Chapter 14: Q.21558-14-67P (page 567)
Question. Compound O has a molecular formula C10H12O and shows an IR absorption at 1687 . The 1H -NMR spectrum of O is given below. What is the structure of O?

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Chapter 14: Q.21558-14-67P (page 567)
Question. Compound O has a molecular formula C10H12O and shows an IR absorption at 1687 . The 1H -NMR spectrum of O is given below. What is the structure of O?

Answer

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The 1H NMR spectrum of CH3OH recorded on a 500 MHz NMR spectrometer consists of two signals, one due to the CH3 protons at 1715 Hz and one due to the OH proton at 1830 Hz, both measured downfield from TMS. (a) Calculate the chemical shift of each absorption. (b) Do the CH3 protons absorb upfield or downfield from the OH proton?
How many signals are present in the 1HNMR spectrum for each molecule? What splitting is observed in each signal?
a.

b.

c.

Propose a structure for a compound of molecular formula C7H14O2 with an IR absorption at 1740 cm-1 and the following 1HNMR data:
Question. Treatment of (CH3)2 CHCH2CH(OH)CH2CH3 with TsOH affords two products (M and N) with the 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.

Rank each group of protons in order of increasing chemical shift.
a.



b.

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