6. Fill in the boxes with appropriate reagents or products to achieve the synthesis show. In some cases it may be helpful to work backwards from the indicated products. (TIP: Consider these as a series of individual reactions) Br Br2 CH3 CH3 CH3 CH3 5. Nobu CH3 CH3 H CH3 CH3 1. NBS hv 2. HE PIC 3. CH3 TsO CH3 4. H NH3 THE CH3 CH3 27

What is a successful synthetic strategy for this transformation? OH O 1. XS MeMgBr, 2. H2O 1. SOCI2, 2. CH3Br O 1. DMSO, C202C12, 2. MeMgBr, 3. H3O+ O NaBH4 OH

R Indicate the correct set of reactions from the choice below that would accomplish the following synthesis. H-=CH3 Product Starting Material 1. NaNH2 2. CH3CH2CH2BR 3. 9-BBN-THF 4. HO-,H2O2, H2O 1. NaNH2 2. CH2=CHCH2B 3. Na/NH3(liq) 4. MCPBA 1. NaNH2 2. CH2=CHCH2Br 3. H2, Pd/C 4. BH3/THF 5. H0-H,O2, H20 1. NaNH2 2. CH;CH2CH2B 3. BH3/THF 4. HO-,H2O2, H2O 1. NaNH2 2. CH2=CHCH2B 3. MCPBA PrtScn F8 Home End F10 PgUp PgDn F2 F4 F5 F7 & %23 2$ C 3. 4. 5. 9- 7. 8. 6 E. P. K G. 7. H.

3. Provide the order of addition of reagents added for the following conversions in the correct order. O₂N CH3