Chemistry 9701 · AS & A Level · States of matter

States of matter — practice question

The three substances shown each exhibit some acidic behaviour: propanoic acid, propan-1-ol and phenol.
(a)[1]

Write an equation for the reaction of propan-1-ol with sodium metal.

(b(i))[1]

State the relative acidities of propanoic acid, propan-1-ol and phenol, with the most acidic first.

(b(ii))[2]

Explain your response to (i).

(c)[2]

Methanoic acid, $\text{HCO}_2\text{H}$, has an acidity similar to propanoic acid. Describe a chemical test that can be used to distinguish between these two acids. Name the acid that gives a positive result in this test and describe the observations that would be seen.

(d)[3]

The ester phenyl propanoate, $\text{C}_2\text{H}_5\text{CO}_2\text{C}_6\text{H}_5$, can be prepared from phenol and propanoic acid by a two-step synthesis. The first step forms an acyl chloride. For this two-step synthesis: - draw the structure of the product formed in the first step, - state the reagents and conditions required for each stage of the synthesis.

(e(i))[1]

Identify Z from the proton NMR spectrum.

(e(ii))[2]

Give one feature that would be observed, and explain why, in the proton NMR spectra of each of the two compounds that are not Z.

(e)

An unknown compound, Z, is propan-1-ol, propanal or propanoic acid. The proton NMR spectrum of Z in $\text{CDCl}_3$ is shown.

Worked solution & mark scheme

This 12-mark question has a full step-by-step worked solution and mark scheme. One marking point: $2C_3H_7OH + 2Na \to 2C_3H_7ONa + H_2$

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