Identify the reagents necessary to achieve the transformation below. ?hoose from

Question

Identify the reagents necessary to achieve the transformation below.

?hoose from reagents (A-H):

A

B

C

D

E

F

G

H

If a reaction can be achieved by multiple reagents above, place answers in ascending order separated by a comma (e.g. A,C).

A

B

C

D

1) NaNH2
2) MeI
3) NaNH2 4) MeI
5) Na, NH3 (l)
6) OsO4, NMO       1) Na, NH3 (l)
2) Br2       1) Na, NH3 (l)
2) OsO4, NMO       1) H2, Lindlar's catalyst
2) Br2      

E

F

G

H

1) H2, Lindlar's catalyst
2) MCPBA
3) H3O+ 1) H2, Lindlar's catalyst
2) OsO4, NMO 1) Na, NH3 (l)
2) MCPBA
3) H3O+ 1) NaNH2
2) MeI
3) NaNH2 4) MeI
5) H2, Lindlar's catalyst
6) OsO4, NMO
OH OH

Explanation / Answer

F.

1) H2, Lindlar's catalyst
2) OsO4, NMO

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