Nitriles and hydroxynitriles
Cambridge A-Level Chemistry (9701) · Unit 19: Nitrogen compounds · 8 flashcards
Nitriles and hydroxynitriles is topic 19.2 in the Cambridge A-Level Chemistry (9701) syllabus , positioned in Unit 19 — Nitrogen compounds , alongside Primary amines.
Marked as A2 Level: examined at A Level in Paper 4 (A Level Structured Questions) and Paper 5 (Planning, Analysis and Evaluation). It is not tested on the AS-only papers (Papers 1, 2 and 3).
The deck below contains 8 flashcards — 7 key concepts and 1 calculation — covering the precise wording mark schemes reward.
What the Cambridge 9701 syllabus says
2025-2027 syllabus, in our words · A2 LevelWhat the syllabus expects you to be able to do in this topic, in plain English. For the exact wording, see the official syllabus (PDF).
- Recall how nitriles can be made: by heating a halogenoalkane in ethanol with KCN.
- Recall how hydroxynitriles can be made: by heating an aldehyde or ketone with HCN, using KCN as a catalyst.
- Describe how nitriles are hydrolysed to carboxylic acids using dilute alkali or dilute acid, followed by acidification.
Cambridge syllabus keywords to use in your answers
These are the official Cambridge 9701 terms tagged to this section. Mark schemes credit responses that use the exact term — weave them into your answers verbatim rather than paraphrasing.
What reagents and conditions are required to produce a nitrile from a halogenoalkane?
A halogenoalkane reacts with potassium cyanide (KCN) in ethanol, under reflux (heat). The cyanide ion acts as a nucleophile, replacing the halogen.
Write a balanced chemical equation for the production of propanenitrile from chloroethane.
CH₃CH₂Cl + KCN → CH₃CH₂CN + KCl. The cyanide ion replaces the chlorine, so the carbon chain is lengthened by one carbon atom, giving propanenitrile.
Outline the mechanism for the formation of a hydroxynitrile from propanone.
HCN reacts with propanone (in the presence of KCN catalyst and heat) via nucleophilic addition. The cyanide ion (CN⁻) attacks the carbonyl carbon, followed by protonation by HCN to form the hydroxynitrile.
Why is KCN used as a catalyst in the formation of hydroxynitriles from aldehydes and ketones with HCN?
KCN provides cyanide ions (CN⁻), which are better nucleophiles than HCN itself. This increases the rate of nucleophilic attack on the carbonyl carbon.
Describe the hydrolysis of a nitrile by heating with dilute acid.
Heating a nitrile under reflux with dilute acid (e.g. HCl or H₂SO₄) hydrolyses it directly to a carboxylic acid. The nitrogen ends up as ammonium ions (NH₄⁺).
Describe the hydrolysis of a nitrile with dilute alkali, followed by acidification.
Heating a nitrile with dilute alkali (
What is the product of the alkaline hydrolysis of propanenitrile, followed by acidification with hydrochloric acid?
The product is propanoic acid (CH₃CH₂COOH). Propanenitrile is first hydrolysed to sodium propanoate, which is then protonated to form propanoic acid upon acidification.
Give the IUPAC name and structural formula of the product formed from the reaction of ethanal with HCN (with KCN as catalyst).
The product is 2-hydroxypropanenitrile, with the structural formula CH₃CH(OH)CN.
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Nitriles and hydroxynitriles sits alongside these A-Level Chemistry decks in the same syllabus unit. Each uses the same spaced-repetition system, so progress in one informs the next.
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