NEETChemistryAldehydes and Ketones
An acyclic dicarbonyl compound 'X' undergoes intramolecular aldol condensation in the presence of dilute NaOH and heat to give 1-acetylcyclopentene as the major product. The compound 'X' is:
Options
- A2,6-Heptanedione
- B2,7-Octanedione
- C6-Oxoheptanal
- D5-Oxohexanal
Correct answer
C. 6-Oxoheptanal
Step-by-step solution
To find the acyclic precursor 'X', we perform a retro-aldol analysis on the given product, 1-acetylcyclopentene. Identify the , -unsaturated system. In 1-acetylcyclopentene, the double bond is between C1 and C2 of the cyclopentene ring, and the acetyl group is at C1. This means C1 was the nucleophilic -carbon and C2 was the electrophilic carbonyl carbon. Hydrate the double bond (retro-dehydration). Break the C1=C2 double bond, adding two hydrogen atoms to the -carbon (C1) and an oxygen atom to the -carbon (C2). Thi