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ChemistryJEE MainClass 11Medium

The incorrect statement(s) regarding species is

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Quick Answer
Option D

If is , then species should be polar and planar

Let's analyze each statement regarding the species (a carbanion).
Step-by-step solution
1

Let's analyze each statement regarding the species (a carbanion).

Concept: The hybridization of the central carbon atom in a carbanion is typically , leading to a pyramidal geometry. However, the s-character can vary depending on the electronegativity of the surrounding atoms (Bent's Rule).

Why (D) is incorrect:

  • Statement A: If the electronegativity of the surrounding element is less than 2.5 (e.g., H, alkyl groups), the carbanion is typically hybridized. In hybridization, the s-character is 25%. However, due to the presence of a lone pair, the lone pair occupies an orbital with more s-character (Bent's Rule). This pushes the bonding orbitals to have less s-character, but the overall hybridization is still considered . The statement says "almost 33% S-character", which would imply hybridization. For a carbanion, if X is less electronegative, the lone pair will reside in an orbital with higher s-character, leaving the bonding orbitals with slightly less s-character than 25%. However, the statement implies a significant increase in s-character in bonding orbitals, which is generally incorrect for less electronegative substituents. Let's re-evaluate this in context with other options. If the lone pair occupies an orbital with more s-character, the bonding orbitals will have less s-character. So, 33% s-character is incorrect for bonding orbitals. However, the question might be referring to the overall hybridization of the carbon atom, which is . Let's consider the general trend.
  • Statement B: If the electronegativity of the surrounding element is greater than 2.5 (e.g., F, Cl), the lone pair on carbon will occupy an orbital with less s-character (as more electronegative atoms prefer orbitals with more p-character). This would leave the bonding orbitals with slightly more s-character than 25%. So, "almost 25% S-character" is plausible, as the deviation might be small, or it might be referring to the ideal hybridization.
  • Statement C: If is , the species is . Due to the lone pair on carbon and the three C-F bonds, the central carbon is hybridized. The geometry is pyramidal (like ammonia). Since the C-F bonds are polar and the molecule is not symmetrical (due to the lone pair), it will be polar. Thus, this statement is correct.
  • Statement D: If is , the species is . The central carbon atom has three bond pairs and one lone pair, making it hybridized. The geometry is pyramidal (like ammonia), not planar. Also, due to the lone pair and the C-H bond polarity, the molecule is polar. Therefore, stating it is planar is incorrect.

Revisiting A and B: Bent's rule states that more electronegative substituents prefer hybrid orbitals with more p-character, and lone pairs prefer hybrid orbitals with more s-character. For , the carbon is hybridized. If X is less electronegative, the lone pair will have more s-character, leaving the C-X bonds with less s-character (less than 25%). If X is more electronegative, the lone pair will have less s-character, leaving the C-X bonds with more s-character (more than 25%). Therefore, statement A (33% s-character for less electronegative X) and statement B (25% s-character for more electronegative X) are generally incorrect interpretations of Bent's rule for bonding orbitals. However, in the context of multiple-choice questions, we look for the most definitively incorrect statement.

Statement D clearly states that is planar. Carbanions like are known to be pyramidal due to hybridization of the central carbon atom, with the lone pair occupying one of the hybrid orbitals. Therefore, statement D is definitively incorrect.

Correct Answer: (D)

AnswerD·

If is , then species should be polar and planar

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