21. Draw the mechanism of each of the following solvolysis reactions: EIOH Br (solvolysis) но (solvolysis) CI

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter30: Orbitals And Organic Chemistry: Pericyclic Reactions
Section30.SE: Something Extra
Problem 14MP: Plastic photochromic sunglasses are based on the following reversible rearrangement of a dye inside...
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21. Draw the mechanism of each of the following solvolysis reactions:
ELOH
Br
(solvolysis)
CI
OH
(solvolysis)
Transcribed Image Text:21. Draw the mechanism of each of the following solvolysis reactions: ELOH Br (solvolysis) CI OH (solvolysis)
Carbocation Rearrangement with proton transfer process:
Here is an example of an Sy1 process that is accompanied by all three additional steps:
H3Oʻ/MEOH
ÖH
:OMe
Proton
transfer
Proton transfer
Nucleophilic
attack
Loss of leaving
Carbocation
group
rearrangement
- H20
Me
H
H.
Me
2° carbocation
3° carbocation
Energy diagram for carbocation rearrangement with proton transfer
Loss of
LG
Nucleophillic
attack
Proton
Carbocation
Proton
transfer
rearrangement
transfer
carbocation
Potential
energy
carbocation
Me e
H-O
OH
OMe
Reaction coordinate
Transcribed Image Text:Carbocation Rearrangement with proton transfer process: Here is an example of an Sy1 process that is accompanied by all three additional steps: H3Oʻ/MEOH ÖH :OMe Proton transfer Proton transfer Nucleophilic attack Loss of leaving Carbocation group rearrangement - H20 Me H H. Me 2° carbocation 3° carbocation Energy diagram for carbocation rearrangement with proton transfer Loss of LG Nucleophillic attack Proton Carbocation Proton transfer rearrangement transfer carbocation Potential energy carbocation Me e H-O OH OMe Reaction coordinate
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