Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

Curcumin is the substance that gives turmeric its yellow colour. Its molecular structure can be determined from the reaction sequence shown below. The $\text{CH}_3\text{O}$- group in curcumin may be treated as unreactive.
(a(i))

Name the functional group that curcumin shares with compounds A and D.

(a(ii))[2]

Name the functional group that is shared by compounds A and B.

(b(i))

Suggest the structures of compounds B, C and D, and draw their structural formulae in the relevant boxes opposite.

(b(ii))[4]

Suggest suitable reagents and conditions for reaction 4.

(c(i))

Name the type of reaction for reaction 2.

(c(ii))

Suggest a reagent for reaction 2.

(c(iii))[3]

Suggest the structure of compound A, and draw its structural formula in the relevant box opposite.

(d(i))

Name the functional group in curcumin that reacts with cold dilute acidified $\text{KMnO}_4$.

(d(ii))[2]

Name two functional groups in curcumin that react with $\text{Br}_2(\text{aq})$.

(e)[2]

Suggest a structure for curcumin, and draw its structural formula in the relevant box opposite.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: Ketone carbonyl correctly identified

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