MHT CET202526 Apr 2025Evening ShiftChemistryAldehydes and KetonesActual
Identify the product formed when Hex-3-enenitrile is reduced with diisobutylaluminium hydride followed by acid hydrolysis?
Options
- AHexanal
- BHexan - 3 - one
- CHex - 3 - enal
- DHexanoic acid
Correct answer
C. Hex - 3 - enal
Step-by-step solution
Structure identification: Hex-3-ennenitrile corresponds to CH₃-CH₂-CH=CH-CH₂-CN . Reduction with DIBAL-H selectively reduces the nitrile to an imine without affecting the isolated alkene: CH₃-CH₂-CH=CH-CH₂-CN DIBAL-H CH₃-CH₂-CH=CH-CH₂-CH=NH . Acid hydrolysis converts the imine to the aldehyde: CH₃-CH₂-CH=CH-CH₂-CH=NH H₃ O^+ CH₃-CH₂-CH=CH-CH₂-CHO + NH₃ . The product CH₃-CH₂-CH=CH-CH₂-CHO is hex-3-enal. Option comparison: A: Hexanal ( CH₃(CH₂)₄CHO , saturated) B: Hexan-3-one ( CH₃CH₂COCH₂CH₂CH₃ , ketone) C: Hex-3-ena