen substituents, for instance, stabilize an alkoxide ion by spreading the charge over a larger volume, thus making the alcohol more acidic. Compare, for instance, the acidities of ethanol ( $\mathrm{p} K_{\mathrm{a}}=16$ ) and 2,2,2-trifluoroethanol ( $\mathrm{p} K_{\mathrm{a}}=12.43$ ), or of tert-butyl alcohol ( $\mathrm{p} K_{\mathrm{a}}=18$ ) and nonafluoro-tert-butyl alcohol $\left(\mathrm{p} K_{\mathrm{a}}=\right.$ 5.4).


Electron-withdrawing groups stabilize the alkoxide ion and lower the $\mathrm{p} K_{\mathrm{a}}$ of the alcohol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0564.jpg?height=215&width=578&top_left_y=971&top_left_x=996)


Because alcohols are weak acids, they don't react with weak bases, such as amines or bicarbonate ion, and they only react to a limited extent with metal hydroxides such as NaOH . Alcohols do, however, react with alkali metals and with strong bases such as sodium hydride ( NaH ), sodium amide ( $\mathrm{NaNH}_{2}$ ), and Grignard reagents ( RMgX ). Alkoxides are themselves bases that are frequently used as reagents in organic chemistry. They are named systematically by adding the -ate suffix to the name of the alcohol. Methanol becomes methanolate, for instance.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0564.jpg?height=920&width=1018&top_left_y=1421&top_left_x=548)


Phenols are about a million times more acidic than alcohols (TABLE 17.1). They are therefore soluble in dilute aqueous NaOH and can often be separated from a mixture simply by basic extraction into aqueous solution, followed by reacidification.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0565.jpg?height=277&width=941&top_left_y=187&top_left_x=592)


Phenols are more acidic than alcohols because the phenoxide anion is resonance-stabilized. Delocalization of the negative charge over the ortho and para positions of the aromatic ring results in increased stability of the phenoxide anion relative to undissociated phenol and in a consequently lower $\Delta G^{\circ}$ for dissociation. FIGURE 17.3 compares electrostatic potential maps of an alkoxide ion $\left(\mathrm{CH}_{3} \mathrm{O}^{-}\right)$with phenoxide ion to show how the negative charge in phenoxide ion is delocalized from oxygen to the ring.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0565.jpg?height=573&width=890&top_left_y=689&top_left_x=609)


FIGURE 17.3 The resonance-stabilized phenoxide ion is more stable than an alkoxide ion. Electrostatic potential maps show how the negative charge is concentrated on oxygen in the methoxide ion but is spread over the aromatic ring in the phenoxide ion.


Substituted phenols can be either more acidic or less acidic than phenol itself, depending on whether the substituent is electron-withdrawing or electron-donating (Section 16.4). Phenols with an electron-withdrawing substituent are more acidic because these substituents delocalize the negative charge; phenols with an electron-donating substituent are less acidic because these substituents concentrate the charge. The acidifying effect of an electron-withdrawing substituent is particularly noticeable in phenols with a nitro group at the ortho or para position.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0565.jpg?height=345&width=1674&top_left_y=1627&top_left_x=231)


(8) WORKED EXAMPLE 17.1 -

Predicting the Relative Acidity of a Substituted Phenol
Is $p$-hydroxybenzaldehyde more acidic or less acidic than phenol?


Strategy -

Identify the substituent on the aromatic ring, and decide whether it is electron-donating or electronwithdrawing. Electron-withdrawing substituents make the phenol more acidic by stabilizing the phenoxide anion, and electron-donating substituents make the phenol less acidic by destabilizing the anion.


Solution -


Solution -

PROBLEM The following data for isomeric four-carbon alcohols show that there is a decrease in boiling point
17-3 with increasing substitution of the OH -bearing carbon. How might you account for this trend?


Solution -

$$
\begin{aligned}
& \text { 1-Butanol, bp } 117.5^{\circ} \mathrm{C} \\
& \text { 2-Butanol, bp } 99.5^{\circ} \mathrm{C} \\
& \text { 2-Methyl-2-propanol, bp } 82.2^{\circ} \mathrm{C}
\end{aligned}
$$


Solution -

PROBLEM Rank the following substances in order of increasing acidity:
17-4 (a) $\left(\mathrm{CH}_{3}\right)_{2} \mathrm{CHOH}, \mathrm{HC} \equiv \mathrm{CH},\left(\mathrm{CF}_{3}\right)_{2} \mathrm{CHOH}, \mathrm{CH}_{3} \mathrm{OH}$
(b) Phenol, $p$-methylphenol, $p$-(trifluoromethyl)phenol
(c) Benzyl alcohol, phenol, $p$-hydroxybenzoic acid


Solution -

PROBLEM $p$-Nitrobenzyl alcohol is more acidic than benzyl alcohol, but p-methoxybenzyl alcohol is less 17-5 acidic. Explain.


Solution - 17.3 Preparation of Alcohols: A Review

Alcohols occupy a central position in organic chemistry. They can be prepared from many other kinds of compounds (alkenes, alkyl halides, ketones, esters, and aldehydes, among others), and they can be transformed into an equally wide assortment of compounds (FIGURE 17.4).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0566.jpg?height=565&width=879&top_left_y=1322&top_left_x=626)

FIGURE 17.4 The central position of alcohols in organic chemistry. Alcohols can be prepared from, and converted into, many other kinds of compounds.


We've already seen several methods of alcohol synthesis:


- Alcohols can be prepared by hydration of alkenes. Because the direct hydration of alkenes with aqueous acid is generally a poor reaction in the laboratory, two indirect methods are commonly used. Hydroboration-oxidation yields the syn, non-Markovnikov hydration product (Section 8.5), whereas oxymercuration-demercuration yields the Markovnikov hydration product (Section 8.4).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0567.jpg?height=641&width=1264&top_left_y=181&top_left_x=460)
- 1,2-Diols can be prepared either by direct hydroxylation of an alkene with $\mathrm{OsO}_{4}$ followed by reduction with $\mathrm{NaHSO}_{3}$ or by acid-catalyzed hydrolysis of an epoxide (Section 8.7). The $\mathrm{OsO}_{4}$ reaction occurs with syn stereochemistry to give a cis diol, and epoxide opening occurs with anti stereochemistry to give a trans diol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0567.jpg?height=679&width=1145&top_left_y=948&top_left_x=514)


PROBLEM Predict the products of the following reactions:
17-6 (a)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0567.jpg?height=193&width=552&top_left_y=1698&top_left_x=472)
(c)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0567.jpg?height=155&width=793&top_left_y=1901&top_left_x=479)


Solution - 17.4 Alcohols from Carbonyl Compounds: Reduction

The most general method for preparing alcohols, both in the laboratory and in living organisms, is by reduction of a carbonyl compound. Just as reduction of an alkene adds hydrogen to a $\mathrm{C}=\mathrm{C}$ bond to give an alkane (Section 8.6), reduction of a carbonyl compound adds hydrogen to a $\mathrm{C}=\mathrm{O}$ bond to give an alcohol. All kinds of carbonyl compounds can be reduced, including aldehydes, ketones, carboxylic acids, and esters.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0568.jpg?height=131&width=665&top_left_y=192&top_left_x=773)


A carbonyl compound -

An alcohol


Reduction of Aldehydes and Ketones -

Aldehydes are easily reduced to give primary alcohols, and ketones are reduced to give secondary alcohols.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0568.jpg?height=215&width=1181&top_left_y=521&top_left_x=472)


Reduction of Aldehydes and Ketones -

Dozens of reagents are used in the laboratory to reduce aldehydes and ketones, depending on the circumstances, but sodium borohydride, $\mathrm{NaBH}_{4}$, is usually chosen because of its safety and ease of handling. Sodium borohydride is a white, crystalline solid that can be weighed in the open atmosphere and used in either water or alcohol solution.


Aldehyde reduction -


Butanal -

1-Butanol (85\%)
(a $1^{\circ}$ alcohol)


Ketone reduction -


Ketone reduction -

Lithium aluminum hydride, $\mathrm{LiAlH}_{4}$, is another reducing agent often used for reduction of aldehydes and ketones. A grayish powder that is soluble in ether and tetrahydrofuran, $\mathrm{LiAlH}_{4}$ is much more reactive than $\mathrm{NaBH}_{4}$ but also much more dangerous. It reacts violently with water and decomposes explosively when heated above $120^{\circ} \mathrm{C}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0568.jpg?height=188&width=508&top_left_y=1830&top_left_x=792)


Ketone reduction -

2-Cyclohexenone
2-Cyclohexenol (94\%)
We'll defer a detailed discussion of these reductions until Chapter 19. For the moment, we'll simply note that they involve the addition of a nucleophilic hydride ion $\left(: \mathrm{H}^{-}\right)$to the positively polarized, electrophilic carbon atom of the carbonyl group. The initial product is an alkoxide ion, which is protonated by addition of $\mathrm{H}_{3} \mathrm{O}^{+}$in a second step to yield the alcohol product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0569.jpg?height=272&width=741&top_left_y=184&top_left_x=687)


Ketone reduction -

In living organisms, aldehyde and ketone reductions are carried out by either of the coenzymes NADH (reduced nicotinamide adenine dinucleotide) or NADPH (reduced nicotinamide adenine dinucleotide phosphate). Although these biological "reagents" are much more complex structurally than $\mathrm{NaBH}_{4}$ or $\mathrm{LiAlH}_{4}$, the mechanisms of laboratory and biological reactions are similar. The coenzyme acts as a hydride-ion donor to give an alkoxide anion, and the intermediate anion is then protonated by acid. An example is the reduction of acetoacetyl ACP to $\beta$-hydroxybutyryl ACP, a step in the biological synthesis of fats (FIGURE 17.5). Note that the pro- $R$ hydrogen of NADPH is the one transferred in this example. Enzyme-catalyzed reactions usually occur with high specificity, although it's not usually possible to predict the stereochemical result before the fact.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0569.jpg?height=885&width=1337&top_left_y=818&top_left_x=394)


Ketone reduction -

FIGURE 17.5 The biological reduction of a ketone (acetoacetyl ACP) to an alcohol ( $\beta$-hydroxybutyryl ACP) by NADPH.


Reduction of Carboxylic Acids and Esters -

Carboxylic acids and esters are reduced to give primary alcohols.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0569.jpg?height=161&width=692&top_left_y=1876&top_left_x=706)


A carboxylic acid
An ester
A primary alcohol
These reactions aren't as rapid as the reductions of aldehydes and ketones. $\mathrm{NaBH}_{4}$ reduces esters very slowly and does not reduce carboxylic acids at all. Instead, carboxylic acid and ester reductions are usually carried out with the more reactive reducing agent $\mathrm{LiAlH}_{4}$. All carbonyl groups, including acids, esters, ketones, and aldehydes, are reduced by $\mathrm{LiAlH}_{4}$. Note that one hydrogen atom is delivered to the carbonyl carbon atom during aldehyde and ketone reductions but that two hydrogens become bonded to the former carbonyl carbon during carboxylic acid and ester reductions. We'll defer a discussion of the mechanisms of these reactions until Chapter 21.


Carboxylic acid reduction
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0570.jpg?height=201&width=1115&top_left_y=252&top_left_x=538)


Ester reduction
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0570.jpg?height=102&width=1099&top_left_y=556&top_left_x=540)


Methyl 2-pentenoate 2-Penten-1-ol (91\%)


WORKED EXAMPLE 17.2 -


Identifying a Reactant, Given the Product -


Strategy -

Identify the target alcohol as primary, secondary, or tertiary. A primary alcohol can be prepared by reduction of an aldehyde, an ester, or a carboxylic acid; a secondary alcohol can be prepared by reduction of a ketone; and a tertiary alcohol can't be prepared by reduction.


Solution -

(a) The target molecule is a secondary alcohol, which can be prepared only by reduction of a ketone. Either $\mathrm{NaBH}_{4}$ or $\mathrm{LiAlH}_{4}$ can be used.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0570.jpg?height=131&width=879&top_left_y=1428&top_left_x=620)
(b) The target molecule is a primary alcohol, which can be prepared by reduction of an aldehyde, an ester, or a carboxylic acid. $\mathrm{LiAlH}_{4}$ is needed for the ester and carboxylic acid reductions.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0570.jpg?height=403&width=993&top_left_y=1666&top_left_x=563)


Solution -


Solution - 17.5 Alcohols from Carbonyl Compounds: Grignard Reaction

Grignard reagents (RMgX), prepared by reaction of organohalides with magnesium (Section 10.6), react with carbonyl compounds to yield alcohols in much the same way that hydride reducing agents do. Just as carbonyl reduction involves addition of a hydride ion nucleophile to the $\mathrm{C}=\mathrm{O}$ bond, Grignard reaction involves addition of a carbanion nucleophile ( $\mathrm{R} \mathrm{P}^{-+} \mathrm{MgX}$ ).


$$
\left[\mathrm{R}-\mathrm{X}+\mathrm{Mg} \longrightarrow \underset{\begin{array}{c}
\text { A Grignard } \\
\text { reagent }
\end{array}}{\stackrel{\delta^{-}}{\mathrm{R}-\mathrm{ingX}} \mathrm{\delta}^{+}}\left\{\begin{array}{l}
\mathrm{R}=1^{\circ}, 2^{\circ}, \text { or } 3^{\circ} \text { alkyl, aryl, or vinylic } \\
\mathrm{X}=\mathrm{Cl}, \mathrm{Br}, \mathrm{I}
\end{array}\right]\right.
$$


The nucleophilic addition reaction of Grignard reagents to carbonyl compounds has no direct counterpart in biological chemistry because organomagnesium compounds are too strongly basic to exist in an aqueous medium. Nevertheless, the reaction is worth understanding for two reasons. First, the reaction is an unusually broad and useful method of alcohol synthesis and demonstrates again the relative freedom with which chemists can operate in the laboratory. Second, the reaction does have an indirect biological counterpart, for we'll see in Chapter 23 that the addition of stabilized carbon nucleophiles to carbonyl compounds is used in almost all metabolic pathways as the major process for forming carbon-carbon bonds.


As examples of their addition to carbonyl compounds, Grignard reagents react with formaldehyde, $\mathrm{H}_{2} \mathrm{C}=\mathrm{O}$, to give primary alcohols, with aldehydes to give secondary alcohols, and with ketones to give tertiary alcohols.


Formaldehyde reaction -


Aldehyde reaction -


Aldehyde reaction -

Ketone reaction
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0572.jpg?height=264&width=1045&top_left_y=947&top_left_x=513)


Aldehyde reaction -

Esters react with Grignard reagents to yield tertiary alcohols in which two of the substituents bonded to the hydroxyl-bearing carbon have come from the Grignard reagent, just as $\mathrm{LiAlH}_{4}$ reduction of an ester adds two hydrogens.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0572.jpg?height=225&width=1259&top_left_y=1362&top_left_x=430)


Aldehyde reaction -

Carboxylic acids don't give addition products when treated directly with Grignard reagents because the acidic carboxyl hydrogen reacts with the basic Grignard reagent to yield a hydrocarbon and the magnesium salt of the acid.


Aldehyde reaction -

$$
[R-X+M g \quad R-M g X]
$$


A carboxylic acid -

A carboxylic acid salt
Carboxylic acids do, however, react with Grignard reagents to give ketones if they are first treated with $i-\mathrm{Pr}_{2} \mathrm{NMgCl}-\mathrm{LiCl}$, called the turbo-Hauser base, to form a complex and increase the electrophilicity of the carboxylate anion toward nucleophilic addition with a Grignard reagent.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0573.jpg?height=375&width=836&top_left_y=187&top_left_x=642)


A carboxylic acid -

The Grignard reaction, although useful, does have limitations. One major problem is that a Grignard reagent can't be prepared from an organohalide if other reactive functional groups are present in the same molecule. For example, a compound that is both an alkyl halide and a ketone can't form a Grignard reagent because it would react with itself. Similarly, a compound that is both an alkyl halide and a carboxylic acid, alcohol, or amine can't form a Grignard reagent because the acidic $\mathrm{RCO}_{2} \mathrm{H}, \mathrm{ROH}$, or $\mathrm{RNH}_{2}$ hydrogen present in the same molecule would react with the basic Grignard reagent as rapidly as it forms. In general, Grignard reagents can't be prepared from alkyl halides that contain the following functional groups (FG):
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0573.jpg?height=416&width=966&top_left_y=887&top_left_x=582)


A carboxylic acid -

As with the reduction of carbonyl compounds discussed in the previous section, we'll defer a detailed treatment of the Grignard reactions until Chapter 19. For the moment, it's sufficient to note that Grignard reagents act as nucleophilic carbanions ( $: \mathrm{R}^{-}$) and that their addition to a carbonyl compound is analogous to the addition of hydride ion. The intermediate is an alkoxide ion, which is protonated by addition of $\mathrm{H}_{3} \mathrm{O}^{+}$in a second step.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0573.jpg?height=277&width=739&top_left_y=1496&top_left_x=693)


WORKED EXAMPLE 17.3 -


Using a Grignard Reaction to Synthesize an Alcohol -

How could you use the addition of a Grignard reagent to a ketone to synthesize 2-phenyl-2-butanol?


Strategy -

Draw the product, and identify the three groups bonded to the alcohol carbon atom. One of the three will have come from the Grignard reagent, and the remaining two will have come from the ketone.


Solution -

2-Phenyl-2-butanol has a methyl group, an ethyl group, and a phenyl group ( $-\mathrm{C}_{6} \mathrm{H}_{5}$ ) attached to the alcohol carbon atom. Thus, the possibilities are addition of ethylmagnesium bromide to acetophenone, addition of methylmagnesium bromide to propiophenone, and addition of phenylmagnesium bromide to 2-butanone.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0574.jpg?height=592&width=1131&top_left_y=192&top_left_x=494)


WORKED EXAMPLE 17.4 -


How could you use the reaction of a Grignard reagent with a carbonyl compound to synthesize 2-methyl-2-pentanol?


Strategy -

Draw the product, and identify the three groups bonded to the alcohol carbon atom. If the three groups are all different, the starting carbonyl compound must be a ketone. If two of the three groups are identical, the starting carbonyl compound could be either a ketone or an ester.


Solution -

In the present instance, the product is a tertiary alcohol with two methyl groups and one propyl group. Starting from a ketone, the possibilities are addition of methylmagnesium bromide to 2 -pentanone and addition of propylmagnesium bromide to acetone.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0574.jpg?height=353&width=958&top_left_y=1534&top_left_x=578)


Acetone -

Starting from an ester, the only possibility is addition of methylmagnesium bromide to an ester of butanoic acid, such as methyl butanoate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0574.jpg?height=199&width=1047&top_left_y=2055&top_left_x=539)


Acetone -

PROBLEM Show the products obtained from addition of methylmagnesium bromide to the following 17-9 compounds:
(a) Cyclopentanone
(b) Benzophenone (diphenyl ketone)
(c) 3-Hexanone


Acetone -

PROBLEM Use a Grignard reaction to prepare the following alcohols:
17-10 (a) 2-Methyl-2-propanol (b) 1-Methylcyclohexanol (c) 3-Methyl-3-pentanol


(d) 2-Phenyl-2-butanol (e) Benzyl alcohol (f) 4-Methyl-1-pentanol -

PROBLEM Use the reaction of a Grignard reagent with a carbonyl compound to synthesize the following 17-11 compound:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0575.jpg?height=305&width=537&top_left_y=379&top_left_x=439)


(d) 2-Phenyl-2-butanol (e) Benzyl alcohol (f) 4-Methyl-1-pentanol - 17.6 Reactions of Alcohols

We've already seen several reactions of alcohols-their conversion into alkyl halides and tosylates in Section 10.5 and their dehydration to give alkenes in Section 8.1-albeit without mechanistic details. Let's now look at those details.


Conversion of Alcohols into Alkyl Halides -

Tertiary alcohols react with either HCl or HBr at $0^{\circ} \mathrm{C}$ by an $\mathrm{S}_{\mathrm{N}} 1$ mechanism through a carbocation intermediate. Primary and secondary alcohols are much more resistant to acid, however, and are best converted into halides by treatment with either $\mathrm{SOCl}_{2}$ or $\mathrm{PBr}_{3}$ through an $\mathrm{S}_{\mathrm{N}} 2$ mechanism.


The reaction of a tertiary alcohol with HX takes place by an $\mathrm{S}_{\mathrm{N}} 1$ mechanism when acid protonates the hydroxyl oxygen atom. Water is expelled to generate a carbocation, and the cation reacts with nucleophilic halide ion to give the alkyl halide product.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0575.jpg?height=337&width=1139&top_left_y=1311&top_left_x=493)


The reactions of primary and secondary alcohols with $\mathrm{SOCl}_{2}$ and $\mathrm{PBr}_{3}$ take place by $\mathrm{S}_{\mathrm{N}} 2$ mechanisms. Hydroxide ion itself is too poor a leaving group to be displaced by nucleophiles in $\mathrm{S}_{\mathrm{N}} 2$ reactions, but reaction of an alcohol with $\mathrm{SOCl}_{2}$ or $\mathrm{PBr}_{3}$ converts the -OH into a much better leaving group, either a chlorosulfite (-OSOCl) or a dibromophosphite $\left(-\mathrm{OPBr}_{2}\right)$, which is readily expelled by backside nucleophilic substitution.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0575.jpg?height=581&width=1280&top_left_y=1840&top_left_x=425)


Conversion of Alcohols into Tosylates -

Alcohols react with $p$-toluenesulfonyl chloride (tosyl chloride, $p$ - TosCl ) in pyridine solution to yield alkyl
tosylates, ROTos (Section 11.1). Only the $\mathrm{O}-\mathrm{H}$ bond of the alcohol is broken in this reaction; the $\mathrm{C}-\mathrm{O}$ bond remains intact, so no change of configuration occurs if the oxygen is attached to a chirality center. The resultant alkyl tosylates behave much like alkyl halides, undergoing both $\mathrm{S}_{\mathrm{N}} 1$ and $\mathrm{S}_{\mathrm{N}} 2$ substitution reactions.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0576.jpg?height=302&width=1337&top_left_y=342&top_left_x=394)


Conversion of Alcohols into Tosylates -

One of the most important reasons for using tosylates in $S_{N} 2$ reactions is stereochemical. The $S_{N} 2$ reaction of an alcohol with an alkyl halide proceeds with two inversions of configuration-one to make the halide from the alcohol and one to substitute the halide-and yields a product with the same stereochemistry as the starting alcohol. The $\mathrm{S}_{\mathrm{N}} 2$ reaction of an alcohol with a tosylate, however, proceeds with only one inversion and yields a product of opposite stereochemistry to the starting alcohol. FIGURE 17.6 shows a series of reactions on the $R$ enantiomer of 2 -octanol that illustrates these stereochemical relationships.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0576.jpg?height=527&width=1503&top_left_y=924&top_left_x=314)

FIGURE 17.6 Stereochemical consequences of $\mathbf{S}_{\mathbf{N}} \mathbf{2}$ reactions on derivatives of ( $\boldsymbol{R}$ )-2-octanol. Substitution through the halide gives a product with the same stereochemistry as the starting alcohol; substitution through the tosylate gives a product with opposite stereochemistry to the starting alcohol.


Conversion of Alcohols into Tosylates -

PROBLEM How would you carry out the following transformation, a step used in the commercial synthesis of 17-12 (S)-ibuprofen?
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0576.jpg?height=211&width=926&top_left_y=1659&top_left_x=407)


Dehydration of Alcohols to Yield Alkenes -

A third important reaction of alcohols, both in the laboratory and in biological pathways, is their dehydration to give alkenes. Because of the usefulness of the reaction, a number of methods have been devised for carrying out dehydrations. One method that works particularly well for tertiary alcohols is the acid-catalyzed reaction discussed in Section 8.1. For example, treatment of 1-methylcyclohexanol with warm, aqueous sulfuric acid in a solvent such as tetrahydrofuran results in loss of water and formation of 1-methylcyclohexene.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0576.jpg?height=199&width=513&top_left_y=2188&top_left_x=784)


1-Methylcyclohexanol 1-Methylcyclohexene (91\%) -

Acid-catalyzed dehydrations usually follow Zaitsev's rule (Section 11.7) and yield the more stable alkene as the major product. Thus, 2-methyl-2-butanol gives primarily 2-methyl-2-butene (trisubstituted double bond)
rather than 2-methyl-1-butene (disubstituted double bond).
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0577.jpg?height=158&width=936&top_left_y=260&top_left_x=578)


2-Methyl-2-butanol
2-Methyl-2-butene 2-Methyl-1-butene (trisubstituted) (disubstituted) Major product Minor product
This reaction is an E1 process (Section 11.10) and occurs by the three-step mechanism shown in FIGURE 17.7 on the next page. Protonation of the alcohol oxygen is followed by unimolecular loss of water to generate a carbocation intermediate and final loss of a proton from the neighboring carbon atom to complete the process. As with most E1 reactions, tertiary alcohols react fastest because they lead to stabilized, tertiary carbocation intermediates. Secondary alcohols can be made to react, but the conditions are severe $\left(75 \% \mathrm{H}_{2} \mathrm{SO}_{4}, 100^{\circ} \mathrm{C}\right)$ and sensitive molecules don't survive.


FIGURE 17.7 MECHANISM
Mechanism for the acid-catalyzed dehydration of a tertiary alcohol to yield an
alkene. The process is an E1 reaction and involves a carbocation intermediate.
(1) Two electrons from the oxygen atom bond to $\mathrm{H}^{+}$, yielding a protonated alcohol intermediate.
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(2) The carbon-oxygen bond breaks, and the two electrons from the bond stay with oxygen, leaving a carbocation intermediate.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0577.jpg?height=190&width=350&top_left_y=1786&top_left_x=1256)


To circumvent the need for strong acid and allow the dehydration of secondary alcohols in a gentler way, reagents have been developed that are effective under mild, basic conditions. One such reagent, phosphorus oxychloride $\left(\mathrm{POCl}_{3}\right)$ in the basic amine solvent pyridine, is often able to effect the dehydration of secondary and
tertiary alcohols at $0^{\circ} \mathrm{C}$.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0578.jpg?height=171&width=660&top_left_y=256&top_left_x=711)


1-Methylcyclohexanol
1-Methylcyclohexene (96\%)
Alcohol dehydrations carried out with $\mathrm{POCl}_{3}$ in pyridine take place by an E2 mechanism, as shown in FIGURE 17.8. Because hydroxide ion is a poor leaving group (Section 11.3), direct E 2 elimination of water from an alcohol does not occur. On reaction with $\mathrm{POCl}_{3}$, however, the -OH group is converted into a dichlorophosphate $\left(-\mathrm{OPOCl}_{2}\right)$, which is a good leaving group and is readily eliminated. Pyridine is both the reaction solvent and the base that removes a neighboring proton in the E2 elimination step.


FIGURE 17.8 MECHANISM


Mechanism for the dehydration of secondary and tertiary alcohols by reaction with $\mathrm{POCl}_{3}$ in pyridine. The reaction is an E2 process.
(1) The alcohol hydroxyl group reacts with $\mathrm{POCl}_{3}$ to form a dichlorophosphate intermediate.


As noted in Section 11.11, biological dehydrations are also common and usually occur by an E1cB mechanism on a substrate in which the - OH group is two carbons away from a carbonyl group. One example occurs in the biosynthesis of the aromatic amino acid tyrosine. A base (:B) first abstracts a proton from the carbon adjacent to the carbonyl group, and the anion intermediate then expels the - OH group with simultaneous protonation by an acid (HA) to form water.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0579.jpg?height=450&width=1705&top_left_y=184&top_left_x=229)


Conversion of Alcohols into Esters -

Alcohols react with carboxylic acids to give esters, a reaction that is common in both the laboratory and living organisms. In the laboratory, the reaction can be carried out in a single step if a strong acid is used as catalyst. More frequently, though, the reactivity of the carboxylic acid is enhanced by first converting it into a carboxylic acid chloride, which then reacts with the alcohol.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0579.jpg?height=530&width=1139&top_left_y=1421&top_left_x=490)


Conversion of Alcohols into Esters -

In living organisms, a similar process occurs, though a thioester or acyl adenosyl phosphate acts as substrate rather than a carboxylic acid chloride. We'll look at the mechanisms of these reactions in Chapter 21.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0579.jpg?height=351&width=741&top_left_y=2058&top_left_x=692)


Conversion of Alcohols into Esters -

An acyl adenosyl phosphate


Conversion of Alcohols into Esters - 17.7 Oxidation of Alcohols

Perhaps the most valuable reaction of alcohols is their oxidation to give carbonyl compounds-the opposite of the reduction of carbonyl compounds to give alcohols. Primary alcohols are oxidized either to aldehydes or carboxylic acids, and secondary alcohols are oxidized to ketones, but tertiary alcohols don't normally react with most oxidizing agents.


Primary alcohol
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0580.jpg?height=190&width=741&top_left_y=458&top_left_x=838)

Secondary alcohol
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0580.jpg?height=142&width=400&top_left_y=685&top_left_x=841)


A ketone


Tertiary alcohol
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0580.jpg?height=153&width=434&top_left_y=910&top_left_x=840)


Primary and secondary alcohols can be oxidized by any of a number of reagents, including $\mathrm{CrO}_{3}$ in aqueous acetic acid and $\mathrm{KMnO}_{4}$ in aqueous NaOH , but chromium-based reagents are rarely used today because of their toxicity and fire danger. Today, primary and secondary alcohols are oxidized to aldehydes and ketones, respectively, using the iodine-containing Dess-Martin periodinane in dichloromethane solution.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0580.jpg?height=782&width=1090&top_left_y=1254&top_left_x=512)

Primary alcohols are oxidized to carboxylic acids by heating with $\mathrm{KMnO}_{4}$ in a basic aqueous solution. An aldehyde is involved as an intermediate in the $\mathrm{KMnO}_{4}$ reaction but can't usually be isolated because it is further oxidized too rapidly.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0580.jpg?height=166&width=822&top_left_y=2183&top_left_x=646)


All these oxidations occur by a mechanism that is closely related to the E2 reaction (Section 11.8). In the Dess-Martin oxidation, for instance, the first step involves a substitution reaction between the alcohol and the $\mathrm{I}(\mathrm{V})$ reagent to form a new periodinane intermediate, followed by expulsion of reduced $\mathrm{I}(\mathrm{III})$ as the leaving group. Similarly, when a $\mathrm{Cr}(\mathrm{VI})$ reagent, such as $\mathrm{CrO}_{3}$, is the oxidant, reaction with the alcohol gives a chromate
intermediate followed by expulsion of a reduced $\mathrm{Cr}(\mathrm{VI})$ species.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0581.jpg?height=435&width=1345&top_left_y=254&top_left_x=390)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0581.jpg?height=399&width=1315&top_left_y=684&top_left_x=405)


Biological alcohol oxidations are the opposite of biological carbonyl reductions and are facilitated by the coenzymes $\mathrm{NAD}^{+}$and $\mathrm{NADP}^{+}$. A base removes the -OH proton, and the alkoxide ion transfers a hydride ion to the coenzyme. An example is the oxidation of sn-glycerol 3-phosphate to dihydroxyacetone phosphate, a step in the biological metabolism of fats (FIGURE 17.9). Note that addition occurs exclusively on the Re face of the NAD ${ }^{+}$ ring, adding a hydrogen with pro- $R$ stereochemistry.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0581.jpg?height=392&width=1289&top_left_y=1319&top_left_x=410)
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0581.jpg?height=465&width=1297&top_left_y=1719&top_left_x=414)

FIGURE 17.9 The biological oxidation of an alcohol (sn-glycerol 3-phosphate) to give a ketone (dihydroxyacetone phosphate). This mechanism is the exact opposite of the ketone reduction shown previously in FIGURE 17.5.


PROBLEM What products would you expect from oxidation of the following compounds with the Dess-Martin 17-15 periodinane?
(a) 1-Hexanol
(b) 2-Hexanol
(c) Hexanal


Conversion of Alcohols into Esters - 17.8 Protection of Alcohols

It often happens, particularly during the synthesis of complex molecules, that one functional group in a molecule interferes with an intended reaction on another functional group elsewhere in the same molecule. We saw earlier in this chapter, for instance, that a Grignard reagent can't be prepared from an alcohol-containing halidel because the $\mathrm{C}-\mathrm{Mg}$ bond is not compatible with the presence of an acidic -OH group in the same molecule.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0582.jpg?height=194&width=814&top_left_y=651&top_left_x=653)


When this kind of incompatibility arises, it's sometimes possible to circumvent the problem by protecting the interfering functional group. Protection involves three steps: (1) introducing a protecting group to block the interfering function, (2) carrying out the desired reaction, and (3) removing the protecting group.


One of the more common methods of alcohol protection involves reaction with a chlorotrialkylsilane, $\mathrm{Cl}^{2}-\mathrm{SiR}_{3}$, to yield a trialkylsilyl ether, $\mathrm{R}^{\prime}-\mathrm{O}-\mathrm{SiR}_{3}$. (Chloro-tert-butyldimethylsilane), usually abbreviated either TBS or TBDMS is often used, as is chlorotrimethylsilane (TMS), and the reaction is carried out in the presence of a base, such as triethylamine, to help form the alkoxide anion from the alcohol and to remove the HCl by-product from the reaction.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0582.jpg?height=326&width=1136&top_left_y=1233&top_left_x=519)


For example:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0582.jpg?height=270&width=1059&top_left_y=1643&top_left_x=525)


The ether-forming step is an $\mathrm{S}_{\mathrm{N}} 2$-like reaction of the alkoxide ion on the silicon atom, with concurrent loss of the leaving chloride anion. Unlike most $\mathrm{S}_{\mathrm{N}} 2$ reactions, though, this reaction takes place at a tertiary center-a trialkyl-substituted silicon atom. The reaction occurs because silicon, a third-row atom, is larger than carbon and forms longer bonds. In addition, three alkyl substituents attached to silicon offer little steric hindrance to ether formation.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0583.jpg?height=792&width=1212&top_left_y=192&top_left_x=462)


Like most other ethers, which we'll study in the next chapter, trialkylsilylethers are relatively unreactive. They have no acidic hydrogens and don't react with oxidizing agents, reducing agents, or Grignard reagents. They do, however, react with aqueous acid or with fluoride ion to regenerate the alcohol. Tetrabutylammonium fluoride is often used.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0583.jpg?height=250&width=1164&top_left_y=1168&top_left_x=475)


To solve the problem posed at the beginning of this section, note that it's possible to use an alcohol-containing halide in a Grignard reaction by employing a protection sequence. For example, we can add 3-bromo-1-propanol to acetaldehyde by the route shown in FIGURE 17.10.


Step 1 Protect alcohol:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0583.jpg?height=77&width=1041&top_left_y=1628&top_left_x=504)


Step 2a Form Grignard reagent:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0583.jpg?height=76&width=850&top_left_y=1797&top_left_x=513)

Step 2b Do Grignard reaction:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0583.jpg?height=139&width=974&top_left_y=1963&top_left_x=505)


Step 3 Remove protecting group:
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0583.jpg?height=114&width=1259&top_left_y=2171&top_left_x=506) FIGURE 17.10 Use of a trialkylsilyl-protected alcohol during a Grignard reaction.
PROBLEM Propose a mechanism for the reaction of cyclohexyl TMS ether with LiF to deprotect the silyl ether. 17-16


Conversion of Alcohols into Esters - 17.9 Phenols and Their Uses

The outbreak of World War I provided a stimulus for the industrial preparation of large amounts of synthetic phenol, which was needed as a raw material to manufacture the explosive, picric acid (2,4,6-trinitrophenol). Today, approximately 132 million tons of phenol is manufactured worldwide each year for use in such products as Bakelite resin and adhesives for binding plywood.


Phenol was manufactured for many years by the Dow process, in which chlorobenzene reacts with NaOH at high temperature and pressure (Section 16.7). Now, however, an alternative synthesis uses isopropylbenzene, commonly called cumene. Cumene reacts with air at high temperature by benzylic oxidation through a radical mechanism to form cumene hydroperoxide, which is converted into phenol and acetone by treatment with acid. This is a particularly efficient process because two valuable chemicals are prepared at the same time.
![](https://cdn.mathpix.com/cropped/2025_02_06_5556f7656cbdcaa0f9a7g-0584.jpg?height=316&width=1297&top_left_y=685&top_left_x=414)