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Chapter 5:
Structure and Preparation of Alkenes.
Elimination Reactions
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Alkenes
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.
Structure:
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The alkene functional group consists of two sp2 hybridised C
atoms bonded to each other via a s and a p
bond.
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In ethene, four other s bonds between the sp2
hybridised C and H 1s make 4 C-H bonds to complete the s
bond framework.
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The p bond is produced by the side-to-side overlap
of the p-orbitals not utilised in the hybrids (see left).
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The 2 C of the C=C and the 4 atoms attached directly to the C=C
are all in the same plane.
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For more details, you should review the
section in Chapter 2
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Reactivity:
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A p bond is a region of high electron
density (red) so alkenes are typically
nucleophiles.
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Alkenes typically undergo addition reactions in which the p
bond is converted to two new s bonds.
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