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Alcohols, Phenols, and Ethers: Answers To Questions

The document discusses various aspects of alcohols, phenols, and ethers, including the Lucas test's applicability to short-chain alcohols, the oxidation resistance of tertiary alcohols and ethers with potassium permanganate, and the relationship between the structures of phenolic compounds and their pH values. It explains that the Lucas test is effective for alcohols with five or fewer carbons due to solubility and steric factors. Additionally, it highlights how the presence and position of electron-withdrawing groups influence the acidity of phenolic compounds.

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4 views1 page

Alcohols, Phenols, and Ethers: Answers To Questions

The document discusses various aspects of alcohols, phenols, and ethers, including the Lucas test's applicability to short-chain alcohols, the oxidation resistance of tertiary alcohols and ethers with potassium permanganate, and the relationship between the structures of phenolic compounds and their pH values. It explains that the Lucas test is effective for alcohols with five or fewer carbons due to solubility and steric factors. Additionally, it highlights how the presence and position of electron-withdrawing groups influence the acidity of phenolic compounds.

Uploaded by

Sunshine KSN
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as DOCX, PDF, TXT or read online on Scribd
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Chemistry 31.

1 (2025) Page |1

Alcohols, Phenols, and Ethers


ANSWERS TO QUESTIONS

1. Give the balanced equations for all the reactions.

2. Explain why Lucas test is applicable only to alcohols containing 5 or less carbons.
- The Lucas test works best for alcohols with five or fewer carbon atoms due to differences in
solubility and reaction efficiency. The Lucas reagent, a mixture of concentrated hydrochloric
acid (HCl) and zinc chloride (ZnCl₂), is a polar medium. Alcohols with shorter carbon chains are
more soluble in this reagent, allowing the reaction to proceed efficiently. On the other hand,
alcohols with longer carbon chains become less soluble because their non-polar hydrocarbon
regions dominate, reducing their ability to interact with the reagent. Additionally, the Lucas test
relies on the formation of alkyl chlorides through either an SN1 or SN2 mechanism, depending
on the type of alcohol. Tertiary alcohols react quickly and produce cloudiness almost
immediately, while secondary alcohols react more slowly, and primary alcohols may take
significantly longer or show minimal reaction. Alcohols with longer carbon chains tend to react
inefficiently in the Lucas test due to both reduced solubility and increased steric hindrance,
making the test most suitable for detecting alcohols with five or fewer carbon atoms.

3. Explain why tertiary alcohols and ethers cannot undergo oxidation upon reaction with potassium
permanganate.
- Tertiary alcohols and ethers do not undergo oxidation with potassium permanganate (KMnO₄)
due to the absence of a hydrogen atom on the carbon directly bonded to the oxygen. In tertiary
alcohols, the carbon atom bearing the -OH group is attached to three other carbon atoms,
leaving no hydrogen atom available for oxidation. Since KMnO₄ requires this hydrogen to initiate
the oxidation process, tertiary alcohols remain unreactive. Meanwhile, in ethers, the oxygen
atom is bonded to two carbon chains, meaning there are no hydrogen atoms directly attached
to the oxygen-bearing carbon. Without this hydrogen, the typical oxidation pathway cannot
proceed, making ethers resistant to oxidation under standard KMnO₄ conditions.

4. Explain the relationship between the structures of the phenolic compounds with their expected pH
values.
- The pH values of phenolic compounds are closely linked to their molecular structures,
particularly the presence of electron-withdrawing or electron-donating groups and their
influence on acidity. Phenol, with a pH of around 5, is a weak acid because its phenoxide ion is
stabilized through resonance once the hydrogen from the hydroxyl group is lost. However, since
phenol lacks strong electron-withdrawing groups, its acidity remains relatively mild. Additionally,
p-Nitrophenol also has a pH of approximately 5 despite it containing a nitro group (-NO₂) at the
para position. Although the nitro group is an electron-withdrawing group that stabilizes the
phenoxide ion through resonance and inductive effects, its distant position limits its impact,
resulting in minimal improvement in acidity compared to phenol. In contrast, picric acid has a
significantly lower pH of around 3. This stronger acidity is attributed to the presence of three
powerful electron-withdrawing nitro groups, which greatly stabilize the phenoxide ion and
enhance the compound’s ability to release a proton. Lastly, β-naphthol has a pH of about 4,
which is slightly lower than phenol’s pH. This is due to its extended aromatic system, which
enhances resonance stabilization of the phenoxide ion, moderately increasing its acidity.
Overall, the pH values of these phenolic compounds are strongly influenced by the presence,
number, and position of electron-withdrawing groups, as well as resonance stabilization.

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