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Basics of Organic Chemistry question

2019 · 9 Jan · Shift 1 · Q7
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Basics of Organic Chemistry question

2019 · 9 Jan · Shift 1 · Q7

JEE MainChemistryBasics of Organic ChemistryMCQ+4 / −1
Which amongst the following is the strongest acid ?
  1. A
    CHBr3CHBr_3CHBr3​
  2. B
    CHI3CHI_3CHI3​
  3. C
    CH(CN)3CH(CN)_3CH(CN)3​
  4. D
    CHCl3CHCl_3CHCl3​
View written solutionFree

Correct answer: C

  1. We compare acidity by stability of the conjugate base.

    For each compound, the acidic proton is the hydrogen attached to carbon. On deprotonation:

    R-CH→R-C−+H+\text{R-CH} \rightarrow \text{R-C}^- + H^+R-CH→R-C−+H+

    The stronger acid is the one whose conjugate base is more stabilized.

  2. Examine each option.

    (A) CHBr3CHBr_3CHBr3​

    Its conjugate base is CBr3−CBr_3^-CBr3−​. The three bromine atoms exert a −I-I−I (electron-withdrawing inductive) effect, which stabilizes the negative charge.

    (B) CHI3CHI_3CHI3​

    Its conjugate base is CI3−CI_3^-CI3−​. Iodine also shows a −I-I−I effect, but it is weaker than bromine and chlorine due to lower electronegativity. So CHI3CHI_3CHI3​ is less acidic than CHBr3CHBr_3CHBr3​ and CHCl3CHCl_3CHCl3​.

    (D) CHCl3CHCl_3CHCl3​

    Its conjugate base is CCl3−CCl_3^-CCl3−​. Chlorine has a stronger −I-I−I effect than bromine and iodine, so among haloforms:

    CHCl3>CHBr3>CHI3CHCl_3 > CHBr_3 > CHI_3CHCl3​>CHBr3​>CHI3​

    in acidity.

    (C) CH(CN)3CH(CN)_3CH(CN)3​

    Its conjugate base is (CN)3C−(CN)_3C^-(CN)3​C−. Each −CN-CN−CN group is a very strong electron-withdrawing group due to both:

    • strong inductive effect (−I-I−I), and
    • additional stabilization because the adjacent nitrile groups strongly delocalize/polarize electron density.

    Thus the carbanion is much more stabilized than in haloforms.

  3. Compare overall acid strengths.

    Since −CN-CN−CN is much more electron-withdrawing than halogens, three cyano groups stabilize the conjugate base far more effectively than three halogens.

    Therefore:

    CH(CN)3 is the strongest acidCH(CN)_3 \text{ is the strongest acid}CH(CN)3​ is the strongest acid

  4. Option check

    • (A) CHBr3CHBr_3CHBr3​ — not strongest
    • (B) CHI3CHI_3CHI3​ — not strongest
    • (C) CH(CN)3CH(CN)_3CH(CN)3​ — strongest
    • (D) CHCl3CHCl_3CHCl3​ — stronger than (A), (B) but weaker than (C)
  5. Final answer

    The strongest acid is:

    CH(CN)3\boxed{CH(CN)_3}CH(CN)3​​

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