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 bonds (P, Q, R, and S).
Which of these bonds will undergo heterolytic cleavage most readily to form a carbocation?
Options
- ABond Q
- BBond S
- CBond P
- DBond R
Correct answer
C. Bond P
Step-by-step solution
The ease of heterolytic cleavage of a bond depends on the stability of the carbocation formed after the departure of the chloride ion (). 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 -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 hybridized orbital that is perpendicular to the -system of the benzene ring, meaning it cannot be stabilized by resonance. Furthermore, the bond here has partial double bond character due to resonance, making it difficult to break.
4. Bond S: Cleavage forms a primary alkyl carbocation (). 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
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 -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 hybridized orbital that is perpendicular to the -system of the benzene ring, meaning it cannot be stabilized by resonance. Furthermore, the bond here has partial double bond character due to resonance, making it difficult to break.
4. Bond S: Cleavage forms a primary alkyl carbocation (). 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