Ch_322a_11.017

Ch_322a_11.017 - 2CH 3 CH 2 Br + H 2 O aryl alkyl ethers...

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Cleavage of Ethers by Acids Ethers are Lewis bases and react with acids to form oxonium ions : CH 3 CH 2 OCH 2 CH 3 : + H-Br CH 3 CH 2 OCH 2 CH 3 H + + Br - oxonium ion Strong acids (HI, HBr, H 2 SO 4 ) cleave dialkyl ethers: ROR' + HX R-X + R'OH HX R'X where R and R' are alkyl
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Example: Heating diethyl ether in conc. HBr gives two equivalents of ethyl bromide. CH 3 CH 2 OCH 2 CH 3 : + HBr CH 3 CH 2 OCH 2 CH 3 H + + Br - CH 3 CH 2 O-CH 2 CH 3 H + + Br - good leaving group CH 3 CH 2 OH + CH 3 CH 2 Br CH 3 CH 2 OH + HBr CH 3 CH 2 Br + H 2 O overall CH 3 CH 2 OCH 2 CH 3 + 2HBr
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Unformatted text preview: 2CH 3 CH 2 Br + H 2 O aryl alkyl ethers cleave in a specific direction O-CH 3 : + HBr O-CH 3 H + + Br-O-CH 3 H + + Br-O-H CH 3 Br + no further reaction alternative nucleophilic substitution reaction does not occur: O-CH 3 H + + Br-X Quiz 11.017 Provide all the organic products of the following reaction. CH 3 OCH 2-OCH 3 conc. HBr CH 3 Br + BrCH 2 OH...
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Ch_322a_11.017 - 2CH 3 CH 2 Br + H 2 O aryl alkyl ethers...

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