[neurones]

Hello,

In my class notes, it says that TNT is 2,4,6-trinitrotoluene.

I was thinking, and shouldn't it be 2-methyl-1,3,5-trinitrilbenzene?

I know that the one in the notes makes sense since it's shorter and since toluene is benzene with a methyl group.

But my reasoning for the way I was thinking is that an amide/amine (always confused between those two) has a higher priority than a methyl group. No?

Thanks

[Dan]

I was thinking, and shouldn't it be 2-methyl-1,3,5-trinitrilbenzene?

But my reasoning for the way I was thinking is that an amide/amine (always confused between those two) has a higher priority than a methyl group. No?

Yes, the IUPAC name is 2-methyl-1,3,5-trinitrobenzene.

The NO₂ groups are nitro groups, not amides or amines.

[neurones]

Ah ok, nice !

So for an amide and amine:

Amide is NH3
Amine is NH2

?

And which one has the most priority in naming? I would say Amide because there's 2 electrons on the Nitrogen to react, but wikipedia says it's Amine. (they didn't give a reason why)

[Dan]

Amide is NH3
Amine is NH2

No. It would take you seconds to google that.

As far as numbering goes, compounds are generally named to give the lowest possible numbers in the structure. So, 6-methyl-1,3,5-trinitrobenzene and 4-methyl-1,3,5-trinitrobenzene are exactly the same as 2-methyl-1,3,5-trinitrobenzene, but the latter is preferable because it keeps the locant numbers to the minimum.

If you have a choice because the locant numbers for two names are the same, for example:

1-chloro-2-iodobenzene vs 2-chloro-1-iodobenzene

Locants are 1 and 2 in both names, but the first one is chosen as it gives the lowest locant to the first substituent alphabetically.

Note that if you have:

4-bromo-2-chloro-1-iodobenzene vs 1-bromo-3-chloro-4-iodobenzene

The first name is chosen because it gives overall lower locants (1,2,4 vs 1,3,4) - the lower locants win, even though it means the first substituent alphabetically does not take position 1.

These are brief rules, things can get more complicated so it's better to look at them on a case by case basis if you have any more specific examples you'd like explained.

[jlbradfi]

go over your priority rules and then name