Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 1-bromobutane. First, select the reagents necessary for the transformation shown, using no more than four steps in the synthesis. In part 2, you will synthesize any carbon reagents (other than acetylene) that were used in the synthesis. 2 H -H Br The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. A B C MeONa NaNH2 t-BuOK D E EtBr H₂, Lindlar's cat. Br2, hv G H 1 HBr, ROOR H₂, Pt HBr

Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 1-bromobutane. First, select the reagents necessary for the transformation shown, using no more than four steps in the synthesis. In part 2, you will synthesize any carbon reagents (other than acetylene) that were used in the synthesis. The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer.

Using acetylene as your only source of carbon atoms, identify a synthetic route for the production of 2-bromobutane. First, select the reagents necessary for the transformation shown, using no more than four steps in the synthesis. In part 2, you will synthesize any carbon reagents (other than acetylene) that were used in the synthesis. H- -H Br The transformation above can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) in the correct order, as a string of letters (without spaces or punctuation, such as “EBF"). If there is more than one correct solution, provide just one answer. A В МeONa NaNH2 t-BUOK E F EtBr H2, Lindlar's cat. Br2, hv G H HBr, ROOR H2, Pt HBr

Choose one of the multistep synthesis reactions. You must use the starting material provided and any additional carbons must be from acetylene or simple alcohol of four or fewer carbons. All carbons on your final compound must be from the materials listed. Complete the synthesis by showing all of the reagents necessary and intermediates on your paper. list the reagents for each step in the following format: 1) reagent(s) 2) reagent(s).. HO H2N