Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

Compounds $J$, $K$, $L$ and $M$ are isomers with the molecular formula $\text{C}_9\text{H}_{11}\text{NO}$. Each of the four contains a benzene ring, and two of the isomers also have a chiral centre. The outcomes of six tests on $J$, $K$, $L$ and $M$ are shown in the table.
(a)[5]

From the experimental results in the table above, work out which group(s), as well as the benzene ring, are present in each of the four isomers $J$, $K$, $L$ and $M$. Fill in the table below by identifying the group(s) in each isomer.

(b(i))[1]

What reaction type occurs in test 5 when $M$ is changed into $P + Q$?

(b(ii))[2]

Suggest possible structures for compounds $P$ and $Q$. $P$ ($\text{C}_6\text{H}_7\text{N}$) $Q$ ($\text{C}_3\text{H}_5\text{O}_2\text{Na}$)

(c)[5]

Isomers $J$, $K$, $L$ and $M$ all share molecular formula $\text{C}_9\text{H}_{11}\text{NO}$. Using the information in (a), suggest a structure for each isomer and draw them in the boxes. Circle every chiral centre in $K$ and $L$.

(d)[1]

Compound $N$ is another isomer with the same molecular formula $\text{C}_9\text{H}_{11}\text{NO}$ and it also contains a benzene ring. $N$ has the same functional group as $M$. When $N$ is heated with $\text{NaOH(aq)}$, ethylamine and a sodium salt $W$ are formed. 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: Functional groups of J, K, L and M identified correctly

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