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NEET 2026
Exam
NEET
Year
2026
Subject
Chemistry
Chapter
Chapter

NEET 2026 · Chemistry · Chapter

Consider the given molecule with four labeled C-Cl bonds (P, Q, R,...

Consider the given molecule with four labeled C-Cl bonds (P, Q, R, and S). Which of these bonds will undergo
Consider the given molecule with four labeled C−Cl\text{C}-\text{Cl} bonds (P, Q, R, and S).

Which of these bonds will undergo heterolytic cleavage most readily to form a carbocation?

Options

  1. ABond Q
  2. BBond S
  3. CBond P
  4. DBond R

Correct answer

C. Bond P

Step-by-step solution

The ease of heterolytic cleavage of a C−Cl\text{C}-\text{Cl} bond depends on the stability of the carbocation formed after the departure of the chloride ion (Cl−\text{Cl}^-). The more stable the carbocation, the more readily the bond will cleave.

Let us analyze the carbocations formed by the cleavage of each labeled bond:

1. Bond P: Cleavage forms a tertiary benzylic carbocation. This carbocation is highly stabilized by resonance with the benzene ring and by hyperconjugation from the six α\alpha-hydrogens of the two methyl groups.

2. Bond Q: Cleavage forms a primary benzylic carbocation. It is stabilized by resonance with the benzene ring, but it is less stable than the tertiary benzylic carbocation formed from P.

3. Bond R: Cleavage forms a phenyl cation. This is highly unstable because the positive charge resides in an sp2sp^2 hybridized orbital that is perpendicular to the π\pi-system of the benzene ring, meaning it cannot be stabilized by resonance. Furthermore, the C−Cl\text{C}-\text{Cl} bond here has partial double bond character due to resonance, making it difficult to break.

4. Bond S: Cleavage forms a primary alkyl carbocation (-CH2-CH2+\text{-CH}_2\text{-CH}_2^+). This carbocation lacks resonance stabilization and is relatively unstable.

Comparing the stabilities of the resulting carbocations, the order is:
Tertiary benzylic (from P) > Primary benzylic (from Q) > Primary alkyl (from S) > Phenyl (from R).

Since the carbocation formed from the cleavage of bond P is the most stable, bond P will undergo heterolytic cleavage most readily.

Answer: Bond P
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