1.Compound X has a molecular formula of C₅H₁₁CIO. The infrared spectrum of Compound X is shown below.

a. Use item 22 of the Data Book to identify the bond type in Compound X that has the highest wave number.

b. The mass spectrum of Compound X, C₅H₁₁CIO, is shown below.

i. Identify the m/z of the base peak. Page 23 of 36 1 mark

ii. Identify the formula of the species that is responsible for the peak at
m/z = 73.

Solution

c. The ¹³C NMR spectrum for Compound X is shown below.

What information do the four peaks in the ¹³C NMR spectrum provide about the arrangement of the five carbon atoms in the structure of Compound X? Justify your answer. (3 marks)

Solution

d. The high-resolution ¹H NMR spectrum for Compound X is shown below.

i. Each peak in the ¹H NMR spectrum for Compound X is a singlet. Each peak has an associated integration curve. In general, what feature of a ¹ H NMR peak is represented by its integration curve?

ii. ¹H NMR spectral analysis can provide information about the molecular structure of compounds. In general, what information does the relative size of the integration curves for any given ¹H NMR spectrum provide about the molecular structure of the compound analysed?

Solution

The expected integration curves for Compound X are shown in the table below.

iii. State what the relative size of the integration curves in the table above indicates about the molecular structure of Compound X.

iv. Consider the chemical shift and the size of the integration curve for the peak at 0.96 ppm. Refer to item 24 of the Data Book. What does this information indicate about the structure of Compound X?

Solution

e. In the space provided below, draw the structural diagram of Compound X, using the information provided in parts a-d.

Solution