CHEM 120 Part III: Multi-step synthesis Recitation Provide reagents needed for the following transformations. More than one step is required for each reaction. 1 Provide missing reagents 2 Provide missing reagents 3 OH Provide missing reagents OH -Br RC9

Draw Intermediate CH3OH₂+ protonation H H3C -0 H Q CH3OH deprotonation loss of H₂O elimination H3C :0 ÖH -CH3 Draw Intermediate CH3OH deprotonatio Please select a drawing or reag

Minoxidil is a molecule that causes hair growth in some people. It was originally synthesized as a vasodilator for the treatment of hypertension (high blood pressure). Most of the patients taking the drug for hypertension were seen to grow body hair. Due to other side effects, its oral use was stopped, but it became popular as a topical cream to promote hair growth. NH2 N-OH NH Minoxidil The first key reaction in one synthesis of minoxidil follows. Draw the product of this reaction. NH NC.

5 Select the reagents that will allow the following transformation to occur. ? as he 1) 03 2) DMS mCPBA 1) BH3 2)H₂O2, NaOH dilute H₂SO4 H

Identify the suitable reagents for the given reaction and arrange them accordingly. OH A+&+F OEt 1 2 OEt OEt 1) EtOH, H₂SO4; 2) EtOH, H₂SO4 1) EtONa followed by H₂O; 2) TsCl/py followed by EtONa 1) EtONa followed by H₂O; 2) NaH followed by EtBr O 1) EtOH, H₂SO4; 2) NaH followed by EtBr O 1) EtOH, H₂SO4; 2) TsCmy followed by EtONa

Identify the missing reagent, 1) ???? 2) NaCN OH CN O PB13 O TSCI (Ts: Tosyl) O CISIME3 (Trimethyl silyl chloride) socI2 O sOCi2

Select the most appropriate reagent combination to successfully execute the following reaction. ? OH OH + enantiomer A) H₂SO4, H₂O B) i) RCO3H, ii) H3O+ C) i) 03, ii) DMS

Complete the following reaction of hydrolysis using arrows and drawing the intermediate products Catión estabilizado por resonancia Catión oxonio MeO OMe - MeOH R R Acetal Catión oxonio Catión oxonio Meo OH R- R Hemiacetal MeOH Catión estabilizado por resonancia -H® R R Compuesto carbonilico

3 CHEM 120 Part III: Multi-step synthesis Recitation Provide reagents needed for the following transformations. More than one step is required for each reaction. 1 Provide missing reagents 2 Provide missing reagents LOH Provide missing reagents Br OH RC9

What is the major product to the following elimination reaction? Br DBN nts ations aculty