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
Official 2025-2027 spec · A2 LevelThese are the exact learning outcomes Cambridge sets for this topic. The candidate is expected to be able to do each of these on the relevant paper.
- recall the reactions by which nitriles can be produced: (a) reaction of a halogenoalkane with KCN in ethanol and heat
- recall the reactions by which hydroxynitriles can be produced: (a) the reaction of aldehydes and ketones with HCN, KCN as catalyst, and heat
- describe the hydrolysis of nitriles with dilute acid or dilute alkali followed by acidification to produce a carboxylic acid
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.
Tips to avoid common mistakes in Nitriles and hydroxynitriles
- › Classify reaction products accurately; condensation with 2,4-DNPH produces an organic orange precipitate, whereas dichromate reduction produces inorganic green Cr3+ ions.
- › Include H2O and H+ on the left-hand side and NH4+ on the right when writing balanced equations for acid hydrolysis of amides.
- › Identify all gaseous products, including water vapour, to determine the true mass of the remaining solid residue.
- › Remember that while amine groups can be protonated to -NH3+, amide groups (-CONH2) remain neutral and do not accept protons easily.
- › Remember that alkyl groups are electron-donating; this concentrates negative charge on the oxygen, making the ethoxide ion a stronger base.
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 ethanenitrile from chloroethane.
CH₃CH₂Cl + KCN → CH₃CH₂CN + KCl
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 with dilute acid, followed by acidification.
Heating a nitrile with dilute acid (
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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All Chemistry FlashcardsMore topics in Unit 19 — Nitrogen compounds
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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