Key Terms

  • anti periplanar
  • bimolecular
  • E1 reaction
  • E1cB reaction
  • E2 reaction
  • first-order reaction
  • kinetics
  • leaving group
  • nucleophilic substitution reaction
  • periplanar
  • rate-determining step
  • rate-limiting step
  • second-order reaction
  • SN1 reaction
  • SN2 reaction
  • solvation
  • syn periplanar
  • tosylate
  • unimolecular
  • Zaitsev’s rule

Summary of Reactions

1. Nucleophilic substitutions

  • SN1 reaction of 3°, allylic, and benzylic halides (Section 7.4 and Section 7.5)

The S N 1 reaction of tertiary halide forms a carbocation intermediate, which further reacts with a nucleophile to yield a halide ion and a substitution product.

 

 

  • SN2 reaction of 1° and simple 2° halides (Section 7.2 and Section 7.3)

The S N 2 reaction between an alkyl halide and nucleophile forms a halide ion and substitution product with inversion of configuration.

 

 

2. Eliminations

  • E1 reaction (Section 7.10)

The E 1 reaction of an alkyl halide forms a carbocation intermediate, which is deprotonated to yield an alkene and H-X.

 

 

 

  • E1cB reaction (Section 7.10)

The E 1 C B reaction of an alkyl halide in concentrated base forms a carbanion intermediate through abstraction of hydrogen alpha to carbonyl, which reacts to produce an allylic carbonyl.

 

 

 

  • E2 reaction (Section 7.8)

The E 2 reaction mechanism of bromoalkane with a base such as K O H forms an alkene in one step.

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Fundamentals of Organic Chemistry Copyright © by Kirsten Kramer and Cassandra Lilly is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License, except where otherwise noted.

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