Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products (M and N) with

Chapter 14, Problem 14.63

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Treatment of (CH3)2CHCH(OH)CH2CH3 with TsOH affords two products (M and N) with molecular formula C6H12. The 1 H NMR spectra of M and N are given below. Propose structures for M and N and draw a mechanism to explain their formation. 3 H 2 H 3 H 1 H ppm 1H NMR of M 9 0 8 1234567 3 H 3 H 3 H 2 H 2 H ppm 1H NMR of N 9 0

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