[bobafettswife]

I ran an experiment where I hydrogenated Ethyl cinnamate to make ethyl 3-pheynylpropanoate
I ran IR
and took a tlc of both material in two different parts
the Rf values of both ended up being about the same
The reason or such small Rf differences between the starting material and product is that because they are very smiler in molecular structure minus one double bond (the product) so the structures are both just about the same about of polar so they streak up the tlc about the same?

My other question is ethyl cinnamate stains with potassium permanganate but the product does not (ethyl 3-pheynylpropanoate)
I think that is because potassium permanganate causes double bond cleavage. So since ethyl cinnamate has two double bonds It breaks down the but c=c double bond not the c=O were is in the case of staining ethyl 3-pheynylpropanoate the oxygen cleavages and thus does not stain and show up under uv?
Based off the the judgment of that
the reaction was done (hydrogenation) with trans-ehtyl cinnamate if we used cis-ethyl cinnamate would we see a different product. I say yes because the location of the double bond would change but i am not entirely sure.
It has been  while since I took O chem help would be greatly appreciated.

[discodermolide]

If you hydrogenate the trans and cis cinnamic acid esters you end up with the same compound.

[spirochete]

I ran an experiment where I hydrogenated Ethyl cinnamate to make ethyl 3-pheynylpropanoate
I ran IR
and took a tlc of both material in two different parts
the Rf values of both ended up being about the same
The reason or such small Rf differences between the starting material and product is that because they are very smiler in molecular structure minus one double bond (the product) so the structures are both just about the same about of polar so they streak up the tlc about the same?

My other question is ethyl cinnamate stains with potassium permanganate but the product does not (ethyl 3-pheynylpropanoate)
I think that is because potassium permanganate causes double bond cleavage. So since ethyl cinnamate has two double bonds It breaks down the but c=c double bond not the c=O were is in the case of staining ethyl 3-pheynylpropanoate the oxygen cleavages and thus does not stain and show up under uv?
Based off the the judgment of that
the reaction was done (hydrogenation) with trans-ehtyl cinnamate if we used cis-ethyl cinnamate would we see a different product. I say yes because the location of the double bond would change but i am not entirely sure.
It has been  while since I took O chem help would be greatly appreciated.

Besides Disco's corrections the other parts of your question answers all seem to be correct, unless I misread something.

[bobafettswife]

could you explain why you end up with the same compound I dont seem to understand why is it because it is not adding any steriocenters?

[discodermolide]

Here is the hydrogenation reaction:Hydrogenation removes double bonds.