Complete the following retrosynthetic analysis (the final product is shown first, and the initial starting material is benzene). Supply all required reagents and precursors. • are all correct and consist of the fewest possible reactions. Save ŅH2 Br

Propose a mechanism for the conversion of E to F. The reagent used in this synthesis is ethyl chloroformate. The other product of this conversion is chloromethane, CH3Cl. Your mechanism should show how the CH3Cl is formed.

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

4. As shown below, compound 2 can be made from compound 1 in two steps. Provide the reagents, A, and draw the product B for the first step. Then, provide the reagents C that lead to the final product. (Hint: Product B has a peak in its 'H NMR spectrum at 11.1 ppm that integrates to 1H.) 1 OH A C B

Current Attempt in Progress Starting with benzene and using any other necessary reagents of your choice, design a synthesis the following compound. Note: some of these problems have more than one plausible answer. Br CBr: The transformation above can be performed with some reagent or 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"). If there is more than one correct solution, provide just one answer. A. CH₂CI, AICI 3 D.CH;CI, NaNH, B. excess NBS, heat E. Br₂, FeBr3 C. 1) Mg: 2) CHBrg F. CHBr 3, AlCl3