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Chapter 12: Q.56. (page 491)

Question: One compound that contributes to the 鈥渟eashore smell鈥漚t beaches in Hawai鈥檚 is dictyopterene D鈥� with excess H2in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2,HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D鈥�?

Short Answer

Expert verified

Answer

The possible structures for compound D are as shown.

Step by step solution

01

Reduction

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

The reaction proceeds as shown below.

Reduction reaction

02

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

03

Ozonolysis

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

Ozonolysis

04

Structure of D

The possible structures of compound D are shown below.

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