[LightningShotz]

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.

[sjb]

(racemic, I think)

What are your thoughts. How can you eliminate water?

[LightningShotz]

I came up with this but wasn't sure.

[sjb]

Seems sensible but check the nitrogen and the conformation

[Babcock_Hall]

When -OH is lost from one carbon, what else is lost, and where is it lost?

[LightningShotz]

Seems sensible but check the nitrogen and the conformation

I’m not sure what you mean here?

[Babcock_Hall]

Look at the groups on nitrogen.

[LightningShotz]

Look at the groups on nitrogen.

I believe from the original InChi that it’s NH2.

[Babcock_Hall]

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.

[sjb]

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)

[sjb]

What is the mechanism of the dehydration?