5) Using the carbon-containing starting material(s), propose a synthesis the following retrosynthetic analysis. Provide structures for all intermediates. The carbon atoms in the product must originate from the starting material(s), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know (note: no mechanisms are required). CI CI Br

Provide a reasonable multistep synthesis of the following molecule from the indicated starting material, using any reagents necessary. Please include both a retrosynthesis and a forward synthesis (that includes the product and reagents of each individual step in your synthesis).

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

7) Using the carbon-containing starting material(s), propose a synthesis the following retrosynthetic analysis. Provide structures for all intermediates. The carbon atoms in the product must originate from the starting material(s), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know (note: no mechanisms are required). Br OH racemic = = + -Br

Starting from acetylene, propose a synthesis for the following compound. Use any other organic or inorganic reagents as needed. HO.

Propose an efficient synthesis for the given transformation. OH This transformation can be performed with some reagent or combination of the reagents listed below. Give the necessary reagent(s) i 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 Br₂, hv F 1) MeMgBr; 2) H3O+ K dilute H₂SO4 B 1); 2) H3O+ G Na, NH3 (1) L DMP or PCC 1); 2) H3O+ H MCPBA (RCO 3H) M SOCI2, pyridine D Mg, diethyl ether I 1) EtMgBr; 2) H3O+ N EtBr E H₂, Lindlar's cat. J HBr (xs), heat O 1) BH3-THF; 2) H₂O2, NaOH

Suggest an efficient synthesis for the following transformation: OH OH H- ? ŌH OH The synthesis above can be performed with some combination of the reagents listed below. Give the necessary reagents in the correct order, as a string of letters (without spaces or punctuation, such as "EBF"). There is more than one correct solution, but provide just one answer. A Mel B C EtBr cat. OsO4, NMO D E F NaNH, H2, Lindlar's cat. H2, Pt G H I 1) R₂BH; 2) H2O2, NaOH 1) RCO3 H; 2) H3O+ Na, NH3 (1)

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.

3. Provide a synthetic scheme for the transformation below. Your scheme must include all reagents & intermediates and account for stereochemistry & regiochemistry where appropriate. All carbon atoms in the product must come from the starting materials provided or from methanol. A retrosynthetic analysis is not required but may prove to be helpful. Hint: the shortest route to complete this transformation involves three reactions. OH OMe OH

10) Using the carbon-containing starting material(s), propose a synthesis the following retrosynthesis scheme. Provide structures for all intermediates. The carbon atoms in the product must originate from the starting material(s), but you may use as many equivalents of each starting material as you would like, and any reagent/reaction you know. (note: no mechanisms are required). E