Chemistry 9701 · AS & A Level · An introduction to A Level organic chemistry

An introduction to A Level organic chemistry — practice question

Acebutolol is a medicine that can be used to reduce blood pressure.
(a)[3]

Give the complete names of the circled functional groups P, Q and R in acebutolol.

(b)[1]

On the diagram of acebutolol below, circle any chiral carbon atoms.

(c(i))[1]

When warmed with dilute hydrochloric acid, acebutolol breaks apart to give two molecules. Draw a line through the bond that is cleaved by heating with dilute hydrochloric acid.

(c(ii))[1]

Draw the structure of the smaller molecule produced by this reaction.

(d)[3]

Suggest what would be observed when acebutolol reacts with the following reagents. If no reaction occurs, write ‘none’. Reagents: alkaline iodine solution; universal indicator solution; 2,4-dinitrophenylhydrazine; Tollens’ reagent.

(e(i))[1]

Butanoic acid can be reduced to make compound N. Compound N reacts with sodium. Suggest a suitable reducing agent for this reaction.

(e(ii))[1]

Draw the skeletal formula of the isomer of N that exists as a pair of optical isomers.

(e(iii))[1]

Another isomer of N does not react with acidified dichromate(VI) solution, but it does react with sodium. Draw the structure of this isomer.

Worked solution & mark scheme

This 12-mark question has a full step-by-step worked solution and mark scheme. One marking point: P is amide, Q is ketone, and R is secondary alcohol

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