Question:
Identify the substrate ' A ' in the following conversion.
A $\xrightarrow[\text{H}_3\text{O}^+]{\text{AlH}(i-\text{Bu})_2}$ Pent-3-enal}
Identify the substrate ' A ' in the following conversion.
A $\xrightarrow[\text{H}_3\text{O}^+]{\text{AlH}(i-\text{Bu})_2}$ Pent-3-enal}
A $\xrightarrow[\text{H}_3\text{O}^+]{\text{AlH}(i-\text{Bu})_2}$ Pent-3-enal}
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$\text{DIBAL-H}$ + Nitrile $\to$ Aldehyde. It does not reduce the $\text{C}=\text{C}$ double bond.
Updated On: Apr 26, 2026
- Pentanenitrile
- Pent-3-enenitrile
- Pent-3-en-1-amine
- Pent-3-ynenitrile
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The Correct Option is B
Solution and Explanation
Step 1: Concept
$\text{DIBAL-H}$ [$\text{AlH}(i-\text{Bu})_2$] is a selective reducing agent that reduces nitriles ($-\text{CN}$) and esters to aldehydes ($-\text{CHO}$).
Step 2: Matching Product and Substrate
- Product: Pent-3-enal (contains 5 carbons, an aldehyde group, and a double bond at position 3). - To obtain this, the substrate must have the same carbon skeleton and double bond position but with a nitrile group instead of the aldehyde.
Step 3: Conclusion
Pent-3-enenitrile ($CH_3-CH=CH-CH_2-CN$) will be reduced by $\text{DIBAL-H}$ to Pent-3-enal.
Final Answer: (B)
$\text{DIBAL-H}$ [$\text{AlH}(i-\text{Bu})_2$] is a selective reducing agent that reduces nitriles ($-\text{CN}$) and esters to aldehydes ($-\text{CHO}$).
Step 2: Matching Product and Substrate
- Product: Pent-3-enal (contains 5 carbons, an aldehyde group, and a double bond at position 3). - To obtain this, the substrate must have the same carbon skeleton and double bond position but with a nitrile group instead of the aldehyde.
Step 3: Conclusion
Pent-3-enenitrile ($CH_3-CH=CH-CH_2-CN$) will be reduced by $\text{DIBAL-H}$ to Pent-3-enal.
Final Answer: (B)
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