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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)
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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