Question

Determine the ratios of the chemically non-equivalent protons in a compound if the steps of the integration curves measure $\mathbf{40}\mathbf{.5}\mathbf{,}\mathbf{27}\mathbf{,}\mathbf{13}$ and$\mathbf{118}\mathbf{mm}$ , from left to right across the spectrum. Draw the structure of a compound whose ${}^{\mathbf{1}}\mathbf{H}$NMR spectrum would show these integrals in the observed order.

Short answer

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

Step-by-step solution

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.,

• $\frac{40.5}{13}=3.1$

• $\frac{27}{13}=2.1$

• $\frac{13}{13}=1$

• $\frac{118}{13}=9.1$
  

So, the combined ratio of non-equivalent protons will be$3:2:1:9$ .

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