Chemistry 9701 · AS & A Level · Organic synthesis

Organic synthesis — practice question

3-aminobenzoic acid may be prepared from methylbenzene in three steps.
(a(i))[2]

In the boxes, draw the structures of $\text{M}$ and $\text{N}$.

(a(ii))[3]

Suggest suitable reagents and conditions for each stage of the synthesis. step $1$ step $2$ step $3$

(b(i))[3]

Draw the structures of the two structural isomers with molecular formula $\text{C}_6\text{H}_{12}\text{N}_2\text{O}_5$ that may be present in the product mixture. The functional group formed in each one should be shown.

(b(ii))[1]

Predict how many different structural isomers with the molecular formula $\text{C}_9\text{H}_{19}\text{N}_3\text{O}_4$ may be present in the product mixture.

(c(i))[1]

On the glutathione diagram, place an asterisk $(*)$ on each chiral centre.

(c(ii))[2]

Draw the structures of the three products formed by complete acid hydrolysis of glutathione. Assume the thiol group, $\text{-SH}$, does not react.

(c(iii))[1]

Glutathione dissolves in water. Using the structure of glutathione, explain why glutathione is soluble in water.

Worked solution & mark scheme

This 13-mark question has a full step-by-step worked solution and mark scheme. One marking point: accurate structures for M and N

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