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Carbocations |
Chapter 8: Nucleophilic Substitution |
Stability:
The general stability order of simple alkyl carbocations is: (most stable) 3o
> 2o > 1o > methyl (least stable)
This is because alkyl groups are weakly electron donating due to hyperconjugation and inductive effects. Resonance effects can further stabilize carbocations when present.
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Alkyl carbocations
are sp2 hybridized, planar systems at the cationic C center.
The p-orbital that is not utilized in the hybrids is empty and is often shown bearing the positive charge since it represents the orbital available to accept electrons. |
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As they have an incomplete
octet, carbocations are excellent electrophiles and react readily with
nucleophiles. Alternatively, loss of H+ can generate a p bond.
The electrostatic
potential diagrams clearly show the cationic center in blue,
this is where the nucleophile will attack. |
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Rearrangements:
Carbocations are prone to rearrangement via 1,2-hyride or 1,2-alkyl shifts if
it generates a more stable carbocation
Reactions
involving carbocations:
1. Substitutions via the SN1
2. Eliminations via the E1
3. Additions to alkenes and alkynes (HX, H3O+)