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Question: Answered & Verified by Expert
Arrange the carbanions, $\left(\mathrm{CH}_3\right)_3 \overline{\mathrm{C}}, \overline{\mathrm{C}} \mathrm{Cl}_3,\left(\mathrm{CH}_3\right)_2 \overline{\mathrm{C}} \mathrm{H}, \mathrm{C}_6 \mathrm{H}_5 \overline{\mathrm{C}} \mathrm{H}_2$, in order of their decreasing stability :
ChemistryGeneral Organic ChemistryJEE MainJEE Main 2009
Options:
  • A
    $\mathrm{C}_8 \mathrm{H}_5 \overline{\mathrm{C}} \mathrm{H}_2>\overline{\mathrm{C}} \mathrm{Cl}_3>\left(\mathrm{CH}_3\right)_3 \overline{\mathrm{C}}>\left(\mathrm{CH}_3\right)_2 \overline{\mathrm{C}} \mathrm{H}$
  • B
    $\left(\mathrm{CH}_3\right)_2 \overline{\mathrm{C}} \mathrm{H}>\overline{\mathrm{C}} \mathrm{Cl}_3>\mathrm{C}_6 \mathrm{H}_5 \overline{\mathrm{C}} \mathrm{H}_2>\left(\mathrm{CH}_3\right)_3 \overline{\mathrm{C}}$
  • C
    $\overline{\mathrm{C}} \mathrm{Cl}_3>\mathrm{C}_8 \mathrm{H}_5 \overline{\mathrm{C}} \mathrm{H}_2>\left(\mathrm{CH}_3\right)_2 \overline{\mathrm{C}} \mathrm{H}>\left(\mathrm{CH}_3\right)_3 \overline{\mathrm{C}}$
  • D
    $\left(\mathrm{CH}_3\right)_3 \overline{\mathrm{C}}>\left(\mathrm{CH}_3\right)_2 \overline{\mathrm{C}} \mathrm{H}>\mathrm{C}_6 \mathrm{H}_5 \overline{\mathrm{C}} \mathrm{H}_2>\overline{\mathrm{C}} \mathrm{Cl}_3$
Solution:
2901 Upvotes Verified Answer
The correct answer is:
$\overline{\mathrm{C}} \mathrm{Cl}_3>\mathrm{C}_8 \mathrm{H}_5 \overline{\mathrm{C}} \mathrm{H}_2>\left(\mathrm{CH}_3\right)_2 \overline{\mathrm{C}} \mathrm{H}>\left(\mathrm{CH}_3\right)_3 \overline{\mathrm{C}}$
$2^{\circ}$ carbanion is more stable than $3^{\circ}$ and $\mathrm{Cl}$ is $-1$ effect group.

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