
Interpretation:
The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion is to be explained.
Concept introduction:
The attack of the base on the carbonyl carbon of the ester and subsequent elimination of ester and protonation of the anion leads to products in a reverse Claisen reaction. However if the ester has acidic α-hydrogen atoms, the base can abstract it giving a stable resonance stabilized anion. In such cases the reverse Claisen reaction will not takes place readily at room temoerature.
To explain:
The difference in reactivity between ethyl acetoacetate (cleaves at 150°C) and ethyl dimethylacetoacetate (cleaves at room temperature) with ethoxide ion.

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Chapter 23 Solutions
Organic Chemistry - With Access (Custom)
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