Amide Formation - Online Tutor, Practice Problems & Exam Prep

Amide formation is a type of condensation reaction where a carboxylic acid and an amine combine, resulting in the loss of water and the creation of an amide. In the process, the carboxylic acid's hydroxyl group (OH) and one hydrogen from the amine are removed to form water. This reaction requires an H⁺ catalyst to initiate. The remaining carboxylic acid and amine bond together, with the carbon from the carboxylic acid and the nitrogen from the amine forming a new bond. The resulting amide structure features a carbonyl group (C=O) single-bonded to a nitrogen. This reaction is essential in organic chemistry for synthesizing amides, which are common in various organic compounds and biological molecules.

Amide Formation

In this video we're going to talk about amide formation. Now under this type of reaction, a carboxylic acid and an amine undergo a condensation reaction to form an amide. Now recall a condensation reaction results in the loss of water. To do this, the carboxylic acid loses its OH group or OH portion and amine nitrogen loses its one hydrogen. OK, so for this to work, nitrogen needs to possess at least one hydrogen.

Now here for this to start we need an H⁺ catalyst. So jump starts this whole process. If we take a look here at a typical amide formation general reaction, we have our carboxylic acid. And remember, squiggly line means it's connected to something else which we don't care about at this moment. And then we have our amine, which again it also has a squiggly line, meaning it's connected to something else. Again, we're not concerned with that for focusing on the carboxylic acid portion and the amine portion.

We're going to lose water. So the OH from the carboxylic acid and the H from the amine, we lose those to produce water. This carbon needs to make up for the bond it just lost and so does this nitrogen. So what they do is they bond to each other and in that way we create an amide. Remember an amide is when we have a carbonyl connected single bonded to a nitrogen group, right? So this would be how we form an amide through a condensation reaction between a carboxylic acid and an amine.

Amide Formation Example

Determine the amide product form when 4 methylpentanoic acid reacts with butylamine. Now we know that the carbacillic acid and the amine will undergo a condensation reaction where we lose the OH from the carbolic acid and one of the hydrogens from the amine.

What's left behind connects together to form our my product. So here we have our carbonyl. We're making the amide connection now. This nitrogen loses one of its HS, but it still has another one and it's still connected to this butyl chain.

O . This would represent our my product again formed through the condensation reaction of our starting carbacillic acid and amine.

Predict the amide product formed when 2,2-dimethylpropanoic acid reacts with dimethylamine.

• A.
• B.
• C.
• D.

Here’s what students ask on this topic:

Which of the following reactions leads to the formation of an amide?

The formation of an amide typically occurs through a reaction known as the acyl substitution reaction. In this process, an acyl group (derived from an acid) reacts with a nitrogen-containing compound such as an amine. One of the most common ways to form an amide is by reacting a carboxylic acid with an amine. The general equation for this reaction is:

$R-{\mathrm{COOH}}_{\text{(carboxylic acid)}}+{\mathrm{R\text{'}}}_{-}\to R_{-}+H_2$

Another common method is the reaction of an acid chloride with an amine:

$R-{\mathrm{COCl}}_{\text{(acid chloride)}}+{\mathrm{R\text{'}}}_{-}\to R_{-}+{\mathrm{HCl}}_{\text{(hydrochloric acid)}}$

Both of these reactions involve the nucleophilic attack of the nitrogen atom on the carbon atom of the carbonyl group, followed by the elimination of a leaving group (water in the case of carboxylic acids, and HCl in the case of acid chlorides), leading to the formation of an amide bond.

Which of the following reactions does not yield an amine?

To determine which reaction does not yield an amine, we need to consider typical reactions that produce amines and those that do not. Common reactions that yield amines include the reduction of nitro compounds, reductive amination, the Gabriel synthesis, and the alkylation of ammonia or an amine.

A reaction that does not yield an amine would be one that either doesn't involve nitrogen-containing starting materials or does not result in the formation of a C-N bond. For example, the SN₂ reaction of an alkyl halide with a hydroxide ion would yield an alcohol rather than an amine. Similarly, the oxidation of an alcohol does not produce an amine; it typically leads to the formation of an aldehyde or a ketone. The hydration of an alkyne also does not yield an amine; instead, it produces an aldehyde or a ketone, depending on the specific conditions and the structure of the alkyne.