Carvone occurs in spearmint and a stereoisomer of carvone occurs in caraway seeds. Treating either isomer with hydrogen over a nickel catalyst produces a mixture of isomers with the structural formula X. [Figure X.X]

1. (a)(i)State the type of stereoisomerism carvone can show. Explain your answer.[1]
2. (a)(ii)Write an equation, using molecular formulae, for this conversion of carvone to X.[2]
3. (b)(i)X can be synthesised from methylbenzene by the following route. [Figure X.X] Name the mechanism in step 1.[1]
4. (b)(ii)What type of reaction is occuring in the following steps? step 3 ______________ step 5 ______________[2]
5. (b)(iii)Suggest reagents and conditions for each of the following steps. step 1 ______________ step 2 ______________ step 3 ______________ step 4 ______________[6]
6. (c)(i)During step 6, hydrogen is added to the benzene ring to produce the cyclohexane ring in X. The six hydrogen atoms are all added to the same side of the benzene ring. State the reagents and conditions needed for this reaction.[1]
7. (c)(ii)Complete the part structure to show the structure of the isomer of X that would most likely be obtained during this reaction. [Figure X.X][2]

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