Tert- Naming

[Dianna Grigorian 1C]

I'm a little confused on when we include the prefix tert- in the naming of an organic molecule. Why in the example from the course reader the molecule has to have the perpendicular bond and be named tert-butyl? Can it not be linear instead of adding this type bond?

[Chem_Mod]

The prefix tert- indicates the carbon in the substituent bonded to the principal structure is tertiary (it is connected to three other carbons other than what it connects to in the principal structure). The second structure on page 96 of the course reader is simply an example of a structure with a tert-butyl substituent.

[Ariana de Souza 4C]

when we name something, for example, "tert butyl" does the t count in the alphabetical order? or does it not? I thought it would, since it's a common name, and for other common names like isopropyl or neopentyl, we include the prefix for alphabetic consideration?

And for number 1.17 in the book, we have a cyclohexane and attached to one of the carbons is a tert-butyl substituent, and to two other carbons are methyl groups. We numbered it so that tert-butyl was number 4 and the methyl groups were 1 and 2. I was thinking that if we weren't considering the t in tert-butyl and instead considered the b, the reason we would have still numbered it that way was because it would be 1,2,4 versus 1,3,4, and 1,2,4 was more favorable. Is this correct?

[Nick_OConnell_2F]

when we name something, for example, "tert butyl" does the t count in the alphabetical order? or does it not? I thought it would, since it's a common name, and for other common names like isopropyl or neopentyl, we include the prefix for alphabetic consideration?

And for number 1.17 in the book, we have a cyclohexane and attached to one of the carbons is a tert-butyl substituent, and to two other carbons are methyl groups. We numbered it so that tert-butyl was number 4 and the methyl groups were 1 and 2. I was thinking that if we weren't considering the t in tert-butyl and instead considered the b, the reason we would have still numbered it that way was because it would be 1,2,4 versus 1,3,4, and 1,2,4 was more favorable. Is this correct?

Hi Ariana,
In response to your first question, I believe the "t" in "tert" does not count in the alphabetical order because it is a prefix regarding the numerical amount of carbons bonded together. Likewise other prefixes such as the "di" for a dimethyl... (2 methyl substituents), refers to the number of methyl groups. In terms of common names, the prefixes "iso" and "neo" refer to a physical/structural motif or arrangement of substituent groups around a carbon rather than just the physical amount. Because these identify number AND structure, they must be included in alphabetizing.

[Ariana de Souza 4C]

when we name something, for example, "tert butyl" does the t count in the alphabetical order? or does it not? I thought it would, since it's a common name, and for other common names like isopropyl or neopentyl, we include the prefix for alphabetic consideration?

And for number 1.17 in the book, we have a cyclohexane and attached to one of the carbons is a tert-butyl substituent, and to two other carbons are methyl groups. We numbered it so that tert-butyl was number 4 and the methyl groups were 1 and 2. I was thinking that if we weren't considering the t in tert-butyl and instead considered the b, the reason we would have still numbered it that way was because it would be 1,2,4 versus 1,3,4, and 1,2,4 was more favorable. Is this correct?

Hi Ariana,
In response to your first question, I believe the "t" in "tert" does not count in the alphabetical order because it is a prefix regarding the numerical amount of carbons bonded together. Likewise other prefixes such as the "di" for a dimethyl... (2 methyl substituents), refers to the number of methyl groups. In terms of common names, the prefixes "iso" and "neo" refer to a physical/structural motif or arrangement of substituent groups around a carbon rather than just the physical amount. Because these identify number AND structure, they must be included in alphabetizing.

Okay, that makes sense. Thanks a lot! :)