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 :0: H H HH Na → CH3CH2ONA, CH3CH2OH H H H H :0: Select to Add Arrows Η :0: H 0:0 :0: H ☑ CH3CH2ONA, CH3CH2OH H 0:0 :0: H :0: Select to Add Arrows Η CH3CH2ONA, CH3CH2OH :0: :0 H Select to Add Arrows H

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°• 1 H Drawing Arrows NaOH, H₂O heat :I:0 > H. Na Ⓒ :O:

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 first step of this reaction sequence. Be sure to account for all bond-breaking and bond- making steps. I H BH₂ H B H Select to Add Arrows > H Bll H BH₂

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: H HH NaOH, H2O :0: H Na → Select to Add Arrows CH3CH2CH2CH О HH :0: 'H H H HH Na ◉H Select to Add Arrows NaOH, H2O :0: 60• NaOH, H₂O H H HHI I Select to Add Arrows Select to Add Arrows NaOH, H2O H NaOH, H₂O Hi HH Select to Add Arrows > HH :0: H 1 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.

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. Drawing Arrows H H H H :CI:0 H. :Ö:

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 steps. Be sure to account for all bond-breaking and bond-making steps.

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 to show the interconversion between resonance hybrid contributors. Be sure to account for all bond-breaking and bond-making steps.

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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. Drawing Arrows C H HH :CHO ww M