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Unformatted text preview: a linear chain instead of a branched one. 3) A laboratory student added 1-bromobutane to a flask containing dry ether and Mg turnings. An exothermic reaction resulted, and the ether boiled vigorously for several minutes. Then she added acetone to the reaction mixture, and the ether boiled even more vigorously. She added dilute acid to the mixture, and separated the layers. She evaporated the ether layer, and distilled a liquid that boiled at 143 °C. GC–MS analysis of the distillate showed one major product with a few minor impurities. The mass spectrum of the major product is shown below. Show the structure of this major product. Mg/ether MgBr Br O H+ OH O- The molecular ion peak should be at 116, but the loss of a carbon from the quatenary C forms a stable carbocation at 101. 1) One of the following compounds is responsible for the IR spectrum shown. Draw the structure of the responsible compound. 1-butene, 1-butanol, 4-hydroxy-1-butene, methyl propyl ether, butanoic acid. First thing to notice is the presence of an alcohol at 3200-3600 cm -1, which narrows our choices down to 1-butanol, 4-hydroxy-1-butene a...
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