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Alcohols Phenols and Ethers question

2019 · 12 Apr · Shift 2 · Q19
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Alcohols Phenols and Ethers question

2019 · 12 Apr · Shift 2 · Q19

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
What will be the major product when m-cresol is reacted with propargyl bromide (HC ≡\equiv≡ C–CH2BrCH_2BrCH2​Br) in presence of K2CO3K_2CO_3K2​CO3​ in acetone?
  1. A
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Alcohols, Phenols and Ethers Question 125 English Option 1
  2. B
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Alcohols, Phenols and Ethers Question 125 English Option 2
  3. C
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Alcohols, Phenols and Ethers Question 125 English Option 3
  4. D
    JEE Main 2019 (Online) 12th April Evening Slot Chemistry - Alcohols, Phenols and Ethers Question 125 English Option 4
View written solutionFree

Correct answer: A

  1. Identify the reaction conditions

    We have m-cresol reacting with propargyl bromide HC≡C−CH2BrHC\equiv C-CH_2BrHC≡C−CH2​Br in presence of K2CO3K_2CO_3K2​CO3​ in acetone.

    These are standard Williamson ether synthesis conditions:

    • K2CO3K_2CO_3K2​CO3​ acts as a mild base.
    • It deprotonates the phenol to form cresoxide ion.
    • Acetone is a polar aprotic solvent, favoring SN2S_N2SN​2 substitution.
  2. Formation of nucleophile

    m-Cresol is: m−CH3C6H4OHm-CH_3C_6H_4OHm−CH3​C6​H4​OH

    In presence of K2CO3K_2CO_3K2​CO3​, it forms the phenoxide: m−CH3C6H4O−m-CH_3C_6H_4O^-m−CH3​C6​H4​O−

  3. Nature of electrophile

    Propargyl bromide is a primary alkyl halide: HC≡C−CH2BrHC\equiv C-CH_2BrHC≡C−CH2​Br

    Primary halides react readily by SN2S_N2SN​2 with phenoxide ions.

  4. Site of attack

    The phenoxide oxygen attacks the CH2BrCH_2BrCH2​Br carbon of propargyl bromide via SN2S_N2SN​2.

    So the product is: m−CH3C6H4OCH2C≡CHm-CH_3C_6H_4OCH_2C\equiv CHm−CH3​C6​H4​OCH2​C≡CH

    This is m-cresyl propargyl ether.

  5. Why not C-alkylation on the ring?

    Although phenoxide activates the ring, under these conditions:

    • mild base (K2CO3K_2CO_3K2​CO3​),
    • primary alkyl halide,
    • polar aprotic solvent,

    O-alkylation is strongly favored over ring alkylation.

  6. Major product

    Therefore the major product is the propargyl ether of m-cresol: m−CH3C6H4OCH2C≡CH\boxed{m-CH_3C_6H_4OCH_2C\equiv CH}m−CH3​C6​H4​OCH2​C≡CH​

  7. Comparison with stored answer

    The stored correct answer is A. Since the actual option structures are not shown, I infer that option A corresponds to the ether: m−CH3C6H4OCH2C≡CHm-CH_3C_6H_4OCH_2C\equiv CHm−CH3​C6​H4​OCH2​C≡CH

    Hence, my derived answer agrees with the stored answer.

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