Octet / Reactions
Hydrohalogenation (HX Addition)
Hydrohalogenation (HX Addition) (Electrophilic Addition Addition.) Converts CC=C to CC(C)Br using HBr (or HCl, HI).
Reaction details
Hydrohalogenation (HX Addition)
Addition
Electrophilic Addition
CC=C
CC(C)Br
HBr (or HCl, HI)
- Smiles
CC=C
- Description
Propene: π electrons are nucleophilic
- Smiles
CC=C
- Description
H⁺ adds to less substituted carbon (forms more stable carbocation)
- Smiles
C[CH+]C
- Description
Secondary carbocation intermediate
- Smiles
CC(C)Br
- Description
Halide attacks carbocation (shown: Br⁻)
Markovnikov: H adds to carbon with more H's, X to more substituted carbon
Carbocation stability determines regiochemistry
Rearrangements possible with carbocation intermediate
Follows Markovnikov's rule
Mechanism shown for HBr; HCl and HI work analogously
hydroboration
halohydrin-formation
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