substituted phenethylamines/amphetamines: numbered counter-clockwise or clockwise, and why?

[Mindlusion]

Put it to the test, in my drawing:

·the fisrt molecule depicts clockwise 2,5-dimethoxy-4-x-amphetamine, and the double bonds in the benzene ring reflect this.
· the second molecule depicts counter-clockwise 2,5-dimethoxy-4-x-phenethylamine and just as it appears that the methoxy orientations have switched, so to do the orientations of the double bonds, as you rotated the molecule on its axis.
·The third molecule depicts 3,6-dimethoxy-4-x-amphetamine, which can be distinguished from a clockwise 2,5-dimethoxy-4-x-amphetamine by the orientation of its double bonds

Take counter-clockwise numbered 2,5-dimethoxy-4-x-phenethylamine in 3-D, spin it on its axis until it appears that the methoxy substitutions have switched to clockwise orientation, keep your eye on the double bonds in the benzene ring as you rotate the molecule, the orientation of the double bonds in the benzene ring "switches" with the methoxy groupings.

-eg

This is literal insanity. You haven't taken in a word that I or DFZ have said, and you keep repeating the same old and wrong ideas over and over again and posting the same pictures without taking account of any new information.


But I will summarize it for you again, because I must be just as insane.

-double bonds do not have an orientation
-the molecule is symmetric, if 2,5 have the same substituents then shifting them over to 3,6 just gives the same molecule but flipped.

 

[entheogenic-gnosis]

there are 6 available carbon atoms, all of which are just as viable for substitution as the last...

If what you ate saying is correct than how do you explain 2,5-dimethoxy-3,4-dimethyl-phenethylamine?

If 2 and 5 and 3 and 6 are the same atom, than how can position 3 have a methyl group attatched? Because if what your saying is correct it would already be filled by a methoxy group.




-eg

Think about it.

Ask yourself. Is this molecule symmetric in the same way as 4 bromo 2,5diMeO?

Don't memorize, apply the knowledge

You never answered any of my questions.

-eg

-eg

 

[entheogenic-gnosis]

Put it to the test, in my drawing:

·the fisrt molecule depicts clockwise 2,5-dimethoxy-4-x-amphetamine, and the double bonds in the benzene ring reflect this.
· the second molecule depicts counter-clockwise 2,5-dimethoxy-4-x-phenethylamine and just as it appears that the methoxy orientations have switched, so to do the orientations of the double bonds, as you rotated the molecule on its axis.
·The third molecule depicts 3,6-dimethoxy-4-x-amphetamine, which can be distinguished from a clockwise 2,5-dimethoxy-4-x-amphetamine by the orientation of its double bonds

Take counter-clockwise numbered 2,5-dimethoxy-4-x-phenethylamine in 3-D, spin it on its axis until it appears that the methoxy substitutions have switched to clockwise orientation, keep your eye on the double bonds in the benzene ring as you rotate the molecule, the orientation of the double bonds in the benzene ring "switches" with the methoxy groupings.

-eg

This is literal insanity. You haven't taken in a word that I or DFZ have said, and you keep repeating the same old and wrong ideas over and over again and posting the same pictures without taking account of any new information.

Because you are not listening.

You have not preformed a single task which I asked which would illustrate what I'm saying, nor have you answered a single question which I proposed.

-eg

 

[Mindlusion]

i've explained to you countless times why the question your asking has no meaning and no right answer. You refuse to let go of it.

If you UNDERSTOOD how aromaticity and symmetry worked, then you would understand why your question doesn't make any sense.

That is why I answer your question by trying to teach you aromaticity and symmetry.

--

The biggest barrier to learning anything is hanging on to our old and wrong ideas. Everyone suffers from this. This is part of being human. Myself included, no one is exempt, even the greatest minds all experience this.

We must be ready and constantly vigilant, ready to throw away everything we think we know about anything.

 

[pitubo]

Entheogenic-gnosis please reconsider yourself a bit.

The double bonds depicted on symbolic drawings of aromatic ring systems do not really exist as such. To equate them to regular unsaturated carbon bonds and to draw inferences from that is quite an elementary mistake.

Some of the few chemically knowledgable people on the nexus have been trying to kindly explain things to you and your reactions reflect only yourself, not them. I'm sure that you'll appreciate their intentions more properly once you have seen the conceptual misunderstanding that kept you in error.

Be well, take some rest and read some of the chemistry books that you have been shelving for a while. Electron delocalization and resonance is an interesting subject for study. Benzene rings are just the entrance to the rabbit hole...

 

[downwardsfromzero]

Thanks mindlusion and pitubo for joining me in my frustration here.

We really have done all that we can to explain this here, it is now up to you, EG, to move forward.

Fortunately I feel these threads have helped me to learn a couple of things. So, thanks for getting me to use my molecular modelling software. This will be coming in useful in the near future.