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Predict the best outcome of the following reaction by identifying A, B, and the final product, diethyl malonate NaOE EtOH (omit all H's and byproducts) B (charged form)

Chemistry Dec 29, 2020

Predict the best outcome of the following reaction by identifying A, B, and the final product, diethyl malonate NaOE EtOH (omit all H's and byproducts) B (charged form)

Expert Solution

1.Explanation | Common mistakes | Hint for next step

When diethyl malonate is treated with sodium ethoxide, the ethoxide ion functions as a base and removes the acidic hydrogen atom from diethyl malonate to form the reactive carbanion.

2.Explanation | Common mistakes | Hint for next step

The carbanion formed from the removal of a proton from diethyl malonate acts as a nucleophile and attacks the electrophilic carbon of the epoxide ring at the less substituted side. This leads to opening of the epoxide ring, to form an alkoxide ion.

3.

Explanation | Common mistakes

The alkoxide formed by the opening of the epoxide ring acts as a nucleophile and attacks the electrophilic carbon of one of the ester group of the same molecule, along with loss of the ethoxide ion. It leads to the formation of a lactone having a molecular formula c9h14o4

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