Textbook Problem

Compound A , C₁₁H₁₆O, 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 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. How many degrees of unsaturation does A have? Write the reactions, and identify A , B , and C .