MHB Thioester Isomer Count: ${C}_{4}{H}_{8}OS$ - 4 Possibilities

AI Thread Summary
The discussion centers on the number of thioester isomers for the formula C4H8OS, with initial confusion about the structures drawn. Two isomers were identified, but the answer key indicated there are four. Clarification was provided that thioesters can have hydrogen as a valid R group, which allows for additional isomers. This understanding resolves the confusion regarding the structures that include hydrogen. Ultimately, it is confirmed that hydrogen can indeed count as an R group in thioester formation.
MermaidWonders
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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:

View attachment 8117

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?
 

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  • Screen Shot 2018-05-19 at 20.25.17.png
    Screen Shot 2018-05-19 at 20.25.17.png
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MermaidWonders said:
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'.
View attachment 8118


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

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  • 150px-Thioester-2D-A.svg.png
    150px-Thioester-2D-A.svg.png
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I like Serena said:
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?
 
Wait... does H count as an R group?
 
Yep. H counts as an R-group. (Nod)
 
I like Serena said:
Yep. H counts as an R-group. (Nod)

Makes sense now. Thanks! :)
 
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