Hello, I would appreciate some help with this question, thank you!Screenshot 2026-01-12 at 10.28.28 PM.png
To convert the cyclohexene (ring double bond) into the major alcohol shown (anti-Markovnikov on the ring):
1. BH₃·THF
2. H₂O₂, NaOH (hydroboration–oxidation)
This puts OH at the less substituted ring carbon (as drawn).
Step effects
TsCl, pyridine: converts the ring –OH → –OTs (same carbon).
Oxymercuration in water: adds OH Markovnikov to the terminal alkene side chain.
NaBD₄ (demercuration): delivers D to the carbon that originally held Hg → for a terminal alkene this ends up as D on the terminal carbon.
Dess–Martin oxidizes the side-chain secondary alcohol → ketone (tosylate stays unchanged).
reaction sequence problems hydroboration tosylation oxymercuration Dess Martin.jpg