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SN1 SN2 E1 E2 Chart (Big Daddy Flowchart) definitions

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  • Nucleophile
    A species with a negative or neutral charge that donates electrons to form a new bond, initiating substitution or elimination.
  • Base
    A compound that removes protons, with strength and bulkiness influencing whether elimination or substitution occurs.
  • Alkyl Halide
    An organic molecule containing a halogen atom bonded to an sp3 carbon, serving as a common substrate in these mechanisms.
  • Leaving Group
    An atom or group that departs with a pair of electrons, enabling the formation of a new bond or carbocation.
  • Spectator Ion
    A cation, often from Group 1 metals, that dissociates in solution and does not participate in the reaction mechanism.
  • Carbocation
    A positively charged carbon intermediate formed during unimolecular substitution or elimination, stabilized by alkyl groups.
  • Bulky Base
    A large, sterically hindered base like tert-butoxide, LDA, or LiTMP, favoring elimination by preventing backside attack.
  • Backside Attack
    A nucleophilic approach from the side opposite the leaving group, essential for bimolecular substitution.
  • Primary Alkyl Halide
    A halide where the carbon attached to the halogen is bonded to only one other carbon, favoring direct substitution.
  • Secondary Alkyl Halide
    A halide with the halogen-bearing carbon bonded to two other carbons, allowing for both substitution and elimination.
  • Tertiary Alkyl Halide
    A halide where the halogen is attached to a carbon bonded to three other carbons, favoring carbocation pathways.
  • Heat
    A condition that increases the likelihood of elimination reactions by providing energy for proton removal.
  • Oxide
    A strong base with the general formula OR−, highly effective at promoting elimination in secondary alkyl halides.
  • Alkynide
    A strong base featuring a negatively charged carbon in a triple bond, promoting elimination due to instability.
  • Flowchart
    A stepwise decision tool guiding the selection of substitution or elimination mechanisms based on reactant features.