Q.56. - Organic Chemistry

Question

Question: One compound that contributes to the “seashore smell”at beaches in Hawai’s is dictyopterene D’ with excess ${\mathit{H}}_{\mathbf{2}}$ in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with ${\mathit{O}}_{\mathbf{3}}$  followed by  ${\left(C{H}_3\right)}_{\mathbf{2}}\mathit{S}$  forms $\mathit{C}{\mathit{H}}_{\mathbf{2}}{\left(CHO\right)}_{\mathbf{2}}$ ,$\mathit{H}\mathit{C}\mathit{O}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}\mathit{H}{\left(CHO\right)}_{\mathbf{2}}$ , and $\mathit{C}{\mathit{H}}_{\mathbf{3}}\mathit{C}{\mathit{H}}_{\mathbf{2}}\mathit{C}\mathit{H}\mathit{O}$. What are possible structures of dictyopterene D’?

Step-by-Step Solution

Answer

Answer

The possible structures for compound D are as shown.

Step 1: Reduction

The reaction of alkenes with hydrogen in the presence of palladium catalyst produces alkanes.

The reaction proceeds as shown below.

Reduction reaction

Step 2: Reverse of ozonolysis

During ozonolysis, the double bond in alkene undergoes a reaction and forms carbonyl compounds.

The structure of compound D can be determined by joining all the given carbonyl compounds and removing the carbonyl oxygen.

Retrosynthetic route

Step 3: Ozonolysis

Compound D undergoes ozonolysis to give the below-shown products.

Ozonolysis

Step 4: Structure of D

The possible structures of compound D are shown below.