---
title: "Hydrolysis of a nitrile Template – Chemistry Diagram | MolDraw"
url: https://www.moldraw.com/templates/nitrile-hydrolysis/
description: "Hydrolysis of a nitrile template: Ethanenitrile in hot aqueous acid: N-protonation, water addition, loss of H⁺ to the imidic acid and tautomerism give…"
lang: en
publisher: Scidart Academy
generated: 2026-11-13
---
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# Hydrolysis of a nitrile template

![Hydrolysis of a nitrile template: Ethanenitrile in hot aqueous acid: N-protonation, water addition, loss of H⁺ to the imidic acid and tautomerism give ethanamide, then ethanoic acid.](https://www.moldraw.com/templates/nitrile-hydrolysis.webp)

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Ethanenitrile in hot aqueous acid: N-protonation, water addition, loss of H⁺ to the imidic acid and tautomerism give ethanamide, then ethanoic acid.

## Mechanism step by step

Water adds to the protonated C≡N; tautomerism gives the amide, which hydrolyses on to the acid

1. **N-Protonation** – The nitrile N takes H⁺
2. **Water adds** – Attack on the nitrile carbon
3. **Deprotonation** – An imidic acid (the enol-like tautomer of the amide)
4. **N-Protonation** – The O lone pair helps H⁺ onto N
5. **Deprotonation** – Ethanamide; it hydrolyses further (see amide hydrolysis)

## Key points

- RX + KCN then hydrolysis adds one carbon: a way to lengthen the chain (bromoethane → propanoic acid).
- Acid gives the carboxylic acid and NH₄⁺; alkali gives the carboxylate and NH₃ (acidify to get the acid).
- The imidic acid → amide step is a tautomerism, like enol → ketone.
- Milder conditions can stop at the amide.

Drawn with 63 atoms, 18 arrows, 7 shapes – every one editable in MolDraw.

## Sources

- [Clayden, Greeves & Warren, Organic Chemistry, 2nd ed., OUP 2012, ch. 10](https://openlibrary.org/isbn/9780199270293) Textbook
- [Smith, March's Advanced Organic Chemistry, 8th ed., Wiley 2020, ch. 16](https://openlibrary.org/isbn/9781119371809) Textbook

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### What is a curly-arrow mechanism template?

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