Chemistry 9701 · AS & A Level · An introduction to A Level organic chemistry

An introduction to A Level organic chemistry — practice question

Ibuprofen and paracetamol are medicines used for pain relief.
(a)[2]

Ibuprofen and paracetamol each contain the aryl (benzene) functional group. State the other functional groups found in each molecule. ibuprofen ................................................ paracetamol ................................................

(b(i))[1]

Ibuprofen has a chiral centre and shows stereoisomerism. State what is meant by the term chiral centre.

(b(ii))[2]

Draw the pair of stereoisomers of ibuprofen.

(c)[2]

Draw the structures of the organic products formed when ibuprofen and paracetamol each react separately with $\text{LiAlH}_4$.

(d(i))[2]

A student performed reactions on solutions of ibuprofen and paracetamol with reagents D and E, and the results below were recorded (✓ means a reaction occurred). Suggest a possible identity for each reagent D and E.

(d(ii))[1]

Give the structure of the organic product formed when reagent D reacted with ibuprofen.

(d(iii))[1]

Give the structure of the organic product formed when reagent E reacted with paracetamol.

(e(i))[1]

One stage in the manufacture of ibuprofen is shown. Write an equation for the reaction between $\text{CH}_3\text{COCl}$ and $\text{AlCl}_3$.

(e(ii))[3]

Complete the mechanism for the conversion of X into Y. Include all necessary curly arrows, any relevant dipoles and charges.

(e(iii))[1]

Name the mechanism in part (ii).

Worked solution & mark scheme

This 16-mark question has a full step-by-step worked solution and mark scheme. One marking point: Ibuprofen has a carboxylic acid group; paracetamol has phenol and amide

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