Chemical properties of ethers

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  • 1. Ethers are quite stable chemical compounds which do not react with bases, active metals, dilute acids, oxidising agents and reducing agents. Generally, they are of low chemical reactivity, but they are more reactive than alkanes (epoxides, ketals, and acetals are unrepresentative classes of ethers and are discussed in separate articles). Important reactions are listed after.

2. Acidic Cleavage Ethers are generally unreactive Strong acid will cleave an ether at elevated temperature HI, HBr produce an alkyl halide from less hinderedcomponent by SN2 (tertiary ethers undergo SN1) ROCH3 + HBr CH3Br + ROH3 3. Claisen Rearrangement Specific to allyl aryl ethers, ArOCH2CH=CH2 Heating to 200250C leads to an o-allylphenol Result is alkylation of the phenol in an ortho position 4. Peroxide Formation When stored in the presence of air or oxygen, ethers tend to form explosive peroxides, such as diethyl ether peroxide. The reaction is accelerated by light, metal catalysts, and aldehydes. In addition to avoiding storage conditions likely to form peroxides, it is recommended, when an ether is used as a solvent, not to distill it to dryness, as any peroxides that may have formed, being less volatile than the original ether, will become concentrated in the last few drops of liquid. 5. Lewis Bases Ethers serve as Lewis bases and Bronsted bases. Strong acids protonate the oxygen to give "onium ions." For instance, diethyl ether forms a complex with boron trifluoride, i.e. diethyl etherate (BF3.OEt2). Ethers also coordinate to Mg(II) center in Grignard reagents. Polyethers, including many antibiotics, cryptands, and crown ethers, bind alkali metal cations stron.Alpha-halogenation This reactivity is akin to the tendency of ethers with alpha hydrogen atoms to form peroxides. Chlorine gives alpha-chloroethers. 6. Done by: Bleona oba