Chapter 20: Problem 39

One of the published syntheses of warburganal begins with the following Diels- Alder reaction. Propose a structure for compound A.

Short Answer

Expert verified

Answer: Compound A contains the diene structure in the product after performing a retro Diels-Alder reaction. It has the following structure: [ \begin{array}{c} \chemfig{*6(=-=(-[::60]-[::-60])=-(=[::60]-[::-60]*5(-=(-)-(<[::-60]R)-(<[::-60]))))}\\\\ \end{array} ] Where R represents the rest of the warburganal molecule, excluding the six-membered ring formed by the Diels-Alder reaction.

Step by step solution

Understand the Diels-Alder Reaction

The Diels-Alder reaction is a cycloaddition reaction that occurs between a conjugated diene (a molecule with alternating double and single bonds) and a dienophile (an electron-poor alkene or alkyne). This reaction results in the formation of a new six-membered ring.

Identify the Diene and Dienophile

In order to propose the structure for compound A, we first need to recognize the product structure (the warburganal) and identify which component of this structure would have been the diene and which the dienophile in the Diels-Alder reaction. Chemical structure of warburganal: [Here is the structure of warburganal](https://pubchem.ncbi.nlm.nih.gov/compound/Warburganal). From the molecule, we can recognize a six-membered ring that could be a result of a Diels-Alder reaction. We need to figure out which two parts of the ring structure were the diene and dienophile.

Retro Diels-Alder Reaction to Obtain Reactants

To find compound A which was involved in the Diels-Alder reaction, we need to do a retro Diels-Alder reaction which is breaking the six-membered ring into its two original parts (diene and dienophile). Break one of the double bonds in the six-membered ring, and the other connecting the fused 5-membered ring. Assign the double bonds correctly to obtain the diene and dienophile.

Find the Structure of Compound A

Based on the retro Diels-Alder reaction, compound A should be the structure that contains the diene. Therefore, compound A has the following structure: Chemical structure of compound A (retro Diels-Alder product containing the diene): [ \begin{array}{c} \chemfig{*6(=-=(-[::60]-[::-60])=-(=[::60]-[::-60]*5(-=(-)-(<[::-60]R)-(<[::-60]))))}\\\\ \end{array} ] Where R is the rest of the warburganal molecule excluding the six-membered ring created by the Diels-Alder reaction.

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One of the published syntheses of warburganal begins with the following Diels- Alder reaction. Propose a structure for compound A.

Short Answer

Step by step solution

Understand the Diels-Alder Reaction

Identify the Diene and Dienophile

Retro Diels-Alder Reaction to Obtain Reactants

Find the Structure of Compound A

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