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Aldehydes Ketones and Carboxylic Acids question

2019 · 9 Jan · Shift 2 · Q4
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Aldehydes Ketones and Carboxylic Acids question

2019 · 9 Jan · Shift 2 · Q4

JEE MainChemistryAldehydes Ketones and Carboxylic AcidsMCQ+4 / −1
The products formed in the reaction of cumene with O2O_2O2​ followed by treatment with dil. HClHClHCl are :
  1. A
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 209 English Option 1
  2. B
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 209 English Option 2
  3. C
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 209 English Option 3
  4. D
    JEE Main 2019 (Online) 9th January Evening Slot Chemistry - Aldehydes, Ketones and Carboxylic Acids Question 209 English Option 4
View written solutionFree

Correct answer: C

  1. Identify the reaction

    Cumene is isopropyl benzene: C6H5−CH(CH3)2\mathrm{C_6H_5-CH(CH_3)_2}C6​H5​−CH(CH3​)2​

    When cumene is treated with oxygen, it undergoes autoxidation to form cumene hydroperoxide.

    C6H5−CH(CH3)2→O2C6H5−C(CH3)2−OOH\mathrm{C_6H_5-CH(CH_3)_2 \xrightarrow{O_2} C_6H_5-C(CH_3)_2-OOH}C6​H5​−CH(CH3​)2​O2​​C6​H5​−C(CH3​)2​−OOH

  2. Acidic cleavage of cumene hydroperoxide

    On treatment with dilute acid (here dil. HCl), cumene hydroperoxide undergoes cleavage, known as the cumene process.

    The products are:

    • Phenol: C6H5OH\mathrm{C_6H_5OH}C6​H5​OH
    • Acetone: CH3COCH3\mathrm{CH_3COCH_3}CH3​COCH3​

    Overall reaction: C6H5−CH(CH3)2→dil. HClO2C6H5OH+CH3COCH3\mathrm{C_6H_5-CH(CH_3)_2 \xrightarrow[\text{dil. HCl}]{O_2} C_6H_5OH + CH_3COCH_3}C6​H5​−CH(CH3​)2​O2​dil. HCl​C6​H5​OH+CH3​COCH3​

  3. Conclusion

    Therefore, the products formed are: Phenol and acetone\boxed{\text{Phenol and acetone}}Phenol and acetone​

  4. Comparison with stored answer

    The stored correct answer is C. Since the cumene process gives phenol and acetone, option C must correspond to these products.

    Hence, my derived answer agrees with the stored answer.

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