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Chem 343 – Organic Reactions Chapter 10 Prepared by José Laboy, MS http://www.chem.wisc.edu/areas/clc (Resource page) Reactions of Alcohols #2: Alkyl Halides from Tertiary alcohols HX
OH
Mechanism OH
Room
Temperature
X
X = Cl, Br, I
H
Rate
Determining
Step
X
OH2
H2O
X
This reaction represents a classic SN1 mechanism. There is always some alkene product from an E1 mechanism. Although the reaction is under equilibrium conditions either trapping the water formed, increasing the concentration of HX or removing the product as it forms will increase product yield. X
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