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Question

Assume general laboratory reagents and butadiene are available.
Which of the following sequences could accomplish the following synthesis?


A
1: Dissolved metal reduction of butadiene;
2; Catalytic hydrogenation
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B
1: Kolbe's electrolysis;
2; Catalytic hydrogenation
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C
1: Stephen's aldehyde synthesis;
2; Catalytic hydrogenation
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D
1: Diels-Alder of butadiene and the substrate;
2; Catalytic hydrogenation
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Solution

The correct option is D 1: Diels-Alder of butadiene and the substrate;
2; Catalytic hydrogenation

Observe the stereochemical data on either side of the equation – both Cl and COOH groups remain trans;
This points to a nifty implementation of the Diels-Alder reaction:


The product from above on catalytic hydrogenation completes the synthesis.
Watch the video for more on the Diels-Alder reaction – a reaction that won
the scientist duo Otto Diels and Kurt Alder a Nobel prize in Chemistry in 1950.


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