15 pts) Fill in with the appropriate reagent or product for the controlled synthesis below. Enter your final answers next to the letters provided below the scheme, not in the scheme itself. A B C D Br2 UV light D NaOH OCH3 B A C KCN

The following synthesis requires more than one step. Specify the reagents you would use to carry it out. Specify reagents using letters from the table, first reagent on the left. Example: ab CH3CH₂CH₂C=CH a b C d Br₂ CH31 CH3CH₂1 CH3CH₂CH₂Br The reagents are (in order of use): f ? CH3CH,CH,CHO e CH₂l2/Zn(Cu) / ether h Reagents H₂/ Lindlar catalyst g H₂ over Pd/C 1. BH3 in THF 2. H₂O₂ in NaOH i j k I 1. 03 2. Zn/H3O+ Li in NH3 KOH / ethanol NaNH2 / NH3

Provide a synthesis of the target compound from the provided starting material. You may use any additional reagents you need. Clearly separate the reagents used for each step of these multistep syntheses. Br Br но вг

Use RSA, including disconnections, synthons and synthetic equivalents to show how to prepare the following target molecule. You can only use those organic molecules found in the Toolbox below and any inorganic reagents. Br Toolbox H CH3 H. Br

Provide the major product in each box for the multistep synthesis below. Mg° H2SO4 Br Et,0 2. aq NH4CI 80 °C

Propose a sequence of reactions to prepare the specified target compound from the indicated starting materials.  All of the carbon atoms in the target must originate in the specified starting materials.  Keeping this restriction in mind, you may use any other organic or inorganic reagents necessary to complete the synthesis. It is only necessary to show the overall transformations involved in your proposed synthesis.