Electronic Displacement Effects - Problem 2

Description:

Q2. Which among the given compounds is more stable and why?

O₂N - CH₂CH₂ - O^- or CH₃CH₂O^-

Explanation −

O₂N − CH₂ − CH₂ − O⁻ > more stable  > CH₃CH₂O⁻

The presence of electron-withdrawing nitro group decreases the charge density on the small oxygen atom via −I effect. Alkyl groups (CH₃CH₂ −) in contrast increases the electron density on oxygen atom via +I effect thereby making it highly unstable.