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Compound A , C 11 H 16 O, 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 , C 11 H 14 , was the major product. Alkene B , on ozonolysis, gave two products. One product was identified as propanal, CH 3 CH 2 CHO. Compound C , the other product, was shown to be a ketone, C 8 H 8 O. How many degrees of unsaturation does A have? Write the reactions, and identify A , B , and C .

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Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485
BuyFind

Organic Chemistry

9th Edition
John E. McMurry
Publisher: Cengage Learning
ISBN: 9781305080485

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Chapter
Section
Chapter 8.SE, Problem 72AP
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 .

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Chapter 8 Solutions

Organic Chemistry
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