Chemistry 9701 · AS & A Level · Carboxylic acids and derivatives

Carboxylic acids and derivatives — practice question

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

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

(b(i))[1]

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

(b(ii))[2]

Explain your answer to (i).

(c)[2]

Methanoic acid, $\text{HCO}_2\text{H}$, has a similar acid strength to propanoic acid. Describe a chemical test that can 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 produces an acyl chloride. For this two-step synthesis, • draw the structure of the product from the first step, • state the reagents and conditions required for each step of the synthesis.

(e(i))[1]

Identify $Z$ from the proton NMR spectrum.

(e(ii))[2]

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

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 \rightarrow 2C_3H_7ONa + H_2

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