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MHT CET Medical202624 April 2026Evening ShiftChemistryAldehydes and KetonesActual

What is the product obtained when Pent-3-enenitrile is treated with DIBAL-H followed by acid hydrolysis?

Options

  1. ACH ₃ -CH=CH-CH ₂ -CHO
  2. BCH ₃ -(CH ₂)₂ -CH ₂ -CHO
  3. CCH ₃ -CH=CH-CH ₂ -COOH
  4. DCH ₃ -(CH ₂)₂ -CH ₂ OH

Correct answer

A. CH ₃ -CH=CH-CH ₂ -CHO

Step-by-step solution

The structure of Pent-3-enenitrile is CH ₃ -CH=CH-CH ₂ -CN . DIBAL-H (Diisobutylaluminium hydride) is a selective reducing agent that reduces nitriles to imines. Upon subsequent acid hydrolysis, the imine is converted to an aldehyde. DIBAL-H does not reduce isolated carbon-carbon double bonds. Therefore, the -CN group is converted to a -CHO group, while the double bond remains intact. The product formed is Pent-3-enal, which has the structure CH ₃ -CH=CH-CH ₂ -CHO . Answer: CH ₃ -CH=CH-CH ₂ -CHO

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