Chemistry 9701 · AS & A Level · Carbonyl compounds

Carbonyl compounds — practice question

The reaction scheme shows a number of reactions of compound P, $\text{C}_5\text{H}_8\text{O}$.
(a(i))[4]

State the structures of the organic compounds Q, R, S and T.

(a(ii))[1]

State the systematic name of compound P.

(a(iii))[1]

What do you observe when compound P is treated with 2,4-dinitrophenylhydrazine (2,4-DNPH)?

(b)[4]

Compound U has a chiral centre and the same molecular formula as compound P, $\text{C}_5\text{H}_8\text{O}$. Compound U decolourises a sample of bromine water readily. Compound U does not display cis-trans isomerism. When compound U is heated under reflux with excess acidified potassium dichromate(VI), the organic product gives the infra-red spectrum shown. Use the information given to suggest a structure for compound U. Explain your answer.

Worked solution & mark scheme

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