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1. The sex attractant of the common housefly is a hydrocarbon with the formula C23H36. On treatment with aqueous basic KMnO4, followed by H3O+, two products are obtained as followed, CH3(CH2)12CO2H and CH3(CH2)7CO2H. Propose structures for the two stereoisomers for the sex attractants.

2. Compound A, C10H18O undergoes reaction with dilute H2SO4 at 250°C to yield a mixture of two alkenes, C10H16. The major alkene product, B, gives only cyclopentanone after ozone treatment followed by reduction with zinc in acetic acid. Identify A and B, and write the reaction.

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