**Compound A**, \( \text{C}_{11}\text{H}_{16}\text{O} \), 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 \( \text{H}_2\text{SO}_4 \), dehydration occurred and an optically inactive alkene **B**, \( \text{C}_{11}\text{H}_{14} \), was produced as the major product. Alkene B, on ozonolysis, gave two products. Product **C**, \( \text{C}_{7}\text{H}_{6}\text{O} \), was shown to be an aldehyde while product **D**, \( \text{C}_{4}\text{H}_{8}\text{O} \), was shown to be a ketone.**Task:** 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.

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

**Compound A**, \( \text{C}_{11}\text{H}_{16}\text{O} \), 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 \( \text{H}_2\text{SO}_4 \), dehydration occurred and an optically inactive alkene **B**, \( \text{C}_{11}\text{H}_{14} \), was produced as the major product. Alkene B, on ozonolysis, gave two products. Product **C**, \( \text{C}_{7}\text{H}_{6}\text{O} \), was shown to be an aldehyde while product **D**, \( \text{C}_{4}\text{H}_{8}\text{O} \), was shown to be a ketone.

**Task:** 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.

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