Core Logic
The stability of a carbanion increases when electron-withdrawing groups (EWG) are present, as they help disperse the negative charge through -I or -M effects.
Electron-donating groups (EDG) decrease stability by intensifying the negative charge through +I or +M effects.
Evaluating the para-substituents:
IV. -CHO$-\text{CHO}$: Strong -M effect. Highly stabilizing.
I. -Br$-\text{Br}$: Weak +M effect, but prominent -I effect. Overall stabilizing relative to hydrogen.
II. -H$-\text{H}$: (Plain benzyl anion) Neutral baseline.
III. -OCH₃$-\text{OCH}_3$: Strong +M effect. Highly destabilizing.
V. -CH₃$-\text{CH}_3$: +I and +H (hyperconjugation) effects. Destabilizing, but less so than strong +M.
Step 1: Final Conclusion
Based on the effects, the stability order is:
-CHO (-M) > -Br (-I) > -H > -CH₃ (+I, +H) > -OCH₃ (+M)$-\text{CHO} (-M) > -\text{Br} (-I) > -\text{H} > -\text{CH}_3 (+I, +H) > -\text{OCH}_3 (+M)$
Therefore: IV > I > II > V > III$\text{IV} > \text{I} > \text{II} > \text{V} > \text{III}$.
Pattern Recognition
For carbanions, think: "EWG stabilizes, EDG destabilizes". This is the exact opposite of carbocation stability rules.
Chapter Mix
Class 11 Chemistry: Organic Chemistry - Some Basic Principles and Techniques