Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methylcyclohexanol to a secondary position? A) 1. KOtBu; 2. Hg(OAc)₂, H₂O; 3. NaBH₄ B) 1. TsCl, pyr; 2. KOtBu; 3. BH₃-THF; 4. H₂O₂, NaOH C) 1. H₂SO₄, heat; 2. BH₃∙THF; 3. H₂O₂, NaOH D) 1. TsCl, pyr; 2. NaOH; 3. BH₃∙THF; 4. H₂O₂, NaOH E) C and D will both work

Question

Quizplus · Accepted Answer

Options C and D both describe processes that can move an alcohol functional group from a tertiary to a secondary position. Option C involves a rearrangement via a sulfonyl group, while option D uses tosylate formation followed by nucleophilic substitution and reduction, both viable for the desired transformation.

Which of the Following Sequences of Reagents Will Move the Alcohol