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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: LightningShotz on June 17, 2020, 07:05:00 AM

Title: Question on correct chemical structure
Post by: LightningShotz on June 17, 2020, 07:05:00 AM
Hi

Please redirect if I have submitted in the wrong location.

I wanted to confirm how you would draw the correct structure for the following compound after undergoing a "water loss" in a mass spectrometer collision cell.

The molecule InChi is:
InChI=1S/C14H21NO2/c1-17-13-7-4-6-11(9-13)14(16)8-3-2-5-12(14)10-15/h4,6-7,9,12,16H,2-3,5,8,10,15H2,1H3/t12-,14-/m0/s1

Thanks for your help.



Title: Re: Question on correct chemical structure
Post by: sjb on June 17, 2020, 07:58:04 AM
CN(C)C[C@@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O (racemic, I think)

What are your thoughts. How can you eliminate water?
Title: Re: Question on correct chemical structure
Post by: LightningShotz on June 17, 2020, 08:14:22 AM
I came up with this but wasn't sure.
Title: Re: Question on correct chemical structure
Post by: sjb on June 17, 2020, 09:13:04 AM
Seems sensible but check the nitrogen and the conformation
Title: Re: Question on correct chemical structure
Post by: Babcock_Hall on June 17, 2020, 09:35:33 AM
When -OH is lost from one carbon, what else is lost, and where is it lost?
Title: Re: Question on correct chemical structure
Post by: LightningShotz on June 17, 2020, 03:39:20 PM
Seems sensible but check the nitrogen and the conformation
I’m not sure what you mean here?
Title: Re: Question on correct chemical structure
Post by: Babcock_Hall on June 18, 2020, 09:23:04 AM
Look at the groups on nitrogen.
Title: Re: Question on correct chemical structure
Post by: LightningShotz on June 18, 2020, 03:34:42 PM
Look at the groups on nitrogen.

I believe from the original InChi that it’s NH2.
Title: Re: Question on correct chemical structure
Post by: Babcock_Hall on June 18, 2020, 05:23:07 PM
Look at the groups on nitrogen.

I believe from the original InChi that it’s NH2.
The drawing in the second post (by sjb) showed two methyl groups.  Also, you have not addressed my comment.
Title: Re: Question on correct chemical structure
Post by: sjb on June 19, 2020, 03:04:06 AM
I confess, I'm not sure if my translation of the InChi is correct. Looking at it again, it is probably the primary amine and a pure enantiomer (http://www.chemspider.com/Chemical-Structure.23976885.html)
Title: Re: Question on correct chemical structure
Post by: sjb on June 22, 2020, 11:55:45 AM
What is the mechanism of the dehydration?