[Eternal_Fire]

Hi all,
I have an assignment in which such a question was asked. This is the only organic chemistry question I have been stuck at. I have been staring at this problem and writing all the possible structures but still can't get all the possible isomers. Any guidance to derive all the possible isomers will be appreciated.

Thanks

Structural isomerism and stereoisomerism should be considered when attempting this question.
How many isomeric compounds with molecular formula C5H6O4 contain two -CO2H groups and one C=C double bond?
A)   5
B)   6
C)   7
D)   8
 

[Borek]

Show structures you got and we will start from there.

You can use SMILES or just draw and attach the image (note: file can't be too large, typical picture taken with mobile is too large, so you will need to edit it and make it smaller).

[Eternal_Fire]

https://imgur.com/a/qPxTv3B

Here you go. I can't seem to think of any others.

[mjc123]

Well, for a start, those aren't -CO2H groups. Conventionally, -CO2H means a carboxylic acid, not a formate ester.

Have you considered branched chain molecules?

[Eternal_Fire]

I fixed that and found a branched one. But I am not sure how it's considered as an isomer

[Borek]

So as far as I can tell you mean these two?





You marked these as having two stereoisomers, can you mark which carbon is the chiral one in both cases?

I am not sure how it's considered as an isomer

What is the isomer definition?

[Babcock_Hall]

Have you thought about the degree of substitution of the vinyl group?