Question 6 of 34intermediate🔍 AnalyzeShort Answer2 marks

Which of the two: O₂NCH₂CH₂O⁻ or CH₃CH₂O⁻ is expected to be more stable and why?

Correct Answer

O2NCH2CH2O−O_2NCH_2CH_2O^- is expected to be more stable.

Exercise: EXERCISES | Q: 8.9
For More Understanding

Explanation

The nitro group (−NO2-NO_2) is highly electronegative and exerts an electron-withdrawing inductive effect, which stabilizes the negative charge on the oxygen atom. Conversely, the ethyl group (−CH2CH3-CH_2CH_3) is electron-donating, which destabilizes the negative charge.

Solution Steps

  1. Step 1: Compare the groups attached to the alkoxide oxygen. In O2NCH2CH2O−O_2NCH_2CH_2O^-, a nitro group (−NO2-NO_2) is present, while in CH3CH2O−CH_3CH_2O^-, an ethyl group is present.

  2. Step 2: The −NO2-NO_2 group contains electronegative atoms and exerts an electron-withdrawing inductive effect, which stabilizes the negative charge on the oxygen atom.

  3. Step 3: The −CH2CH3-CH_2CH_3 group is electron-donating, which intensifies the negative charge on the oxygen atom, making CH3CH2O−CH_3CH_2O^- less stable. Therefore, O2NCH2CH2O−O_2NCH_2CH_2O^- is more stable.

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