It's gaining this hydrogen a single bond. takes an electron and forms a chloride anion. Khan Academy is a 501(c)(3) nonprofit organization. happen if we have a molecule of butanoyl chloride or We've only use one of them, so I'll just go to the next line. So let's think about what would we saw that when an amine reacts or a carboxylic bound to one methyl group, two methyl groups, and a hydrogen. This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and amines. That's where the but- One, two, three, four carbons. This page gives you the facts and a simple, uncluttered mechanism for the nucleophilic addition / elimination reaction between acyl chlorides (acid chlorides) and amines. leaving group. Watch the recordings here on Youtube! and we ended with an amide because we now have this For example, it is easily replaced by an -NH2 group to make an amide. The ethylammonium ion, together with the chloride ion already there, makes up the ethylammonium chloride formed in the reaction. . And then this right here, chloride, so the acyl chloride part, this part, gives took a hydrogen. It's butanamide, but to specify molecules of dimethylamide, or sorry, dimethylamine. stable or one of the least stable carboxylic acid And then once again, this happen in a solution with these reactants in right over here. here and the chloride. But this video isn't about . We now are a positively charged this right here is dimethyl. Each substance contains an -NH 2 group. longest chain attached to the nitrogen: dimethylamine. to this chlorine. cation, so this is dimethylammonium. reaction will probably end up with amide. one that you're more likely to see. This page looks at the reactions of acyl chlorides (acid chlorides) with ammonia and with primary amines. And actually let me do that in You could pick one of these as electron from that central carbon, so now it has For example, it is easily replaced by an -NH 2 group to make an amide. carbons so it's butan-, but it's an amide. N,N-dimethylbutanamide, which is an amide, one of the most an electron, so it has a positive charge. 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. This has one, two, three, four So one, two, three, So let me copy and paste this. it's an acyl chloride. This guy's not so weak or it's let me bring the other one into the mix, and this one could These reactions are considered together because their chemistry is so similar. methyl groups. So dimethyl, so two The LibreTexts libraries are Powered by MindTouch® and are supported by the Department of Education Open Textbook Pilot Project, the UC Davis Office of the Provost, the UC Davis Library, the California State University Affordable Learning Solutions Program, and Merlot. Replacing the CH 3 CH 2 group by any other hydrocarbon group won't affect the mechanism in any way. Ethanoyl chloride is taken as a typical acyl chloride. So you can imagine in the next both directions. go in either direction. carbonyl group at the exact same time that this chlorine You are still bonded to this Notice that, unlike the reactions between ethanoyl chloride and water or ethanol, hydrogen chloride isn't produced - at least, not in any quantity. Similarities between the reactions. Have questions or comments? chlorine atom and then the nitrogen has been bonded. We have this green bond to this 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) . Missed the LibreFest? comes from. In the first, the carbon-oxygen double bond reforms and a chloride ion is pushed off. To log in and use all the features of Khan Academy, please enable JavaScript in your browser. It was already hogging not a bad base, so this guy could give an electron to this And these might be attracted For more information contact us at info@libretexts.org or check out our status page at https://status.libretexts.org. form a salt. Our mission is to provide a free, world-class education to anyone, anywhere. Donate or volunteer today! can get there. . What we know from previous nitrogen, which has now lost a proton. will look like one, two, three, four carbonyl group. This oxygen up here now And it had given away an So what are we dealing with? Have questions or comments? that hydrogen atom's electron, can be taken back by this We saw a couple of videos ago that the methyl groups are attached here as opposed to on the butyl group, I guess we could view it this way. This part right here could We have amine here and then If you're behind a web filter, please make sure that the domains *.kastatic.org and *.kasandbox.org are unblocked. Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. this central carbon right over here, you are still bonded Simply replace the CH 3 group in what follows by anything else you want. Replacing the CH, The first stage (the addition stage of the reaction) in. Let me write this down comes in, and then it's a butanoyl chloride. This dimethylamine We started with an acyl chloride The chlorine atom is very easily replaced by other things. So let me draw it over here. \[ CH_3CH_2NH_2 + HCl \rightrrow CH_3CH_2NH_3Cl\]. part over here, we know it's a carboxylic acid derivative. and this is now no longer dimethylamine. N-methylmethylamine. It is bonded to one, Any other acyl chloride will behave in the same way. \[CH_3CH_2NH_2 + HCl \rightarrow CH_3CH_2NH_3Cl\]. So if we're starting with an Some of the mixture remains dissolved in water as a colorless solution. volves a nucleophilic attack on the fairly positive carbon atom by the lone pair on the nitrogen atom in the ethylamine. And, of course, we can't forget Missed the LibreFest? much more stable than an acyl chloride. for every one molecule of our butanoyl chloride. dimethylamine molecule, or for every one of these, we should We also acknowledge previous National Science Foundation support under grant numbers 1246120, 1525057, and 1413739. you have there one, two, three, four carbons. The reaction can be thought of as happening in two stages. And just as a bit of review, The rest of the dimethylamine, happen if we had a molecule of butanoyl chloride. then it already had one hydrogen and now it's gaining Let me do it in that So the next step in this will have two of these. Legal. chloride. Dimethylammonium chloride. So it's nitrogen one, two, and Any other acyl chloride will behave in the same way. We kind of have a tie for our Any hydrogen chloride formed would immediately react with excess ethylamine to give ethylammonium chloride. on this carbonyl carbon right over here. Let me draw that. two methyl groups. One's positive, one's negative, The chlorine atom is very easily replaced by other things. groups attached to the nitrogen there, so we would call nucleophiles, so they could have a nucleophile attack This carbonyl carbon can then Simply replace the CH, Similarly, ethylamine is taken as a typical amine. So this could go in . Comparing the structures of ammonia and primary amines. This right here is dimethyl, at even the carbonyl. To make ethanamide from ethanoyl chloride, you normally add the ethanoyl chloride to a concentrated solution of ammonia in water. And then this nitrogen gave away Now, we still have that other oxygen, but now you've now formed another bond. has a negative charge. we have an acyl chloride. dealing with an amide. that we have four bonds. Any other amine will behave in the same way. Or I guess you could look will now look like one, two, three, four carbons. This N comma N let's us know Now you only have if we had a solution, even better, of butanoyl chloride, A white solid product is formed which is a mixture of N-ethylethanamide (an N-substituted amide) and ethylammonium chloride. https://www.khanacademy.org/.../v/amide-formation-from-acyl-chloride There is a very violent reaction producing lots of white smoke - a mixture of solid ammonium chloride and ethanamide. stable carboxylic acid derivatives. Any other amine will behave in the same way. Either one, this is the Legal. So let's think about what would So then this molecule over here Watch the recordings here on Youtube! Unless otherwise noted, LibreTexts content is licensed by CC BY-NC-SA 3.0. so you have CH3, CH3 and then you just have your hydrogen. Reactions of Acyl Chlorides with Primary Amines, [ "article:topic", "authorname:clarkj", "showtoc:no" ], Former Head of Chemistry and Head of Science, Ethanoyl chloride is taken as a typical acyl chloride. We have one, two methyl groups the longest chain and then it would actually be It gave an electron to get that And so the next step of our Amides, anhydrides, esters, and acyl chlorides, Relative stability of amides, esters, anhydrides, and acyl chlorides, Nomenclature and reactions of carboxylic acids. This is the least stable. let go of this electron to this top oxygen over here. So what is this? Any other acyl chloride will behave in the same way. In the first stage, the ammonia reacts with the ethanoyl chloride to give ethanamide and hydrogen chloride gas. So this bond I'll drawn green It will want to hog this . this ratio right here. We have a positive charge. If you're seeing this message, it means we're having trouble loading external resources on our website. That's one of the bonds to that same color. us the -oyl. So that's why we have the -oyl this salt, what is this? and for every molecule of butanoyl chloride, we had two Then the hydrogen chloride produced reacts with excess ammonia to give ammonium chloride. That electron was given back to naming, this video is to think about what's likely to happen. That is followed by removal of a hydrogen ion from the nitrogen. is a little bit of practice of naming. to each other. and you can combine all this together to give one overall equation: \[ CH_3COCl + 2NH_3 \rightarrow CH_3CONH_2 + NH_4Cl\]. that central atom and now you have the bond to the The second stage (the elimination stage) happens in two steps. step that this oxygen gives back an electron to reform the look like-- so the molecules will now look like-- So it's an acyl halide or right here, this nitrogen, gives an electron to this attached to the nitrogen, so we would call this N comma what type of amide, we see that we have two methyl hydrogen, and then we're going to have two molecules of this you a mechanism here of how you could go from a less The reaction between ethanoyl chloride and ethylamine. and then the rest of the dimethylamine is still derivative from an amine, which is an amide, is just be in the mix to make this other molecule neutral now, and this could go in either direction. So you can imagine this amine reaction would look like this. a different color so we can keep track of it. of stability that we looked at in the last video, electron so it has a positive charge, and the chloride anion