Nitrogen Compound

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CIE AS Chemistry Your notes
3.7 Nitrogen Compounds

Contents
3.7.1 Primary Amines
3.7.2 Nitriles & Hydroxynitriles
Page 1 of 8
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3.7.1 Primary Amines

Your notes
Production of Amines
Amines are compounds with the amine (-NH2 ) functional group
They can be produced as a result of nucleophilic substitution reactions of halogenoalkanes
when they are heated under pressure with ethanolic ammonia (NH3 in ethanol)
The halogen atom in halogenoalkanes is more electronegative than the carbon atom it is
bonded to
The halogen, therefore, draws electron density from the C-X bond (where X is the halogen)
towards itself
The carbon, therefore, has a partial positive charge and the halogen itself has a partial negative
charge
The lone pair of electrons on the nitrogen atom (in NH3) acts as a nucleophile and attacks the
partial positively charged carbon
As a result of this nucleophilic attack, the C-X bond is broken and the halogen is substituted by an
amine group
Amine replaces the halogen in halogenoalkanes in a nucleophilic substitution reaction
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3.7.2 Nitriles & Hydroxynitriles

Your notes
Production of Nitriles
Nitriles are compounds with a -CN functional group
They can be prepared from the nucleophilic substitution of halogenoalkanes
Propanenitrile, an example of a nitrile

Reaction with KCN
The nucleophile in this reaction is the cyanide, CN- ion
Ethanolic solution of potassium cyanide (KCN in ethanol) is heated under reflux with the
halogenoalkane
The product is a nitrile
If an aqueous solution of potassium cyanide (KCN (aq)) is heated under reflux with the
halogenoalkane, an alcohol can be formed instead of the nitrile
Bromoethane reacts with ethanolic potassium cyanide when heated under reflux to form propanenitrile
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Exam Tip
Your notes
The nucleophilic substitution of halogenoalkanes with KCN adds an extra carbon atom to the
carbon chain.This reaction can therefore be used by chemists to make a compound with one
more carbon atom than the best available organic starting material.
Page 4 of 8
Production of Hydroxynitriles
Hydroxynitriles are compounds with both a hydroxy (-OH) and cyanide (-CN) functional group Your notes
They can be prepared from the nucleophilic addition of aldehydes and ketones
2-hydroxy-2-methylpropanenitrile
Reaction with HCN
The nucleophilic addition of hydrogen cyanide to carbonyl compounds is a two-step process
In step 1, the cyanide ion attacks the carbonyl carbon to form a negatively charged intermediate
In step 2, the negatively charged oxygen atom in the reactive intermediate quickly reacts with
aqueous H+ (either from HCN, water or dilute acid) to form a 2-hydroxynitrile
Page 5 of 8
Your notes
The cyanide ion attacks the carbonyl carbon to form a negatively charged intermediate which quickly
reacts with a proton to form a 2-hydroxynitrile compound
Exam Tip
The actual negative charge on the cyanide ion is on the carbon atom and not on the nitrogen
atom.
Page 6 of 8
Hydrolysis of Nitriles
Nitriles are hydrolysed by either dilute acid or dilute alkali followed by acidification to give a Your notes
carboxylic acid
Hydrolysis is the breakdown of a compound using water
Hydrolysis of nitriles
Nitriles are hydrolysed by either dilute acid or dilute alkali followed by acidification
Hydrolysis by dilute acid results in the formation of a carboxylic acid and ammonium salt
Hydrolysis by dilute alkali results in the formation of a sodium carboxylate salt and ammonia;
Acidification is required to change the carboxylate ion into a carboxylic acid
The -CN group at the end of the hydrocarbon chain is converted to a -COOH group
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Hydrolysis of nitriles by either dilute acid (1) or dilute alkali and acidification (2) will form a carboxylic acid
Your notes
Exam Tip
Unlike the formation of nitriles which add an extra carbon atom to the carbon chain, hydrolysis
doesn’t change the number of carbon atoms.
Page 8 of 8

Nitrogen Compound

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CIE AS Chemistry Your notes

3.7 Nitrogen Compounds

3.7.1 Primary Amines

Amine replaces the halogen in halogenoalkanes in a nucleophilic substitution reaction

3.7.2 Nitriles & Hydroxynitriles

Propanenitrile, an example of a nitrile

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