Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Ibuprofen and paracetamol are medicines used to relieve pain. Their structural formulae are shown.
(a)[2]

Ibuprofen and paracetamol both include the aryl (benzene) functional group. Name the other functional groups found in each molecule.\n\nibuprofen ...............................................................\n\nparacetamol ...............................................................

(b(i))[1]

Ibuprofen contains a chiral centre and exhibits 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 react separately with $\text{LiAlH}_4$.

(d(i))[2]

A student carried out some reactions on solutions of ibuprofen and paracetamol using reagents D and E, and the results below were obtained (✓ means a reaction took place). Suggest a possible identity for each reagent D and E.\n\nD ...............................................................\n\nE ...............................................................

(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 step 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 required curly arrows, along with any relevant dipoles and charges.

(e(iii))[1]

Name the mechanism in (ii).

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