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
Correct Answer:
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