During this laboratory session we will use the Claisen rearrangement to transform phenyl allyl ether (1)...
During this laboratory session we will use the Claisen rearrangement to transform phenyl allyl ether (1) into 2- allyl phenol (2). The phenol results from the tautomerization of the initial product of the Claisen rearrangement to restore aromaticity as shown below. You have yet to learn that keto-enol tautomerization usually favors the ketone, but in this case the restoration of aromaticity provides a driving force for the formation of the enol). OH Claisen Rearrangement Tautomerization Re-aromatization H 2 Scheme 2. Synthesis of 2-allyl phenol from phenyl allyl ether The transformation of 1 to 2 requires 6 hours of heating at reflux to reach completion. We will monitor the