Question

Select the reagent(s) that would efficiently convert the starting material to the product for the following transformations (if more than one reagent is needed, list them in order separated by commas with NO spaces. For example, e,d,c). Сhoose from reagents (A-L): A B C D CH3NH2, H H3O O3, DMS H2SO4, H2O, HgSO4 E F G H PCC, CH2Cl2 1) CH3MgBr 2) H2O H , HOCH2CH2OH NaOH I J K L 1) NH2NH2 2) KOH, H2O, Heat H , HSCH2CH2SH 1) LAH 2) H2O 1) CH3CH2MgBr 2) H2O

Answer 1

CH3NH2, H+ H3O+ O3, DMS H2SO4, H2O, HgSO4

E

F

G

H

PCC, CH2Cl2 1) CH3MgBr

2) H2O HOCH2CH2OH, H+ NaOH

I

J

K

L

1) NH2NH2

2) KOH, H2O, Heat 1) HSCH2CH2SH, H+

2) Raney Ni 1) LAH

2) H2O 1) CH3CH2MgBr

2) H2O