Chemistry 9701 · AS & A Level · Carbonyl compounds

Carbonyl compounds — practice question

Ethanal undergoes reaction with a mixture of HCN and NaCN to form 2-hydroxypropanenitrile, $\text{CH}_3\text{CH(OH)CN}$. The mechanism for this reaction is nucleophilic addition.
(a)[2]

Explain what is meant by the term nucleophile and identify the species that functions as the nucleophile in this reaction.

(b(i))[1]

Name the type of stereoisomerism displayed by $\text{CH}_3\text{CH(OH)CN}$.

(b(ii))[3]

Draw three-dimensional diagrams for this pair of stereoisomers. Show the chiral centre on one of the structures drawn with an asterisk ($*$).

(c)[1]

Give the structure of the organic product formed when $\text{CH}_3\text{CH(OH)CN}$ reacts with dilute sulfuric acid.

Worked solution & mark scheme

This 7-mark question has a full step-by-step worked solution and mark scheme. One marking point: donor of a lone pair / electron pair

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