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Alcohols Phenols and Ethers question

2023 · Shift 1 · Q7
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Alcohols Phenols and Ethers question

2023 · Shift 1 · Q7

JEE AdvancedChemistryAlcohols Phenols and EthersMCQ+3 / −1
In the given reaction scheme, P\mathbf{P}P is a phenyl alkyl ether, Q\mathbf{Q}Q is an aromatic compound; R\mathbf{R}R and S\mathbf{S}S are the major products. JEE Advanced 2023 Paper 1 Online Chemistry - Alcohols, Phenols and Ethers Question 6 English The correct statement about S\mathbf{S}S is :
  1. A
    It primarily inhibits noradrenaline degrading enzymes.
  2. B
    It inhibits the synthesis of prostaglandin.
  3. C
    It is a narcotic drug.
  4. D
    It is ortho-acetylbenzoic acid.
View written solutionFree

Correct answer: B

  1. Identify the likely reaction sequence

    The final options are about the identity/properties of compound S\mathbf{S}S. Among the options:

    • option A refers to a drug like selegiline / MAO inhibitors,
    • option B refers to aspirin,
    • option C refers to a narcotic drug like heroin/morphine,
    • option D is a chemical name: ortho-acetylbenzoic acid.

    In standard organic chemistry reaction schemes involving a phenyl alkyl ether P\mathbf{P}P giving an aromatic compound Q\mathbf{Q}Q and then a major product S\mathbf{S}S, a very common path is:

    anisole or phenyl alkyl ether→cleavageHIphenol (Q)\text{anisole or phenyl alkyl ether} \xrightarrow[\text{cleavage}]{HI} \text{phenol } (\mathbf{Q})anisole or phenyl alkyl etherHIcleavage​phenol (Q)

    Then phenol on further reaction can lead to salicylic acid and then acetylation gives aspirin.

  2. Interpret the compounds

    Since P\mathbf{P}P is a phenyl alkyl ether, cleavage of aryl-alkyl ether occurs at the alkyl–oxygen bond, producing:

    ArOR→HIArOH+RI\mathrm{ArOR} \xrightarrow{HI} \mathrm{ArOH} + \mathrm{RI}ArORHI​ArOH+RI

    Thus, Q\mathbf{Q}Q is most plausibly phenol, an aromatic compound.

  3. Formation of S\mathbf{S}S from phenol-derived pathway

    A standard sequence is:

    • phenol →\rightarrow→ sodium phenoxide
    • Kolbe reaction →\rightarrow→ salicylic acid
    • acetylation with acetic anhydride →\rightarrow→ acetylsalicylic acid (aspirin)

    Therefore, S\mathbf{S}S is most likely aspirin.

  4. Check the statements about aspirin

    Aspirin acts by inhibiting the enzyme cyclooxygenase, thereby reducing the synthesis of prostaglandins.

    So statement B is correct:

    Aspirin inhibits the synthesis of prostaglandins.\text{Aspirin inhibits the synthesis of prostaglandins.}Aspirin inhibits the synthesis of prostaglandins.

  5. Reject other options

    • A: MAO inhibition is not the action of aspirin.
    • C: Aspirin is not a narcotic drug.
    • D: Aspirin is 2-acetoxybenzoic acid, not ortho-acetylbenzoic acid.
  6. Final answer

    The correct statement about S\mathbf{S}S is Option B.

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