NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND AMINES

NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND AMINES

This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and amines. If you want the mechanism explained to you in detail, there is a link at the bottom of the page.
Ethanoyl chloride is taken as a typical acyl chloride. Any other acyl chloride will behave in the same way. Simply replace the CH₃ group in what follows by anything else you want.
Similarly, ethylamine is taken as a typical amine. Any other amine will behave in the same way. Replacing the CH₃CH₂ group by any other hydrocarbon group won't affect the mechanism in any way.
The reaction between ethanoyl chloride and ethylamine The facts
Ethanoyl chloride reacts violently with a cold concentrated solution of ethylamine. A white solid product is formed which is a mixture of N-ethylethanamide (an N-substituted amide) and ethylammonium chloride.

Notice that, unlike the reactions between ethanoyl chloride and water or ethanol, hydrogen chloride isn't produced - at least, not in any quantity. Any hydrogen chloride formed would immediately react with excess ethylamine to give ethylammonium chloride.

The mechanism
The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by the lone pair on the nitrogen atom in the ethylamine.

The second stage (the elimination stage) happens in two steps. In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off.

That is followed by removal of a hydrogen ion from the nitrogen. This might happen in one of two ways:
It might be removed by a chloride ion, producing HCl (which would immediately react with excess ethylamine to give ethylammonium chloride as above) . . .

and

. . . or it might be removed directly by an ethylamine molecule.

The ethylammonium ion, together with the chloride ion already there, makes up the ethylammonium chloride formed in the reaction.

NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND AMMONIA

NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND AMMONIA

This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and ammonia. If you want the mechanism explained to you in detail, there is a link at the bottom of the page.
Ethanoyl chloride is taken as a typical acyl chloride. Any other acyl chloride will behave in the same way. Simply replace the CH₃ group in what follows by anything else you want.
The reaction between ethanoyl chloride and ammonia The facts
Ethanoyl chloride reacts violently with a cold concentrated solution of ammonia. A white solid product is formed which is a mixture of ethanamide (an amide) and ammonium chloride.

Notice that, unlike the reactions between ethanoyl chloride and water or ethanol, hydrogen chloride isn't produced - at least, not in any quantity. Any hydrogen chloride formed would immediately react with excess ammonia to give ammonium chloride.

The mechanism
The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by the lone pair on the nitrogen atom in the ammonia.

The second stage (the elimination stage) happens in two steps. In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off.

That is followed by removal of a hydrogen ion from the nitrogen. This might happen in one of two ways:
It might be removed by a chloride ion, producing HCl (which would immediately react with excess ammonia to give ammonium chloride as above) . . .

and

. . . or it might be removed directly by an ammonia molecule.

The ammonium ion, together with the chloride ion already there, makes up the ammonium chloride formed in the reaction.

NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND ALCOHOLS

NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND ALCOHOLS This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and alcohols. If you want the mechanism explained to you in detail, there is a link at the bottom of the page. Ethanoyl chloride is taken as a typical acyl chloride. Any other acyl chloride will behave in the same way. Simply replace the CH3 group in what follows by anything else you want. Similarly, ethanol is taken as a typical alcohol. If you are interested in another alcohol, you can replace the CH3CH2 group by any other alkyl group. The reaction between ethanoyl chloride and ethanol The facts Ethanoyl chloride reacts instantly with cold ethanol. There is a very exothermic reaction in which a steamy acidic gas is given off (hydrogen chloride). Ethyl ethanoate (an ester) is formed. The mechanism The first stage (the addition stage of the reaction) involves a nucleophilic attack on the fairly positive carbon atom by one of the lone pairs on the oxygen of an ethanol molecule.
	Note:  Only one of the two lone pairs on the oxygen in the ethanol is shown. This is to avoid cluttering an already complicated diagram with things that aren't relevant.
The second stage (the elimination stage) happens in two steps. In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off. That is followed by removal of a hydrogen ion by the chloride ion to give ethyl ethanoate and hydrogen chloride.