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18 Cards in this Set

  • Front
  • Back
Occur when one functional group replaces another.
Sn1 reaction
Two step reaction with a rate dependent on only one of the reactants.
Slow step
Rate determining step of reaction
Sn2 reaction
One step reaction with a rate dependent on the concentration of the nucleophile and the substrate
Sterical Hinderance
Sn2 reactions typically do not occur in tertiary substrates.
"The nucleophile and the 5 Ss"
Differences between Sn1 and Sn2 reactions
"The Nucleophile"
Sn2 requires strong nucleophile while Sn1 is not affected by nucleophile strength
1st S- Substrate
Sn2 reactions dont occur with sterically hindered substrate. Sn2 requires methyl, primary or secondary substrate while Sn2 requires secondary or tertiary.
2nd S- Solvent
Highly polar solvent increases reaction rate of Sn1 by stabilizing the carbocation, but slows down Sn2 reactions by stabilizing the nucleophile
3rd S- Speed
Speed of Sn2 depends on concentration of substrate and the nucleophile, while speed of Sn1 depends only on the substrate.
4th S- Stereochemistry
Sn2 inverts stereochemistry about chiral center while Sn1 creates a racemic mixture.
5th S- Skeleton
Sn1 may be accompanied by carbon skeleton rearrangement but Sn2 never rearranges the carbon skeleton.
Loss of H2, addition of O or O2, addition of X2
Addition of H2, loss of O or O2, loss of X2
Formation of sulfonates
Nucleophilic substitution where alcohol acts as a nucleophile.
Tosylates and mesylates
commonly used sulfonates (draw)
Pinacol arrangement
Dehydration of an alcohol that results in a unexpected product
Polar, relatively non reactive substances that can hydrogen bond with compounds that contain hydrogen attached to an N, O, or F atom.