A laboratory student added 1-bromobutane to a flask containing dry ether and magnesium 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 here.

(a) Draw out the reactions that took place and show the product that was formed.

(b) Explain why the molecular ion is or is not visible in the mass spectrum, and show what ions are likely to be responsible for the strong peaks at m/z 59 and 101.

Transcribed Image Text:

100 59 80 60 101 40 20 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 m/z abundance