:0: CH3CH2ONA, CH3CH2OH Select to Add Arrows 0:0 .H :0: Q CH3CH2ONA, CH3CH2OH CH3CH2ONA, CH3CH2OH Version: 3.136.3 +5049 production H 0:- :0: do :O: Select to Add Arrows CH3CH₂ONA, CH3CH2OH :OH: :0: Q Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. H H H Na CH3CH2ONA, CH3CH2OH :0: H H Select to Add Arrows :0: H Η H Select to Add Arrows CH3CH₂ONA, CH3CH2OH H .H CH3CH2ONA, CH3CH2OH :0: Select to Add Arrows CH3CH₂ONA, CH3CH2OH, CH2CHC(O)CH3 O: H :0: :0: Select to Add Arrows CH3CH2ONA, CH3CH2OH :0: 0:0- H H

Below you will find five reaction products (labeled product 1, product 2, etc.), but you will only find four reaction schemes. Your job is to match the reaction scheme with the correct product. Simply fill in the blank with the product number (i.e. 1, 2, 3, 4, or 5). Then, state the regio-control that governs the reaction (i.e. Markovnikov or anti-Markovnikov). If the reaction does not have any regio-control then enter none. OH OH OH - OH d OH Product 2 Product 3 Product 4 Product 5 1. Hg(OAc)2, H₂O 2. NaBH4 H₂O Product 1 a. regiocontrol: Br b. regiocontrol: C. H₂O+

(Practice Problems) CI 1) CH, - OH H;C CH, H,C - H,C CH, - Br 6) OH H CH,CH3 H,C 2) CH - (CH3)2 7) H. H,C F- H,C CH,CH, H,C, 3) CH = CH2 8) H;C - H,C H,C H. 4) Br с — CН, CH,CH,CH3 CH, - CH %3D Cн, 5) H,C OH

The compound shown below has a molecular formula of [x] and has a total of [Y] SP carbon/s.