[HaroTaro]

Provide the reagents and write out the steps for the following multi-step synthetic transformation.

I have problem starting this question. I don't know which step to start. I know that since H and D are added to form in trans fashion, they should be added using sodium/lithium liquid ammonia.But how do I added it to the phenol group? How do I deprotonate. Very confused...

[nj_bartel]

I'd alkylate before reducing.

[oc dummy]

What I did first was adding NaNH2 first, to take off the H... then I have an nucleophilic C which will then add that entire group in.
Then deal with the H's and D's.

[azmanam]

Why do you suppose the deuterium atoms were necessarily added trans?

[oc dummy]

is it because its added on as X2.. (halide)
so it has to go on trans?

[nj_bartel]

Dislike problems like this, seeing as how that could just as easily be a syn addition with bond rotation.

[HaroTaro]

still confused...

[HaroTaro]

So does D adds to alkyne/alkene in the same fashion as H? Or does it add like Br2 and Cl2?

[azmanam]

same fashion as H.  All reactions that are available to H₂ are available to D₂

[oc dummy]

 would it be correct to just write D2?
Or do I need a catayst?
like H2, Pd...
so D2, Pd??