Question

Treatment of ethyl acetoacetate with NaOEt (2 equiv) and BrCH2CH2Br forms compound X. This reaction is the first step in the synthesis of illudin-S, an antitumor substance isolated from the jack-o'-lantern, a saffron-colored mushroom. What is the structure of X

Answer 1

Answer:

See explanation below

Explanation:

In this reaction we have the ethyl acetoacetate which is reacting with 2 eq of sodium etoxide. The sodium etoxide is a base and it usually behaves as a nucleophyle of many reactions. Therefore, it will atract all the acidics protons in a molecule.

In the case of the ethyl acetoacetate, the protons that are in the methylene group (CH3 - CO - CH2 - COOCH2CH3) are the more acidic protons, therefore the etoxide will substract these protons instead of the protons of the methyl groups. This is because those hydrogens (in the methylene group) are between two carbonile groups, which make them more available and acidic for any reaction. As we have 2 equivalents of etoxide, means that it will substract both of the hydrogen atoms there, and then, reacts with the Br - CH2CH2 - Br and form a product of an aldolic condensation.

The mechanism of this reaction to reach X is shown in the attached picture.