Identify the reagents you would use to accomplish the following transformation:
The transformation above can be performed with some reagent or combination of the reagents below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer.
A. 1) O₃; 2) DMS
B. 1) R₂BH; 2) H₂O₂, NaOH
C. MeI
D. H₂, Lindlar's cat.
E. Na, NH₃ (l)
F. NaNH₂
G. CH₃CH₂Br
H. H₂SO₄, H₂O, HgSO₄
I. MeONa
To accomplish the transformation of to , you can first reduce the alkyne to a trans-alkene and then perform hydroboration followed by oxidation. Here are the necessary steps:
So, the string of letters indicating the correct order of reagents is "EB".
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