Calcitriol is a steroid hormone found in human blood. [Figure showing structure of calcitriol]

1. (a)Give the number of primary, secondary and tertiary alcohol groups in one molecule of calcitriol.[1]
2. (b)Give the number of chiral carbon atoms in one molecule of calcitriol.[1]
3. (c)Calcitriol shows geometrical isomerism. Give the number of geometrical isomers of calcitriol, including calcitriol.[1]
4. (d)(i)Predict the number of peaks in the carbon-13 NMR spectrum of X.[1]
5. (d)(ii)For the carbon-13 NMR spectrum of X, state the expected chemical shift ranges (δ) of the peaks predicted in (i) and the number of peaks in each range.[3]
6. (d)(iii)Predict the number of peaks this compound would show in its proton NMR spectrum.[1]
7. (d)(iv)For each of the peaks in the proton NMR spectrum you have identified in (iii) give the expected splitting pattern. Explain your reasoning.[2]
8. (e)(i)Of these two other carbon-containing products, identify the product with the smaller molecular mass. Explain how this product is formed.[2]
9. (e)(ii)Of these two other carbon-containing products, identify the product with the larger molecular mass by drawing its skeletal formula in the space below.[1]

This question uses a diagram from the original paper, which isn't shown here. Open the full paper from the past papers archive to see it.