Help chemistry urgent

what exam board is this from?

Help I. Don’t get this q my exam final is in a week… the red is correct ans but idk how to do it I know that d2o removed OH but how do I know the rest

I don’t get the chemical shift I part why is it 2-3 isn’t that a c double bond o.
I mean for the first one the it’s A H attached to a So isn’t it 1-2??

When you shake it with D₂O, some of the hydrogens get replaced by deuteriums.
The hydrogens this happens to are hydroxyl (-OH) and amine group ones – the hydroxyl one can be deprotonated (so you get –O^-) and the amine one can be protonated/deuterated (so you get –NH₃⁺, –NH₂D⁺, NHD₂⁺, ND₃⁺ – remember in solution there is interchange)… so these groups will not appear in the ¹H NMR spectrum.

The remaining hydrogens are the ones attached to the carbons.
For the CH hydrogen, there is only one hydrogen atom in this environment, so the relative peak area = 1. There are two hydrogens attached to the adjacent carbon, so the splitting pattern is a triplet (as n + 1 = 2 + 1 = 3).
For the CH₂ hydrogens, the same applies. There are two of these hydrogens, so relative peak area = 2. There is one "adjacent" hydrogen, so the splitting pattern is a doublet (1 + 1 = 2).


https://en.wikipedia.org/wiki/Hydrogen–deuterium_exchange
https://www.chemguide.co.uk/analysis/nmr/highres.html (see "A clever way of picking out the -OH peak")
https://chemguide.co.uk/organicprops/aminoacids/acidbase.html

And
https://cpb-us-e1.wpmucdn.com/sites.ucsc.edu/dist/9/291/files/2015/11/IR-Table-1.pdf
At the top of page 3 there is a nice little diagram of approximate chemical shifts

Thank uuu
but I still don’t get the chemical shift part… in the exam I’m not gonna be given any thing apart from the pt and the nmr data and I’m still stuck on how to get 2-3 and 3.3-4.4 for the chemiscal shift paft