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Functional groups

MermaidWonders

Active member
Feb 20, 2018
113
How many isomers are there with the following description?
- Thioesters with the formula ${C}_{4}{H}_{8}OS$?

I was able to draw 2 of them, but apparently, the answer key showed and stated that there are 4. I am confused about why the following two are possibliities:

Screen Shot 2018-05-19 at 20.25.17.png

I thought that thioesters are the functional groups where a C double-bonded to O is attached to both an R group and S, with S itself being attached to an R group. So, I was wondering how the 2 structures in the above attachment could be thioesters when the C that is double-bonded to O isn't attached to an R group but is instead to an H?
 

Klaas van Aarsen

MHB Seeker
Staff member
Mar 5, 2012
8,780
How many isomers are there with the following description?
- Thioesters with the formula ${C}_{4}{H}_{8}OS$?

I was able to draw 2 of them, but apparently, the answer key showed and stated that there are 4. I am confused about why the following two are possibliities:



I thought that thioesters are the functional groups where a C double-bonded to O is attached to both an R group and S, with S itself being attached to an R group. So, I was wondering how the 2 structures in the above attachment could be thioesters when the C that is double-bonded to O isn't attached to an R group but is instead to an H?
Hi MermaidWonders !

From https://en.wikipedia.org/wiki/Thioester:

In chemistry thioesters are compounds with the functional group R–S–CO–R'.
150px-Thioester-2D-A.svg.png

So we can have both an R-group at the double-bonded C, and we can have another R'-group at the S.
 

MermaidWonders

Active member
Feb 20, 2018
113
Hi MermaidWonders !

From https://en.wikipedia.org/wiki/Thioester:

In chemistry thioesters are compounds with the functional group R–S–CO–R'.

So we can have both an R-group at the double-bonded C, and we can have another R'-group a the S.
Right. So doesn't it mean that there must be an R group attached to the double-bonded C, which means that the above isomers in the attached image are not valid structures since C is attached to H in both?
 

MermaidWonders

Active member
Feb 20, 2018
113
Wait... does H count as an R group?
 

Klaas van Aarsen

MHB Seeker
Staff member
Mar 5, 2012
8,780
Yep. H counts as an R-group. (Nod)
 

MermaidWonders

Active member
Feb 20, 2018
113