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Compound A (C7H10) exhibits a lmax of 230 nm in its UV

Chapter 17, Problem 17.49

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QUESTION:

Compound A (C7H10) exhibits a lmax of 230 nm in its UV absorption spectrum. Upon hydrogenation with a metal catalyst, compound A will react with two equivalents of hydrogen gas. Ozonolysis of compound A yields the following two compounds. Identify two possible structures for compound A. H H O O H O O Compound A H 1) O3 2) DMS +

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QUESTION:

Compound A (C7H10) exhibits a lmax of 230 nm in its UV absorption spectrum. Upon hydrogenation with a metal catalyst, compound A will react with two equivalents of hydrogen gas. Ozonolysis of compound A yields the following two compounds. Identify two possible structures for compound A. H H O O H O O Compound A H 1) O3 2) DMS +

ANSWER:

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This exercise is challenging. It presents us with an unknown compound \(\mathbf{A}\) (molecular formula \(\mathrm{C}_{7} \mathrm{H}_{10}\) ) that has a \(\lambda_{\max }\) of \(230 \mathrm{~nm}\) in its UV absorption spectrum. Upon hydrogenation with a metal catalyst, compound \(A\) reacts with two equivalents of hydrogen gas. Ozonolysis of \(A\) yields the following compounds (shown below). We're challenged to identify two possible structures for the compound \(\mathrm{A}\).

                                         

 

 

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