Nitriles and hydroxynitriles
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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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