Alcohols, Phenols & Ethers

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| By Tanmay Shankar

Tanmay Shankar

Community Contributor

Quizzes Created: 491 | Total Attempts: 1,783,262

Questions: 15 | Attempts: 3,008 | Updated: Apr 1, 2024

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Chemical reactions are part and parcel to chemistry. Do you think that you know about alcohols phenols and ethers? Take the quiz below and find out how much you really know about them. All the best.

Questions and Answers

1.

The structure of iso-butyl alcohol is:
- A.
- B.
- C.
- D.
Correct Answer
B.

Explanation
The structure of iso-butyl alcohol is a branched chain compound with a hydroxyl group (-OH) attached to the second carbon atom in the chain. It has four carbon atoms in total, with three of them forming a linear chain and the fourth carbon branching off from the second carbon. The presence of the hydroxyl group makes it an alcohol.

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2.

Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields.
- A.
  
  O- Cresol
- B.
  
  M- Cresol
- C.
  
  2, 4- Dihydroxytoulene
- D.
  
  Benzyl alcohol
Correct Answer
D. Benzyl alcohol

Explanation
The monochlorination of toluene in sunlight results in the formation of benzyl chloride. When benzyl chloride is hydrolyzed with aqueous sodium hydroxide (NaOH), it undergoes a nucleophilic substitution reaction to form benzyl alcohol. Therefore, the correct answer is benzyl alcohol.

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3.

The process of converting alkyl halides into alcohols involves:
- A.
  
  Addition Reaction
- B.
  
  Substitution Reaction
- C.
  
  Dehydrohalogenation Reaction
- D.
  
  Rearrangement Reaction
Correct Answer
B. Substitution Reaction

Explanation
The process of converting alkyl halides into alcohols involves substitution reaction. In this reaction, the halogen atom of the alkyl halide is replaced by a hydroxyl group (-OH) to form an alcohol. This substitution reaction occurs through the nucleophilic attack of a hydroxide ion (OH-) on the carbon atom bonded to the halogen. The halogen is displaced and replaced by the hydroxyl group, resulting in the formation of an alcohol.

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4.

The reaction which involves dicholrocabene as an electrophile is:
- A.
  
  Reimer-Teimann Reaction
- B.
  
  Kolbe’s Reaction
- C.
  
  Freidel–Craft’s Acylation
- D.
  
  Kolbe–Schmidt Reaction
Correct Answer
A. Reimer-Teimann Reaction

Explanation
The Reimer-Teimann reaction involves the use of dichlorocarbene as an electrophile. In this reaction, a phenol or an enolizable aldehyde or ketone reacts with chloroform in the presence of a base to form a carbonyl compound with a substituted hydroxyl group. The dichlorocarbene acts as an electrophile by attacking the carbon of the carbonyl group, leading to the formation of a new carbon-carbon bond. This reaction is commonly used for the synthesis of salicylaldehydes and salicylic acids.

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5.

Guess the compound A:
- A.
- B.
- C.
- D.
Correct Answer
C.
6.

Anisole reacts with Br₂ in ethanoic acid, predominantly give:
- A.
  
  Only p- bromoanisole
- B.
  
  2, 4, 6- tribromo anisole
- C.
  
  Mixture of o- bromoanisole and p- bromoanisole
- D.
  
  Only o- bromoanisole
Correct Answer
A. Only p- bromoanisole

Explanation
Anisole reacts with Br2 in ethanoic acid to predominantly give only p-bromoanisole. This is because the reaction follows an electrophilic aromatic substitution mechanism, where the bromine molecule acts as the electrophile. The bromine molecule attacks the benzene ring of anisole, and due to the presence of electron-donating methoxy group (-OCH3), the attack occurs at the para position, resulting in the formation of p-bromoanisole as the major product. The ortho position is less favored due to steric hindrance caused by the methoxy group. Therefore, the reaction predominantly produces only p-bromoanisole.

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7.

In the following compounds:
- A.
  
  III > IV > I > II
- B.
  
  I > IV > III > II
- C.
  
  II > I > III > IV
- D.
  
  IV >III > I > II
Correct Answer
D. IV >III > I > II

Explanation
The given answer suggests that compound IV is the most reactive, followed by compound III, compound I, and finally compound II. This order is determined by the reactivity of the compounds, with compound IV being the most reactive and compound II being the least reactive.

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8.

Phenol on nitration with conc. HNO₃ form:
- A.
  
  2-nitrophenol
- B.
  
  4-nitrophenol
- C.
  
  3-nitrophenol
- D.
  
  2,4.6-nitrophenol
Correct Answer
B. 4-nitrophenol

Explanation
When phenol undergoes nitration with concentrated nitric acid (HNO3), it results in the formation of 4-nitrophenol. This is a chemical reaction where a nitro group (-NO2) is added to the ortho position of the phenolic ring, producing 4-nitrophenol as the major product.

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9.

The reaction of sodium benezene sulphonate with NaOH followed by acidification gives:
- A.
  
  Phenol
- B.
  
  Benzoic Acid
- C.
  
  Benzene
- D.
  
  1,2-dihydroxy benzene
Correct Answer
A. Phenol

Explanation
When sodium benzene sulphonate reacts with NaOH, it forms sodium phenoxide. This is because the sodium ion from NaOH replaces the hydrogen ion in the sulphonate group, resulting in the formation of sodium phenoxide. When this solution is acidified, the phenoxide ion accepts a proton from the acid, forming phenol. Therefore, the correct answer is Phenol.

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10.

Haloform reaction does not take place with:
- A.
  
  Acetone
- B.
  
  2-chloropropane
- C.
  
  Ethanol
- D.
  
  Methanol
Correct Answer
C. Ethanol

Explanation
The haloform reaction, a type of halogenation reaction, does not occur with ethanol because it lacks a methyl ketone group (CH3-CO-), which is essential for the formation of the haloform product. This reaction typically involves methyl ketones like acetone, not alcohols such as ethanol.

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11.

Propene on hydroboration-oxidation produces:
- A.
  
  CH₃CH₂CH₂OH
- B.
  
  CH₃CHOHCH₂OH
- C.
  
  CH₃CH₂CHO
- D.
  
  CH₃CHOHCH₃
Correct Answer
A. CH₃CH₂CH₂OH

Explanation
Propene on hydroboration-oxidation undergoes anti-Markovnikov addition, where the boron atom adds to the less substituted carbon atom, resulting in the formation of an alcohol. In this case, the less substituted carbon atom is the terminal carbon, so the boron atom adds to it. After oxidation, the boron atom is replaced by a hydroxyl group (OH), resulting in the formation of CH3CH2CH2OH, which is the correct answer.

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12.

Among the following compounds, strongest acid is:
- A.
- B.
  
  C₆H₆
- C.
  
  C₂H₆
- D.
  
  CH₃OH
Correct Answer
D. CH₃OH

Explanation
The strongest acid among the given compounds is CH3OH (methanol). Methanol is a weak acid but it is stronger than the other two compounds listed. C6H6 (benzene) is a nonpolar compound and does not have any acidic properties. C2H6 (ethane) is also a nonpolar compound and does not exhibit any acidic behavior. Methanol, on the other hand, can donate a proton (H+) and therefore has weak acidic properties.

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13.

Among the following four compounds: (i) Phenol (ii) Methylphenol (iii) meta-nitrophenol (iv) para-nitrophenol The decreasing acidity order is:
- A.
  
  (iv) > (iii) > (i) > (ii)
- B.
  
  (iii) > (iv) > (i) > (ii)
- C.
  
  (i) > (iv) > (iii) > (ii)
- D.
  
  (ii) > (i) > (iii) > (iv)
Correct Answer
A. (iv) > (iii) > (i) > (ii)

Explanation
The correct answer is (iv) > (iii) > (i) > (ii). This is because the acidity of a compound is determined by the stability of its conjugate base. In this case, para-nitrophenol (iv) has the highest acidity because the nitro group stabilizes the negative charge on the phenoxide ion through resonance. Meta-nitrophenol (iii) is next in acidity because the nitro group can still stabilize the negative charge, although to a lesser extent. Phenol (i) is less acidic than the nitrophenols because it lacks any electron-withdrawing groups to stabilize the negative charge. Methylphenol (ii) is the least acidic because the methyl group does not have any electron-withdrawing effect.

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14.

During dehydration of alcohols to alkenes by heating with conc. H₂SO₄, the initial step is:
- A.
  
  Formation of an ester
- B.
  
  Protonation of alcohol molecule
- C.
  
  Formation of carbocation
- D.
  
  Elimination of water
Correct Answer
B. Protonation of alcohol molecule

Explanation
In the dehydration of alcohols to alkenes, the initial step is the protonation of the alcohol molecule. This involves the transfer of a proton from the concentrated sulfuric acid (H2SO4) to the alcohol molecule, resulting in the formation of a protonated alcohol. This protonation increases the electrophilicity of the alcohol molecule, making it more susceptible to elimination of water and formation of a carbocation. Therefore, the correct answer is the protonation of the alcohol molecule.

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15.

What are the products of the following reactions?
- A.
- B.
- C.
- D.
Correct Answer
A.

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Current Version
Apr 01, 2024

Quiz Edited by
ProProfs Editorial Team
Jan 23, 2014

Quiz Created by
Tanmay Shankar

Alcohols, Phenols & Ethers

The structure of iso-butyl alcohol is:

Monochlorination of toluene in sunlight followed by hydrolysis with aq. NaOH yields.

The process of converting alkyl halides into alcohols involves:

The reaction which involves dicholrocabene as an electrophile is:

Guess the compound A:

Anisole reacts with Br2 in ethanoic acid, predominantly give:

In the following compounds:

Phenol on nitration with conc. HNO3 form:

The reaction of sodium benezene sulphonate with NaOH followed by acidification gives:

Haloform reaction does not take place with:

Propene on hydroboration-oxidation produces:

Among the following compounds, strongest acid is:

Among the following four compounds: (i) Phenol (ii) Methylphenol (iii) meta-nitrophenol (iv) para-nitrophenol The decreasing acidity order is:

During dehydration of alcohols to alkenes by heating with conc. H2SO4, the initial step is:

What are the products of the following reactions?

Anisole reacts with Br₂ in ethanoic acid, predominantly give:

Phenol on nitration with conc. HNO₃ form:

During dehydration of alcohols to alkenes by heating with conc. H₂SO₄, the initial step is: