Q60P. Unknown X, C5 H9 Br, does not re... [FREE SOLUTION]

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Chapter 8: Q60P. (page 460)

Unknown X, C5 H9 Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5 H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis鈥搑eduction of Y gives dialdehyde Z, C5 H8 O2. 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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Proposed structures with reactions are shown below.

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Organic Reactions

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Since compound X (C₅H₉Br) does not react with bromine or dilute KMnO4 which means compound is saturated (i.e., no double or triple bond is present in the structure X).

Also, X upon treatment with tBuOK gives one product Y. This is the dehydrobromination reaction which results in the removal of hydrogen bromide and double bond formation takes place in compound Y. As now, double bond (unsaturated bond) is present in compound Y, it decolorizes bromine and changes KMnO4 from purple to brown.

Further, catalytic hydrogenation (H2, Pd-C) of Y gives methylcyclobutane. At last, ozonolysis-reduction of Y gives dialdehyde Z (C₅H₈O₂).