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Chem 343 – Organic Reactions Chapter 11 Prepared by José Laboy, MS http://www.chem.wisc.edu/areas/clc (Resource page) Alkene Reactions #5: Haloether Synthesis X = Cl or Br
Mechanism RO
X2
R-OH
an alcohol
X
racemic
R-OH
R
H
R-OH
O
δ+
X
X
X
X
X
racemic
racemic
R-OH2+
OR
X
The process is an anti stereospecific addition. The halonium three-­‐membered ring has a greater positive charge on the most substituted carbon atom therefore the nucleophile, in this case the alcohol solvent, attacks the side which has a greater positive charge. This works quite well with small chain alcohols. The reaction is also regioselective. The major product is a results of a Markovnikov addition. racemic
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