Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide,X gives only one product, Y, C5H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown.Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5H8O2. Proposeconsistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide,X gives only one product, Y, C5H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown.Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5H8O2. Proposeconsistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

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

Chapter19: Enolate Anions And Enamines

Section: Chapter Questions

Problem 19.40P: Enamines normally react with methyl iodide to give two products: one arising from alkylation at...

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Concept explainers

Sulfur Functional Groups

Many organic molecules contain sulfur functional groups and have their own importance in chemistry as well as biology. Some of the organic molecules which contain sulfur functional groups and the corresponding sulfur functionality is given below:

Question

Unknown X, C5H9Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide,
X gives only one product, Y, C5H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown.
Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5H8O2. Propose
consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

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