Most Important Selected Qs for JEE AdvancedChemistryAldehydes and Ketones
Paragraph: Consider the following mechanism of an aldol condensation reaction: Answer the following questions based on the above mechanism and your knowledge about aldol condensation. Question: If all the alpha hydrogen in X is replaced by deuterium "D" atom. Which of the following would be observed? (Assuming high concentration of base)
Options
- AEnolate I is more stable than II, since it is formed by deprotonation of more acidic hydrogen.
- BEnolate I is more stable than II, since it is less substituted.
- CEnolate II is more stable than I, since it is formed by deprotonation of more stable than acidic hydrogen.
- DEnolate II is more stable than I, since it is more substituted.
Correct answer
D. Enolate II is more stable than I, since it is more substituted.
Step-by-step solution
C - H bond is broken in non rate determining step, therefore, substitution of - H by deuterium doesn't affect the rate of reaction.