Which of the Following Sequences of Reagents Will Move the Alcohol

question 46

Multiple Choice

Which of the following sequences of reagents will move the alcohol functional group from the tertiary position of 1-methyl-1-cyclohexanol 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

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