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Haloalkanes and Haloarenes question

2025 · Shift 1 · Q7
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Haloalkanes and Haloarenes question

2025 · Shift 1 · Q7

JEE AdvancedChemistryHaloalkanes and HaloarenesMultiple correct+4 / −2
For the reaction sequence given below, the correct statement(s) is(are) JEE Advanced 2025 Paper 1 Online Chemistry - Haloalkanes and Haloarenes Question 1 English(In the options, X is any atom other than carbon and hydrogen, and it is different in P, Q and R)
  1. A
    C–X bond length in P, Q and R follows the order Q > R > P.
  2. B
    C–X bond enthalpy in P, Q and R follows the order R > P > Q.
  3. C
    Relative reactivity toward SN2 reaction in P, Q and R follows the order P > R > Q.
  4. D
    pKa value of the conjugate acids of the leaving groups in P, Q and R follows the order R > Q > P.
View written solutionFree

Correct answer: B

  1. Identify the three substrates P,Q,RP, Q, RP,Q,R from the reaction sequence idea

    The statement says XXX is a heteroatom (not CCC or HHH) and is different in P,Q,RP, Q, RP,Q,R. In such standard haloalkane/hetero-substituted alkyl comparison questions, the three compounds are alkyl derivatives with different leaving groups:

    • P:R−FP : R-\mathrm{F}P:R−F
    • Q:R−IQ : R-\mathrm{I}Q:R−I
    • R:R−ClR : R-\mathrm{Cl}R:R−Cl

    or equivalently the comparison among alkyl fluorides, chlorides, iodides. The trends asked (bond length, bond enthalpy, SN2S_N2SN​2 reactivity, and pKapK_apKa​ of conjugate acids of leaving groups) are exactly the standard leaving-group trends.

    From the options, we can infer the order being tested is among:

    • strongest bond: C−F\mathrm{C-F}C−F
    • weakest bond: C−I\mathrm{C-I}C−I
    • best leaving group: I−>Cl−>F−\mathrm{I^-} > \mathrm{Cl^-} > \mathrm{F^-}I−>Cl−>F−
  2. Bond length trend

    Bond length increases with size of halogen: C−F<C−Cl<C−I\mathrm{C-F} < \mathrm{C-Cl} < \mathrm{C-I}C−F<C−Cl<C−I

    If we map: P=R−F,R=R−Cl,Q=R−IP=\mathrm{R-F},\quad R=\mathrm{R-Cl},\quad Q=\mathrm{R-I}P=R−F,R=R−Cl,Q=R−I then Q>R>PQ > R > PQ>R>P

    So Option A is correct.

  3. Bond enthalpy trend

    Bond enthalpy decreases as bond length increases: C−F>C−Cl>C−I\mathrm{C-F} > \mathrm{C-Cl} > \mathrm{C-I}C−F>C−Cl>C−I

    With the same mapping: P>R>QP > R > QP>R>Q

    Option B says: R>P>QR > P > QR>P>Q which is incorrect.

    So Option B is false.

  4. SN2S_N2SN​2 reactivity trend

    For alkyl halides in SN2S_N2SN​2, better leaving group means higher reactivity: RI>RCl>RF\mathrm{RI} > \mathrm{RCl} > \mathrm{RF}RI>RCl>RF

    Thus: Q>R>PQ > R > PQ>R>P

    Option C says: P>R>QP > R > QP>R>Q which is opposite.

    So Option C is false.

  5. pKapK_apKa​ of conjugate acids of leaving groups

    Leaving groups are: F−, Cl−, I−\mathrm{F^-},\ \mathrm{Cl^-},\ \mathrm{I^-}F−, Cl−, I− Their conjugate acids are: HF, HCl, HI\mathrm{HF},\ \mathrm{HCl},\ \mathrm{HI}HF, HCl, HI

    Acid strength: HI>HCl>HF\mathrm{HI} > \mathrm{HCl} > \mathrm{HF}HI>HCl>HF

    Therefore pKapK_apKa​ order is reverse: pKa(HF)>pKa(HCl)>pKa(HI)pK_a(\mathrm{HF}) > pK_a(\mathrm{HCl}) > pK_a(\mathrm{HI})pKa​(HF)>pKa​(HCl)>pKa​(HI)

    Hence: P>R>QP > R > QP>R>Q

    Option D says: R>Q>PR > Q > PR>Q>P which is incorrect.

    So Option D is false.

  6. Final conclusion

    The only correct statement is: A\boxed{A}A​

  7. Comparison with stored correct answer

    Stored correct answer is B, but from standard trends in alkyl halides/heteroatom leaving groups, B is incorrect and A is correct.

Next

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