Predict the major product when each reagent reacts with ethylene oxide.

(a) NaOCH₂CH₃(Sodium ethoxide)

(b) NaNH₂(sodium amide)

(c) NaSPh (sodium thiophenoxide)

(d) PhNH₂(aniline)

(e) KCN (potassium cyanide)

(f) NaN₃(soidum azide)

Epoxides are considered to be more reactive since opening the epoxide ring relieves the strain of the three-membered ring. Strong bases can attack and open epoxides, even though the leaving group is an alkoxide. Amines can also open epoxides.

(a) Ethylene oxide when reacts with sodium ethoxide gives 2-ethoxy ethanol as the major product.

(b) Ethylene oxide when reacts with sodium amide gives 2-amino ethanol (ethanolamine) as the major product.

(c) Ethylene oxide when reacts with sodium phenoxide gives 2-(phenylthio)ethanol as the major product.

(d) Ethylene oxide when reacts with aniline gives N-phenyl ethanolamine as the major product.

(e) Ethylene oxide when reacts with potassium cyanide gives 2-cyanoethanol as the major product.

(f) Ethylene oxide when reacts with sodium azide gives 2-azidoethanol as the major product.