Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Cumin is a spice used to add flavour to food. Two compounds that contribute to that flavour are cuminaldehyde and cuminyl alcohol.
(a(i))[1]

Deduce how many peaks would appear in the $^{13}\text{C}$ NMR spectrum of cuminyl alcohol.

(a(ii))[2]

Identify two bonds that account for the differences in the infra-red spectra of cuminaldehyde and cuminyl alcohol, and give their absorption ranges in the infra-red spectrum (in $\text{cm}^{-1}$).

(b(i))[4]

Suggest reagents and conditions for steps 1-4 in the synthesis of cuminyl alcohol from benzene.

(b(ii))[2]

Name the mechanism of step 2 and state the type of reaction in step 4.

Worked solution & mark scheme

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