- A
- B
- C
- D
View written solutionFree
Correct answer: C
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We compare acidity by stability of the conjugate base.
For each compound, the acidic proton is the hydrogen attached to carbon. On deprotonation:
The stronger acid is the one whose conjugate base is more stabilized.
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Examine each option.
(A)
Its conjugate base is . The three bromine atoms exert a (electron-withdrawing inductive) effect, which stabilizes the negative charge.
(B)
Its conjugate base is . Iodine also shows a effect, but it is weaker than bromine and chlorine due to lower electronegativity. So is less acidic than and .
(D)
Its conjugate base is . Chlorine has a stronger effect than bromine and iodine, so among haloforms:
in acidity.
(C)
Its conjugate base is . Each group is a very strong electron-withdrawing group due to both:
- strong inductive effect (), and
- additional stabilization because the adjacent nitrile groups strongly delocalize/polarize electron density.
Thus the carbanion is much more stabilized than in haloforms.
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Compare overall acid strengths.
Since is much more electron-withdrawing than halogens, three cyano groups stabilize the conjugate base far more effectively than three halogens.
Therefore:
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Option check
- (A) — not strongest
- (B) — not strongest
- (C) — strongest
- (D) — stronger than (A), (B) but weaker than (C)
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Final answer
The strongest acid is:
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