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Chapter 5: Structure and Preparation of Alkenes: Elimination Reactions



Summary | Alkenes | Preparation of Alkenes | Elimination Reactions | Self Assessment | Quiz |


Alkenes

Chapter 5: Structure and Preparation of Alkenes. Elimination Reactions

Nomenclature:
Functional group suffix = -ene (review)
Simple 1,2-alkenes can be described as cis- or trans- (review)
More complex alkenes are best described as E- or Z- based on the Cahn-Ingold-Prelog priority rules (review)

Stability:
There are 3 factors that influence alkene stability:
1. Degree of substitution: more highly alkylated alkenes are more stable, so tetra > tri > di > mono-substituted.
2. Stereochemistry: trans > cis due to reduced steric interactions when R groups are on opposite sides of the double bond.
3. Conjugated alkenes are more stable than isolated alkenes.
 

more stable than
trans-2-butene
cis-2-butene

Structure:
 

pi bond molecular orbital
  • The alkene functional group consists of two sp2 hybridized C atoms bonded to each other via a s and a p bond.
  • The p bond is produced by the side-to-side overlap of the p-orbitals not utilized in the hybrids (see left).
  • The substituents are attached to the C=C unit via s bonds.
  • The 2 C of the C=C and the 4 atoms attached directly to the C=C are all in the same plane.

Reactivity:

  • A  p bond  is a region of high electron density (red) so alkenes are typically nucleophiles.
  • Alkenes typically undergo addition reactions in which the p bond  is converted to two new s bonds.
electrostatic potential of ethene

 

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