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The oxidation of toluene to benzoic acid can be stopped at the aldehyde stage, to give benzadehyde, The reagent used for the purpose is one of the following.
- a)Chromyl chloride
- b)Carbon monoxide and hydrogen chloride
- c)Chlorine
- d)Chromic oxide
Correct answer is option 'A'. Can you explain this answer?
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The oxidation of toluene to benzoic acid can be stopped at the aldehyd...
This is Etard Reaction.
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The oxidation of toluene to benzoic acid can be stopped at the aldehyd...
The oxidation of toluene to benzoic acid can be stopped at the aldehyde stage, to give benzaldehyde, using chromyl chloride as the reagent.
Explanation:
Toluene can be oxidized to benzoic acid through a two-step process. The first step involves the oxidation of toluene to benzaldehyde, and the second step involves the further oxidation of benzaldehyde to benzoic acid.
In order to stop the oxidation at the aldehyde stage and obtain benzaldehyde, a selective oxidizing agent is required. Chromyl chloride (CrO2Cl2) is one such reagent that can selectively oxidize toluene to benzaldehyde without further oxidation to benzoic acid.
Chromyl Chloride (CrO2Cl2):
Chromyl chloride is a dark red, volatile, and toxic compound. It is a powerful oxidizing agent that contains a chromium(VI) center. It can be prepared by reacting chromate(VI) salts with concentrated hydrochloric acid. Chromyl chloride is commonly used in organic chemistry for selective oxidations.
Mechanism:
The oxidation of toluene to benzaldehyde using chromyl chloride proceeds through a free radical mechanism. The chromyl chloride molecule is reduced to chromic chloride (CrCl3) during the reaction. The mechanism involves the following steps:
1. Initiation: The reaction is initiated by the homolytic cleavage of chromyl chloride to yield a chlorine radical (Cl•) and a chromium(V) species (CrO2•):
CrO2Cl2 → Cl• + CrO2•
2. Propagation: The chlorine radical abstracts a hydrogen atom from the methyl group of toluene, forming a benzyl radical:
Cl• + CH3C6H5 → HCl + CH2C6H5•
3. Termination: The benzyl radical reacts with another chromyl chloride molecule, leading to the formation of benzaldehyde and the regeneration of the chromium(VI) species:
CH2C6H5• + CrO2Cl2 → CH2C6H5CHO + CrCl3
The use of chromyl chloride as the reagent allows for the selective oxidation of toluene to benzaldehyde, as further oxidation to benzoic acid does not occur. This is because the benzaldehyde formed is not a strong enough reducing agent to reduce the chromium(VI) species back to chromyl chloride.
Therefore, option A, chromyl chloride, is the correct reagent to stop the oxidation of toluene at the aldehyde stage and obtain benzaldehyde.
Explanation:
Toluene can be oxidized to benzoic acid through a two-step process. The first step involves the oxidation of toluene to benzaldehyde, and the second step involves the further oxidation of benzaldehyde to benzoic acid.
In order to stop the oxidation at the aldehyde stage and obtain benzaldehyde, a selective oxidizing agent is required. Chromyl chloride (CrO2Cl2) is one such reagent that can selectively oxidize toluene to benzaldehyde without further oxidation to benzoic acid.
Chromyl Chloride (CrO2Cl2):
Chromyl chloride is a dark red, volatile, and toxic compound. It is a powerful oxidizing agent that contains a chromium(VI) center. It can be prepared by reacting chromate(VI) salts with concentrated hydrochloric acid. Chromyl chloride is commonly used in organic chemistry for selective oxidations.
Mechanism:
The oxidation of toluene to benzaldehyde using chromyl chloride proceeds through a free radical mechanism. The chromyl chloride molecule is reduced to chromic chloride (CrCl3) during the reaction. The mechanism involves the following steps:
1. Initiation: The reaction is initiated by the homolytic cleavage of chromyl chloride to yield a chlorine radical (Cl•) and a chromium(V) species (CrO2•):
CrO2Cl2 → Cl• + CrO2•
2. Propagation: The chlorine radical abstracts a hydrogen atom from the methyl group of toluene, forming a benzyl radical:
Cl• + CH3C6H5 → HCl + CH2C6H5•
3. Termination: The benzyl radical reacts with another chromyl chloride molecule, leading to the formation of benzaldehyde and the regeneration of the chromium(VI) species:
CH2C6H5• + CrO2Cl2 → CH2C6H5CHO + CrCl3
The use of chromyl chloride as the reagent allows for the selective oxidation of toluene to benzaldehyde, as further oxidation to benzoic acid does not occur. This is because the benzaldehyde formed is not a strong enough reducing agent to reduce the chromium(VI) species back to chromyl chloride.
Therefore, option A, chromyl chloride, is the correct reagent to stop the oxidation of toluene at the aldehyde stage and obtain benzaldehyde.
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The oxidation of toluene to benzoic acid can be stopped at the aldehyde stage,to give benzadehyde, The reagent used for the purpose is one of the following.a)Chromyl chlorideb)Carbon monoxide and hydrogen chloridec)Chlorined)Chromic oxideCorrect answer is option 'A'. Can you explain this answer?
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