Which of the Following Reaction Series Will Result in the Formation

Multiple Choice

Which of the following reaction series will result in the formation of a new secondary (2°) alcohol from the beginning alcohol listed at the top?

A) Ethanol
1) Na°
2) CH₃CH₂I


B) t-butyl alcohol
1) K₂Cr₂O₇/acetic acid
2) CH₃-MgBr
3) H₃O⁺


C) 2-propanol
1) K₂Cr₂O₇/acetic acid
2) CH₃-MgBr
3) H₃O⁺


D) n-butanol
1) H₂SO₄/heat
2) Hg(OAc) ₂ (aq)
3) NaBH₄


E) 2-methylcycloxexanol
1) H₂SO₄/heat
2) OsO₄/H₂O₂
3) H₂SO₄/heat