Question:
Cumene is industrially used for the preparation of phenol. During the manufacture of phenol from cumene, which of the following compounds is obtained as a valuable by-product?
Cumene is industrially used for the preparation of phenol. During the manufacture of phenol from cumene, which of the following compounds is obtained as a valuable by-product?
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Always remember the industrial reaction:
\[
\text{Cumene}
\rightarrow
\text{Phenol + Acetone}
\]
CUET frequently asks either the by-product or the intermediate (cumene hydroperoxide) involved in this process.
Updated On: Jun 8, 2026
- Acetaldehyde
- Acetone
- Formaldehyde
- Benzaldehyde
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Verified By Collegedunia
The Correct Option is B
Solution and Explanation
Concept:
The industrial preparation of phenol from cumene is one of the most important commercial processes discussed in NCERT Organic Chemistry. This method is commonly known as the Cumene Process or Hock Process. The process involves oxidation of cumene followed by acidic hydrolysis of the intermediate hydroperoxide.
Students often focus only on the formation of phenol, but CUET frequently asks conceptual questions regarding the by-products formed during industrial reactions.
The complete reaction sequence is:
\[
\text{Cumene}
\xrightarrow{O_2}
\text{Cumene Hydroperoxide}
\xrightarrow{H^+}
\text{Phenol + Acetone}
\]
Thus, both phenol and acetone are important products obtained from this industrial process.
Step 1: Formation of cumene hydroperoxide.
Cumene is isopropyl benzene. Its structure is: \[ C_6H_5CH(CH_3)_2 \] When exposed to air in the presence of oxygen, oxidation occurs to form cumene hydroperoxide. \[ C_6H_5CH(CH_3)_2 \xrightarrow{O_2} C_6H_5C(CH_3)_2OOH \] This intermediate is highly reactive.
Step 2: Acidic cleavage of hydroperoxide.
The hydroperoxide undergoes acid-catalyzed rearrangement. The O-O bond breaks and molecular rearrangement occurs. As a result: \[ C_6H_5C(CH_3)_2OOH \xrightarrow{H^+} C_6H_5OH + (CH_3)_2CO \] Products obtained are: \[ \text{Phenol} \] and \[ \text{Acetone} \]
Step 3: Analysis of all options.
• Acetaldehyde is not produced during the cumene process.
• Acetone is formed directly along with phenol.
• Formaldehyde is not generated in this reaction.
• Benzaldehyde is not formed during hydroperoxide cleavage. Hence the correct answer is: \[ \boxed{\text{Acetone}} \]
Step 1: Formation of cumene hydroperoxide.
Cumene is isopropyl benzene. Its structure is: \[ C_6H_5CH(CH_3)_2 \] When exposed to air in the presence of oxygen, oxidation occurs to form cumene hydroperoxide. \[ C_6H_5CH(CH_3)_2 \xrightarrow{O_2} C_6H_5C(CH_3)_2OOH \] This intermediate is highly reactive.
Step 2: Acidic cleavage of hydroperoxide.
The hydroperoxide undergoes acid-catalyzed rearrangement. The O-O bond breaks and molecular rearrangement occurs. As a result: \[ C_6H_5C(CH_3)_2OOH \xrightarrow{H^+} C_6H_5OH + (CH_3)_2CO \] Products obtained are: \[ \text{Phenol} \] and \[ \text{Acetone} \]
Step 3: Analysis of all options.
• Acetaldehyde is not produced during the cumene process.
• Acetone is formed directly along with phenol.
• Formaldehyde is not generated in this reaction.
• Benzaldehyde is not formed during hydroperoxide cleavage. Hence the correct answer is: \[ \boxed{\text{Acetone}} \]
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