what happens when ethyl amine reacts with acetyl chloride?
Answers
Answer:
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.
Answer:
It is known as the nucleophilic addition of carbonyl compounds. The nucleophile attacks the electron-deficient carbonyl carbon of acetyl chloride and fives the final product i.e., N-ethylacetamide or N-acetylethylamine.
Explanation:
The given reaction occurs in the presence of a base such as pyridine.
Pyridine abstracts the acidic proton of the ethyl amine (C₂H₅NH₂). It results in the formation of an anion of nitrogen.
The carbonyl carbon of acetyl chloride (CH₃COCl) is electron-deficient so it can easily undergo a nucleophilic addition reaction.
The anion of nitrogen attacks the electron-deficient carbonyl carbon of acetyl chloride and results in the formation of a tetrahedral intermediate.
With the elimination of the chloride ion, we get our desired product i.e., an amide.
The name of the amide is N-ethylacetamide or N-acetylethylamine. It is a secondary amide as the nitrogen is attached with two carbons and one hydrogen.
The reaction is as follows below:
C₂H₅NH₂ + CH₃COCl → (C₂H₅)HN-COCH₃ + HCl
When ethyl amine reacts with acetyl chloride, it results in the formation of a monoacetyl derivative, N-ethylacetamide or N-acetylethylamine.
Hence, when ethyl amine reacts with acetyl chloride it gives N-ethylacetamide or N-acetylethylamine as the final product.
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