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Haloalkanes and Haloarenes question

2006 · Shift 0 · Q13
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  5. /2006 · Shift 0 · Q13

Haloalkanes and Haloarenes question

2006 · Shift 0 · Q13

JEE MainChemistryHaloalkanes and HaloarenesMCQ+4 / −1
Fluorobenzene (C6H5FC_6H_5FC6​H5​F) can be synthesized in the laboratory
  1. A
    by heating phenol with HF and KF
  2. B
    from aniline by diazotisation followed by heating the diazonium salt with HBF4HBF_4HBF4​
  3. C
    by direct fluorination of benzene with F2F_2F2​ gas
  4. D
    by reacting bromobenzene with NaF solution
View written solutionFree

Correct answer: B

  1. Identify the reliable laboratory method for preparing fluorobenzene

    Aryl fluorides are not usually prepared by simple nucleophilic substitution on haloarenes, because the C−FC-FC−F bond is very strong and direct fluorination with F2F_2F2​ is too violent and uncontrolled.

    The standard laboratory method is the Balz–Schiemann reaction:

    • Convert aniline to benzene diazonium salt by diazotisation.
    • Treat with HBF4HBF_4HBF4​ to form benzene diazonium tetrafluoroborate.
    • On heating, it decomposes to give fluorobenzene.

    C6H5NH2→0−5∘CNaNO2/HClC6H5N2+Cl−C_6H_5NH_2 \xrightarrow[0-5^\circ C]{NaNO_2/HCl} C_6H_5N_2^+Cl^-C6​H5​NH2​NaNO2​/HCl0−5∘C​C6​H5​N2+​Cl− C6H5N2+Cl−+HBF4→C6H5N2+BF4−C_6H_5N_2^+Cl^- + HBF_4 \rightarrow C_6H_5N_2^+BF_4^-C6​H5​N2+​Cl−+HBF4​→C6​H5​N2+​BF4−​ C6H5N2+BF4−→ΔC6H5F+BF3+N2C_6H_5N_2^+BF_4^- \xrightarrow{\Delta} C_6H_5F + BF_3 + N_2C6​H5​N2+​BF4−​Δ​C6​H5​F+BF3​+N2​

  2. Evaluate each option

    A: by heating phenol with HF and KF

    • Phenol does not get converted directly to fluorobenzene by this method.
    • The −OH-OH−OH group in phenol is not replaced by FFF under these conditions.
    • Incorrect.

    B: from aniline by diazotisation followed by heating the diazonium salt with HBF4HBF_4HBF4​

    • This is exactly the Balz–Schiemann reaction, the standard laboratory preparation of fluorobenzene.
    • Correct.

    C: by direct fluorination of benzene with F2F_2F2​ gas

    • Direct fluorination is highly reactive, explosive, and not a controlled laboratory method for preparing fluorobenzene.
    • Incorrect.

    D: by reacting bromobenzene with NaF solution

    • Haloarenes do not undergo such simple halogen exchange with NaFNaFNaF solution.
    • Incorrect.
  3. Final answer

    The correct option is: B\boxed{\text{B}}B​

  4. Comparison with stored correct answer

    Stored correct answer = B.

    My derived answer also = B.

    Therefore, they agree.

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