Compound A, CuH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CuH was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C-HO, was shown to be an aldehyde while product D, CH0, was shown to be a ketone. Draw the structure of compound C.

Compound A, CuH10, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/C catalyst. On treatment of A with dilute H,SO, dehydration occurred and an optically inactive alkene B, CuH was produced as the major product. Alkene B, on ozonolysis, gave two products. Product C, C-HO, was shown to be an aldehyde while product D, CH0, was shown to be a ketone. Draw the structure of compound C.

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter22: Carbonyl Alpha-substitution Reactions

Section22.SE: Something Extra

Problem 26MP: Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium...

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