Question

A variation of the acetamidomalonate synthesis can be used to synthesize threonine. The process involves the following steps: Ethoxide ion deprotonates diethyl acetamidomalonate, forming enolate anion 1; Enolate anion 1 makes a nucleophilic attack on acetaldehyde, forming tetrahedral intermediate 2; Protonation of the oxyanion forms alcohol 3; Acid hydrolysis yields dicarboxyamino alcohol 4; Decarboxylation leads to the final amino acid. Write out the mechanism on a separate sheet of paper, and then draw the structure of tetrahedral intermediate 2.

Answer 1

Answer:

See figure 1

Explanation:

For this reaction, we have the production of a carbanion as the first step. The base "ethoxide" can remove a hydrogen-producing a negative charge in the carbon (enolate anion 1). Then this negative charge can attack the carbon of the carbonyl group in the molecule acetaldehyde and the tetrahedral intermediate 2 is form. In the next step, we have the protonation of the oxygen to produce alcohol 3. A continuation we have the hydrolysis of the ester groups to produce the Dicarboxyamino alcohol and finally, we have a decarboxylation reaction we will produce the amino acid Threonine.

To further explanations see figure 1

I hope it helps!