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.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Organomagnesium compounds

The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.

Hydrolysis Grignard Reactions and Reduction

Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.

Question

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Compound A, CH10, 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, CH4 was produced as the major
product. Alkene B, on ozonolysis, gave two products. Product C, C,H,0, was shown to be an aldehyde while product D, CHg0, 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, jtust draw one.

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