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When treated with hydrogen and a platinum catalyst, an

Chapter 21, Problem 38SP

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QUESTION:

When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to given-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

Equation Transcription:

Text Transcription:

H-C-CH-CH_{2}-C-C-H

H-C-C-H

H-C-C-OH

H-C-OH

Questions & Answers

QUESTION:

When treated with hydrogen and a platinum catalyst, an unknown compound X absorbs 5 equivalents of hydrogen to given-butylcyclohexane. Treatment of X with an excess of ozone, followed by dimethyl sulfide and water, gives the following products:

Propose a structure for the unknown compound X. Is there any uncertainty in your structure?

Equation Transcription:

Text Transcription:

H-C-CH-CH_{2}-C-C-H

H-C-C-H

H-C-C-OH

H-C-OH

ANSWER:

Solution 38SP

Step 1

The structure of unknown compound (x) is given below:

The structure X reacts with 5 equivalents of  to form n-butyl cyclohexane.

There is uncertainty in structure because the structure can be cis or trans.

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