1.1. Four samples containing alcohols were studied by ¹³C NMR spectroscopy. The alcohols all have the formula C₄H₁₀O.

i) Draw the four alcohol isomers of C₄H₁₀

ii) For each isomer, deduce the number of chemical peaks expected in the ¹³C spectrum.

iii) The ¹³C NMR spectra of one of the isomers is shown below in Figure 1.

Figure 1

Deduce which of the isomers produced the spectra shown in Figure 1 and explain your answer with reference to the chemical shift pattern.

1.2. State the number of peaks in the proton NMR spectra of CH₃CH₂CH₂CH₂OH and of HOOCCH₂CH₂COOH. Analysis of peak splitting is not required.

1.3. Compound A can be converted into compound B via an intermediate species as shown in Figure 1 below;

Figure 1

Suggest how you would be able to determine the difference between compounds A and B by analysis of their ¹H NMR spectra.

1.4. Compound X was studied using ¹H NMR spectroscopy. The formula of Compound X is shown in Figure 2.

Figure 2

i) State the number of peaks in the ¹H NMR spectrum of X.

ii) State the splitting pattern of the protons labelled with the *.

iii) State the IUPAC name of X.

iv) Identify a solvent in which X can be dissolved in before obtaining its ¹H NMR spectrum.