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Chem 343 – Organic Reactions Chapter 11 Prepared by José Laboy, MS http://www.chem.wisc.edu/areas/clc (Resource page) Synthesis and Reactions of Ethers #2: Ethers from 3° Alcohols Mechanism OH
CH3OH
Traces of H2SO4
OH
OCH3
OSO3H
H2O
O
H
O
S
OH
OH2
O
CH3
O
CH3OH
H
OCH3
CH3OH
This reaction is a classic SN1 mechanism. It’s done at room temperature. Some E1 product is expected. If the carbon atom that bears the alcohol group is stereogenic then expect a racemic mixture.
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