Nitrile reduction
Hydride additions reduce the carbon-nitrogen triple bond; the separate aqueous work-up protonates the nitrogen-containing intermediates. The nitrile carbon becomes CH2NH2, preserving the enlarged three-carbon skeleton.
- Reagents
- 1. LiAlH4; 2. Aqueous work-up
- Conditions
- Dry ether during reduction; work-up afterwards
- Reaction class
- Nitrile reduction
- Equation
- CH3CH2CN + 4[H] -> CH3CH2CH2NH2
Overview
Hydride additions reduce the carbon-nitrogen triple bond; the separate aqueous work-up protonates the nitrogen-containing intermediates. The nitrile carbon becomes CH2NH2, preserving the enlarged three-carbon skeleton.
Transformation
- Equation
- CH3CH2CN + 4[H] -> CH3CH2CH2NH2
- Reagents
- 1. LiAlH4; 2. Aqueous work-up
- Environment
- Dry ether during reduction; work-up afterwards
- Reaction class
- Nitrile reduction
- Mechanism
- hydride reduction followed by protonation
- Evidence level
- source-backed molecular example
Scope and limitations
- Scope
- The nitrile carbon becomes the terminal CH2NH2 carbon.
- Limitations
- [H] is formal reduction bookkeeping; water must be absent from the hydride stage.
Related reactions
- Cyanide substitution: Bromoethane → Propanenitrile
The carbon end of cyanide attacks the primary carbon of bromoethane as bromide leaves. The new C-C bond joins cyanide’s carbon to the original chain, giving a three-carbon nitrile rather than acetonitrile.
- Nitrile hydrolysis: Propanenitrile → Propanoic acid
Acid-assisted water addition converts the nitrile through an amide before hydrolysis gives the acid. The nitrile carbon becomes the carboxyl carbon, while its nitrogen leaves the organic skeleton as ammonium.
References
- Organic Chemistry: Synthesis of AminesJohn McMurry · OpenStax Organic Chemistry · 2023
Supports functional-group chemistry used to curate the linked examples. Checked 2026-09-16; named examples are applications of textbook scope, without claimed experimental yields.