Compound A, C 11 H 16 0, was found to be an optically active alcohol. Despite its

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Compound A, C11H160, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a palladium catalyst. On treatment of A with dilute sulfuric acid, dehydration occurred and an optically inactive alkene B, C11H14, was produced as the major product. Alkene B, on ozonolysis, gave two products. One product was identified as propanal, CH3CH2CHO. Compound C, the other product, was shown to be a ketone, C8H8O. 1 Low many degrees of unsaturation does A have? Write the reactions, and identify A, B, and C.

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