(a)
Interpretation:
The reactivity of cyclohexanol and phenol with aqueous
Concept introduction:
The phenol is an aromatic compound having a formula,
Answer to Problem 18.53AP
Phenol is more reactive than cyclohexanol with an aqueous
Explanation of Solution
The sodium hydroxide is a strong base. It abstracts a proton from the stronger acidic compound and forms its sodium salt. In the given case, sodium hydroxide abstracts a proton from phenol and cyclohexanol and form phenoxide ion and cyclohexanol conjugate base respectively. The phenoxide ion gets stabilized by resonance structures, but this is not possible in case of cyclohexanol conjugate base. It is known that more the stability of the conjugate base more the acidity of the compound. In the given case, phenoxide ion is more stable due to this phenoxide is more acidic. Therefore, phenoxide ion is more reactive toward an aqueous
Figure 1
The reactivity of phenol is more as compared to cyclohexanol with an aqueous solution of
(b)
Interpretation:
The reactivity of cyclohexanol and phenol with
Concept introduction:
The phenol is an aromatic compound having a formula,
Answer to Problem 18.53AP
Phenol is more reactive than cyclohexanol with an aqueous
Explanation of Solution
The sodium hydride is a strong base. It abstracts a proton from the stronger acidic compound and forms its sodium salt and hydrogen gas is evolved. In the given case, sodium hydroxide abstracts a proton from phenol and cyclohexanol and form phenoxide ion and cyclohexanol conjugate base respectively. The phenoxide ion gets stabilized by resonance structures, but this is not possible in case of cyclohexanol conjugate base. It is known that more the stability of the conjugate base more the acidity of the compound. In the given case, phenoxide ion is more stable due to this phenoxide is more acidic. Therefore, phenoxide ion is more reactive toward an aqueous
Figure 2
The reactivity of phenol is more as compared to cyclohexanol with an aqueous solution of
(c)
Interpretation:
The reactivity of cyclohexanol and phenol with triflic anhydride in pyridine at
Concept introduction:
The triflic anhydride is a chemical compound which is also known as Trifluoromethanesulfonic anhydride. It has a molecular formula
Answer to Problem 18.53AP
The presence of the more nucleophilic character of cyclohexanol makes it more reactive towards triflic anhydride in pyridine at
Explanation of Solution
In the given case, when triflic acid reacts with cyclohexanol and phenol in the presence of pyridine at
Figure 3
The reactivity of cyclohexanol is more as compared to phenol with triflic acid in pyridine at
(d)
Interpretation:
The reactivity of cyclohexanol and phenol with concentrated aqueous
Concept introduction:
The phenol is an aromatic compound having a formula,
Answer to Problem 18.53AP
The deactivation of the aromatic ring of phenol makes it less reactive toward concentrated aqueous
Explanation of Solution
Cyclohexanol is more nucleophilic as compared to phenol. It is due to the participation of the lone pair of electrons on oxygen in resonance structures of phenol. Therefore, in the given conditions cyclohexanol reacts more rapidly as compared to phenol. When cyclohexanol undergoes protonation in the presence of
Figure 4
In the case of phenol, it undergoes electrophilic aromatic substitution reaction with
The reactivity of phenol is less with concentrated aqueous
(e)
Interpretation:
The reactivity of cyclohexanol and phenol with
Concept introduction:
The phenol is an aromatic compound having a formula,
Answer to Problem 18.53AP
The phenol is more reactive toward
Explanation of Solution
The phenol is an aromatic compound which shows similar reactions as
Figure 5
Whereas no such reaction is possible with cyclohexanol because this compound gives addition reaction.
The phenol is an aromatic compound which undergoes electrophilic substitution reaction. Due to this, it is more reactive toward
(f)
Interpretation:
The reactivity of cyclohexanol and phenol with
Concept introduction:
Oxidation is defined as the addition of oxygen atom or removal of the hydrogen atom. The oxidizing agent is the substance that causes oxidation and itself get reduced. The reagent
Answer to Problem 18.53AP
The phenol is an aromatic compound which loses its aromatic character on reaction with
Explanation of Solution
In the given conditions, both the given compounds undergo an oxidation reaction. The reaction of cyclohexanol with
Figure 6
The reaction of phenol with
Figure 7
When phenol undergoes oxidation reaction, it loses its aromatic character which means it loses its stability. Therefore, cyclohexanol is more reactive toward
The phenol on reaction with
(g)
Interpretation:
The reactivity of cyclohexanol and phenol with
Concept introduction:
The phenol is an aromatic compound having a formula,
Answer to Problem 18.53AP
The deactivation of the aromatic ring of phenol due to protonation of the hydroxyl group makes it less reactive toward
Explanation of Solution
Cyclohexanol is more nucleophilic as compared to phenol. It is due to the participation of the lone pair of electrons on oxygen in resonance structures of phenol. Therefore, in the given conditions cyclohexanol reacts more rapidly as compared to phenol. When cyclohexanol undergoes protonation in the presence of
Figure 8
The less nucleophilic character makes phenol less reactive toward
The reactivity of phenol is less with
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Chapter 18 Solutions
Organic Chemistry
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- Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning