Sodium pentothal is a short-acting barbiturate derivative used as a general anesthetic and known in popular culture as truth serum. It is synthesized like other barbiturates, but uses thiourea, (H2N)2C=S, in place of urea. The mechanism involves the following steps: 1. Ethoxide ion deprotonates malonic ester, forming enolate anion 1;
2. Enolate anion 1 acts as a nucleophile in an SN2 reaction with ethyl bromide, forming alkylated intermediate 2;
3. Ethoxide ion deprotonates alkylated intermediate 2, forming enolate anion 3;
4. Enolate anion 3 acts as a nucleophile in an SN2 reaction with 2-bromopentane, forming alkylated intermediate 4;
5. Alkylated intermediate 4 reacts with thiourea to form tetrahedral intermediate 5;
6. Tetrahedral intermediate 5 collapses, expelling ethoxide ion and forming intermediate 6;
7. Intermediate 6 reacts with sodium hydroxide to form sodium pentothal.
Draw the mechanism out on a separate sheet of paper and then draw the structure of enolate anion 1. You do not have to consider stereochemistry. You do not have to explicitly draw H atoms. Do not include lone pairs in your answer. They will not be considered in the grading.