Compound A, C₁1 H160, was found to be an optically active alcohol. Despite its apparent unsaturation, no hydrogen was absorbed on catalytic reduction over a Pd/Ccatalyst. On treatment of A with dilute H₂SO4, dehydration occurred and an optically inactive alkene B, C₁₁H₁4 was produced as the major product. Alkene B, onozonolysis, gave two products. Product C, C7H6O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone.Draw the structure of compound C.• You do not have to consider stereochemistry.• You do not have to explicitly draw H atoms.• In cases where there is more than one answer, just draw one.

Since, alcohol A on catalytic reduction over Pd/C not absorbed any hydrogen suggests that in alcohol…

Compound A, C₁1H160, 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 H₂SO4, dehydration occurred and an optically inactive alkene B, C₁1H14 was produced the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.

Compound A, C₁1H160, 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 H₂SO4, dehydration occurred and an optically inactive alkene B, C₁1H14 was produced the major product. Alkene B, on ozonolysis, gave two products. Product C, C,H,O, was shown to be an aldehyde while product D, C4H8O, was shown to be a ketone. Draw the structure of compound C. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one.

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions

Section: Chapter Questions

Problem 20.43P

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