In this organic chemistry laboratory experiment, students perform two different alkylations of a-methylcyclohexanone. Conditions have been established that allow the students to achieve efficient anion formation using lithium diisopropylamide in tetrahydrofuran. First, the enolate is alkylated with either allyl bromide or benzyl bromide and the product analyzed by GC/MS. Subsequently, a competitive alkylation is performed using both electrophiles and the reaction mixture analyzed by GC/MS.
Padías et al. (Mon,) studied this question.