Pyrethrins are a group of naturally occurring insecticidal substances found in the

Chapter 24, Problem 24.20

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Pyrethrins are a group of naturally occurring insecticidal substances found in the flowers of various plants of the chrysanthemum family. The following is the structure of a typical pyrethrin, cinerin I (exclusive of stereochemistry): O O O (a) Locate any isoprene units present in cinerin I. (b) Hydrolysis of cinerin I gives an optically active carboxylic acid, (+)-chrysanthemic acid. Ozonolysis of (+)-chrysanthemic acid, followed by oxidation, gives acetone and an optically active dicarboxylic acid, ()-caronic acid (C7H10O4). What is the structure of ()-caronic acid? Are the two carboxyl groups cis or trans to each other? What does this information tell you about the structure of (+)-chrysanthemic acid?

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