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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

Nitriles are a piece of cake when it comes to naming. It's as easy as adding the word "nitrile" to our name. Let's take a look.

Concept #1: Nitrile Nomenclature


Let's learn how to name nitriles. Nitriles are honestly the easiest functional group to name because there's nothing tricky about them. All you’re going to do is you’re going to take the name of your alkane chain and you’re going to add the suffix nitrile to the name. You're not even going to drop the e, so don’t. Don't drop the e. Just literally add the word nitrile at the end. Substituents are named using numbers. They're located using numbers. In this case, this would be five-carbon chain that has a nitrile group on it. This would be pentane nitrile. Notice that I kept the e. Don't drop it because then it’s going to look weird. Pentane nitrile, and that’s it. We’ve got a practice problem. Go ahead and see if you can name it and then I'll give you the answer.

Example #1: Name the structure


So guys, the only possibly tricky thing about naming nitriles is that you have to remember to include that first carbon in the carbon chain, okay? Meaning, this is your first carbon and it's part of a four carbon chain, this is going to be a butane nitrile and now we just need to name my substituents, which appear to be a 2, 3 dimethyl. So, it's going to be 2, 3 dimethylbutanenitrile. So easy, don't you wish every topic goes like this in orgo? Okay, so then here's another one, go ahead and try to draw it and that will give you the answer.

Example #2: Draw the molecule


And here we go, six carbon chain 1, 2, 3, 4, 5, 6. Now, that six carbon is part of the nitrile. So, then I would draw triple bond N, okay? Six carbons, this is my one carbon. So, then I have a two amino, that's going to be NH2 and a 4 bromo, that's it. Alright, let's move on to the next topic.