Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

In medicine, procaine is employed as an anaesthetic. As illustrated in Fig. 7.1, it may be prepared from methylbenzene in five steps.
(a(i))[1]

Identify all functional groups in procaine.

(a(ii))[1]

A procaine molecule contains 13 carbon atoms. State how many of the carbon atoms are $sp$, $sp^2$ and $sp^3$ hybridised in procaine.

(b)[1]

The proton ($^1\text{H}$) NMR spectrum for procaine in $\text{D}_2\text{O}$ is obtained. Predict how many peaks will be seen.

(c)[1]

State why procaine is able to act as a base.

(d(i))[1]

Use the box provided to draw the structure of compound W.

(d(ii))[2]

State the reagents and conditions used in step 1 and step 2.

(e)[3]

Procaine is prepared from X in three steps. Suggest the reagents and conditions for step 4 and for step 5 in Fig. 7.1.

(f(i))[2]

Explain the meaning of partition coefficient, $K_{pc}$.

(f(ii))[2]

The partition coefficient of procaine between octan-1-ol and water is $1.77$. Octan-1-ol and water are immiscible. A solution containing $0.500\,\text{g}$ of procaine in $75.0\,\text{cm}^3$ of water is shaken with $50.0\,\text{cm}^3$ of octan-1-ol. Calculate the mass of procaine that is extracted into the octan-1-ol.

Worked solution & mark scheme

This 14-mark question has a full step-by-step worked solution and mark scheme. One marking point: Includes phenylamine, amine and ester groups

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