Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

The compounds J, K, L and M are isomers with the molecular formula $\text{C}_9\text{H}_{11}\text{NO}$. Each of the four isomers includes a benzene ring. Two of the isomers have a chiral centre. The findings from six tests on J, K, L and M are presented in the table.
(a)[5]

Using the experimental results in the table above, determine which group(s), besides the benzene ring, are present in each of the four isomers J, K, L and M. Complete the table below by identifying the group(s) in each isomer.

(b(i))[1]

Name the reaction type in test 5 that changes M into P + Q.

(b(ii))[2]

Suggest structures for compounds P and Q. P has molecular formula $\text{C}_6\text{H}_7\text{N}$ and Q has molecular formula $\text{C}_3\text{H}_5\text{O}_2\text{Na}$.

(c)[5]

Isomers J, K, L and M each have molecular formula $\text{C}_9\text{H}_{11}\text{NO}$. Use the information in (a) to propose a structure for every isomer and draw them in the boxes. Put circles around all chiral centres in K and L.

(d)[1]

Compound N is a further isomer with the same molecular formula $\text{C}_9\text{H}_{11}\text{NO}$, and it also has a benzene ring. N has the same functional group as M. On heating with $\text{NaOH}(aq)$, N forms ethylamine and a sodium salt W. Suggest the structure of W.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Correctly identified functional groups for J-M

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