Question

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.

Answer 1

Answer:

Figure 1

Explanation:

In this case, we have to ester with a "malonic synthesis" in which we have to add a strong (ethoxide) to produce an enolate ion that would form a new C-C bond with an alkyl halide (ethyl bromide and bromo pentane). Then a "nucleophilic acyl substitution reaction" takes place to add thiourea, in this step two ethanol groups are eliminated to form a cyclic structure. Finally, an "elimination reaction" happen by the addition of sodium hydroxide generating a double bond and a negative charge in the sulfur atom that is neutralized with the positive charge of sodium.

See figure 1 for the total mechanism

I hope it helps!