Help! You start with two overall neutral molecules and, if you forgot the positive charge, you would end up with a negative ion. In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off. 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. Ethanoyl chloride is taken as a typical acyl chloride. Any other amine will behave in the same way. In the case we are discussing, an ethyl group has replaced one of the hydrogens on the nitrogen - hence N-ethylethanamide. As the electron pair moves back to form a bond with the carbon, the pair of electrons in the carbon-chlorine bond are forced entirely onto the chlorine to give a chloride ion. . The removal by another ethylamine molecule is probably the major route as long as the ethylamine is in excess - which it almost certainly will be. That produces a significant amount of negative charge on the nitrogen atom. Make sure you understand that mechanism before you go any further with this one. You may well feel that this is less daunting than the other route. In the first, the carbon-oxygen double bond reforms. In fact, it isn't any more difficult than the mechanism for the reaction between acyl chlorides and ammonia. Nucleophiles are either fully negative ions, or else have a strongly - charge somewhere on a molecule. A nucleophile is a species (an ion or a molecule) which is strongly attracted to a region of positive charge in something else. The corresponding reaction with an acyl chloride is: The reaction with phenylamine (aniline) Phenylamine is the simplest primary amine where the -NH 2 group is attached directly to a benzene ring. Similarities between the reactions The ethylammonium ion, together with the chloride ion already there, makes up the ethylammonium chloride formed in the reaction. This page guides you through the mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid 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. In the addition stage, an ethylamine molecule becomes attached to the carbon in the ethanoyl chloride. You can put both things right with a positive charge on the nitrogen. The reaction happens in two main stages - an addition stage, followed by an elimination stage. Changing either the acyl choride or the amine won't affect the mechanism in any way. Nitrogen can only form four bonds if it carries a positive charge. Similarly, ethylamine is taken as a typical amine. Ethanoyl chloride is taken as a … Replacing the CH3CH2 group by any other hydrocarbon group won't affect the mechanism in any way. Facts and mechanism for the reaction between an acyl chloride (acid chloride) and an amine to produce an N-substituted amide - nucleophilic addition / elimination NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND AMINES Ethanoyl chloride is taken as a typical acyl chloride. Ethanoyl chloride is taken as a typical acyl chloride. A white solid product is formed which is a mixture of N-ethylethanamide (an N-substituted amide) and ethylammonium chloride. They both pull electrons towards themselves, leaving the carbon atom quite positively charged. This mechanism also looks extremely complicated! Both of these are very electronegative. Any other acyl chloride will behave in the same way. . It is that carbon atom which is attacked by the lone pair on the nitrogen atom in an ethylamine molecule. NUCLEOPHILIC ADDITION / ELIMINATION IN THE REACTION BETWEEN ACYL CHLORIDES AND AMINES. Simply replace the CH3 group in what follows by anything else you want. N-ethylethanamide is an N-substituted amide. Ethanoyl chloride is taken as a typical acyl chloride. Ethanamide (a simple amide) has the formula CH3CONH2.