Explain the fact that cyclohexanone enolate reacts with 2-bromobutane giving rise to two reaction products, while only one is formed with 2-bromo-2-methylpropane.


The important basicity of the enolates produces eliminations in secondary and tertiary substrates. In the case of 2-bromobutane, two alkenes and some alkylation product can be formed. 2-Bromo-2-methylpropane is a tertiary substrate that will remove 100% generating a single alkene.