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Ch. 20 - Carboxylic Acid Derivatives: NAS WorksheetSee all chapters
All Chapters
Ch. 1 - A Review of General Chemistry
Ch. 2 - Molecular Representations
Ch. 3 - Acids and Bases
Ch. 4 - Alkanes and Cycloalkanes
Ch. 5 - Chirality
Ch. 6 - Thermodynamics and Kinetics
Ch. 7 - Substitution Reactions
Ch. 8 - Elimination Reactions
Ch. 9 - Alkenes and Alkynes
Ch. 10 - Addition Reactions
Ch. 11 - Radical Reactions
Ch. 12 - Alcohols, Ethers, Epoxides and Thiols
Ch. 13 - Alcohols and Carbonyl Compounds
Ch. 14 - Synthetic Techniques
Ch. 15 - Analytical Techniques: IR, NMR, Mass Spect
Ch. 16 - Conjugated Systems
Ch. 17 - Aromaticity
Ch. 18 - Reactions of Aromatics: EAS and Beyond
Ch. 19 - Aldehydes and Ketones: Nucleophilic Addition
Ch. 20 - Carboxylic Acid Derivatives: NAS
Ch. 21 - Enolate Chemistry: Reactions at the Alpha-Carbon
Ch. 22 - Condensation Chemistry
Ch. 23 - Amines
Ch. 24 - Carbohydrates
Ch. 25 - Phenols
Ch. 26 - Amino Acids, Peptides, and Proteins
Ch. 26 - Transition Metals
Carboxylic Acid Derivatives
Naming Carboxylic Acids
Diacid Nomenclature
Naming Esters
Naming Nitriles
Acid Chloride Nomenclature
Naming Anhydrides
Naming Amides
Nucleophilic Acyl Substitution
Carboxylic Acid to Acid Chloride
Fischer Esterification
Acid-Catalyzed Ester Hydrolysis
Lactones, Lactams and Cyclization Reactions
Decarboxylation Mechanism
Additional Guides
Carboxylic Acid

Amides aren't horribly difficult to name. Once we figure out the suffix, then all that is left is to name the R groups that come off the nitrogen. So don't be suprised if N,N is in your name somewhere.

Concept #1: Amide Nomenclature


Time to learn how to name amides. Amides are carboxylic acid derivatives. Again, pretty much
everything that applies from a carboxylic acid derivative applies to an amide. We're going to replace the e ending of the parent chain with the suffix -amide. That's pretty straightforward. The only thing that complicates an amide is that you've got the possibility for multiple R groups on end. It's not like an ester for example. Remember that an ester, you can only have one R group on an O and that's it. It’s easy. But for nitrogen compounds, you can form three bonds. Sometimes you can have up to three things coming out with that end. You’re going to name them as substituents either on the N or N,N positions. It's just easier if I show you an example. This general structure would be N,N-dimethyl, notice because I have methyl groups coming off of it. Then it would be alkanamide. Of course, I'm waiting to know what the identity of that R group is to figure out what I put here. You could use common names or IUPAC names. Just remember to change your descriptions with numbers or Greek letters depending on which one you’re using. You guys are all set to start this example. Go ahead and try to name it and then I’ll help out. 

Example #1: Name the molecule


Alright guys, let's do the IUPAC name first so the IUPAC name would be 4 carbons, I would have a butanoic acid, wow that is not butanoic, butanoic, but I'm going to change it to butanamide, right? Awesome, this becomes to a butanamide, what substituents do I have? Well, because the fact that this is IUPAC I can just use numbers, so it would be 2, 3, so this is looking like a dimethyl and a hydroxy, h comes before m. So, it's going to be in terms of the root name, it's going to be 2, a hydroxy comes first. So, it's gonna be 3 hydroxy 2, 3 dimethyl butanamide, perfect, but we're not done, we need to name the alkyl group on the N and that always comes first, okay? So, did you guys have any problems naming this? this is called the vinyl group guys, that's just a common substituent you should know. So, this would be N- vinyl and then the rest of the name, okay? So, N-vinyl and then you got your root, cool? Let's do common. So, common is going to be a butyric acid. So, instead of butyric acid it would be butramide, butyramide, I'm sorry, butyramide okay? And we know that the substituents are going to be names using Greek symbols. So, pretty much I'm actually going to move this over because I drew it too far out, I want to move it back in. So, I can have space everything else the N-vinyl doesn't change guys. So, N-vinyl stays the same but now I'm going to have all these substituents with Greek symbols and the Greek symbols I'm going to be using are alpha and beta, okay? So, on in alphabetical order it would be beta hydroxy and then alpha beta dimethyl butyramide. Alright guys, awesome. So, not so bad, let's move on to the next problem.

Example #2: Draw the amide


Okay. So, for this one, maybe the most challenging thing was that you might have forgotten what a benzyl group looks like, remember, that's not a phenol, phenol is a benzene ring directly attached, you're like, oh shoot, I forgot. So, benzyl is a phenol with an extra CH2, let's draw our amide. So, our amide it looks like this for general formula right, now in terms of the root, acetamide, that's just a two carbon chain so this is drawn correctly, I'm just going to keep it like this CH3, that's my acetamide. Now, I just need that N alkyl groups and that's going to be two benzyl group. So, it's going to be 1, 2 like this and 1, 2 like this, awesome, and that's my compound. Now, guys one thing that actually didn't come up in any of these examples but I want to make sure you know it, it's just what happens if you have two different substituents, then you'd put those in alphabetical order on N. So, if I had, let's say an ethyl and a methyl then that would turn into N-ethyl-N-methyl, okay? You would not put N comma N ethyl methyl, that's wrong, you have to put the N before every substituent, other than that you should be good to go. Alright guys, so let's move on to the next topic.