IUPAC Nomenclature of Organic Substituents (cyclo, sec-, iso-, tert-, hydroxy, phenyl, etc)

In today’s lesson, we are going to discuss naming different types of substituents on organic compounds, including both their name and drawing. Note that all substituents are highlighted in blue in the pictures below. Sometimes, some of these groups are not substituents, but rather they are the main functional family – it depends what other functional families are in your compound. I will be introducing other functional families in later lessons, so we will do examples on what to do when we have multiple families in our shape. For now, let’s just consider that all of these act as substituents.

(a) C: Alkyl groups which are just carbons and hydrogens, are named using the regular prefixes of meth, eth, prop, etc (click here for a list of prefixes in my other post)

These would be methyl (1 carbon), ethyl (2 carbon), and propyl (3 carbon) substituents

(b) Cyclic Compounds: These use the same prefix system as alkyl groups, but with a “cyclo” in front of the name

These blue substituents would be cyclopentane, cyclobutane, and cyclopropane (I have numbered each ring so you can see how many carbons are in each of them)

(c) Benzene: A benzene as a substituent is called a Phenyl

Both of these substituents in blue are benzenes which will be called “phenyl” as a substituent in the name of the compound. Benzene can be drawn in two different ways as I showed above

(d) OH group: An alcohol group substituent is called a Hydroxy

2-hydroxybutane

(e) F, Br, Cl, I: Halogen substituents have their endings changed – respectively, these would be Fluoro, Bromo, Chloro, and Iodo

2-bromobutane (or if it was a Cl, F, or I in its place, it would respectively be 2-chlorobutane, 2-fluorobutane, or 2-iodobutane)

(f) NO2: Nitro

2-nitrobutane

(g) N3: Azido

Azidobutane

(h) S-H: Mercapto

2-mercaptobutane

These following groups are carbons bonded together in specific ways, and instead of naming these certain branches we have given them the following names if they are substituents:

(i) Isopropyl

5-isopropyldecane

(j) Sec-butyl

5-(sec-butyl)decane

(k) Tert-butyl

5-(tert-butyl)decane

(l) Isobutyl

5-isobutyldecane

(m) Neopentane

5-neopentyldecane

(n) Isopentane

5-isopentyldecane