Eliminations Reactions: E1, E2, E1cB
Start with the big picture
E1 proceeds in two steps: the leaving group departs to form a carbocation, then a base removes a β-hydrogen. Its rate depends on substrate concentration, and carbocation rearrangements may occur. E2 is a concerted, one-step pathway whose rate depends on both substrate and base; it requires an anti-periplanar β-hydrogen and gives a stereospecific outcome. E1cB proceeds through deprotonation to form a carbanion before leaving-group departure, and is associated with a poor leaving group and an acidic β-hydrogen. The topic also connects mechanism choice with substrate reactivity, base and solvent conditions, leaving-group ability, and competition with substitution. Regioselectivity, stereochemistry, and reaction energy profiles provide further ways to distinguish the pathways.
What you'll learn
- Compare the steps, intermediates, and rate dependence of E1, E2, and E1cB.
- Relate substrate, base, solvent, and leaving-group properties to pathway preference.
- Explain the anti-periplanar requirement and stereochemical outcomes of E2 elimination.
- Distinguish alkene regioselectivity and rearrangement possibilities among elimination pathways.
- Describe how elimination conditions can compete with substitution reactions.
Continue your study
Work through the complete notes and reinforce the topic with the study tools available in the full lesson.