12 Chemistry – Alcohols, Phenols and Ethers
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Examples include reactions with hydrogen halides or phosphorus halides.
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1. Which reaction type involves the cleavage of the C–O bond in alcohols?
This is wrong answer.
Yes. You are Correct.
Reactions involving cleavage of the C-O bond include reaction with hydrogen halides and phosphorus halides, or dehydration. The Lucas test is an example of a C-O bond cleavage reaction.
This biological process yields “grain alcohol”.
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2. What is the industrial process by which ethanol is prepared from sugars?
Industrial preparation of ethanol often occurs via the fermentation of sugars.
This reagent is highly selective for tertiary alcohols.
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3. Which reagent combination constitutes the Lucas test, used for the classification and distinction of primary, secondary, and tertiary alcohols?
The Lucas test uses concentrated $text{HCl}$ and anhydrous $text{ZnCl}_2$ (Lucas reagent) to distinguish between 1°, 2°, and 3° alcohols based on reactivity.
The -OH group pushes electron density into the ring.
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4. The hydroxyl group (-OH) in phenol is strongly activating and directs incoming electrophiles to which positions?
The -OH group is ortho and para directing in electrophilic aromatic substitution reactions.
Consider the nature of the two alkyl or aryl groups attached to the oxygen.
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5. Ethers are classified into simple and mixed based on:
Ethers are classified as simple (symmetrical) or mixed (unsymmetrical) depending on whether the alkyl/aryl groups attached to the oxygen atom are the same or different.
Catechol has two -OH groups adjacent to each other on the benzene ring.
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6. What is the IUPAC name for the dihydric phenol commonly known as catechol?
Dihydric phenols include catechol (Benzene-1,2-diol), resorcinol, and quinol.
NO2 is a strong electron-withdrawing group.
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7. A nitro group (NO2) attached to the benzene ring in a nitrophenol structure affects the acidity of the phenol by:
Electron-withdrawing substituents, like $text{NO}_2$, increase the acidity of phenols by stabilizing the phenoxide ion.
Alkyl groups are electron-donating, affecting conjugate base stability.
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8. How does the acidity of alcohols compare to that of water?
Alcohols are generally weaker acids than water.
This test relies on the characteristic color formation of phenoxide ions with specific salts.
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9. Which test is used to distinguish between an alcohol and a phenol?
The neutral $text{FeCl}_3$ test yields a characteristic color (violet/purple) with phenols but not with alcohols, allowing for distinction.
This reaction involves the reduction of the -OH group.
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10. What product is formed when phenol reacts with zinc dust?
Although not explicitly listed in the main reactions, phenol can be reduced to benzene using zinc dust. (If phenol undergoes reduction, it forms cyclohexanol, mentioned in. However, zinc dust leads to benzene, an established concept relating to the ring).
Ethers lack the crucial -OH bond.
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11. Why are the boiling points of ethers significantly lower than those of isomeric alcohols?
Ethers have lower boiling points because they cannot form intermolecular hydrogen bonds, unlike alcohols.
Cumene is isopropylbenzene.
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12. Which industrial method for the preparation of phenol involves the decomposition of cumene hydroperoxide?
Phenol is prepared industrially from cumene (isopropylbenzene).
Consider the single bonds around the C atom.
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13. What type of hybridization is exhibited by the carbon atom bonded to the hydroxyl group in an alcohol?
In alcohols, the carbon atom bonded to the -OH functional group is $sp^3$ hybridized.
This is the versatile reaction discovered in 1850.
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14. Which of the following is the most suitable method for synthesizing both symmetrical and unsymmetrical ethers using an alkyl halide and an alkoxide?
The most common and versatile method for preparing ethers is the Williamson synthesis.
Strong agents like KMnO4 lead to carboxylic acids; milder, selective agents are needed for aldehydes.
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15. Which oxidizing agent is commonly used to convert a primary alcohol into an aldehyde (without further oxidation to carboxylic acid)?
Strong oxidizing agents yield carboxylic acids, but milder or specific reagents are needed to stop at the aldehyde stage. ($text{CrO}_3$ is often used to stop oxidation at the aldehyde stage).
Ethers are systematically named by treating the smaller alkyl group and oxygen as a substituent.
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16. What is the IUPAC nomenclature method for naming ethers?
Ethers are named as alkoxyalkanes in the IUPAC system.
Focus on the number of hydroxyl groups present.
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17. Which class of alcohol includes methanol and ethanol?
Alcohols containing only one hydroxyl (-OH) group are classified as monohydric alcohols.
A specific hydrogen atom is missing in tertiary compounds.
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18. Tertiary alcohols are resistant to oxidation under neutral conditions because:
Tertiary alcohols resist oxidation because the carbon atom bearing the -OH group does not have a hydrogen atom attached directly to it.
Look for the strongest intermolecular force alcohols can form.
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19. Why do alcohols have higher boiling points compared to hydrocarbons of comparable molecular mass?
Alcohols exhibit significantly higher boiling points due to the presence of the -OH group, allowing them to form strong intermolecular hydrogen bonds.
This is a well-known reaction involving formylation of the ring.
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20. Treatment of phenol with aqueous NaOH and CHCl3 followed by acidification yields salicylaldehyde. This reaction is known as:
This reaction, resulting in the introduction of an aldehyde group, is the Reimer-Tiemann reaction.
This name reflects its preparation via destructive distillation.
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21. What is methanol commonly known as, in reference to its historical preparation method?
Methanol ($text{CH}_3text{OH}$) is commonly known as wood spirit.
The -OR group is activating.
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22. Aromatic ethers, such as anisole (methoxybenzene), undergo electrophilic substitution reactions primarily at which ring positions?
The alkoxy group (-OR) is strongly activating and directs electrophiles to the ortho and para positions.
Reaction of RMgX with formaldehyde yields the simplest alcohols.
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23. What is the expected product when formaldehyde reacts with a Grignard reagent (RMgX) followed by hydrolysis?
Reaction of Grignard reagents with formaldehyde yields primary alcohols. Using other aldehydes produces secondary alcohols, and ketones yield tertiary alcohols.
Alkyl halides react with aqueous base or moisture to replace the halogen with -OH.
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24. When an alkyl halide is used as a starting material, which type of reaction typically forms an alcohol?
Alcohols can be prepared from alkyl halides via a substitution reaction, where the halogen is replaced by a hydroxyl group.
Ethers undergo cleavage with strong acids like HI or HBr.
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25. When diethyl ether reacts with cold, concentrated HI, what is the cleavage product?
Ethers undergo C-O bond cleavage upon reaction with HI or HBr, forming alkyl halides. Diethyl ether forms ethyl iodide ($text{CH}_3text{CH}_2text{I}$).
Oxidation of the aromatic ring leads to a dione structure.
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26. What is the final product when phenol is oxidized using chromic acid (Na₂Cr₂O₇ and H2SO4)?
Phenols undergo oxidation to form quinones.
This process changes its tax status and prevents misuse.
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27. What is the primary purpose of adding substances like pyridine or copper sulphate to ethanol to create denatured alcohol?
Denatured alcohol is ethanol made unfit for drinking to prevent consumption and exempt it from heavy excise duties.
This is a highly facile electrophilic substitution reaction.
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28. Phenol reacts readily with bromine water (aqueous Br2) to give a white precipitate of 2,4,6-tribromophenol. This indicates that:
The formation of a tri-substituted product shows that the -OH group strongly activates the ring towards electrophilic substitution (Halogenation of phenol).
Consider how the benzene ring handles the charge of the conjugate base.
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29. The enhanced acidity of phenol compared to ethanol is explained by:
The phenoxide ion, the conjugate base of phenol, is stabilized by resonance, making phenol more acidic than alcohols.
Ethers form via intermolecular dehydration, which requires mild conditions.
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30. What temperature condition favors the formation of an ether over an alkene during the acid-catalyzed dehydration of an alcohol?
Dehydration of alcohols yields ethers at lower temperatures (around 413 K or 140°C), favoring intermolecular dehydration. Higher temperatures (443 K) favor alkene formation.
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