Chapter 1, Problem 1.9E

Consider the reaction of a propanoate ester with hydroxide ion shown below. A series of four alcohol leaving groups were tested to determine which would be the best leaving group. Based on the pKa values of the alcohols, predict which alcohol would produce the fastest hydrolysis reaction. HO FOR A Alcohol I, pKa =16.0 B Alcohol II, pKa =10.0 C Alcohol III, pKa = 7.2 + ROH D Alcohol IV, pKa = 6.6

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. :0: NaOH, H₂O 00:4 Na O heat NaO Select to Add Arrows Select to Add Arrows :0: Na a NaOH, H2O :0: NaOH, H2O heat heat Na ONH Select to Add Arrows

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 CH3NH3+ :0: :0: HO CH3NH2 HH iSelect to Add Arrows i Select to Add Arrows i HH CH3NH3+ CH3NH2 Select to Add Arrows i CH3NH3 CH3NH2 ايكدا HH Select to Add Arrows