Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Spearmint contains carvone, while caraway seeds contain a stereoisomer of carvone. If either isomer is treated with hydrogen over a nickel catalyst, a mixture of isomers with structural formula X is produced.
(a(i))[1]

State which type of stereoisomerism carvone is capable of showing. Explain your answers.

(a(ii))[2]

Using molecular formulae, write an equation for the conversion of carvone to X.

(b(i))[1]

Name the mechanism in step 1.

(b(ii))[2]

What type of reaction is taking place in the following steps? step 3 step 5

(b(iii))[6]

Suggest reagents and conditions for each of the steps below. step 1 step 2 step 3 step 4

(c(i))[1]

State the reagents and conditions required for this reaction.

(c(ii))[2]

Complete the part structure so that it shows the isomer of X that is most likely to be obtained in this reaction.

Worked solution & mark scheme

This 15-mark question has a full step-by-step worked solution and mark scheme. One marking point: Optical, because it contains a chiral carbon bonded to four different groups

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