Chemical properties of ethoxyethane

Ethers are quite stable compounds. These are not easily attacked by alkalies, dilute mineral acids, active metals, reducing agents or oxidising agents under ordinary conditions.

(i) Reaction with acids : Being Lewis bases, ethers form complexes with Lewis acids such as BF₃, AlCl₃, FeCl₃, etc. These complexes are called etherates.

Similarly, diethyl ether reacts with Grignard reagent forming Grignard reagent etherate.

Due to the formation of the etherate, Grignard reagents dissolve in ether. That is why Grignard reagents are usually prepared in ethers. However, they cannot be prepared in benzene, because benzene has no lone pair of electrons and therefore, cannot form complexes with them.

(ii) Action of hydroiodic acid

(a) With cold HI

Cold

C₂H₅OC₂H₅ + HI —————→ C₂H₅I + C₂H₅OH

^{Diethyl ether Ethyl iodide Ethyl alcohol}

(b) With hot HI

R – O – R' + 2HI ——————→ RI + R'I + H₂O

(iii) Zeisel method : RI + AgNO₃ (alc.) → AgI ↓ + RNO₃

•The silver iodide thus form can be detected and estimated. This is the basis of Zeisel method for the detection and estimation of alkoxy group in a compound.

(iv) Action of PCl₅

R – O – R + PCl₅ ————→ 2RCl + POCl₃. There is no reaction in cold.

(v) Reaction with acetyl chloride

ZnCl₂

CH₃COCl + C₂H₅ . O . C₂H₅ ——————→ CH₃COOC₂H₅

^{Acetylchloride Diethyl ether} heat ^{Ethyl acetate}

(vi) Reaction with acid anhydride

ZnCl₂

CH₃CO . O . OCCH₃ + C₂H₅ . O . C₂H₅ —————→ 2CH₃COOC₂H₅

^{Acetylchloride Diethyl ether} heat ^{Ethyl acetate}

(vii) Dehydration

Al₂O₃

C₂H₅OC₂H₅ ———————→ 2CH = CH₂ + H₂O

300^oC

(viii) Reaction with carbon mono oxide

BF₃/150^oC

C₂H₅OC₂H₅ + CO ———————→ C₂H₅COOC₂H₅

^{Diethyl ehter} 500 atm. ^{Ethyl propionate}

(ix) Action of bases