NEETChemistryAldehydes and Ketones
Consider the following reaction sequence: Ethyl 3-oxobutanoate NaBH ₄ A conc. H ₂ SO ₄, B The major product 'B' is:
Options
- AEthyl 3-hydroxybutanoate
- BBut-2-enoic acid
- CButane-1,3-diol
- DEthyl but-2-enoate
Correct answer
D. Ethyl but-2-enoate
Step-by-step solution
NaBH ₄ is a mild reducing agent that selectively reduces the ketone group to a secondary alcohol but does not reduce the ester group. Therefore, ethyl 3-oxobutanoate is reduced to ethyl 3-hydroxybutanoate (Product A). Heating the -hydroxy ester (A) with concentrated H ₂ SO ₄ leads to acid-catalyzed dehydration. The elimination of a water molecule occurs to form a double bond that is conjugated with the ester carbonyl group, making it highly stable. This yields ethyl but-2-enoate as the major product (Product B). Co