Question

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.

Answer 1

Hi, you have not provided structure of the aldehyde and alkoxide ion.

Therefore i'll show a mechanism corresponding to the proton transfer by considering a simple example.

Explanation: For an example, let's consider that proton transfer is taking place between a simple aldehyde e.g. acetaldehyde and a simple alkoxide base e.g. methoxide.

The hydrogen atom attached to the carbon atom adjacent to aldehyde group are most acidic. Hence they are removed by alkoxide preferably.

After removal of proton from aldehyde, a carbanion is generated. As it is a conjugated carbanion therefore the negative charge on carbon atom can conjugate through the carbonyl group to form an enolate which is another canonical form of the carbanion.

All the structures are shown below.