Question

The following transformation can be carried out in four stepsusing some of the reagents listed.

From the reagent table below, select the reagent(s) you would useto accomplish your goal. (Select "none" if no further reagents areneeded. If there are multiple possibilities, give the shortestroute.)

1° reagent Na,NH3NaNH2,NH3 H2 / LindlarHCl,coldBr2,hν, heatnoneconc.H2SO4NaOCH2CH3,HOCH2CH3Br2, dark, cold	2° reagent H2 /LindlarNaNH2,NH3 Br2, hν,heatNaOCH2CH3,HOCH2CH3Br2, dark, coldnoneHCl, coldNa, NH3conc.H2SO4
3° reagent HCl, coldNa, NH3 NaOCH2CH3,HOCH2CH3conc.H2SO4Br2,dark, coldH2 /LindlarnoneNaNH2, NH3Br2, hν,heat	4° reagent Na,NH3Br2, dark,cold NaNH2, NH3noneHCl, coldH2 / Lindlarconc.H2SO4Br2,hν, heatNaOCH2CH3,HOCH2CH3