Question:
What is the product obtained when Pent-3-enenitrile is treated with DIBAL-H followed by acid hydrolysis?
What is the product obtained when Pent-3-enenitrile is treated with DIBAL-H followed by acid hydrolysis?
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DIBAL-H partially reduces a nitrile to an aldehyde without touching the C=C bond.
Updated On: Nov 12, 2026
- \(\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CHO}\)
- \(\text{CH}_{3}\text{-(CH}_{2})_{2}\text{-CH}_{2}\text{-CHO}\)
- \(\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-COOH}\)
- \(\text{CH}_{3}\text{-(CH}_{2})_{2}\text{-CH}_{2}\text{OH}\)
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The Correct Option is A
Solution and Explanation
Step 1: Understanding the Concept
Pent-3-enenitrile is \(\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CN}\).
Step 2: Action of DIBAL-H
DIBAL-H adds one hydride to the nitrile carbon to give an imine-aluminium complex.
Acid hydrolysis then converts the imine into an aldehyde.
Step 3: Selectivity
DIBAL-H is a selective reagent. It leaves the isolated C=C bond untouched and does not reduce further to the alcohol.
So the product is pent-3-enal, \(\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CHO}\).
Final Answer:
The product is pent-3-enal. \[ \boxed{\text{(A) }\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CHO}} \]
Pent-3-enenitrile is \(\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CN}\).
Step 2: Action of DIBAL-H
DIBAL-H adds one hydride to the nitrile carbon to give an imine-aluminium complex.
Acid hydrolysis then converts the imine into an aldehyde.
Step 3: Selectivity
DIBAL-H is a selective reagent. It leaves the isolated C=C bond untouched and does not reduce further to the alcohol.
So the product is pent-3-enal, \(\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CHO}\).
Final Answer:
The product is pent-3-enal. \[ \boxed{\text{(A) }\text{CH}_{3}\text{-CH=CH-CH}_{2}\text{-CHO}} \]
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