Problems and exercisesElimination Reactions
1. Alcohols and bromides
Explain the following facts: the cis and trans isomers of 4-tert-butylcyclohexanol dehydrate at very similar rates in H2SO4 at high temperature. However, the cis isomer of 1-bromo-4-tert-butylcyclohexane eliminates HBr with a strong base much faster than its trans isomer.
2. Saytzev or Hofmann
Give the major olefin in the elimination of 2-bromo-2-methylbutane with: a) sodium ethoxide in ethanol; b) potassium tert-butoxide in tert-butanol.
3. E2 stereochemistry
Which alkene is formed in the E2 elimination of (2R,3S)-2-bromo-3-methylpentane?