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Consider the above reaction and predict the major product. EtO–C(=O)–CH2–(cyclopentene ring)–CH2CH2CN (i) DIBAL-H (ii) H3O+

1. OHC–H2C–(cyclopentene ring)–CH2CH2CHO
2. EtO–C(=O)–H2C–(cyclopentene ring)–CH2CH2CHO
3. EtO–C(=O)–H2C–(cyclopentene ring)–CH2CH2COOH
4. OHC–H2C–(cyclopentene ring)–CH2CH2COOH

Correct answer: EtO–C(=O)–H2C–(cyclopentene ring)–CH2CH2CHO

Solution

The correct option represents the major product formed after the reaction with DIBAL-H, which selectively reduces the ester to an aldehyde, followed by acid hydrolysis that does not further oxidize the aldehyde, resulting in the formation of the aldehyde product.

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