Question:

Reaction that yields P as the major product is

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Cyclopentadiene gives norbornene derivatives by Diels-Alder reactionNitroalkenes can act as dienophiles, and the nitro group can be converted into a carbonyl group using TiCl$_3$/H$_2$O
Updated On: Jun 1, 2026
  • A
  • B
  • C
  • D
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The Correct Option is A

Solution and Explanation

Step 1: Identify the product skeleton.
Product P has a bicyclic norbornene type skeletonThis type of bicyclic system is commonly formed by Diels-Alder reaction of cyclopentadiene with a suitable dienophile

Step 2: Identify the diene.
In all the given options, cyclopentadiene is used as the dieneCyclopentadiene readily undergoes Diels-Alder reaction because it is locked in the reactive s-cis conformation

Step 3: Analyze the substituents in product P.
Product P contains a carbonyl group and methyl substituentsThe correct dienophile must therefore be capable of giving the same carbon framework and should also be convertible into a ketone after the cycloaddition step

Step 4: Role of nitroalkene in option (A).
In option (A), the dienophile is a nitro-substituted alkeneNitroalkenes are electron-deficient dienophiles and undergo Diels-Alder reaction efficiently with cyclopentadiene

Step 5: Conversion of nitro group into carbonyl group.
After cycloaddition, treatment with TiCl$_3$/H$_2$O converts the nitro functionality into the corresponding carbonyl groupThis transformation gives the ketone present in product P

Step 6: Stereochemical preference.
The Diels-Alder reaction proceeds through the endo transition state as the major pathwayThis gives the required relative orientation of the substituents in the bicyclic product

Step 7: Conclusion.
Thus, cyclopentadiene reacts with the nitroalkene in option (A), followed by TiCl$_3$/H$_2$O workup, to give product P as the major product
\[ \boxed{\text{A}} \]
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