Describe, and give an equation for, the reaction of halogenoalkanes (RX) with cyanide ions, CN-.

Halogenoalkanes are heated in a solution of potassium cyanide in ethanol to form nitriles.


RX + CN- ➔ RCN + X-

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What is the reaction mechanism for the reaction above?

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What is the mechanism for the reaction above?

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Describe, and give an equation for, the reaction of halogenoalkanes with excess concentrated ammonia, NH3.

Halogenoalkanes (RX) are heated under pressure in a solution of excess concentrated ammonia in ethanol to form primary amines.


RX + 2NH3 ➔ RNH2 + NH4X

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How are carboxylic acids produced from nitriles?

Nitriles are hydrolysed by heating under reflux with dilute acid or alkali to produce a carboxylic acid. The products of the alkali hydrolysis must be acidifed to produce the free carboxylic acid from the carboxylate salt. 


For example, ethanoic acid is produced from the hydrolysis of ethanenitrile using hydrochloric acid:

CH3CN + 2H2O + HCl  ➔ CH3COOH + NH4Cl

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How are hydroxynitriles produced from aldehydes and ketones?

Aldehydes and ketones are heated with hydrogen cyanide (HCN), generated in situ. by the reaction of KCN and sulfuric acid. A nucleophilic addition reaction takes place.


For example, 2-hydroxypropanenitrile is produced from ethanal and hydrogen cyanide:

CH3CHO + HCN ➔ CH3CH(OH)CN

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How are nitriles produced from halogenoalkanes?

Halogenoalkanes are heated under reflux in a solution of potassium cyanide in ethanol to form nitriles. A nucleophilic substitution reaction takes place.


For example, propanenitrile is produced from chloroethane and potassium cyanide:

C2H5Cl + KCN ➔ C2H5CN + KCl

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How are amines produced from halogenoalkanes?

Halogenoalkanes are heated under pressure in a solution of excess concentrated ammonia in ethanol to form amines. A nucleophilic substitution reaction takes place.


For example, ethylamine is produced from the reaction of chloroethane and ammonia:

C2H5Cl + 2NH3 ➔ C2H5NH2 + NH4Cl

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