Question

In the 1H NMR of the product of the reduction reaction (4-t-butylcyclohexanol) it is apparent that there is a mixture of 4-t-butylcyclohexanols. In the expanded region between 3.2 and 4.5 ppm, the peak at 4.05 ppm integrates to 1.0, while the peak at 3.52

In the 1H NMR of the product of the reduction reaction (4-t-butylcyclohexanol) it is apparent that there is a mixture of 4-t-butylcyclohexanols. In the expanded region between 3.2 and 4.5 ppm, the peak at 4.05 ppm integrates to 1.0, while the peak at 3.52 ppm integrates to 2.52. Which protons give rise to these peaks? Calculate the percentage of each isomer in the sample by using these values.

Note: the attachments labeled 51 are for the trans 4-t-butylcyclohexanone. The ones labeled 52 are for the 4-t-butylcyclohexanols. The 51 labeled attachments are just for seeing the difference, not to be used to solve the problem.

51 (2).png

52 (1).png

51 (1).png

52 (2).png


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Answer #1

There are mixture of 4-t-butylcyclohexanols (cis and trans) as shown

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In the 1H NMR of the product of the reduction reaction (4-t-butylcyclohexanol) it is apparent that there is a mixture of 4-t-butylcyclohexanols. In the expanded region between 3.2 and 4.5 ppm, the peak at 4.05 ppm integrates to 1.0, while the peak at 3.52
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