Chemistry Reference
In-Depth Information
Figure 7.3 Unlike most carbonyl-based functional groups, nonconjugated esters can react with
nucleophiles and retain the carbonyl unit.
using arrow pushing, is known as an addition-elimination and involves initial addition of a
nucleophile to a carbonyl followed by elimination of an alkoxide leaving group. As a cau-
tionary note, the conversion of esters to ketones can be difficult to control due to sequential
reaction of the newly formed ketones with nucleophiles present in the reaction mixture.
Addition-elimination reactions are not exclusive to esters. In fact, these reactions can
occur with any carbonyl-based system where the leaving group is a weaker nucleophile
Scheme 7.19 The addition-elimination mechanism illustrated with arrow pushing.
