Choose from Unknown - A Chiral Compound

[AGNuke]

A C₈H₁₂ chiral hydrocarbon, X, is reduced by catalytic Hydrogenation to an achiral C₈H₁₄. Ozonolysis (Oxidative) of X gave a chiral C₈H₁₂O₄ dicarboxylic acid. Choose X from the given.

Attempt
I first determined the chirality of the given alternatives. That rules out the 2nd option, as it is clearly symmetric. Then I just removed the double bonds, as asked in the question to see if any achiral hydrocarbon is formed. First one, I think is achiral. But I am not sure about the 3rd and 4th.

How about my attempt and is it something that I am overlooking?

 

[Borek]

I think you are on the right track, but I have been wrong about chiral compounds so many times in the past I no longer trust myself.

 

[AGNuke]

Yeah me too. It was in the test paper earlier, but I had to leave this simple looking question. What a shame.

I couldn't formulate it back then, that 1st one would be achiral after catalytic hydrogenation.

 

[chemisttree]

The 3rd and 4th remain chiral after hydrogenation but I'm sure you already knew that.

 

[AGNuke]

I was unable to think about them in exam.