Solution
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: Strong -M effect. Highly stabilizing. I. -Br: Weak +M effect, but prominent -I effect. Overall stabilizing relative to hydrogen. II. -H: (Plain benzyl anion) Neutral baseline. III. -OCH₃: Strong +M effect. Highly destabilizing. V. -CH₃: +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) Therefore: IV > I > II > V > 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