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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

When naming acid chlorides we will use another functional group to help us get the correct answer. Are you ready to find out which one it is?

Concept #1: Acid Chloride Nomenclature


Let's name some acid chlorides, so guys acid chlorides are not hard to name but it's important to know that the process that you use is going to change a little bit depending on whether you're trying to a common or an IUPAC name, since there's a few rules associated with this I think the best way to learn it is just a drawn example. So, let's go ahead and say that we have a three carbon acid chloride and we're trying to figure out both, the common name and the IUPAC name for it, I'm actually going to move this over. So, I have more room to write, okay. Perfect. So, let's go ahead and start off with the common name, so the rules for the common name are that. Remember, that the common name starts from the carboxylic acid, you're basically in imagining, imagine this is carboxylic acid. Now, how, what would be the prefix that you'd use, what would be the root name, I'm sorry. So, if it's three carbons, we know that would be propionic acid, right? So, let's actually write that down, you're going to need your eraser because we're going to erase it but you can just write it for now, propionic acid. So, why am I writing this? this would be the name of the molecule if it was a carboxylic acid, right? But it's not, it's an acid chloride, so how do we change it? Well, for a common name you replace the -ic ending, ic acid ending with -yl chloride, so that means I would then erase acid and -ic and I would replace it with propionyl chloride, see? So, we're done, all you have to do is you take your common name and just take out the ending and you replace with -yl chloride, you're done. Now, for the IUPAC the process is completely different, because remember that the IUPAC group wouldn't be propionic acid, it would actually just be propane, right? Because it's a three carbon chain 1, 2, 3. So, that means the IUPAC name we're starting from propane. So, you would say, I'm going to start from propane and how am I going to change it? Well, similar to IUPAC rules you take out the e and you add suffix, but the suffix that we're going to add is little different, we're going to actually add an extra o to it. So, instead of being -yl chloride, we're going to end it with -oyl chloride, it actually sounds like motor oil, that's how you pronounce it. So, we would erase the e and we would say propanoyl chloride, and guys this is just a naming convention that's very widely used. So, it's great you should be aware of, alright? Cool. So, in terms of the general names for acid chlorides. Remember, that for common names you're basically using your alkenyl, it's alkenyl chloride and for your IUPAC name it's alkanoyl chloride, alright? Not hard at all just a little bit tricky okay, cool? So, go ahead and move on to the next set of questions and see if you can name and draw the following structures.

Example #1: Provide the IUPAC name for the molecule


Okay guys. So, everything that applies to carboxylic acids still applies to these acid chlorides. So, if you're naming it was common to have to use Greek symbols, you know, something like that, okay? So, let's do the IUPAC first, I know you're thinking, Oh dammit, I forgot that, okay? So, IUPAC. So, two carbons, I actually gave that one to you, man too easy, damn. So, we've got an ethanoyl chloride and this substituent will be a 2-hydroxy, right? So, let's put that all together 2-hydroxy ethanoyl chloride. Now, guys one little minor thing that you might be thinking is, hey Johnny, I remember from Orgo one that we used to always give the alcohol priority but guys those days are over, okay? Carbonyls in general, any carbonyl is always going to get priority over an alcohol, okay? Common name, so the common name is going to be again our acetyl chloride but it's going to be what? it's going to be alpha hydroxy, acetyl chloride, okay? Very good. So, because this is the alpha carbon. So, guys I made that one way too easy. So, let's see how you feel about the next one, go ahead and see if you can draw that molecule, by the way, if you can't recognize that symbol that is not a Y, that is a gamma okay? Okay. So, go for it.

Example #2: Draw the Acid-Chloride


Alright, so I'm going to draw my valeryl chloride, which is going to be a five carbon chain with a Corinne on it, okay? Then I've got gamma ethyl so that means that I'm going to go alpha, beta, gamma and place an ethyl group in that position and that would be the way that you draw that compound, okay? Awesome guys. So, not too bad, let's move on to the next topic