Advertisements
Advertisements
Question
Which of the two: O2NCH2CH2O– or CH3CH2O–is expected to be more stable and why?
Short Note
Solution
NO2 group is an electron-withdrawing group. Hence, it shows –I effect. By withdrawing the electrons toward it, the NO2 group decreases the negative charge on the compound, thereby stabilising it. On the other hand, ethyl group is an electron-releasing group. Hence, the ethyl group shows +I effect. This increases the negative charge on the compound, thereby destabilising it. Hence, O2NCH2CH2O– is expected to be more stable than CH3CH2O–.
shaalaa.com
Fundamental Concepts in Organic Reaction Mechanism - Inductive Effect
Is there an error in this question or solution?
Chapter 12: Organic Chemistry - Some Basic Principles and Techniques - EXERCISES [Page 370]
APPEARS IN
RELATED QUESTIONS
Match the ions given in Column I with their nature given in Column II.
| Column I | Column II |
| (i) \[\ce{CH3 - \overset{\bullet\bullet}{\underset{\bullet\bullet}{O}} - \overset{⊕}{C}H - CH3}\] | (a) Stable due to resonance |
| (ii) \[\ce{F3 - \overset{⊕}{C}}\] | (b) Destabilised due to inductive effect |
|
(iii) \[\begin{array}{cc} |
(c) Stabilised by hyperconjugation |
| (iv) \[\ce{CH3 - \overset{⊕}{C}H - CH3}\] | (d) A secondary carbocation |
