Ethyl isopropyl ether

Ethyl isopropyl ether 110 CsHi O Pyridine 172 C5H5N... 

Ethyl isopropyl ether C.HioO 625547 88.150 1.0625E-I-05 2.9215E-I-02... 

Acidic ether cleavages are typical nucleophilic substitution reactions, either SN1 or Sn2 depending on the structure of the substrate. Ethers with only primary and secondary alkyl groups react by an S 2 mechanism, in which or Br attacks the protonated ether at the less hindered site. This usually results in a selective cleavage into a single alcohol and a single alkyl halide. For example, ethyl isopropyl ether yields exclusively isopropyl alcohol and iodoethane on cleavage by HI because nucleophilic attack by iodide ion occurs at the less hindered primary site rather than at the more hindered secondary site. 

Ethoxy-2-propyne, 1909 f Ethyl isopropyl ether, 2012 f Ethyl propenyl ether, 1956 f Ethyl vinyl ether, 1610... 

Problem 14.55 Prepare the following ethers starting with benzene, toluene, phenol (C H OH), cyclohexanol, any aliphatic compound of three C s or less and any solvent or inorganic reagent a) dibenzyl ether, b) di-/i-butyl ether, (c) ethyl isopropyl ether, d) cyclohexyl methyl ether, (e) p-nitrophenyl ethyl ether, (/) divinyl ether (g) diphenyl ether. <... 

Isopropyl bromide Propene(87%) Ethyl isopropyl ether (13%)... 

Elimination to give propene competes with substitution to give ethyl isopropyl ether. Furthermore, the rate of elimination, like the rate of substitution, is proportional to the concentrations of 2-bromopropane and ethoxide ion. Thus elimination here is a second-order reaction (it may be helpful to review Section 8-4 at this point) ... 

Ethyl isopropyl ether Isobutyl methyl ether... 

The signal of the methine proton in isobutyl methyl ether will be split into more than a septet, however, because in addition to being split by two methyl groups, it is coupled to the two protons in the methylene group. Thus, isobutyl methyl ether does not have the correct splitting pattern to be the answer. The correct answer is ethyl isopropyl ether. 

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