Thursday, February 16, 2017

organic chemistry - Are all amides also amines?


I watched a Khan academy video on organic chemistry functional groups. It mentioned the amine and amide groups.


From what I see, an amide is an amine with a carbonyl group. However, the internet says that that assumption is wrong. I am guessing it has to do with the "R" groups on the amine functional group.


But in the video, he used an example of 2 ethyls (2 carbon chains, not sure what they are called) attached to the nitrogen, and the third R group is just a hydrogen. So what exactly is an R group, and are all amides also amines? Thanks in advance for the help.



Answer



An R group is used in structural formulae as a placeholder for a range of possible subtituents, e.g. hydrogen, alkyl chains or aryl groups etc. It can also be used as an abbreviation when R is a predefined rest.


An amide is a derivative of an organic acid where an $\ce{OH}$ group is substituted by $\ce{NR2}$ (with R = H or any organic rest, see here, for example). An amine is a base, and not formally derived from an acid, but from ammonia. It has the general formula $\ce{NR3}$, with R being H or any organic rest except X=O (X = C, S, etc.) or any other rest derived from an acid. So amides and amines are different classes of compounds. Here are examples for amides of a carboxylic acid, a sulfonic acid (sulfonamide), and an amine (from left to right):


enter image description here


The compound from the video that you have described is diethyl amine. You can formally derive it from ammonia by substituting two hydrogens with ethyl groups:



enter image description here


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