Question:
Identify a final product obtained when Pent-3-enenitrile is treated with \(\text{AlH}(i\text{-Bu})_{2}\) followed by acid hydrolysis.
Identify a final product obtained when Pent-3-enenitrile is treated with \(\text{AlH}(i\text{-Bu})_{2}\) followed by acid hydrolysis.
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DIBAL-H reduces a nitrile to an imine, which hydrolyses to an aldehyde without touching the C=C bond.
Updated On: Nov 12, 2026
- Pent-3-enol
- Pentanoic acid
- But-3-enol
- Pent-3-enal
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The Correct Option is D
Solution and Explanation
Step 1: Understanding the Concept
DIBAL-H, \(\text{AlH}(i\text{-Bu})_2\), is a mild reducing agent that converts a nitrile to an aldehyde (Stephen-type partial reduction followed by hydrolysis).
Step 2: Apply to the nitrile
Pent-3-enenitrile is \(\text{CH}_3\text{CH}=\text{CHCH}_2\text{CN}\).
DIBAL-H adds one hydride to the C\(\equiv\)N to give an imine-aluminium complex, and it does not reduce an isolated C=C.
Step 3: Hydrolysis
Acid hydrolysis converts the imine to an aldehyde, \(\text{CH}_3\text{CH}=\text{CHCH}_2\text{CHO}\).
The 5-carbon chain and the C3 double bond are kept, so the product is pent-3-enal.
Final Answer:
The final product is pent-3-enal. \[ \boxed{\text{(D) }\text{Pent-3-enal}} \]
DIBAL-H, \(\text{AlH}(i\text{-Bu})_2\), is a mild reducing agent that converts a nitrile to an aldehyde (Stephen-type partial reduction followed by hydrolysis).
Step 2: Apply to the nitrile
Pent-3-enenitrile is \(\text{CH}_3\text{CH}=\text{CHCH}_2\text{CN}\).
DIBAL-H adds one hydride to the C\(\equiv\)N to give an imine-aluminium complex, and it does not reduce an isolated C=C.
Step 3: Hydrolysis
Acid hydrolysis converts the imine to an aldehyde, \(\text{CH}_3\text{CH}=\text{CHCH}_2\text{CHO}\).
The 5-carbon chain and the C3 double bond are kept, so the product is pent-3-enal.
Final Answer:
The final product is pent-3-enal. \[ \boxed{\text{(D) }\text{Pent-3-enal}} \]
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