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Chapter 14: Q50P (page 669)

Determine the ratios of the chemically non-equivalent protons in a compound if the steps of the integration curves measure 40.5,鈥�27,鈥�13 and118鈥�mm , from left to right across the spectrum. Draw the structure of a compound whose H1NMR spectrum would show these integrals in the observed order.

Short Answer

Expert verified

Ratio of hydrogen atoms is and the structure of the compound is given below.

Step by step solution

01

Step-by-Step SolutionStep 1: Calculation of ratio of non-equivalent protons

Ratio can be calculated by dividing the integration steps value with the smallest value.

i.e.,

  • 40.513=3.1
  • 2713=2.1
  • 1313=1
  • 11813=9.1

So, the combined ratio of non-equivalent protons will be3:2:1:9 .

02

Drawing structure from the obtained ratio

Since the ratio is 3:2:1:9, it is from highest frequency to lowest frequency. So, the compound may be an ester. Structure of the compound is given below.

Structure of desired compound

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Most popular questions from this chapter

How many signals would you expect to see in the NMR spectrum of each of the following compounds ?

[18]-Annulene shows two signals in its 1 H NMR spectrum: one at 9.25 ppm and the other to the right of the TMS signal at -2.88 ppm. What hydrogens are responsible for each of the signals?

a) For the following compounds which pairs of hydrogen (Ha and Hb) are enantiotopic hydrogens?

b) which pairs are diastereotopic hydrogens?

Without referring to Table 14.1, label the proton or set of protons in each compound that gives the signal at the lowest frequency a, at the next lowest b, and so on.

Propose structures that are consistent with the following spectra. (Integral ratios are given from left to right across the spectrum.)

a. The1HNMR spectrum of a compound with molecular formulaC4H10O2has two singlets with integral ratios of 2: 3.

b. The1HNMR spectrum of a compound with molecular formulaC6H10O2has two singlets with integral ratios of 2: 3.

c. The1HNMR spectrum of a compound with molecular formulaC8H6O2has two singlets with integral ratios of 1: 2.
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