Nomenclature question, Please help

[jirotrom]

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Is N-[3-chlorophenyl] propanamide

the same as m-chlorophenyl propanamide?

 

[whatDATmean]

Nope, the key to this problem is the N before the 3-chlorophenyl propanamide.

N-[3-chlorophenyl] propanamide tells you than the 3-chlorophenyl is attached to the nitrogen hence the N designation.

For m-chlorophenyl propanamide suggests that you take a benzene ring and you have

Benzene ring that has Cl then a meta propanamide with respective to that Cl

But as far as my understanding go you don't use m-, o-,p- unless benzene is your main carbon chain but in this case the propanamide is your main chain so you can't use meta ortho or para names.

 

[jirotrom]

👍 Thanks! you really helped me here

 

[iamgosu]

but they are the same compound if you draw it out i think 😕

 

[Troyvdg]

but they are the same compound if you draw it out i think 😕

no. See above explanation

 

[orgohacks]

but they are the same compound if you draw it out i think 😕

Without the N, it is ambiguous whether the propanamide is bound by the CARBON to the benzene ring or to the nitrogen.

e.g. (3-ClPh)-CH2CH2C(O)NH2 or CH3CH2C(O)NH-(3-ClPh)

See what I mean?

You need the N in the name there to alleviate the confusion. Hence, N-(3-chlorophenyl)-propanamide.

 

[iamgosu]

Without the N, it is ambiguous whether the propanamide is bound by the CARBON to the benzene ring or to the nitrogen.

e.g. (3-ClPh)-CH2CH2C(O)NH2 or CH3CH2C(O)NH-(3-ClPh)

See what I mean?

You need the N in the name there to alleviate the confusion. Hence, N-(3-chlorophenyl)-propanamide.

oh i see, thanks!
i thought it would be normally assumed that the amide functional group would be attached to the phenyl ring via the Nitrogen, and not the C, but you are right.