Question

The acid-catalyzed dehydration of 1-methylcyclohexanol yields a mixture of two alkenes. How could you use 1H NMR to help you decide which was which?

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1^1H NMR spectra can be used to distinguish the two products of the acid-catalyzed dehydration of 1-methylcyclohexanol.

The 1^1H NMR spectrum of product A has four signals\textbf{product A has four signals} corresponding to the four nonequivalent protons of the symmetric molecule. Proton (a) is attributed to the hydrogen of the =CH2_2 group. The three remaining nonequivalent protons (b), (c), and (d) are attributed to the CH2_2 groups of the ring.

On the other hand, the 1^1H NMR spectrum of product B has six signals\textbf{product B has six signals} corresponding to the six nonequivalent protons. Proton (a) is from the CH3_3 group. Proton (b) is from the =CH- group. Protons (c), (d), (e), and (f) are from the CH2_2 groups of the ring.

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