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Chapter 23: Q12P (page 766)

As shown in Figures 23-4, the Claisen reaction is reversible. That is, a饾泝-keto ester can be cleaved by base into two fragments. Using curved arrows to indicate electron flow, show the mechanism by which this cleavage occurs.

Short Answer

Expert verified

When a 饾泝-keto ester reacts with a strong base (NaOH) it can give us two products but one of them is reversible and can鈥檛 give the desired product.

Step by step solution

01

Base (NaOH) can be attacked at two positions of 饾泝-keto ester:

a.When the base (-OH) is attacked at acidic 饾泜-hydrogen the reaction will reverse easily and we can鈥檛 get the desired product.

b.But when (-OH) is attacked at the carbon of the carbonyl group, then the reaction is irreversible and we can easily get the desired product.

02

Cleavage of the 饾泝-keto ester by base like NaOH:

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