A proton transfer reaction can occur when an aldehyde is placed in strong base, such as an alkoxide ion, producing an alcohol and a charged conjugate base that is resonance stabilized. In the left box, draw the curved arrows for the proton transfer. In the middle and right boxes, draw the two structures for the resonance-stabilized product as noted in the box-specific directions. Be sure to include all lone pairs and nonzero formal charges.

(i) Draw curved arrows to show the proton transfer reaction between the aldehyde and the alkoxide ion. (1) Draw the resonance structure with the charge on the OXYGEN. Do not add curved arrows. i) Draw the resonance structure with the charge on the carbon (no curved arrows)