Drawing the structure of 1,3,5 - trimethylphenol

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SUMMARY

The discussion centers on the naming and structure of 1,3,5-trimethylphenol, where participants clarify that the correct structure is actually 2,4,6-trimethylphenol. The confusion arises from the prioritization of functional groups, specifically the hydroxyl (OH) group, which should be assigned the lowest possible number in accordance with IUPAC naming conventions. The reference to 4-chloroaniline illustrates that the NH2 group can take precedence in certain structures, further complicating the naming process. Ultimately, the original homework statement contains an error regarding the correct nomenclature.

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Sunwoo Bae
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Homework Statement
Draw the structure of 1,3,5 - trimethylphenol
Relevant Equations
none
1612368249218.png

The picture above is the correct answer, but I do not understand why.
I thought that the OH group on the top has to be prioritized and be numbered 1.
But then, the structure would have to be named 2,4,6-trimethylphenol, not 1,3,5-trimethylphenol.

For example, 4-chloroaniline structure looks this way. From this structure, it seems likes NH2 group on the top did get priority.
1612368161220.png

Can anyone tell me what I am missing?
 
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Sunwoo Bae said:
Homework Statement:: Draw the structure of 1,3,5 - trimethylphenol
Relevant Equations:: none

View attachment 277372
The picture above is the correct answer, but I do not understand why.
I thought that the OH group on the top has to be prioritized and be numbered 1.
But then, the structure would have to be named 2,4,6-trimethylphenol, not 1,3,5-trimethylphenol.

Agreed. The structure pictured is 2,4,6-trimethylphenol.
https://en.wikipedia.org/wiki/Mesitol

The question is likely in error.
 
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