Alkene Reaction Mechanisms
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Addition of Hydrogen Halide to Alkene
- 1. Protonation to form Carbocation Intermediate
- 2. Halide (EN element) attack protonated Carbon
Reaction: Addition of Hydrogen Halide to Alkene
RCH = CH2 + HX -->
Acid-Catalyzed Addition of Water Mechanism
- 1. Protonation with H+ from H3O+ to least substituted carbon
- 2. Nucleophile (H2O)adds to carbocation creating protonated alcohol
- 3. Excess H2O removes proton from protonated alcohol, regenerating H3O+
Reaction: Acid-Catalyzed Addition of Water
RCH = CH2 + H2O H2SO4>
Mechanism: Acid-Catalyzed Addition of An Alcohol
- 1. Protonation with H+ from alcohol
- 2. Nucleophile (R-O) adds to carbocation creating protonated ether
- 3. Excess alcohol removes proton
Reaction: Acid Catalyzed Addition of Alcohol
RCH = CH2 + CH3OH H2SO4>
Acid catalyzed reaction of an alkene with water creates an:
Acid catalyzed reaction of alkene with alcohol creates an:
Mechanism: Addition of Hydrogen Halide to Alkyne
- 1. Relatively weak pi bond breaks because pi electrons are attracted to electrophilic proton.
- - electrophile add to sp2 carbon bonded to greater number of hydrogens
- 2. Positively charged carbocation intermediate reacts rapidly with negatively charged halide ion.
Give major product of the following reaction:
HC= CCH3 HBr >
Product of addition of electrophilic reagent to an alkyne is an _________, meaning __________ can occur if in the presence of excess hydrogen halide.
second electrophilic addition reaction
Give the major product of the following reaction:
CH3C= CCH3 excess HBr>
The initial product of acid-catalyzed addition of water to an alkyne is:
An enol immediately rearranges into:
A ketone and an enol only differ in the location of a _______ and a ________
___________ are isomers that are in rapid equilibrium
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