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

In summary, there are 2 possible structures for thioesters, one with an R-group at the double-bonded C and another with an R'-group at the S.
  • #1
MermaidWonders
112
0
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?
 

Attachments

  • Screen Shot 2018-05-19 at 20.25.17.png
    Screen Shot 2018-05-19 at 20.25.17.png
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  • #2
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.
 

Attachments

  • 150px-Thioester-2D-A.svg.png
    150px-Thioester-2D-A.svg.png
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  • #3
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?
 
  • #4
Wait... does H count as an R group?
 
  • #5
Yep. H counts as an R-group. (Nod)
 
  • #6
I like Serena said:
Yep. H counts as an R-group. (Nod)

Makes sense now. Thanks! :)
 

1. What is a thioester?

A thioester is a compound that contains a sulfur atom bonded to a carbonyl carbon atom. It is similar to an ester, but instead of an oxygen atom, it contains a sulfur atom in its functional group.

2. How many isomers does ${C}_{4}{H}_{8}OS$ have?

There are four possible isomers for ${C}_{4}{H}_{8}OS$. These are based on the arrangement of the atoms around the central carbon atom.

3. What are the differences between the four isomers of ${C}_{4}{H}_{8}OS$?

The main difference between the four isomers of ${C}_{4}{H}_{8}OS$ is the position of the sulfur atom. In each isomer, the sulfur is bonded to a different carbon atom, resulting in different chemical and physical properties.

4. How do you determine the isomer count of a thioester?

To determine the isomer count of a thioester, you need to identify the number of possible arrangements of the atoms around the central carbon atom. In this case, there are four possible arrangements, resulting in four isomers.

5. What are the applications of thioester isomers?

Thioester isomers have various applications in organic synthesis and biochemistry. They are used to create complex molecules and as intermediates in the synthesis of pharmaceuticals and natural products. They also play a crucial role in biochemical processes, such as protein folding and post-translational modifications.

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