Organic Chemistry Organohalides

Eliminations Reactions: E1, E2, E1cB

Topic overview

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.

Learning objectives

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.
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