Liquids that contain molecules of T smell like lemons. [Figure 3.1]

1. (a)Molecules of T exist as a pair of stereoisomers. Name the type of stereoisomerism shown by molecules of T. Explain your answer.[2]
2. (b)Two organic products are produced when a sample of T is heated under reflux with excess acidified concentrated KMnO₄. Draw the structure of the two organic products, from this reaction, in the boxes.[2]
3. (c)(i)Identify a suitable reagent for reaction 1.[1]
4. (c)(ii)Identify the reagent and conditions needed for reaction 2.[2]
5. (c)(iii)Suggest which product formed in reaction 2 has a higher yield. Explain your answer.[3]
6. (d)(i)Predict the observations for each test-tube. Explain your answer in terms of the functional groups present in Q and R.[3]
7. (d)(ii)When PCl₅(s) is added to separate samples of Q and R at room temperature, both react vigorously. Complete the equation shown in Fig. 3.4 to describe the reaction that occurs when R reacts with PCl₅(s). [Figure 3.4][2]
8. (d)(iii)Suggest why samples of Q and R must be dried before PCl₅ is added. Include a relevant equation to support your answer.[2]

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