Question

Integrated Problem 21.104 Get help answering Molecular Drawing questions Get help answering Molecular Drawing questions. When a malonic ester synthesis is performed using excess base and 1,4-dibromobutane as the alkyl halide, an intramolecular reaction occurs, and the product contains a ring. Draw the product of this process:

Answer 1

Answer:

See explanation below

Explanation:

The malonic ester synthesis is a commonly used reaction to form several products. In this case when we have an excess of base, in presence of an alkyl halide of 4 carbons, this will promoves the formation of a ring.

This synthesis has 4 steps:

1) Enolate formation. In this step the strong base (Such as methoxyde) will substracts the more acidic atom of hydrogen in the molecule. In the malonic ester, it would be the hydrogens from carbon 2.

2) Enolate alkylation. Once the enolate has been formed in the previous step, it will become a nucleophyle, and will attack the alkyl halide to form an enolate alkyl. Then, as we have excess of base, we are going back to step 1 to substract the remaining hydrogen, and then, step 2 again so the remaining bromine leaves the molecule. In this part, it will form the ring.

3) Ester hydrolisis. When the ring is formed, it's time to do an hydrolisis of the ester, so we can convert the ester into carboxilic acids. As we have two ester,we will have two carboxilic acids.

4) Decarboxilation. Finally, a decarboxilation occurs in presence of heat to have the final product with a ring and CO2 there as final products.

See picture attached for products thislllll